Hillsmere Shores Homes for Sale

Hillsmere Shores Homes for Sale

Welcome to Hillsmere Shores, a hidden gem nestled in the heart of Annapolis, Maryland. This charming subdivision is a perfect blend of natural beauty and modern convenience, making it an ideal place to call home. Situated along the picturesque shores of the Chesapeake Bay, Hillsmere Shores offers residents breathtaking waterfront views and easy access to a variety of outdoor activities, including boating, fishing, and hiking.

The community is known for its friendly atmosphere and strong sense of belonging, with neighbors often gathering for seasonal events and enjoying the serene surroundings. Hillsmere Shores boasts a variety of amenities, including a private beach, community park, and playground, ensuring that families and individuals alike can enjoy the great outdoors right at their doorstep.

Homes for sale in Hillsmere Shores reflect the unique character of the neighborhood, ranging from charming single-family homes to modern townhouses that cater to diverse lifestyles. Many of these residences feature spacious layouts, contemporary finishes, and beautifully landscaped yards, perfect for entertaining or relaxing after a long day. With proximity to the vibrant downtown Annapolis, residents have easy access to shopping, dining, and cultural attractions, all while enjoying the tranquility of suburban living.

Whether you're a first-time homebuyer or looking to settle into a peaceful retreat, Hillsmere Shores offers a wonderful opportunity to experience the best of Maryland living. Explore the available homes for sale today and discover your perfect haven in this delightful community!

Newest Hillsmere Shores Homes for Sale

$874,900
3 Beds ⋅ 3 Baths ⋅ MDAA2150956 MLS
Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility, and everyday comfort. The bright, open main level is designed for gathering, featuring a beautifully updated white kitchen with quartz countertops, stainless appliances, custom backsplash, generous workspace, and seamless flow into a dining and seating area accented by shiplap details and French doors opening to an expansive entertaining deck overlooking the oversized, fully fenced backyard. The spacious primary suite includes a sitting area, custom California Closets walk-in, and a bathroom with 4' vanity, an extra large Smart Mirror/Medicine Cabinet and marble shower. The walkout lower level offers exceptional flexibility with a large room currently enjoyed as a family room but could easily serve as a fourth bedroom, complete with fireplace, closet, full egress, and direct access to a private covered deck with hot tub. Two additional bedrooms, both with California Closet systems, a beautifully renovated full bath with double vanity, extended tub and an updated laundry room complete this level. A bonus feature of this house is the separate, flex space adjacent to the garage with its own beautifully renovated powder room, mini-split HVAC, large deck, with endless possibilities as a home office, fitness studio, media room, teen hangout, creative workspace, or guest overflow. Outside, the oversized fenced-in back yard provides rare privacy and room to play, entertain, or garden, complemented by multiple outdoor living areas and a detached shed/workshop with power and air conditioning. The large two car garage features Flow Wall storage system, epoxy floor coating, and an EV charging plug as well as direct access to the rear yard. Extensive renovations throughout include the kitchen, baths, roof, siding, windows, HVAC, flooring, lighting, garage, landscaping, and countless custom details, creating a truly move-in-ready home. Enjoy one of Annapolis' most beloved waterfront communities with a voluntary HOA, private beach on the South River, marina, community pool, playgrounds, and year-round neighborhood events—all just minutes from Downtown Annapolis.

117 Sunset Dr, Annapolis
$730,000
3 Beds ⋅ 2 Baths ⋅ MDAA2150070 MLS
Open House on 9/13 has been cancelled. Please contact listing agent for showings directly. **NEW PRICE — a fresh opportunity to call Hillsmere Shores home!** Just two blocks from the community’s private beach and playground on the South River, this updated 3-bedroom, 2-bath home puts one of Hillsmere’s best amenities practically at your doorstep. Watch the sunrise at the water, afternoons at the beach, and evenings watching sailboats and ships pass along the Chesapeake Bay are all part of the lifestyle here. Inside, the split-level design offers more space and flexibility than you might expect, with multiple living areas to spread out and make your own. The main living room features a cozy pellet fireplace insert, while a spacious family room and additional finished lower-level room provide plenty of options for a home office, gym, playroom, hobby space, or guests. Hardwood flooring extends throughout two levels, complemented by luxury vinyl plank flooring on the remaining two. The updated kitchen features quartz countertops and stainless steel appliances, and both full baths have beautifully renovated showers. A convenient mudroom/laundry room connects directly to the attached one-car garage, while just off the kitchen, a paver patio creates an easy spot for grilling, dining, and entertaining outdoors. And then there’s Hillsmere! Residents enjoy a private beach, marina, community pool, boat ramps, playgrounds, and year-round neighborhood events—all just minutes from downtown Annapolis. **With its new price, flexible living space, garage, updates, and location just two blocks from the South River, this home deserves another look!**

110 Lake View Dr, Annapolis
$1,500,000
5 Beds ⋅ 4 Baths ⋅ MDAA2149706 MLS
Sunsets, Water Views & Effortless Coastal Living in Hillsmere Perfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathtaking water views of Lake Hillsmere in the foreground and the South River beyond—without the expense of waterfront taxes. Designed to embrace its spectacular setting, the home is oriented to the west, delivering unforgettable sunsets from two expansive waterfront-facing decks and covered balconies. Set on a generously sized lot with ample setbacks, the property provides privacy, space, and a rare sense of tranquility. Best of all, the home is outside the floodplain, so flood insurance is not required, and an elevation certificate is available. Inside, over three finished levels, you'll find thoughtfully updated living spaces featuring hardwood floors, 9-foot ceilings, abundant natural light, and multiple indoor and outdoor areas designed for gathering and entertaining. The beautifully updated kitchen features granite countertops, stainless steel appliances, island seating, a pantry with built-in shelving, and sliding doors that open to the deck and water views beyond. The main-level primary suite is a true retreat, complete with private deck access, a custom walk-in closet by California Closets, and a renovated spa-inspired bath with a soaking tub, double vanity, and glass-enclosed shower. Additional bedrooms and flexible living spaces provide endless options for guests, recreation, a home office, or multigenerational living. The lower level offers a welcoming mudroom entry, family room with fireplace and wood stove insert, full bath, dedicated office or optional sixth bedroom, laundry room, and abundant storage. Outdoor living is equally impressive, featuring IPE decking, a rear deck, three-season room overlooking the backyard, kayak and paddleboard racks, two sheds, and a private driveway leading to the oversized two-car garage with additional storage. Meticulously maintained and exceptionally efficient, the home includes newer HVAC systems, a whole-house Generac generator, Cat 8 Ethernet throughout, closed-cell spray foam insulation, LED lighting, energy-efficient windows, and remarkably low utility costs for its size. Just three blocks away, enjoy the community beach for swimming, relaxing, or launching kayaks and paddleboards. Residents of Hillsmere enjoy an unparalleled waterfront lifestyle with a private marina, boat ramps, community pool, parks, playgrounds, waterfront pavilions, and direct access to the 340-acre Quiet Waters Park. This is a rare opportunity to enjoy panoramic water views, extraordinary sunsets, and an exceptional lifestyle—without waterfront taxes or flood insurance requirements.

621 Harbor Dr, Annapolis
$769,900
4 Beds ⋅ 3 Baths ⋅ MDAA2149064 MLS
OPEN HOUSE SUNDAY SEPTEMBER 20TH FROM 12 UNTIL 2! Fall is here and it is time to make your move and be settled in before the holiday season is here! This is your chance to get into Hillsmere Shores, one of Annapolis’ most sought‑after waterfront communities. The exterior is deceiving — step inside to discover an unexpectedly open, bright, and airy interior that buyers don’t see every day. Sellers are highly motivated. If you’ve been waiting for the right Hillsmere home, this is it. The Hillsmere Shores community, offers a private beach, community pool, marina, and multiple launch areas for boats, kayaks, canoes, and paddleboards — the perfect setting for anyone who loves life on the water. The home features four spacious bedrooms and three full baths, all set within an open, airy floor plan designed to capture natural light and create an inviting sense of space. A generously sized kitchen serves as the heart of the home, offering abundant prep areas, modern appliances, and effortless flow into the main living spaces. The living room is anchored by a refined propane fireplace, adding warmth and ambiance throughout the seasons. The lower-level functions as an extension of the home, complete with a private bedroom and full bath—ideal for guests or multigenerational living. A sprawling great room provides endless possibilities for entertaining or relaxation, while a dedicated laundry space and two additional flex rooms offer versatility for a home gym, office, studio, or hobby space. Customizable space based on what works for you and your lifestyle. Sitting on a generous lot, the property backs directly to Quiet Waters Park and includes a private path for easy access and all the park has to offer...hiking trails, a playground, dog park, outdoor summer concerts and several other fun events throughout the year. The fully fenced backyard is designed for entertaining, complete with a bar area and firepit for evenings outdoors. The detached garage/barn provides endless possibilities — workshop, studio, storage, or more. A massive, fully covered deck spans the back of the home, creating an ideal space for crab feasts, cookouts, or simply relaxing and enjoying the peaceful surroundings. This home is truly a must‑see. Looks can be deceiving — it is far more spacious than it appears from the outside, offering room to spread out and enjoy every part of the property and its incredible location. Close to the library, shopping, restaurants and only minutes to Eastport and downtown Historic Annapolis

278 Hillsmere Dr, Annapolis
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