$640,000 Rarely available, all-brick rancher in the amenity-rich, sought-after Hillsmere Shores community. This home has been meticulously cared for and loved, and it will show from the moment you step in!! Gleaming hardwood floors, freshly painted interior, and abundant natural light perfectly framed by custom plantation shutters are your first signs that this is a special home. As you make your way through the dining/eating area, you will begin to realize that there is way more space inside than you might have imagined from the outside. Prepare to be completely wow'd as you step into the four-season room!! Vaulted ceilings, skylights, a brick accent wall, a pellet stove, and a dedicated Mitsubishi split heat and A/C system will quickly make you realize you have found your favorite room in the house. The second bathroom's shower was converted for accessibility to main level laundry - enjoy the convenience, or easily convert back as there is still laundry available in the basement. Speaking of the basement...it is a full basement with 1500+ sq. feet of potential and possibilities. Workshop, rec room, fourth bedroom, third bathroom, etc. It is truly a blank slate that can quickly double the home's square footage. On top of all this awesomeness, we haven't even stepped out back, where you will find an oversized, maintenance-free deck overlooking a flat, cleared, spacious, fully fenced backyard. AND a 2-car all-brick detached garage with a driveway that will have you envisioning having everyone over very easily for fall football and firepits!! Be sure to check out all of the amenities that Hillsmere Shores has to offer....pier, boat ramp, waterfront playground, beach, pavilion, and neighboring access to Quiet Waters Park. This one is priced to sell quickly and is a rare combination of things that a lot of people look for in Annapolis that are rarely available. Don't hesitate!! 3 Beds ⋅ 2 Baths ⋅ MDAA2155652 MLS Rarely available, all-brick rancher in the amenity-rich, sought-after Hillsmere Shores community. This home has been meticulously cared for and loved, and it will show from the moment you step in!! Gleaming hardwood floors, freshly painted interior, and abundant natural light perfectly framed by custom plantation shutters are your first signs that this is a special home. As you make your way through the dining/eating area, you will begin to realize that there is way more space inside than you might have imagined from the outside. Prepare to be completely wow'd as you step into the four-season room!! Vaulted ceilings, skylights, a brick accent wall, a pellet stove, and a dedicated Mitsubishi split heat and A/C system will quickly make you realize you have found your favorite room in the house. The second bathroom's shower was converted for accessibility to main level laundry - enjoy the convenience, or easily convert back as there is still laundry available in the basement. Speaking of the basement...it is a full basement with 1500+ sq. feet of potential and possibilities. Workshop, rec room, fourth bedroom, third bathroom, etc. It is truly a blank slate that can quickly double the home's square footage. On top of all this awesomeness, we haven't even stepped out back, where you will find an oversized, maintenance-free deck overlooking a flat, cleared, spacious, fully fenced backyard. AND a 2-car all-brick detached garage with a driveway that will have you envisioning having everyone over very easily for fall football and firepits!! Be sure to check out all of the amenities that Hillsmere Shores has to offer....pier, boat ramp, waterfront playground, beach, pavilion, and neighboring access to Quiet Waters Park. This one is priced to sell quickly and is a rare combination of things that a lot of people look for in Annapolis that are rarely available. Don't hesitate!! 122 Kuethe Dr, Annapolis
$675,000 Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner. 3 Beds ⋅ 2 Baths ⋅ MDAA2156150 MLS Welcome to 953 Mastline Drive, a spacious ranch style home in the highly sought after 55+ community of Heritage Harbour. Offering just under 2,000 square feet, three bedrooms, two full bathrooms, and a two car garage, this home provides easy single level living with plenty of space to enjoy. Inside, fresh paint and brand new carpet give the home a clean, refreshed feel throughout. Generous living and dining areas offer flexibility for everyday life and entertaining, while the primary suite features its own private bathroom. Updated windows and HVAC, along with new insulation, add to the improvements already completed, allowing you to move right in while still having the opportunity to personalize the home over time. Heritage Harbour offers an impressive collection of amenities, including indoor and outdoor pools, a fitness center, tennis and pickleball courts, a nine hole golf course, community Lodge, library, and an extensive calendar of clubs, activities, and social opportunities. Shopping, dining, healthcare, and everyday conveniences are nearby, with easy access to Routes 50 and 97 and Historic Downtown Annapolis just a short drive away. Combining a spacious ranch layout, valuable updates, and the active lifestyle of one of the Annapolis area’s most established 55+ communities, 953 Mastline Drive is ready to welcome its next owner. 953 Mastline Dr, Annapolis
$755,000 Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level and stairs feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50 1 Baths ⋅ MDAA2156472 MLS Nestled in the sought-after community of Hunt Meadow, and on a quiet cul-de-sac, this perfectly-kept colonial home offers the right blend of comfort and privacy. Featuring 4 bedrooms and 2.5 baths, a family room with a cozy fireplace, raised hearth and framed in brick. Vaulted ceilings, and custom oak hardwood floors. The kitchen features stainless steel appliances, granite counter tops and modern plank flooring. The entire second level and stairs feature all NEW carpeting. The primary bedroom has a spacious en-suite bath. Two additional bedrooms and an additional full bath are on this level. The finished basement offers additional space for recreation with a Movie Room featuring a large TV screen, movie projector and stereo system that all conveys with the property. A walk-in cedar-lined storage closet, a laundry room with front-load washer and dryer, and a fourth bedroom. The exterior features a brand NEW deck, and fire pit - ideal for enjoying the quiet outdoors. The back yard is private, partly wooded, and has trails leading from it for exploration. The garage is equipped with shelves and a workbench for projects. Residents enjoy access to community amenities such as the large outdoor pool, tennis courts, and scenic jog/walk paths that connect to Quiet Waters Park. The neighborhood is well-maintained, with sidewalks for leisurely strolls. Lots of community spirit here with swim meets, 5k runs, food trucks, holiday celebrations and other get-togethers. Hunt Meadow is just minutes from downtown Annapolis and convenient to Rts. 97 and 50 303 Riding Ridge Rd, Annapolis
$849,000 Welcome to 1249 Stillwoods Way, an elegant and exceptionally well-appointed residence offering nearly 4,200 square feet of beautifully finished living space, a full finished lower level, and an enviable combination of comfort, style, and functionality. From the moment you enter, the home presents a sophisticated yet inviting atmosphere. The gourmet kitchen is designed for both everyday living and entertaining, featuring beautiful granite countertops and generous workspace. The main level offers an effortless flow between living and dining spaces, with a screened porch providing a tranquil extension of the home and an ideal setting for morning coffee, leisurely afternoons, or evening gatherings. The private primary suite is a true retreat. The updated primary bath evokes a spa-like experience with a striking freestanding soaking tub, an oversized walk-in shower, and beautifully updated mirrors featuring integrated lighting and built-in defrosting—thoughtful details that elevate the everyday. With four bedrooms, three full baths, and a convenient half bath on the main level, the home offers exceptional flexibility for family, guests, or a dedicated home office. The fully finished basement expands the possibilities even further, providing valuable additional living and entertaining space. A two-car garage adds both convenience and coveted storage, while the screened porch and thoughtfully designed interiors create a seamless balance between indoor comfort and outdoor enjoyment. Ideally situated in Annapolis, 1249 Stillwoods Way offers the rare opportunity to enjoy an elevated residential lifestyle while remaining close to the area’s renowned waterfront, historic charm, dining, shopping, and recreation. 4 Beds ⋅ 4 Baths ⋅ MDAA2156616 MLS ⋅ Stillwoods BLDG. Welcome to 1249 Stillwoods Way, an elegant and exceptionally well-appointed residence offering nearly 4,200 square feet of beautifully finished living space, a full finished lower level, and an enviable combination of comfort, style, and functionality. From the moment you enter, the home presents a sophisticated yet inviting atmosphere. The gourmet kitchen is designed for both everyday living and entertaining, featuring beautiful granite countertops and generous workspace. The main level offers an effortless flow between living and dining spaces, with a screened porch providing a tranquil extension of the home and an ideal setting for morning coffee, leisurely afternoons, or evening gatherings. The private primary suite is a true retreat. The updated primary bath evokes a spa-like experience with a striking freestanding soaking tub, an oversized walk-in shower, and beautifully updated mirrors featuring integrated lighting and built-in defrosting—thoughtful details that elevate the everyday. With four bedrooms, three full baths, and a convenient half bath on the main level, the home offers exceptional flexibility for family, guests, or a dedicated home office. The fully finished basement expands the possibilities even further, providing valuable additional living and entertaining space. A two-car garage adds both convenience and coveted storage, while the screened porch and thoughtfully designed interiors create a seamless balance between indoor comfort and outdoor enjoyment. Ideally situated in Annapolis, 1249 Stillwoods Way offers the rare opportunity to enjoy an elevated residential lifestyle while remaining close to the area’s renowned waterfront, historic charm, dining, shopping, and recreation. 1249 Stillwoods Way, Annapolis
$675,000 Tucked at the end of a private flag-lot driveway and backing to mature woods, this home offers the rare combination of privacy and convenience. A light-filled sunroom overlooks the tree-lined rear yard, while the gas fireplace anchors the main living space for easy year-round comfort. The primary suite is located on the main level, along with a second bedroom/TV den and a hallway full bathroom. Upstairs two more flexible bedrooms can also function as an office, craft room, or workout space, and are joined by another full bathroom upstairs. Freshly painted throughout with brand-new flooring, it's move-in ready from day one. The big-ticket items are already handled: HVAC replaced in 2022, roof approximately three years young, and a tankless water heater installed in 2019 for endless hot water and lower energy costs. An attached two-car garage and in-ground lawn sprinkler system round out the package. Residents of Heritage Harbour enjoy an exceptional array of amenities designed for an active, social, and engaging lifestyle. The list of Heritage Harbour amenities and services is vast, including: a 9-hole, par 3 golf course with pro shop, tennis courts, indoor and outdoor pools, fitness center with exercise classes, sauna, and whirlpool, billiard room, restaurant, library, meeting rooms, auditorium with stage and dance floor, wood shop and craft room, pier with boat slips and kayak storage, RV storage, and a pond - the popular site of remote control boat races. Activities Abound. There’s no excuse for boredom when you live in Heritage Harbour. Residents have access to all kinds of clubs, meetings, and activities, including community college classes on site, bus service to nine standard Annapolis locations and many other special trips, community dances and plays, the Harbour Lights newsletter and HHTV television channel, model boat races, billiard tournaments, community management and leadership, bocce, horseshoes, and lawn games. A Prime Location. The community is located about 10 minutes from Anne Arundel Medical Center and Annapolis Mall. For those who like to snowbird in warmer locations, the Baltimore Washington International airport is about 30 minutes away. 4 Beds ⋅ 3 Baths ⋅ MDAA2156964 MLS Tucked at the end of a private flag-lot driveway and backing to mature woods, this home offers the rare combination of privacy and convenience. A light-filled sunroom overlooks the tree-lined rear yard, while the gas fireplace anchors the main living space for easy year-round comfort. The primary suite is located on the main level, along with a second bedroom/TV den and a hallway full bathroom. Upstairs two more flexible bedrooms can also function as an office, craft room, or workout space, and are joined by another full bathroom upstairs. Freshly painted throughout with brand-new flooring, it's move-in ready from day one. The big-ticket items are already handled: HVAC replaced in 2022, roof approximately three years young, and a tankless water heater installed in 2019 for endless hot water and lower energy costs. An attached two-car garage and in-ground lawn sprinkler system round out the package. Residents of Heritage Harbour enjoy an exceptional array of amenities designed for an active, social, and engaging lifestyle. The list of Heritage Harbour amenities and services is vast, including: a 9-hole, par 3 golf course with pro shop, tennis courts, indoor and outdoor pools, fitness center with exercise classes, sauna, and whirlpool, billiard room, restaurant, library, meeting rooms, auditorium with stage and dance floor, wood shop and craft room, pier with boat slips and kayak storage, RV storage, and a pond - the popular site of remote control boat races. Activities Abound. There’s no excuse for boredom when you live in Heritage Harbour. Residents have access to all kinds of clubs, meetings, and activities, including community college classes on site, bus service to nine standard Annapolis locations and many other special trips, community dances and plays, the Harbour Lights newsletter and HHTV television channel, model boat races, billiard tournaments, community management and leadership, bocce, horseshoes, and lawn games. A Prime Location. The community is located about 10 minutes from Anne Arundel Medical Center and Annapolis Mall. For those who like to snowbird in warmer locations, the Baltimore Washington International airport is about 30 minutes away. 954 Shadewater Way, Annapolis
$1,750,000 If you love a home that breathes history, you’ll fall in love with this one. Ideally situated at 102 Duke of Gloucester Street, the property rests along one of the area’s most historic streets—named in the late 1600s in honor of Prince William, The Duke of Gloucester. Set on one of the most desirable stretches of the street, this classic Annapolis home is one where history, character, and everyday livability come together beautifully. Directly across from St. Mary’s Church, this four-bedroom, 3.5-bath residence offers just under 3,000 square feet perched on a generous lot with ample private parking. Its location places you within effortless walking distance of Spa Creek, Main Street, Ego Alley, the Annapolis Yacht Club, and Eastport—an extraordinary position that puts the very best of Annapolis at your doorstep. From the moment you cross the threshold, the charm is unmistakable. This home is filled with warm natural light and the energy of a true Annapolis residence that has been has been lived in, loved, and appreciated in its time. Rich wood, original details, and an authentic sense of place create an atmosphere that simply cannot be replicated in a new build. Among its most beautiful details are the original panes of glass showcased at the front of the home, along with rare, old-growth Georgia hard-pine edge-grain floors, and an original letter box—craftsmanship and materials that are increasingly difficult, if not impossible, to find today. The second floor showcases an especially inviting primary suite with a huge bath filled with warm morning light— a peaceful place to begin each day surrounded by the character of historic Annapolis. An additional full bath and bedrooms right down the hall. A bright and spacious grand room crowns the 3rd floor to be used as you like for an additional bedroom, exercise, and artist haven, office - you decide! The lower level is fitted with the original brick floors and offers a private full suite—an exceptional space for guests, extended family, or separate living arrangement. Additionally it includes its own secluded workshop, a rare and charming feature for someone who enjoys working with their hands, tackling projects, or simply having a dedicated place to create. Easily accessed from the kitchen breakfast area, the rear yard is one of the property’s most unexpected treasures. This generous outdoor space, not often found in downtown, offers privacy, a place to garden, entertain or simply letting the dog run and play. You will have your own highly desired and remarkably convenient parking for downtown living with room for two full-size vehicles or up to three compact cars, complemented by additional ample street parking. A fire-suppression system adds an additional layer of peace of mind to this historic residence. The sewer line was updated within the last 8 years and the roof was replaced in 2016 with 50 year rated shingles. But perhaps what makes this home most special is what cannot be measured in square footage. It has soul. The wood is rich. The light is warm. The architecture carries the imprint of another era. And the location is nearly impossible to duplicate. For those who appreciate the romance of an old home—the imperfections, the craftsmanship, the history, and the stories embedded within its walls—102 Duke of Gloucester Street offers something increasingly rare: a genuine piece of Annapolis that still still feels like a home. 4 Beds ⋅ 4 Baths ⋅ MDAA2156954 MLS If you love a home that breathes history, you’ll fall in love with this one. Ideally situated at 102 Duke of Gloucester Street, the property rests along one of the area’s most historic streets—named in the late 1600s in honor of Prince William, The Duke of Gloucester. Set on one of the most desirable stretches of the street, this classic Annapolis home is one where history, character, and everyday livability come together beautifully. Directly across from St. Mary’s Church, this four-bedroom, 3.5-bath residence offers just under 3,000 square feet perched on a generous lot with ample private parking. Its location places you within effortless walking distance of Spa Creek, Main Street, Ego Alley, the Annapolis Yacht Club, and Eastport—an extraordinary position that puts the very best of Annapolis at your doorstep. From the moment you cross the threshold, the charm is unmistakable. This home is filled with warm natural light and the energy of a true Annapolis residence that has been has been lived in, loved, and appreciated in its time. Rich wood, original details, and an authentic sense of place create an atmosphere that simply cannot be replicated in a new build. Among its most beautiful details are the original panes of glass showcased at the front of the home, along with rare, old-growth Georgia hard-pine edge-grain floors, and an original letter box—craftsmanship and materials that are increasingly difficult, if not impossible, to find today. The second floor showcases an especially inviting primary suite with a huge bath filled with warm morning light— a peaceful place to begin each day surrounded by the character of historic Annapolis. An additional full bath and bedrooms right down the hall. A bright and spacious grand room crowns the 3rd floor to be used as you like for an additional bedroom, exercise, and artist haven, office - you decide! The lower level is fitted with the original brick floors and offers a private full suite—an exceptional space for guests, extended family, or separate living arrangement. Additionally it includes its own secluded workshop, a rare and charming feature for someone who enjoys working with their hands, tackling projects, or simply having a dedicated place to create. Easily accessed from the kitchen breakfast area, the rear yard is one of the property’s most unexpected treasures. This generous outdoor space, not often found in downtown, offers privacy, a place to garden, entertain or simply letting the dog run and play. You will have your own highly desired and remarkably convenient parking for downtown living with room for two full-size vehicles or up to three compact cars, complemented by additional ample street parking. A fire-suppression system adds an additional layer of peace of mind to this historic residence. The sewer line was updated within the last 8 years and the roof was replaced in 2016 with 50 year rated shingles. But perhaps what makes this home most special is what cannot be measured in square footage. It has soul. The wood is rich. The light is warm. The architecture carries the imprint of another era. And the location is nearly impossible to duplicate. For those who appreciate the romance of an old home—the imperfections, the craftsmanship, the history, and the stories embedded within its walls—102 Duke of Gloucester Street offers something increasingly rare: a genuine piece of Annapolis that still still feels like a home. 102 Duke Of Gloucester St, Annapolis
$1,300,000 A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind. 5 Beds ⋅ 4 Baths ⋅ MDAA2156894 MLS A rare opportunity to own a fully metered triplex in the heart of Downtown Annapolis where historic charm, prime location, and remarkable versatility come together. Steeped in character and offering exceptional flexibility, this distinctive property presents an array of possibilities for both lifestyle and investment. With separately metered electricity, the property can be enjoyed as a multigenerational residence, with each family member having their own private space; an owner-occupied home with additional rental income from the remaining units; or a pure investment property with multiple income producing residences. For those envisioning something truly extraordinary, the entire building could be transformed back into a stunning single-family home. With original architecture and showcasing hardwood floors throughout, this property strikes the perfect balance between historic character and modern livability. The first floor features two bedrooms, each with an en-suite bath, kitchen, and living room, ideal for an owner-occupant or long-term tenant. The second floor offers one bedroom, a full bath, kitchen, living room, and access to a private balcony. The third floor impresses with two bedrooms, a full bath, kitchen, and living room, plus its own private balcony. An unfinished basement provides excellent storage space. A fenced backyard complete with a paver patio, provides an outdoor retreat ideal for relaxing or entertaining. Add to that the coveted off-street parking, a true rarity in Downtown Annapolis, and this property is as practical as it is beautiful. Whether you're an investor seeking immediate income potential, a buyer looking to offset your mortgage, or a multigenerational family wanting separate yet connected living spaces, this home checks every box. All of this just steps from the vibrant shops, restaurants, waterfront, and history that make Downtown Annapolis truly one of a kind. 135 Conduit St, Annapolis
$2,300,000 Simultaneously Listed and SOLD 3 Beds ⋅ 2 Baths ⋅ MDAA2156842 MLS Simultaneously Listed and SOLD 3260 Harness Creek Rd, Annapolis
$3,375,000 Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifestyle. Built in 2012, this stunning detached home showcases timeless architectural elegance with its brick and HardiPlank exterior, inviting you into a world of sophistication. Step inside to discover an expansive open floor plan adorned with rich hardwood and tile flooring, creating a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, featuring a commercial-grade range, stainless steel appliances, and a spacious island, perfect for culinary creations and entertaining. The butler's pantry adds an extra touch of convenience, while the adjoining dining area flows seamlessly into the living space, highlighted by an elegant gas fireplace that provides a cozy ambiance. Waterfront views from every room.The primary suite is a true sanctuary, boasting breathtaking views and a luxurious en-suite bathroom complete with a soaking tub and walk-in shower. Each of the five bedrooms is generously sized with ensuite baths offering ample space for relaxation and privacy. Thoughtful details such as crown moldings, recessed lighting, and wainscoting enhance the home's refined aesthetic. Venture to the fully finished daylight basement, where natural light pours in through large windows, creating an inviting space for recreation or relaxation. This versatile area includes a wet/dry bar, perfect for hosting gatherings or enjoying quiet evenings at home, another bedroom and 2 full baths. Outside, the property is a true oasis. The extensive hardscape is complemented by lush landscaping and an underground lawn sprinkler system, ensuring a vibrant outdoor space year-round. Enjoy evenings on the screened porch or patio, where you can take in the tranquil views of the South River. With private access to the water, indulge in boating, fishing, or simply basking in the beauty of your surroundings. A standout waterfront designed for the boating lifestyle, featuring a 6' × 115' private pier with a spacious 10' × 20' platform and 3' × 12' finger pier - a total of 125 ft. length from the MHWL at the bulkhead. With approximately 10 feet of water at Mean Low Water (MLW) at the slips, the property offers exceptional deep-water access, along with a 12' × 14' boat lift with guide pole and an approximately 18' × 50' mooring slip. A timber bulkhead and riprap-protected shoreline complete this impressive waterfront setting—offering outstanding access to the Chesapeake and everything that comes with life on the water. The pier also includes a dock box, kayak rack, and lighthouse-style power pedestal. Additional features include a two-car attached garage with inside access, energy-efficient appliances, and a comprehensive water treatment system, ensuring comfort and convenience at every turn. This home is not just a residence; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Experience the best of coastal living in this remarkable property, where every detail has been thoughtfully curated for your enjoyment. 5 Beds ⋅ 7 Baths ⋅ MDAA2156764 MLS Nestled in the serene enclave of Cape St. John, this exquisite coastal residence offers a harmonious blend of luxury and comfort, perfectly designed for an elevated lifestyle. Built in 2012, this stunning detached home showcases timeless architectural elegance with its brick and HardiPlank exterior, inviting you into a world of sophistication. Step inside to discover an expansive open floor plan adorned with rich hardwood and tile flooring, creating a warm and inviting atmosphere. The gourmet kitchen is a chef's dream, featuring a commercial-grade range, stainless steel appliances, and a spacious island, perfect for culinary creations and entertaining. The butler's pantry adds an extra touch of convenience, while the adjoining dining area flows seamlessly into the living space, highlighted by an elegant gas fireplace that provides a cozy ambiance. Waterfront views from every room.The primary suite is a true sanctuary, boasting breathtaking views and a luxurious en-suite bathroom complete with a soaking tub and walk-in shower. Each of the five bedrooms is generously sized with ensuite baths offering ample space for relaxation and privacy. Thoughtful details such as crown moldings, recessed lighting, and wainscoting enhance the home's refined aesthetic. Venture to the fully finished daylight basement, where natural light pours in through large windows, creating an inviting space for recreation or relaxation. This versatile area includes a wet/dry bar, perfect for hosting gatherings or enjoying quiet evenings at home, another bedroom and 2 full baths. Outside, the property is a true oasis. The extensive hardscape is complemented by lush landscaping and an underground lawn sprinkler system, ensuring a vibrant outdoor space year-round. Enjoy evenings on the screened porch or patio, where you can take in the tranquil views of the South River. With private access to the water, indulge in boating, fishing, or simply basking in the beauty of your surroundings. A standout waterfront designed for the boating lifestyle, featuring a 6' × 115' private pier with a spacious 10' × 20' platform and 3' × 12' finger pier - a total of 125 ft. length from the MHWL at the bulkhead. With approximately 10 feet of water at Mean Low Water (MLW) at the slips, the property offers exceptional deep-water access, along with a 12' × 14' boat lift with guide pole and an approximately 18' × 50' mooring slip. A timber bulkhead and riprap-protected shoreline complete this impressive waterfront setting—offering outstanding access to the Chesapeake and everything that comes with life on the water. The pier also includes a dock box, kayak rack, and lighthouse-style power pedestal. Additional features include a two-car attached garage with inside access, energy-efficient appliances, and a comprehensive water treatment system, ensuring comfort and convenience at every turn. This home is not just a residence; it's a lifestyle, offering the perfect blend of luxury, comfort, and natural beauty. Experience the best of coastal living in this remarkable property, where every detail has been thoughtfully curated for your enjoyment. 203 Cape St John Rd, Annapolis
$2,499,500 There are houses that simply check the boxes, and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighborhood, this beautifully crafted custom home is filled with the details that make a house memorable: gorgeous millwork, custom built-ins, gracious rooms, beautiful gardens and spaces designed for both gathering and retreat. At the heart of the home is a stunning chef’s kitchen that opens seamlessly to the spacious family room and screened porch, equally suited to busy mornings, relaxed weekends and a house full of friends. Custom built-ins surround the breakfast area, while formal living and dining rooms offer elegant spaces for entertaining without feeling overly formal. Upstairs, the expansive primary suite feels like a true retreat, with an oversized walk-in closet and spa-inspired bath featuring dual vanities, a soaking tub and separate shower. Two additional bedroom suites, a generous bonus room perfect for a family room, library, playroom or home office, and a large laundry room complete the second level. The third floor adds two more bedrooms and a full bath, offering tremendous flexibility for guests, work or hobbies. The lower level adds another layer of versatility, with its own private entrance, living room, full kitchen, bedroom, full bath and separate laundry. Ideal for extended family, an au pair or long-term guests, this completely independent apartment has also historically rented for $2,100 per month. Outside, the grounds are every bit as special as the home itself. Beautifully established English-style gardens surround the property, with professional landscaping, lush plantings and masses of mature hydrangeas creating a setting that feels almost Nantucket-like in the summer. The screened porch overlooks this private garden retreat and may quickly become your favorite room in the house. A circular driveway provides generous off-street parking, while the oversized two-car garage includes custom built-in storage. Significant recent improvements include three new HVAC systems installed approximately three years ago, along with an upgraded sprinkler system. And perhaps the most Annapolis detail of all: step outside in the morning and you can hear reveille from the U.S. Naval Academy; in the evening, taps carries through the air. Downtown Annapolis, the Naval Academy, marinas, restaurants and shopping are all just minutes away, with easy access to Route 50 making commuting simple and convenient. As an added benefit, the entire home has historically rented for approximately $16,000 during Naval Academy Commissioning Week, an exceptional opportunity unique to this sought-after Annapolis location. Beautifully built, wonderfully livable and unmistakably Annapolis, this is a home with room for everyone, and then some. 6 Beds ⋅ 6 Baths ⋅ MDAA2156370 MLS There are houses that simply check the boxes, and then there are houses that have a sense of place. Tucked away at the end of a quiet street in the coveted Wardour neighborhood, this beautifully crafted custom home is filled with the details that make a house memorable: gorgeous millwork, custom built-ins, gracious rooms, beautiful gardens and spaces designed for both gathering and retreat. At the heart of the home is a stunning chef’s kitchen that opens seamlessly to the spacious family room and screened porch, equally suited to busy mornings, relaxed weekends and a house full of friends. Custom built-ins surround the breakfast area, while formal living and dining rooms offer elegant spaces for entertaining without feeling overly formal. Upstairs, the expansive primary suite feels like a true retreat, with an oversized walk-in closet and spa-inspired bath featuring dual vanities, a soaking tub and separate shower. Two additional bedroom suites, a generous bonus room perfect for a family room, library, playroom or home office, and a large laundry room complete the second level. The third floor adds two more bedrooms and a full bath, offering tremendous flexibility for guests, work or hobbies. The lower level adds another layer of versatility, with its own private entrance, living room, full kitchen, bedroom, full bath and separate laundry. Ideal for extended family, an au pair or long-term guests, this completely independent apartment has also historically rented for $2,100 per month. Outside, the grounds are every bit as special as the home itself. Beautifully established English-style gardens surround the property, with professional landscaping, lush plantings and masses of mature hydrangeas creating a setting that feels almost Nantucket-like in the summer. The screened porch overlooks this private garden retreat and may quickly become your favorite room in the house. A circular driveway provides generous off-street parking, while the oversized two-car garage includes custom built-in storage. Significant recent improvements include three new HVAC systems installed approximately three years ago, along with an upgraded sprinkler system. And perhaps the most Annapolis detail of all: step outside in the morning and you can hear reveille from the U.S. Naval Academy; in the evening, taps carries through the air. Downtown Annapolis, the Naval Academy, marinas, restaurants and shopping are all just minutes away, with easy access to Route 50 making commuting simple and convenient. As an added benefit, the entire home has historically rented for approximately $16,000 during Naval Academy Commissioning Week, an exceptional opportunity unique to this sought-after Annapolis location. Beautifully built, wonderfully livable and unmistakably Annapolis, this is a home with room for everyone, and then some. 4 Ridge Rd, Annapolis
$825,000 Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself! 4 Beds ⋅ 4 Baths ⋅ MDAA2156774 MLS Welcome to 2691 Claibourne Road, beautifully presented and ready to impress in the sought-after water-privileged community of Annapolis Roads. This spacious 4-bedroom, 3.5-bath Colonial offers a flexible floor plan, finished lower level, two-car garage and inviting indoor and outdoor spaces designed for everyday living and entertaining. Step inside to hardwood floors and light-filled living spaces that flow comfortably throughout the main level. The updated kitchen features granite countertops and opens to the home's gathering areas, while separate living and dining rooms provide plenty of room for entertaining. Just beyond, the screened-in porch overlooks the peaceful, wooded backyard and offers the perfect spot for morning coffee, outdoor dining or relaxing at the end of the day. Upstairs, the spacious primary suite features a vaulted ceiling, oversized walk-in closet and private bath with a sunken tub and separate shower. Three additional bedrooms and a full hall bath complete the upper level. Downstairs, the finished lower level adds even more flexibility with a family/rec room, full bath and generous storage—ideal for guests, a home office, workout space or additional living area. Additional features include a whole-house generator, newer heat pump, water-softening system, two-car garage and custom shed with electricity. Fresh landscaping and new mulch enhance the home's curb appeal, while the wooded backyard provides a private setting for relaxing and entertaining. Just a short walk down Claibourne Road, take in beautiful sights of Lake Heron—one more reminder of the special setting that surrounds this home. Annapolis Roads residents enjoy an exceptional water-privileged lifestyle with access to the community's private beach, boat ramp, piers, waterfront pavilion and picnic area, playground, fire pit, kayak storage, walking trails and neighborhood events. All of this is just minutes from Downtown Annapolis, shopping, dining and commuter routes. Beautifully staged, refreshed and ready for its next chapter—come experience 2691 Claibourne Road for yourself! 2691 Claibourne Rd, Annapolis
$534,000 A Dutch Colonial on a cul-de-sac inside the Annapolis city line, for $534,000. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. 1017 Hyde Park Drive was built in 1984 in Wilshire. Three bedrooms and a full bath sit upstairs, a fourth bedroom and a second full bath on the main level, with central air for August. Its 1,272 square feet on the top two levels sit over a finished basement, with room for a rec room, a gym or an office. Out back, a deck looks over a yard of your own. The address does the rest. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, and from the restaurants of Eastport, the Annapolis Maritime Museum and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore and the Eastern Shore within reach, for the commute or for the weekend. Coming Soon. Showings begin September 18, 2026. Schedule online through ShowingTime. Cash, conventional, FHA and VA financing considered. 4 Beds ⋅ 2 Baths ⋅ MDAA2152942 MLS A Dutch Colonial on a cul-de-sac inside the Annapolis city line, for $534,000. End the day in the steam shower with full body sprays, then light the wood-burning fireplace and let the blower carry the heat through the room. 1017 Hyde Park Drive was built in 1984 in Wilshire. Three bedrooms and a full bath sit upstairs, a fourth bedroom and a second full bath on the main level, with central air for August. Its 1,272 square feet on the top two levels sit over a finished basement, with room for a rec room, a gym or an office. Out back, a deck looks over a yard of your own. The address does the rest. Wilshire sits off Forest Drive, a short drive from the trails and waterfront at Quiet Waters Park, and from the restaurants of Eastport, the Annapolis Maritime Museum and City Dock. Route 50 and the Bay Bridge put Washington, DC, Baltimore and the Eastern Shore within reach, for the commute or for the weekend. Coming Soon. Showings begin September 18, 2026. Schedule online through ShowingTime. Cash, conventional, FHA and VA financing considered. 1017 Hyde Park Dr, Annapolis
$1,050,000 Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own. 2 Beds ⋅ 2 Baths ⋅ MDAA2155302 MLS Highly Desirable Eastport Peninsula! Experience the best of the Eastport lifestyle in this charming home, ideally located in the heart of the peninsula. Relax on the inviting front porch and watch the world go by, or step out your door and walk to Eastport’s renowned restaurants, lively bars, boutique shopping, marinas, yacht clubs, and the water taxi to historic downtown Annapolis. Inside, beautiful heart pine floors add warmth and character. The spacious rear yard is a rare find in Eastport and offers plenty of room for entertaining, gardening, pets, or simply enjoying your own private outdoor retreat. The chef’s kitchen features Viking refrigerator and stainless steel appliances, creating a wonderful space for both everyday cooking and entertaining. Thoughtful improvements and major updates throughout the years make this home truly move-in ready while still offering the opportunity to add your own personal touches. Notable improvements include: * Pella rear sliding glass door — 2025 * Carrier first-floor HVAC — 2025 * Washer & dryer — 2024 * Viking refrigerator — 2024 * New roof — 2023 * First-floor bathroom remodeled — 2018 * Front porch replaced and metal roof added — 2018 * First-floor floors and stairs refinished by Beers — 2017 * Rinnai tankless water heater — 2016 * Upstairs bathroom and closet remodeled by Gate One Builders — 2011 * HardiePlank siding — 2009 * Fence — 2005 * Brick foundation repointed — 2004 * Shed — 2003 * Renovation and rear addition — 1998 A wonderful opportunity to own a piece of Eastport—move right in, enjoy the lifestyle, and make it your own. 412 Third St, Annapolis
$9,500,000 Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed! 6 Beds ⋅ 10 Baths ⋅ MDAA2154762 MLS Located on a private 2.5-acre lot in Wimbledon Farms, this waterfront estate home, designed by Cathy Purple Cherry and constructed by West River Builders, is truly a masterpiece in design and quality. The 3-level home – complete with elevator -- takes full advantage of its waterfront setting that includes 400 ft of shoreline. Facing Quiet Waters Park, the ever-changing view includes brilliant fall foliage, deer by the water’s edge, and osprey circling overhead. Stroll down to the 100 ft private pier with deep-water slips. There’s 7 ft water depth at the dock; Harness Creek is a recognized hurricane hole so this is the perfect spot for boats to ride out a storm. The 20 ft x 40 ft saltwater pool has a spacious ipe deck and two Hanso pergolas provide shade with wonderful water views. Six bedrooms, each with a private ensuite bath, a gourmet kitchen, and wrap-around screen porches and decks provide space for both casual living and grand entertaining. Upon entering, there is a gracious paneled foyer that opens to the living room. With Brazilian cherry floors, a gas fireplace with marble surround, and built-in bookcases, this room has fabulous water views and opens to one of the screened porches on this level that invite outdoor living. To the right is the heart of the home – the great room. It includes a just remodeled chef’s kitchen with multiple work areas, a family room, and the dining area. The kitchen includes Taj Mahal leathered countertops, two wall ovens, two Bosch dishwashers, a warming drawer, instant hot dispenser, Wolf 5-burner gas cooktop, and KitchenAid side-by-side refrigerator. There’s also a wet bar with beverage cooler. The family room has a wood-burning fireplace with raised hearth and stone surround; there’s also a spacious workspace with built-in bookshelves. The dining area overlooks the water, and there’s access to both screened porches. The main level also features a fabulous guest suite: there is a large bedroom with water views, walk-in closet, and a private bath with radiant heated floor. In addition, there are two powder rooms and a mudroom with three closets and an abundance of storage space. The main level has 10 ft ceilings and 8 ft interior doors. Upstairs, the primary suite is an owner’s dream escape. There’s a spacious bedroom with water views, dark cherry floors and a gas fireplace. The study, with wet bar, built-in shelves and file drawers, leads to a small reading room – with water views. The spa-like bathroom, with radiant heated floor, includes a separate water closet room, jetted tub with marble surround, oversized steam shower, and separate vanities. Step onto the private screened porch to enjoy a cup of coffee in the morning. The primary suite also includes two large walk-in closets and a laundry room. There are three additional water view bedrooms on the second floor, each with private bathroom and walk-in closet. The main laundry is in a dedicated room with ample storage. There’s also a walk-in cedar closet. All of the bedrooms and closets that have carpeting were re-carpeted in 2026. The walk-out lower level has a huge game room that includes a big screen TV, wet bar, and full bathroom. From here, you can step out to the bluestone patio that leads up to the pool. There is a half-bath off the patio, accessible for pool visitors. The 6th bedroom with ensuite bathroom also has peaceful views, and multiple closets. The main utility room houses the commercial grade water treatment system. It has a garage door for easy access to boat supplies and equipment servicing. A secondary utility room houses the elevator mechanism and reverse osmosis treatment system. A third unfinished area has the camera and internet systems. This exceptional home offers sophisticated waterfront living just minutes from the heart of Annapolis and the Chesapeake Bay. The year-round beauty of this scenic setting and unrivaled design is truly unsurpassed! 3285 Harness Creek Rd, Annapolis
$610,000 Come and discover the charm of this beautifully renovated ranch-style home in Hillsmere Estates, where modern comfort meets serene living. Step in to this warm and inviting retreat, featuring solid hardwood flooring on the main floor. With four spacious bedrooms and three full bathrooms, this home is designed to accommodate your lifestyle needs. The cozy and newly updated fireplace in the living room creates a perfect ambiance for gatherings, while the well-appointed kitchen is ready for your culinary adventures along with plenty of cabinets and counter space. Feel free to gather around the kitchen island or in the bright and cheerful dining area. The main floor also includes a bonus sunroom/ family room when you need extra space for game room adventures or to kick your feet up for some quiet time. The fully finished basement offers plenty of room for relaxation in your bedroom/office along with a family room for entertaining and the convenience of a full bathroom. The basement also includes a kitchenette space that can easily be converted to a full kitchen with a laundry area as well as a plentiful amount of storage to store your tools and toys. Step outside to enjoy the expansive 0.32-acre lot, where you can unwind in your private outdoor space or explore the community amenities, including a refreshing pool. For water enthusiasts, the property is just 2 miles from the South River, providing easy access for boating, fishing, and kayaking. With multiple slips available by lease, your aquatic adventures are just a stone's throw away. This home also features a convenient driveway for parking and a shed for additional storage. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities. This is more than just a house; it's a place to create lasting memories. Don't miss your chance to make it your own! 4 Beds ⋅ 3 Baths ⋅ MDAA2156556 MLS Come and discover the charm of this beautifully renovated ranch-style home in Hillsmere Estates, where modern comfort meets serene living. Step in to this warm and inviting retreat, featuring solid hardwood flooring on the main floor. With four spacious bedrooms and three full bathrooms, this home is designed to accommodate your lifestyle needs. The cozy and newly updated fireplace in the living room creates a perfect ambiance for gatherings, while the well-appointed kitchen is ready for your culinary adventures along with plenty of cabinets and counter space. Feel free to gather around the kitchen island or in the bright and cheerful dining area. The main floor also includes a bonus sunroom/ family room when you need extra space for game room adventures or to kick your feet up for some quiet time. The fully finished basement offers plenty of room for relaxation in your bedroom/office along with a family room for entertaining and the convenience of a full bathroom. The basement also includes a kitchenette space that can easily be converted to a full kitchen with a laundry area as well as a plentiful amount of storage to store your tools and toys. Step outside to enjoy the expansive 0.32-acre lot, where you can unwind in your private outdoor space or explore the community amenities, including a refreshing pool. For water enthusiasts, the property is just 2 miles from the South River, providing easy access for boating, fishing, and kayaking. With multiple slips available by lease, your aquatic adventures are just a stone's throw away. This home also features a convenient driveway for parking and a shed for additional storage. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities. This is more than just a house; it's a place to create lasting memories. Don't miss your chance to make it your own! 301 Cedar Ln, Annapolis
$2,695,000 Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas, restaurants, waterfront parks, and the vibrant streets of Downtown Eastport and Annapolis. Lush, thoughtfully designed landscaping brings the property to life, framing the home with color, texture, and greenery and creating an inviting sense of arrival. A gracious front porch sets the tone for the warm and welcoming interiors. Just inside, a dedicated office provides a quiet workspace, while hardwood floors, shiplap accents, custom millwork, and thoughtful details lend character throughout. The open floor plan unfolds into the heart of the home, where a spectacular kitchen features GE Monogram appliances, an expansive island, abundant cabinetry, and generous workspace. The adjoining dining area flows seamlessly into the living room, anchored by a fireplace framed with custom built-ins. Doors extend the living space to a large rear patio surrounded by beautiful landscaping, creating a private and inviting setting for outdoor dining, entertaining, and relaxed evenings at home. The main-level primary suite offers the convenience of one-level living with a beautifully appointed ensuite bath and conveniently located laundry room. A thoughtfully designed mudroom with built-in cubbies provides everyday functionality and an organized transition into the home. Additionally, the home features advanced technology throughout, including a Tesla Powerwall 3 for backup power, Tesla EV charger, and professionally installed Control4 home automation. The integrated system provides centralized control of lighting, climate, security, electronic locks, TVs, and built-in ceiling speakers throughout the home. Upstairs, two spacious bedrooms share a hall bath, while a large finished attic adds a wonderfully flexible dimension to the floor plan. Currently ideal as a bunk room, this charming bonus space can easily adapt as a playroom, additional sleeping quarters, creative studio, or whatever best suits your lifestyle. The finished lower level takes entertaining and recreation to another level with a spacious family room, game area, wet bar, full bath, and golf simulator. A separate bonus room currently serves as a home gym, while an expansive storage area provides the practical space that is often difficult to find in Eastport. Beyond the front door, the best of Annapolis is within easy reach. Launch a kayak from nearby Horn Point Park, stroll to Eastport's celebrated restaurants, pubs, marinas, and street-end parks, or cross the Spa Creek Bridge into Downtown Annapolis and the U.S. Naval Academy. Boaters will appreciate immediate proximity to the Chesapeake Bay and some of the region's most sought-after cruising destinations. Membership at the nearby Annapolis Capital Yacht Club marina also provides permission to enjoy the Chesapeake Landing community swimming pool, adding yet another way to embrace the waterfront lifestyle just steps from home. Offering the charm and personality of an Eastport Craftsman with the advantages of newer construction, beautiful landscaping, a main-level primary suite, exceptional entertaining spaces, and an enviable walkable location, this is a rare opportunity to experience one of Annapolis' most beloved neighborhoods with comfort, style, and ease. Welcome Home! 4 Beds ⋅ 4 Baths ⋅ MDAA2156250 MLS Celebrate the Eastport lifestyle in this beautifully crafted home, where classic Craftsman character meets the comfort and ease of newer construction. Built in 2016 and lightly lived in, the home captures everything that makes Eastport so desirable, from its welcoming front porch, charming architectural details, and beautifully curated landscaping to a location just steps from marinas, restaurants, waterfront parks, and the vibrant streets of Downtown Eastport and Annapolis. Lush, thoughtfully designed landscaping brings the property to life, framing the home with color, texture, and greenery and creating an inviting sense of arrival. A gracious front porch sets the tone for the warm and welcoming interiors. Just inside, a dedicated office provides a quiet workspace, while hardwood floors, shiplap accents, custom millwork, and thoughtful details lend character throughout. The open floor plan unfolds into the heart of the home, where a spectacular kitchen features GE Monogram appliances, an expansive island, abundant cabinetry, and generous workspace. The adjoining dining area flows seamlessly into the living room, anchored by a fireplace framed with custom built-ins. Doors extend the living space to a large rear patio surrounded by beautiful landscaping, creating a private and inviting setting for outdoor dining, entertaining, and relaxed evenings at home. The main-level primary suite offers the convenience of one-level living with a beautifully appointed ensuite bath and conveniently located laundry room. A thoughtfully designed mudroom with built-in cubbies provides everyday functionality and an organized transition into the home. Additionally, the home features advanced technology throughout, including a Tesla Powerwall 3 for backup power, Tesla EV charger, and professionally installed Control4 home automation. The integrated system provides centralized control of lighting, climate, security, electronic locks, TVs, and built-in ceiling speakers throughout the home. Upstairs, two spacious bedrooms share a hall bath, while a large finished attic adds a wonderfully flexible dimension to the floor plan. Currently ideal as a bunk room, this charming bonus space can easily adapt as a playroom, additional sleeping quarters, creative studio, or whatever best suits your lifestyle. The finished lower level takes entertaining and recreation to another level with a spacious family room, game area, wet bar, full bath, and golf simulator. A separate bonus room currently serves as a home gym, while an expansive storage area provides the practical space that is often difficult to find in Eastport. Beyond the front door, the best of Annapolis is within easy reach. Launch a kayak from nearby Horn Point Park, stroll to Eastport's celebrated restaurants, pubs, marinas, and street-end parks, or cross the Spa Creek Bridge into Downtown Annapolis and the U.S. Naval Academy. Boaters will appreciate immediate proximity to the Chesapeake Bay and some of the region's most sought-after cruising destinations. Membership at the nearby Annapolis Capital Yacht Club marina also provides permission to enjoy the Chesapeake Landing community swimming pool, adding yet another way to embrace the waterfront lifestyle just steps from home. Offering the charm and personality of an Eastport Craftsman with the advantages of newer construction, beautiful landscaping, a main-level primary suite, exceptional entertaining spaces, and an enviable walkable location, this is a rare opportunity to experience one of Annapolis' most beloved neighborhoods with comfort, style, and ease. Welcome Home! 507 1st St, Annapolis
$2,795,000 Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home. 3 Beds ⋅ 3 Baths ⋅ MDAA2156508 MLS Live authentically. The Chesapeake Bay is the view, the backdrop and the reason to linger. From the covered bluestone porch, the horizon opens across the Bay with uninterrupted sky and water. Morning coffee, an afternoon breeze through open doors, evenings around the fire—the water sets the pace. Extensively renovated inside and out since 2019, this charming craftsman styled gem in the sought-after Bay Ridge Community offers easy one-floor living and a natural connection to the outdoors. Windows and skylights, French doors and Phantom screens invite the sunshine and bay breeze inside. New Café Elite appliances, induction cooktop, and laundry. Freshly painted, craftsman style trim, molding and shiplap accents. Open floor plan with wide plank hickory flooring. Set on a generous .31 are lot, the flat, manicured backyard leaves plenty of room for games, children and pets. Low-maintenance Ipe deck and rear entry porch made for entertaining. Ample storage for water toys, paddle boards and bikes. Outdoor shower adding another practical touch to life by the water. Oversized parking pad for guests. Detached 2 car garage/studio, heated and cooled, skylight and separate personnel door offers flex space for home gym, office or guests. Functional updates include architectural shingle roofs, Pella windows, Hardie siding, hurricane French doors, blown attic insulation and generator hook- up. Then there is Bay Ridge itself—a walkable waterfront community with the quiet, unhurried character of a New England shore town. Tree lined streets, community beaches, deep water marina, pool and clubhouse are part of the fabric, while effortless biking connects the neighborhood to shoreline points along the South and Severn Rivers. A coveted pool bond conveys. Eastport, with its waterfront restaurants, marinas and distinctly maritime character, is close by, as are the Annapolis Maritime Museum & Park and Quiet Waters Park, with miles of trails and waterfront access. Historic downtown Annapolis, City Dock and the U.S. Naval Academy bring dining, shopping, sailing, history and the traditions of one of the country's most distinctive institutions at your doorstep. Zippy routes south to Washington, DC and Northern Virginia, north toward Baltimore, and across the Chesapeake Bay Bridge to Maryland’s Eastern Shore. BWI Airport and the Amtrak/MARC station are under 35 minutes away. Chesapeake Bay cottage lifestyle with the water in front of you, a community around you and the region within easy reach. Cultivate your existence. The art of uniting human and home. 113 Bay Dr, Annapolis
$750,000 Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience. 4 Beds ⋅ 3 Baths ⋅ MDAA2156594 MLS Welcome to 580 Pinedale Dr, a spacious 4-bedroom, 2.5-bath home set on a beautiful 1.8-acre lot in Annapolis. Offering a comfortable blend of character, functionality, and privacy, this home provides plenty of space for everyday living and entertaining. The impressive lofted living room is filled with natural light and features skylights that create an open, airy atmosphere. The inviting family room offers a propane fireplace, providing a cozy gathering space for relaxing evenings. The spacious kitchen offers plenty of cabinet and counter space, providing a functional and inviting setting for preparing meals and gathering with family and friends. A convenient half bath completes the main level. The spacious primary bedroom features its own ensuite bathroom and private laundry, creating a comfortable retreat with added convenience. Three additional bedrooms provide flexibility for family, guests, a home office, or hobby space. Outside, the expansive 1.8-acre property offers room to enjoy the outdoors and plenty of privacy, while the attached 2-car garage provides ample parking and storage. With its generous lot, versatile floor plan, lofted living space, and sought-after Annapolis location, 580 Pinedale Dr offers an opportunity to enjoy both space and convenience. 580 Pinedale Dr, Annapolis
$575,000 EARLY ACCESS! Be among the first to preview this home before it officially goes Active on the MLS. Private showings are available now. Call Lesa Clark at 301-410-6009 for a private tour. Welcome to this beautifully updated split-foyer home nestled on a gorgeous corner lot in the sought-after Cape St. Claire community of Annapolis. Offering an exceptional combination of modern updates, thoughtful improvements, and outstanding community amenities, this move-in ready home has been meticulously maintained inside and out. Inside, you'll enjoy modern fixtures, recessed lighting, granite countertops, and an updated kitchen featuring stainless steel appliances, including a refrigerator, dishwasher, and electric range replaced in 2022. The kitchen flows seamlessly onto a brand-new wood deck (2023, freshly stained in 2026), creating the perfect space for outdoor dining, entertaining, or simply relaxing. The inviting living room is centered around a beautifully renovated wood-burning fireplace (2023), while major system upgrades provide added peace of mind, including a new HVAC system (2024) and a whole-house humidifier (2025) for year-round comfort. The main level offers three bedrooms, including a primary suite with a private bath and two additional bedrooms with a shared hall bath. The finished lower level features a spacious flex area that can easily serve as a recreation room, home office, workout space, guest area, or potential fourth bedroom, along with a dedicated laundry area and convenient side-entry mudroom. Step outside and discover extensive outdoor improvements completed between 2022 and 2024. The property has been professionally regraded and enhanced with retaining walls, a stone walkway, additional gravel parking, and a completely restructured driveway offering improved functionality and expanded parking. An engineered drainage system, including underground front-yard downspouts and a complete backyard French drain, helps keep the property dry and functional throughout the seasons. Thoughtfully selected native, non-invasive flowers and shrubs provide beautiful color and interest throughout the year. Located in the highly desirable Cape St. Claire community of Annapolis, Maryland, residents enjoy access to outstanding neighborhood amenities, including a private community beach, community marina, boat ramp, fishing and crabbing pier, playgrounds, parks, and community events throughout the year. Conveniently located just minutes from downtown Annapolis, Broadneck Park, Sandy Point State Park, the Chesapeake Bay, the U.S. Naval Academy, shopping, dining, waterfront attractions, and everyday conveniences. Commuters will appreciate easy access to Route 50, I-97, Baltimore, Washington, D.C., Fort Meade, and BWI Airport. Whether you're looking for a beautifully updated home, a move-in ready property with major system upgrades, or the lifestyle that comes with living in one of Annapolis' premier water-access communities, this exceptional Cape St. Claire home offers the perfect opportunity to enjoy the very best of Maryland's Chesapeake Bay lifestyle. 4 Beds ⋅ 2 Baths ⋅ MDAA2153414 MLS EARLY ACCESS! Be among the first to preview this home before it officially goes Active on the MLS. Private showings are available now. Call Lesa Clark at 301-410-6009 for a private tour. Welcome to this beautifully updated split-foyer home nestled on a gorgeous corner lot in the sought-after Cape St. Claire community of Annapolis. Offering an exceptional combination of modern updates, thoughtful improvements, and outstanding community amenities, this move-in ready home has been meticulously maintained inside and out. Inside, you'll enjoy modern fixtures, recessed lighting, granite countertops, and an updated kitchen featuring stainless steel appliances, including a refrigerator, dishwasher, and electric range replaced in 2022. The kitchen flows seamlessly onto a brand-new wood deck (2023, freshly stained in 2026), creating the perfect space for outdoor dining, entertaining, or simply relaxing. The inviting living room is centered around a beautifully renovated wood-burning fireplace (2023), while major system upgrades provide added peace of mind, including a new HVAC system (2024) and a whole-house humidifier (2025) for year-round comfort. The main level offers three bedrooms, including a primary suite with a private bath and two additional bedrooms with a shared hall bath. The finished lower level features a spacious flex area that can easily serve as a recreation room, home office, workout space, guest area, or potential fourth bedroom, along with a dedicated laundry area and convenient side-entry mudroom. Step outside and discover extensive outdoor improvements completed between 2022 and 2024. The property has been professionally regraded and enhanced with retaining walls, a stone walkway, additional gravel parking, and a completely restructured driveway offering improved functionality and expanded parking. An engineered drainage system, including underground front-yard downspouts and a complete backyard French drain, helps keep the property dry and functional throughout the seasons. Thoughtfully selected native, non-invasive flowers and shrubs provide beautiful color and interest throughout the year. Located in the highly desirable Cape St. Claire community of Annapolis, Maryland, residents enjoy access to outstanding neighborhood amenities, including a private community beach, community marina, boat ramp, fishing and crabbing pier, playgrounds, parks, and community events throughout the year. Conveniently located just minutes from downtown Annapolis, Broadneck Park, Sandy Point State Park, the Chesapeake Bay, the U.S. Naval Academy, shopping, dining, waterfront attractions, and everyday conveniences. Commuters will appreciate easy access to Route 50, I-97, Baltimore, Washington, D.C., Fort Meade, and BWI Airport. Whether you're looking for a beautifully updated home, a move-in ready property with major system upgrades, or the lifestyle that comes with living in one of Annapolis' premier water-access communities, this exceptional Cape St. Claire home offers the perfect opportunity to enjoy the very best of Maryland's Chesapeake Bay lifestyle. 1178 Glenwood Dl, Annapolis
$750,000 Pics are up! Pottery Barn Perfect best describes this perfect house in the sought after community of Hunt Meadow! Everything is done! Move right in! This 3/4 bedroom, 2.5 bath home has barn doors, great moldings, newer siding and windows, great deck overlooking a perfect sized fenced yard with Thermospa Hot Tub. Irrigation with rain sensor. Upgraded lighting. Kitchen and baths are renovated, newer deck. Three bedrooms up. 4th bedroom/office in the lower level with a great theater & Murphy Bed in the Lower level. Hvac unit for garage. Absolutely adorable. Community pool, swim team, events and 5 minutes to downtown Annapolis. 3 Beds ⋅ 3 Baths ⋅ MDAA2156486 MLS Pics are up! Pottery Barn Perfect best describes this perfect house in the sought after community of Hunt Meadow! Everything is done! Move right in! This 3/4 bedroom, 2.5 bath home has barn doors, great moldings, newer siding and windows, great deck overlooking a perfect sized fenced yard with Thermospa Hot Tub. Irrigation with rain sensor. Upgraded lighting. Kitchen and baths are renovated, newer deck. Three bedrooms up. 4th bedroom/office in the lower level with a great theater & Murphy Bed in the Lower level. Hvac unit for garage. Absolutely adorable. Community pool, swim team, events and 5 minutes to downtown Annapolis. 304 Saddle Ridge Rd, Annapolis
$525,000 Welcome to 911 Blue Ridge Drive, a freshly painted 4-bedroom, 2-bath split foyer tucked on a private, tree-lined .53-acre lot -noticeably larger than most in the neighborhood - and just a short walk to Broadneck High School. Upstairs, three bedrooms and two full baths include a spacious primary suite, all set off by newer carpet (2024) and a cozy fireplace in the light-filled living room. The eat-in kitchen features oak cabinetry and new stainless steel refrigerator, range, and dishwasher (2025).The updated hall bath offers a clean, modern look with new flooring and fixtures. The walkout lower level adds even more living space, with a large family room centered around a wood-burning stove, a versatile bonus room ideal for a 4th bedroom, office, or den, and a dedicated laundry/utility room with a new whole-home water filtration/Revers Osmosis system (2025). Major systems are already handled, with a new roof (2024), New water heater (2025), Well Tank (2024), and Well Pump (2025) giving buyers real peace of mind. Out back, a large deck overlooks the huge, flat, fenced yard — plenty of room to entertain, garden, or let kids and pets roam — with a low-maintenance turf patio tucked underneath. As a Cape St. Claire resident, you'll enjoy access to the community's sought-after amenities, including beaches, boat ramps, a clubhouse, and playgrounds, all just minutes from Route 50, downtown Annapolis, and Sandy Point State Park. 4 Beds ⋅ 2 Baths ⋅ MDAA2155878 MLS Welcome to 911 Blue Ridge Drive, a freshly painted 4-bedroom, 2-bath split foyer tucked on a private, tree-lined .53-acre lot -noticeably larger than most in the neighborhood - and just a short walk to Broadneck High School. Upstairs, three bedrooms and two full baths include a spacious primary suite, all set off by newer carpet (2024) and a cozy fireplace in the light-filled living room. The eat-in kitchen features oak cabinetry and new stainless steel refrigerator, range, and dishwasher (2025).The updated hall bath offers a clean, modern look with new flooring and fixtures. The walkout lower level adds even more living space, with a large family room centered around a wood-burning stove, a versatile bonus room ideal for a 4th bedroom, office, or den, and a dedicated laundry/utility room with a new whole-home water filtration/Revers Osmosis system (2025). Major systems are already handled, with a new roof (2024), New water heater (2025), Well Tank (2024), and Well Pump (2025) giving buyers real peace of mind. Out back, a large deck overlooks the huge, flat, fenced yard — plenty of room to entertain, garden, or let kids and pets roam — with a low-maintenance turf patio tucked underneath. As a Cape St. Claire resident, you'll enjoy access to the community's sought-after amenities, including beaches, boat ramps, a clubhouse, and playgrounds, all just minutes from Route 50, downtown Annapolis, and Sandy Point State Park. 911 Blue Ridge Dr, Annapolis
$1,925,000 ***Seller will consider owner financing*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best. 4 Beds ⋅ 4 Baths ⋅ MDAA2156430 MLS ***Seller will consider owner financing*** Experience the best of the Annapolis lifestyle from this beautifully reimagined coastal Craftsman in the heart of Eastport. Ideally located within walking distance of downtown Annapolis, the waterfront, restaurants, shops, yacht clubs, marinas, and the many neighborhood amenities that make Eastport one of the area's most desirable communities, this extensively renovated home offers an exceptional combination of location, character, and modern comfort. Offering approximately 4,099 square feet of finished living space, the home features three bedrooms, a dedicated office, four bathrooms, and a versatile floor plan designed for both everyday living and entertaining. A welcoming front porch sets the tone, while James Hardie siding, Andersen 400 Series windows, low-maintenance exterior materials, and extensive improvements provide the benefits of a thoughtfully updated home while preserving its classic Eastport character. Inside, hardwood floors, high ceilings, substantial trim work, a fireplace creates warmth and architectural interest. Generous living and dining spaces flow naturally into the kitchen and family room, creating an inviting setting for entertaining or relaxed everyday living. Dual staircases provide access from both the front and rear portions of the home and add a distinctive architectural element to the floor plan. Upstairs, the spacious primary suite serves as a private retreat with a spa-inspired bath featuring a soaking tub, frameless glass shower, and dual vanity. Two additional bedrooms provide comfortable accommodations, while a separate office offers an ideal space for working from home. Convenient second-floor laundry completes the upper level. The fully finished lower level significantly expands the home's versatility, offering generous space for a recreation room, home gym, media room, or potential fourth bedroom. Full egress provides added flexibility for buyers who need additional sleeping accommodations, while ample storage enhances the functionality of the space. Outside, a large rear deck overlooks the generously sized yard, providing plenty of room for outdoor dining, entertaining, gardening, or simply relaxing at home. Three off-street parking spaces are an exceptional convenience in Eastport, while the property also offers potential for a future garage, accessory dwelling unit, and/or pool, subject to applicable approvals. Beyond the property itself is the lifestyle that makes this location so special. Leave the car at home and explore Eastport's restaurants, marinas, yacht clubs, and waterfront destinations, or stroll across the Spa Creek Bridge into historic downtown Annapolis and City Dock. Spend the morning on the water, meet friends for dinner in Eastport, or walk downtown for an evening along the harbor—all just minutes from your front door. 400 Jefferson Street offers the space and amenities of a substantially renovated home paired with the walkability, waterfront culture, and unmistakable character of Eastport. This is Annapolis living at its best. 400 Jefferson St, Annapolis
$542,900 Welcome to this beautifully updated Cape St. Claire home, where extensive improvements, stylish finishes, and comfortable living spaces come together in a property that has been carefully maintained inside and out. At the heart of the home is an updated kitchen featuring newer appliances, 42-inch cabinetry, quartz countertops, a custom backsplash, and a farmhouse apron sink. The home features two full bathrooms, including one that was completely renovated from top to bottom with a new tub, tile, flooring, toilet, vanity, and sink. The second full bath has also been refreshed with new flooring, vanity, and sink. Newer luxury vinyl plank flooring and carpeting add a fresh, cohesive feel throughout the interior, while all-new custom window treatments installed throughout the home in 2026 provide a polished finishing touch. The finished lower level offers valuable additional living space with the flexibility to function as a recreation room, home office, or a combination of both. A fireplace adds warmth and character, creating an inviting setting for working, relaxing, or entertaining. A dedicated mini-split system installed in 2025 provides independent climate control for this level. The home has benefited from a substantial list of recent improvements, including a new main-level HVAC system installed in 2024, Hardie siding and shutters in 2025, replacement windows in 2022, and a roof replaced in 2018. The home also includes a garage with a new door installed in 2025. A security system was added in 2026, and an owned whole-house water treatment and softener system was installed in 2024, providing added convenience and value for the next owner. Outdoor living is equally appealing. A new deck completed in 2026 provides an ideal setting for dining, entertaining, or relaxing outdoors, while the fully fenced yard offers added privacy, security, and flexibility for pets or play. An expanded driveway and parking area installed in 2025 adds valuable everyday functionality and additional off-street parking. Tucked along a quiet, lightly traveled street with just five homes, the property enjoys a more private neighborhood setting while remaining only a few blocks from the Cape St. Claire community beach. The location also offers convenient access to Annapolis, shopping, dining, recreation, and major commuter routes while retaining the neighborhood atmosphere that makes Cape St. Claire so sought after. The home is served by the highly regarded Broadneck school district. With an updated kitchen, one fully renovated bath, a refreshed second full bath, extensive recent improvements, newer major systems, dedicated climate control on both finished levels, a garage, and substantial exterior upgrades already completed, this home offers the opportunity to simply move in and enjoy. Years of investment, care, and thoughtful enhancement have created a property where very little remains for the next owner to do. 3 Beds ⋅ 2 Baths ⋅ MDAA2156048 MLS Welcome to this beautifully updated Cape St. Claire home, where extensive improvements, stylish finishes, and comfortable living spaces come together in a property that has been carefully maintained inside and out. At the heart of the home is an updated kitchen featuring newer appliances, 42-inch cabinetry, quartz countertops, a custom backsplash, and a farmhouse apron sink. The home features two full bathrooms, including one that was completely renovated from top to bottom with a new tub, tile, flooring, toilet, vanity, and sink. The second full bath has also been refreshed with new flooring, vanity, and sink. Newer luxury vinyl plank flooring and carpeting add a fresh, cohesive feel throughout the interior, while all-new custom window treatments installed throughout the home in 2026 provide a polished finishing touch. The finished lower level offers valuable additional living space with the flexibility to function as a recreation room, home office, or a combination of both. A fireplace adds warmth and character, creating an inviting setting for working, relaxing, or entertaining. A dedicated mini-split system installed in 2025 provides independent climate control for this level. The home has benefited from a substantial list of recent improvements, including a new main-level HVAC system installed in 2024, Hardie siding and shutters in 2025, replacement windows in 2022, and a roof replaced in 2018. The home also includes a garage with a new door installed in 2025. A security system was added in 2026, and an owned whole-house water treatment and softener system was installed in 2024, providing added convenience and value for the next owner. Outdoor living is equally appealing. A new deck completed in 2026 provides an ideal setting for dining, entertaining, or relaxing outdoors, while the fully fenced yard offers added privacy, security, and flexibility for pets or play. An expanded driveway and parking area installed in 2025 adds valuable everyday functionality and additional off-street parking. Tucked along a quiet, lightly traveled street with just five homes, the property enjoys a more private neighborhood setting while remaining only a few blocks from the Cape St. Claire community beach. The location also offers convenient access to Annapolis, shopping, dining, recreation, and major commuter routes while retaining the neighborhood atmosphere that makes Cape St. Claire so sought after. The home is served by the highly regarded Broadneck school district. With an updated kitchen, one fully renovated bath, a refreshed second full bath, extensive recent improvements, newer major systems, dedicated climate control on both finished levels, a garage, and substantial exterior upgrades already completed, this home offers the opportunity to simply move in and enjoy. Years of investment, care, and thoughtful enhancement have created a property where very little remains for the next owner to do. 1155 Spruce Tree Ln, Annapolis
$1,250,000 Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road. 4 Beds ⋅ 4 Baths ⋅ MDAA2155936 MLS Welcome to 700 Miller Road. Discover a truly special property tucked away on a private road, yet just minutes away from historic downtown Annapolis. Located less than a 5-minute walk from the Naval Academy Marine Corps Stadium, this beautifully renovated 2026 home offers the rare combination of privacy, convenience and Annapolis charm. Set on a generous .598-acre tract, the property backs-up to Tawes Gardens, that gives the home a tranquil and private setting. The home has been completely renovated in 2026, both inside and out, offering thoughtful updates while maintaining the integrity of the community. Enjoy the best of Annapolis, all within walking distance or true city living just a short drive away. Welcome home to 700 Miller Road. 700 Miller Rd, Annapolis
$1,625,000 Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living. 2 Beds ⋅ 3 Baths ⋅ MDAA2154154 MLS Rarely does a home of this historical significance become available in the heart of Historic Annapolis. Believed to date to the late 17th century, the extraordinary residence is among the city's oldest surviving homes, seamlessly blending centuries of architectural heritage with sophisticated modern living. Perched at the water end of Market St overlooking Spa Creek, this home is instantly recognizable by its iconic red standing-seam roof and timeless presence. Rich in character, the interior showcases exposed original beams, soaring ceilings, abundant natural light, and thoughtfully designed living spaces that honor the home's remarkable past while embracing contemporary comfort. A nationally recognized renovation in 1977 by Gate One Builders, transformed the residence into a one of a kind masterpiece, preserving its historic integrity while creating an open, light filled floor plan unlike any other in Annapolis. The beautifully appointed Kitchen, inviting living and dining areas, combination gas and wood burning fireplaces and a tranquil large Sunroom addition all flow effortlessly to a private walled courtyard, an intimate outdoor retreat ideal for entertaining or quiet relaxation. Water Views of Spa Creek, exceptional craftsmanship, and architectural details at every turn make this home as captivating as it is livable. Adding to its rarity are amenities seldom found with the Historic District, including two covered off street parking spaces and an unparalleled waterfront setting just moments from City Dock, the USNA, fine dining, boutiques, galleries and yacht club. Whether enjoyed as a full time residence or an exceptional Annapolis retreat, 100 Market Street represents a once in a generation opportunity to own an irreplaceable piece of the city's history, where more than three centuries of heritage meet the very best of coastal luxury living. 100 Market St, Annapolis
$745,000 Welcome to this thoughtfully updated home in the water-privileged community of Admiral Heights. Beautifully maintained and improved over the years, this inviting home combines comfortable everyday living, stylish updates and wonderful outdoor spaces in an exceptionally convenient Annapolis location. The main level is filled with natural light and features warm hardwood floors and an open, easy flow between the living spaces. Unlike the more traditional layout, the kitchen has been opened to the living room, creating a connected space that is perfect for everyday living and entertaining. The eat-in kitchen offers granite countertops, stainless steel appliances, generous cabinetry with updated hardware, recessed lighting and a large multi-level island with bar seating and built-in wine storage. A door from the kitchen leads directly to the deck and rear yard, making outdoor dining and entertaining easy. The bedrooms on this level are served by a beautifully renovated full bath featuring custom cabinetry, open shelving and beautiful tilework throughout the shower and floor. The finished lower level offers even more room to spread out, with a spacious family room centered around a gas fireplace, an additional bedroom and full bath. Sliding doors open directly to the patio and backyard, while unfinished space provides valuable additional storage. The backyard is truly something special. Designed to be enjoyed, this private, fenced setting offers multiple outdoor living spaces surrounded by mature trees and thoughtfully designed landscaping. Gather on the expansive custom paver patio, dine or relax on the Trex deck, tend the raised garden beds or simply enjoy the peaceful setting. String lights add a fun ambiance in the evening, transforming the patio and deck into an especially inviting place to gather after the sun goes down. A shed provides additional storage, while established plantings and garden areas give the entire yard a welcoming, tucked-away feel. Then there is the Admiral Heights lifestyle. This water-privileged community offers access to Weems Creek with opportunities for kayaking, fishing and swimming, along with community kayak racks and a pier. Membership in the Admiral Heights Improvement Association (AHIA) is voluntary. Separate memberships are available for the Admiral Heights Boat Club and Admiral Heights Swim Club. The Boat Club offers access to its dock and private boat slips, while the Swim Club offers a neighborhood pool and swim team — go Dolphins! All of this is just minutes from West Annapolis, Downtown Annapolis, Navy-Marine Corps Memorial Stadium, shopping and dining, with convenient access to Route 50 and I-97. Thoughtfully improved, beautifully cared for and designed to enjoy both indoors and out, 228 Dewey Drive offers a wonderful opportunity to call Admiral Heights home. 3 Beds ⋅ 2 Baths ⋅ MDAA2156310 MLS Welcome to this thoughtfully updated home in the water-privileged community of Admiral Heights. Beautifully maintained and improved over the years, this inviting home combines comfortable everyday living, stylish updates and wonderful outdoor spaces in an exceptionally convenient Annapolis location. The main level is filled with natural light and features warm hardwood floors and an open, easy flow between the living spaces. Unlike the more traditional layout, the kitchen has been opened to the living room, creating a connected space that is perfect for everyday living and entertaining. The eat-in kitchen offers granite countertops, stainless steel appliances, generous cabinetry with updated hardware, recessed lighting and a large multi-level island with bar seating and built-in wine storage. A door from the kitchen leads directly to the deck and rear yard, making outdoor dining and entertaining easy. The bedrooms on this level are served by a beautifully renovated full bath featuring custom cabinetry, open shelving and beautiful tilework throughout the shower and floor. The finished lower level offers even more room to spread out, with a spacious family room centered around a gas fireplace, an additional bedroom and full bath. Sliding doors open directly to the patio and backyard, while unfinished space provides valuable additional storage. The backyard is truly something special. Designed to be enjoyed, this private, fenced setting offers multiple outdoor living spaces surrounded by mature trees and thoughtfully designed landscaping. Gather on the expansive custom paver patio, dine or relax on the Trex deck, tend the raised garden beds or simply enjoy the peaceful setting. String lights add a fun ambiance in the evening, transforming the patio and deck into an especially inviting place to gather after the sun goes down. A shed provides additional storage, while established plantings and garden areas give the entire yard a welcoming, tucked-away feel. Then there is the Admiral Heights lifestyle. This water-privileged community offers access to Weems Creek with opportunities for kayaking, fishing and swimming, along with community kayak racks and a pier. Membership in the Admiral Heights Improvement Association (AHIA) is voluntary. Separate memberships are available for the Admiral Heights Boat Club and Admiral Heights Swim Club. The Boat Club offers access to its dock and private boat slips, while the Swim Club offers a neighborhood pool and swim team — go Dolphins! All of this is just minutes from West Annapolis, Downtown Annapolis, Navy-Marine Corps Memorial Stadium, shopping and dining, with convenient access to Route 50 and I-97. Thoughtfully improved, beautifully cared for and designed to enjoy both indoors and out, 228 Dewey Drive offers a wonderful opportunity to call Admiral Heights home. 228 Dewey Dr, Annapolis
$949,999 Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a refreshing touch for those warm summer days. Parking is a breeze with an attached carport and additional driveway space, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where cherished memories are made. Experience the perfect blend of classic design and modern living in this delightful Admiral Heights gem. Don't miss the opportunity to make this house your home! 5 Beds ⋅ 4 Baths ⋅ MDAA2155716 MLS Nestled in the charming Admiral Heights neighborhood, this stunning split-level home exudes warmth and character, inviting you to experience its unique design and craftsmanship. Built with everyone in mind, this residence boasts timeless appeal with its classic brick-and-vinyl siding exterior, harmoniously blending with the lush surroundings. Step inside to discover a spacious layout that offers both comfort and functionality. With five generous bedrooms and three and a half bathrooms, this home is perfect for those who appreciate space and versatility. The heart of the home features a cozy fireplace, creating an inviting atmosphere for gatherings and quiet evenings alike. The partially finished basement provides endless possibilities, whether you envision a workshop, a play area, or additional storage. The expansive lot offers ample outdoor space for relaxation and recreation, while the community pool adds a refreshing touch for those warm summer days. Parking is a breeze with an attached carport and additional driveway space, ensuring convenience for you and your guests. This home is not just a place to live; it's a sanctuary where cherished memories are made. Experience the perfect blend of classic design and modern living in this delightful Admiral Heights gem. Don't miss the opportunity to make this house your home! 13 Rickover Ct, Annapolis
$750,000 Nestled in the charming Eastport neighborhood, this exceptional property blends warmth, character, and versatility. The main residence features 2 bedrooms and 1.5 bathrooms, with rich wood flooring, a cozy fireplace, and an inviting layout designed for comfortable living. A convenient basement laundry area and attached 1-car garage add everyday functionality. Step outside to discover even more possibilities, including a detached 1-bedroom, 1-bath guest house —perfect for guests, extended living, a home office, or additional storage. Set on a generous 0.17-acre lot, the property offers a wonderful balance of privacy, outdoor space, and neighborhood charm. With its desirable Eastport location, flexible living arrangements, and abundant character, this unique property offers an opportunity to enjoy both comfort and convenience in one of the area’s most appealing communities. 3 Beds ⋅ 3 Baths ⋅ MDAA2156278 MLS Nestled in the charming Eastport neighborhood, this exceptional property blends warmth, character, and versatility. The main residence features 2 bedrooms and 1.5 bathrooms, with rich wood flooring, a cozy fireplace, and an inviting layout designed for comfortable living. A convenient basement laundry area and attached 1-car garage add everyday functionality. Step outside to discover even more possibilities, including a detached 1-bedroom, 1-bath guest house —perfect for guests, extended living, a home office, or additional storage. Set on a generous 0.17-acre lot, the property offers a wonderful balance of privacy, outdoor space, and neighborhood charm. With its desirable Eastport location, flexible living arrangements, and abundant character, this unique property offers an opportunity to enjoy both comfort and convenience in one of the area’s most appealing communities. 906 Jackson St, Annapolis
$879,990 Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. Builder is offering $5,000 toward closing costs with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,411 square feet of above-grade living space and is thoughtfully appointed with the quality features and finishes today’s homebuyers desire. Enjoy a spacious 12’ x 16’ sunroom, 9-foot ceilings on the main level, engineered hardwood flooring throughout the entire first floor, granite or quartz kitchen countertops, and upgraded cabinetry with soft-close doors and drawers. Additional included features include ceramic tile in the bathrooms and laundry room, stainless steel kitchen appliances, a washer and dryer package, upgraded Craftsman-style moldings, Craftsman newel posts with oak handrails and black iron pickets, stone exterior accents, architectural roof shingles, a Wi-Fi-enabled garage door opener, a sodded lawn, a generous landscaping package, and so much more. Best of all, these exceptional features are included as standard! There is also plenty of opportunity to expand your living space with available options, including a finished recreation room, additional basement bedroom, and full bathroom, all available at an additional cost. Come home and enjoy the incredible lifestyle and amenities offered in this water-privileged community. Cape St. Claire offers three community beaches, community docks, a fishing and crabbing pier, picnic areas, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, a community clubhouse, and an outdoor pool available with membership. Conveniently located with easy access to Annapolis, Baltimore, and Washington, D.C., this is a rare opportunity to enjoy new construction in the desirable Cape St. Claire community. A home you will be proud to come home to! Photos and images shown may be representative of the builder’s work, craftsmanship, and quality and may include optional features not included in the base price. Prices, terms, conditions, features, and availability are subject to change without prior written notice. 4 Beds ⋅ 3 Baths ⋅ MDAA2156258 MLS Ameri-Star Homes is proud to offer this exceptional opportunity to build a brand-new Craftsman-style home on a beautiful 9,225-square-foot corner homesite in the sought-after waterfront community of Cape St. Claire in Annapolis. Builder is offering $5,000 toward closing costs with the use of the builder’s approved lender and title company! The exciting Bancroft model offers approximately 2,411 square feet of above-grade living space and is thoughtfully appointed with the quality features and finishes today’s homebuyers desire. Enjoy a spacious 12’ x 16’ sunroom, 9-foot ceilings on the main level, engineered hardwood flooring throughout the entire first floor, granite or quartz kitchen countertops, and upgraded cabinetry with soft-close doors and drawers. Additional included features include ceramic tile in the bathrooms and laundry room, stainless steel kitchen appliances, a washer and dryer package, upgraded Craftsman-style moldings, Craftsman newel posts with oak handrails and black iron pickets, stone exterior accents, architectural roof shingles, a Wi-Fi-enabled garage door opener, a sodded lawn, a generous landscaping package, and so much more. Best of all, these exceptional features are included as standard! There is also plenty of opportunity to expand your living space with available options, including a finished recreation room, additional basement bedroom, and full bathroom, all available at an additional cost. Come home and enjoy the incredible lifestyle and amenities offered in this water-privileged community. Cape St. Claire offers three community beaches, community docks, a fishing and crabbing pier, picnic areas, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, a community clubhouse, and an outdoor pool available with membership. Conveniently located with easy access to Annapolis, Baltimore, and Washington, D.C., this is a rare opportunity to enjoy new construction in the desirable Cape St. Claire community. A home you will be proud to come home to! Photos and images shown may be representative of the builder’s work, craftsmanship, and quality and may include optional features not included in the base price. Prices, terms, conditions, features, and availability are subject to change without prior written notice. 1049 Sun Valley Dr, Annapolis