Annapolis Homes for Sale

Annapolis Homes for Sale

Welcome to Annapolis, Maryland—a city where history meets coastal charm! Nestled in Anne Arundel County, Annapolis is not just the state capital; it’s a vibrant hub of culture, community, and breathtaking waterfront views. Known for its rich maritime heritage, this picturesque city is famous for the United States Naval Academy, historic colonial architecture, and the bustling streets of its downtown area, lined with boutique shops, art galleries, and delightful eateries.

Annapolis offers a unique blend of urban living and small-town warmth, making it an ideal place to call home. Whether you're drawn to the serene beauty of the Chesapeake Bay or the lively atmosphere of the city center, Annapolis has something for everyone. Families appreciate the top-rated schools and abundant parks, while young professionals enjoy the thriving social scene and easy access to major metropolitan areas.

If you’re looking for homes for sale in this enchanting city, you’re in luck! Annapolis boasts a diverse real estate market, featuring everything from charming historic homes to modern waterfront condos. Each neighborhood has its own unique character, whether you prefer the quaint streets of Eastport or the family-friendly vibes of Broadneck. With a range of price points and styles, there’s a perfect home waiting for you in Annapolis.

Discover the unparalleled lifestyle that Annapolis offers, where every day feels like a vacation. Explore the possibilities and find your dream home in this captivating city today!

Newest Annapolis Homes for Sale

$640,000
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
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
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
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
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
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
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
3 Beds ⋅ 2 Baths ⋅ MDAA2156842 MLS
Simultaneously Listed and SOLD

3260 Harness Creek Rd, Annapolis
$3,375,000
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
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
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
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
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