Hillsmere Estates Homes for Sale

Hillsmere Estates Homes for Sale

Welcome to Hillsmere Estates, a picturesque subdivision nestled in the heart of Annapolis, Maryland, within the charming Anne Arundel County. Known for its serene atmosphere and close-knit community, Hillsmere Estates offers a delightful blend of suburban tranquility and vibrant local culture, making it an ideal place to call home.

As you explore the homes for sale in this coveted neighborhood, you'll discover a variety of architectural styles, from classic colonials to modern designs, each boasting unique charm and character. Many of these residences are situated on spacious lots, surrounded by lush greenery and mature trees, providing a peaceful retreat from the hustle and bustle of everyday life. The interiors often feature open floor plans, updated kitchens, and cozy living spaces, perfect for both entertaining and relaxation.

Hillsmere Estates is not just about stunning homes; it also offers residents a wealth of amenities. Enjoy access to community parks, walking trails, and the nearby waterfront, where you can indulge in boating, fishing, or simply soaking in the breathtaking views of the Chesapeake Bay. Families will appreciate the top-rated schools in the area, ensuring a quality education for children of all ages.

Conveniently located just minutes from downtown Annapolis, residents can easily explore the rich history, dining, and shopping options that this vibrant city has to offer. Whether you're a first-time homebuyer or looking to settle down in a welcoming community, Hillsmere Estates presents a unique opportunity to embrace a lifestyle of comfort, convenience, and connection. Come discover your dream home in this enchanting neighborhood today!

Newest Hillsmere Estates Homes for Sale

$850,000
4 Beds ⋅ 3 Baths ⋅ MDAA2157350 MLS
Welcome to 327 Beach Drive, a beautifully updated 4-bedroom, 3-bath home located in the sought-after Hillsmere Shores community of Annapolis. Thoughtfully renovated with an emphasis on quality craftsmanship and timeless finishes, this home is truly move-in ready. The main level features brand-new natural birch flooring throughout, solid wood interior doors, crown molding, and recessed lighting in every bedroom. At the heart of the living room, a custom shiplap fireplace creates a warm and inviting focal point. The beautifully finished hall bathroom features custom details and an elevated design. A fully permitted addition created an impressive primary suite complete with a luxury private bath, providing a spacious and relaxing retreat. The finished lower level adds valuable flexibility with a home office and fourth bedroom, perfect for guests, working from home, or additional living space. The exterior is equally impressive with crisp white board-and-batten siding, an architectural-shingle roof, and great curb appeal. Step outside to a large, flat, fully fenced backyard offering plenty of space for entertaining, pets, play, and gardening. A low-maintenance Trex patio provides the perfect spot for outdoor dining, grilling, or relaxing. Located in desirable Hillsmere Shores, this thoughtfully renovated Annapolis home combines custom finishes, flexible living space, a fantastic backyard, and the coastal community lifestyle buyers are looking for.

327 Beach Dr, Annapolis
$610,000
4 Beds ⋅ 3 Baths ⋅ MDAA2156556 MLS
Welcome to this beautifully updated ranch-style home in Hillsmere Estates... where modern comfort meets serene living. Located on a spacious corner lot with ample driveway parking, this warm and charming retreat boasts four bedrooms and three full bathrooms and is designed to accommodate all your lifestyle needs. The open well-appointed kitchen is ready for your culinary adventures boasting plenty of sleek counter space along with an abundance of cabinets. Gather around the roomy kitchen island or the bright and cheerful dining area for your social events or comforting traditional meals. Cozy up to the newly updated fireplace in the living room that creates the perfect ambiance for quiet evenings or festive gatherings. Hardwood flooring on the main floor adds to the appeal of this home. The inviting sunroom is ready when you need extra space for game time adventures or a moment to lean back with your feet up to revel in your comfy quiet world. The fully finished basement offers plenty of room for your bedroom/office along with a family room for entertainment and the added convenience of a full bathroom. It also features a kitchenette space that can easily be converted to a full kitchen with a laundry area to create an accommodating in-law suite. Not only are there endless options in the basement living areas, this generous space includes plentiful storage room for your handy tools and treasured keepsakes. Stepping out to the back yard, the WOW feature continues as you gaze out to the fully fenced and expansive 0.32-acre flat lot where your options are limitless. A picturesque atmosphere where you can be the host of a special occasion or unwind in your private outdoor oasis. As nature smiles in this abundant space, a large shed has been gently nestled in allowing you to organize some well-deserved lounging furniture, gardening implements as well as your entertaining games and toys for all your pleasures. As you venture out from the sanctuary of your lovely home, the amenities for the Hillsmere Shores community are ready to be enjoyed. Feel the charm as you walk down Hillsmere Drive beneath a canopy of historic cypress trees. Treat yourself with exclusive access to a private marina on the South River, a sandy beach, waterfront pavilions, a community pool, and multiple playgrounds. Potential adventures abound in a community where you are within easy walking distance to Quiet Waters Park sharing its nature trails, dog beach and playgrounds. For water enthusiasts, you are only 2 miles from the South River, providing easy access for boating, fishing and kayaking. Multiple slips are available by lease making your aquatic adventures just a stone's throw away. Embrace the lifestyle you've always wanted in a community that offers both tranquility and recreational opportunities and is conveniently located near schools, a library along with dining and shopping experiences. This is more than just a house... it is your home and community where you can create lasting memories. Don't miss your chance to make this home 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
$679,999
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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