Hillsmere Estates Real Estate

Hillsmere Estates Real Estate

Welcome to Hillsmere Estates, a hidden gem nestled in the heart of Annapolis, Maryland. This charming subdivision offers a perfect blend of tranquility and accessibility, making it an ideal choice for families, retirees, and anyone seeking a peaceful lifestyle just minutes away from the vibrant city life.

Hillsmere Estates boasts a picturesque setting characterized by lush greenery, serene waterways, and a welcoming community atmosphere. Residents enjoy a variety of outdoor activities, with nearby parks, walking trails, and the stunning Chesapeake Bay just a stone's throw away. The community is known for its friendly neighbors and a strong sense of belonging, making it easy to feel at home.

One of the standout features of Hillsmere Estates is its convenient location. Just a short drive from downtown Annapolis, residents can indulge in the city's rich history, eclectic dining options, and unique shopping experiences. Whether you're exploring the historic streets, enjoying a waterfront meal, or attending local events, everything you need is within reach.

Families will appreciate the quality schools in the area, as well as the abundance of recreational facilities. Hillsmere Estates is also in close proximity to major highways, making commuting to Baltimore or Washington D.C. a breeze.

With its serene environment, strong community spirit, and prime location, Hillsmere Estates is more than just a place to live; it’s a lifestyle. Come discover your dream home in this enchanting subdivision and experience the best of Annapolis living!

Newest Listings in Hillsmere Estates

$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
$610,000
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 ​o​n 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
$425,000
3 Beds ⋅ 1 Baths ⋅ MDAA2154980 MLS
Welcome to 293 Cedar Lane, a classic 1963 ranch on a private .27 acre lot in the water privileged community of Hillsmere Estates, steps from Quiet Waters Park and minutes to the South River. Original hardwood floors flow through the main level, where a living room with custom built in shelving opens to a galley kitchen with an electric stove top, wall oven, and dishwasher, full of potential for your personal touch. The full bath keeps its classic pedestal sink charm. Downstairs, a full basement offers a finished rec area and bonus room alongside generous unfinished storage and utility space, ready for however you want to use it. Step outside to a rear deck made for morning coffee or evening unwinding. Ceiling fans keep the main level comfortable, while public sewer and a private well simplify utilities. Sold strictly as is, this well loved home offers real bones in one of Annapolis's most sought after neighborhoods, home to a private beach, marina, and community pool. Come discover what it truly means to Love Being Home.

293 Cedar Ln, Annapolis
$699,990
4 Beds ⋅ 3 Baths ⋅ MDAA2150374 MLS
Some neighborhoods give you an address. Hillsmere gives you a way of life. At 104 Groh Lane, you’ll find a beautifully updated four-bedroom, three-bath home with approximately 2,300 square feet of finished living space, an exceptionally versatile floor plan, and a wonderful level, fenced backyard—all within one of Annapolis’ most beloved waterfront communities. Three bedrooms and two full baths are conveniently located on the main level, including the primary suite, while light-filled living and dining spaces, a fireplace, and a beautifully renovated kitchen create a warm and inviting setting for everyday living and entertaining. The finished walk-out lower level adds nearly 1,000 square feet of additional living space with a fourth bedroom, full bath, recreation area, and laundry, offering wonderful flexibility for guests, a home office, fitness space, or additional living area. Outside, a spacious deck overlooks the expansive backyard framed by mature trees—a private setting for summer dinners, gardening, children at play, and four-legged family members. But what makes this home particularly special is everything waiting just beyond the front door. Hillsmere is the kind of neighborhood where children ride their bikes down tree-lined streets, neighbors walk their dogs and stop to talk, and families head to the beach together on summer evenings. It’s Fourth of July bike parades ending at the water, Halloween parades, ice cream socials, beach gatherings, live music, the annual oyster roast, and Santa making his way through the neighborhood during the holidays. Residents enjoy a sandy community beach overlooking the Chesapeake Bay, marina and boat ramps, waterfront pavilions, playgrounds, and community pool, while the trails, dog park, and natural beauty of Quiet Waters Park are practically next door. Eastport, Historic Annapolis, City Dock, restaurants, shopping, and the waterfront are only minutes away. Beautifully updated and wonderfully livable, 104 Groh Lane offers something increasingly difficult to find: a home you’ll love in a neighborhood that still feels like a community.

104 Groh Ln, Annapolis
$694,999
4 Beds ⋅ 3 Baths ⋅ MDAA2149728 MLS
Stunning 2400 sq ft remodeled home in Hillsmere! Situated on a lovely street and a large flat lot, this breathtaking home has been fully remodeled and offers some of the nicest finishes in the community! Entering through a charming 3 season room, youll be greeted by brand new lvp flooring throughout the home, a spacious family room that opens into your brand new kitchen. Kitchen features include brand new cream shaker cabinets around the kitchen, a brand new shaker island featuring oak finish, quartz counters, and brand new SS appliances. Behind the kitchen is a charming addition with lots of natural light. The main level boast 2 bedrooms, 2 fully renovated and stunning full bathrooms, including an owners suite with 2 closets and a dual vanity. Downstairs youll find 2 more bedrooms, a fully remodeled full bathroom, and an extra and open family room. The home boasts lots of attic storage as well as generous closet space. Outside, youll notice a brand new patio, lovely landscaping, and a large firepit area. The community boasts beaches, pool, pavilion areas, and more. This is a must see and wont last long! Roof replaced in 2022 and HWH in 2025.

117 Pinecrest Dr, Annapolis
$769,900
4 Beds ⋅ 3 Baths ⋅ MDAA2149498 MLS
Price Improvement! Experience the best of Annapolis living in this beautifully updated 4-bedroom, 3-bath home located in a waterfront community. This move-in-ready home offers the perfect blend of modern updates, comfortable living, and an exceptional Chesapeake Bay lifestyle. The heart of the home has also been refreshed with updated kitchen countertops and appliances (2024/2025), making it ideal for everyday living and entertaining. Additional major improvements include a new HVAC system (2025), hot water heater (2025), water conditioning system (2025), and garage door (2025), providing peace of mind for years to come. Outside, the partially fenced backyard offers the perfect space to relax, entertain, or enjoy outdoor activities. All three full bathrooms have been completely renovated with designer tile, new flooring, and modern vanities. The thoughtfully updated interior showcases updated flooring throughout, featuring newly refinished hardwood floors on upper level, new fixtures, and along with a new staircase railing. The inviting fireplace has been refaced on the lower level, creating a stylish focal point in the living space. The home also offers a versatile den/office and a one-car garage. Enjoy Hillsmere’s community amenities including private sandy beaches on the South River, a private marina with boat slips and direct access to the South River, boat ramps, waterfront pavilions, a community swimming pool, playgrounds, volleyball courts, and picnic areas. Whether you're boating, kayaking, fishing, or simply taking in the waterfront scenery, this community offers an unmatched coastal lifestyle. Conveniently located just minutes from historic downtown Annapolis, Quiet Waters Park, shopping, and dining, this exceptional home combines extensive recent updates with one of the area's most desirable waterfront communities. Don't miss the opportunity to make this beautifully renovated home your own.

100 Oak Dr, Annapolis
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