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

$610,000
4 Beds ⋅ 3 Baths
Discover the charm of this beautifully renovated ranch-style home in Hillsmere Estates, where modern comfort meets serene living. Major renovations completed in 2020 have transformed this residence into a warm and inviting retreat, featuring solid hardwood flooring throughout and a fully finished basement that offers ample space for relaxation or entertainment. With four spacious bedrooms and three full bathrooms, this home is designed to accommodate your lifestyle needs. The cozy fireplace in the living area creates a perfect ambiance for gatherings, while the well-appointed kitchen is ready for your culinary adventures. 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

Listing courtesy of ExecuHome Realty. Contact:

$425,000
3 Beds ⋅ 1 Baths
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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$699,990
4 Beds ⋅ 3 Baths
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

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$694,999
4 Beds ⋅ 3 Baths
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

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$799,000
4 Beds ⋅ 3 Baths
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

Listing courtesy of Innovative Properties, Inc.. Contact:

Start Your Search