Hillsmere Estates Real Estate

Hillsmere Estates Real Estate

Welcome to Hillsmere Estates, a hidden gem nestled in the heart of Annapolis, Maryland. This picturesque subdivision offers a harmonious blend of suburban tranquility and vibrant community life, making it the perfect place for families, retirees, and everyone in between.

Hillsmere Estates is ideally situated just minutes away from the iconic Chesapeake Bay, offering residents easy access to stunning waterfront views and recreational activities. Whether you’re kayaking on the bay, strolling along the scenic trails, or enjoying a picnic at the nearby parks, outdoor enthusiasts will find plenty to love about this charming locale.

The community is characterized by its well-maintained homes, lush green spaces, and friendly neighbors. Here, you’ll discover a variety of architectural styles that reflect the unique character of the area, from classic Cape Cods to modern ranch-style homes. The tree-lined streets create a warm and inviting atmosphere, perfect for evening walks or morning jogs.

Families will appreciate the proximity to top-rated schools, as well as a range of amenities including local shops, restaurants, and community centers. Hillsmere Estates is also just a short drive away from historic downtown Annapolis, where you can explore boutique shopping, fine dining, and cultural attractions.

With its perfect blend of nature, community, and convenience, Hillsmere Estates is more than just a place to live; it’s a lifestyle. Come and experience the charm of this enchanting subdivision, where your dream home awaits!

Newest Listings in Hillsmere Estates

123 Maple Dr, Annapolis
$725,000
3 Beds ⋅ 3 Baths
Welcome to 123 Maple Drive in sought-after, amenity-rich Hillsmere Estates! This updated 3-bedroom, 3-full-bath home features a spacious main-level bedroom, new windows, new LVP flooring on the main level, and new carpet on the stairs and upper level. The updated kitchen offers new quartz countertops, stainless steel appliances, and a new stove and microwave. The primary ensuite has been completely renovated, and the other two full baths have also been updated. A new sliding glass door leads to the large, new custom-built deck overlooking a spacious, flat, fenced rear yard—plenty of room for entertaining, playing, or relaxing outdoors. A two-car garage with a new garage door adds convenience and storage. Enjoy all that Hillsmere has to offer, including a community pool, beach, boat ramp, volleyball court, frisbee golf, pavilion, and more, plus adjacent access to Quiet Waters Park. Located approximately a 5-minute walk to Hillsmere Elementary and a 3-minute drive to Key School, this home combines thoughtful updates, great outdoor space, and an incredible Annapolis location!

123 Maple Dr, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

130 Great Lake Dr, Annapolis
$650,000
4 Beds ⋅ 3 Baths
SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 130 Great Lake Drive, an exciting new opportunity in one of Annapolis' most sought-after waterfront communities! Offering wonderful versatility and inviting spaces designed for both everyday comfort and effortless entertaining, this home features 2 fireplaces, a fabulous deck perfect for outdoor gatherings, and a separate in-law, nanny, or au pair suite that provides exceptional flexibility for extended family, guests, or multigenerational living. Imagine cozy evenings beside the fire, summer dinners under the stars, and weekends enjoying everything that makes Hillsmere Shores so special—including its beautiful community beach, marina, pool, and vibrant waterfront lifestyle. All just minutes from Historic Downtown Annapolis, shopping, dining, and everything the Chesapeake Bay region has to offer. A home with character, flexibility, and an address you'll love. More details and photographs coming soon. STAY TUNED!

130 Great Lake Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

416 Walnut Dr, Annapolis
$554,990
3 Beds ⋅ 3 Baths
Imagine starting your morning with coffee in a sun-filled room, looking out over a peaceful backyard framed by trees. Later, you could launch a kayak, head to the community beach, take a walk through Quiet Waters Park, or be in downtown Annapolis in minutes. This is the lifestyle that makes Hillsmere Shores so special. Set near the Chesapeake Bay and the mouth of the South River, this updated 3-bedroom, 2.5-bath home blends comfort, character, and flexibility in one of Annapolis’s most loved waterfront communities. Inside, a thoughtful renovation created spaces that feel open, warm, and easy to enjoy. The expanded kitchen features a center island, eat-in area, custom tile backsplash, solid wood cabinetry, and plenty of room to gather. The primary suite was also expanded and now offers a sitting area, large walk-in closet, brand-new carpeting, and a beautifully renovated bath. But the room you may never want to leave is the four-season sunroom. Fresh paint, new luxury vinyl plank flooring, and views of the fenced backyard make it the perfect place to relax in every season.The finished lower level gives you even more room to spread out. Use it as a recreation room, office, gym, creative space, or potential fourth bedroom. A classic brick fireplace with an insert creates the perfect backdrop for cozy evenings, and a half bath adds extra convenience. Outside, the backyard offers privacy, trees, and room to enjoy the outdoors. And then there’s Hillsmere Shores itself: a private marina, boat ramps, kayak and canoe launch, community beach, swimming pool, playgrounds, picnic areas, and recreation spaces—all just minutes from downtown Annapolis, Key School, and Quiet Waters Park. This isn’t just Annapolis living. This is Chesapeake Bay living at its best.

416 Walnut Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

327 Beach Dr, Annapolis
$850,000
4 Beds ⋅ 3 Baths
Welcome to 327 Beach Drive, where thoughtful design, quality craftsmanship, and the relaxed Annapolis lifestyle come together in the heart of Hillsmere Shores a waterfront community. Completely transformed with a warm, modern aesthetic, this 4-bedroom, 3-bath home offers approximately 2,450 square feet of beautifully finished living space. From the moment you arrive, the crisp white board-and-batten exterior and inviting curb appeal set the tone. Inside, brand-new natural birch flooring, solid wood interior doors, crown molding, recessed lighting, and carefully selected finishes create a bright, cohesive feel throughout the main level. The open living spaces are designed for both everyday living and entertaining, highlighted by a custom shiplap fireplace that adds warmth and character. The kitchen flows naturally into the surrounding living and dining areas, creating an easy gathering space at the center of the home. A fully permitted addition created a stunning primary suite that feels like a private retreat, complete with a spacious bedroom, walk-in closet, and beautifully finished luxury bath. The additional main-level bedrooms are complemented by a custom-designed hall bathroom with timeless finishes and attention to detail. The finished lower level adds even more flexibility with a fourth bedroom, full bath, home office, additional living space, laundry, and storage—ideal for guests, working from home, or creating a separate recreation area. Outside, the large, level .41-acre lot is fully fenced and offers exceptional space for entertaining, pets, play, or gardening. A low-maintenance Trex patio extends the living space outdoors and provides the perfect setting for summer dinners, grilling, and relaxing with friends. Located in sought-after Hillsmere Shores with access to the community’s waterfront lifestyle and amenities of marinas, beach and pool, 327 Beach Drive offers the rare combination of a beautifully renovated home, generous outdoor space, flexible living areas, and an Annapolis location that makes it easy to enjoy everything the area has to offer. https://hillsmereshores.org/pool/ This isn’t simply an updated home—it has been thoughtfully redesigned for the way you want to live.

327 Beach Dr, Annapolis

Listing courtesy of RE/MAX United Real Estate. Contact:

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