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SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 103 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!

4 Beds ⋅ 3 Baths

SOMETHING SPECIAL IS COMING TO HILLSMERE SHORES! Get ready to fall in love with 103 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:

$589,000

Character, comfort, and versatility come together in this beautifully appointed Hillsmere home. Set among large, mature trees within an established waterfront community, the main level offers an open, airy feel with vaulted ceilings, attractive flooring, and a kitchen with stainless steel appliances. Every bathroom has been remodeled, including the primary suite's bath with a spacious shower, tile flooring, and custom shelving. The finished lower level adds a bedroom, an updated half bath, and a rec room wood stove, while a bonus room with its own private entrance offers flexible space for an office, studio, or additional living area and could potentially be converted back to a one-car garage. Outside, an expansive private yard bordered by a creek provides a serene backdrop, along with a spacious deck. Hillsmere is adjacent to Quiet Waters Park, and community amenities include an outdoor pool, marinas, beaches, playgrounds, a boat ramp, and boat storage with downtown Annapolis just minutes away. Updates: 2015 - Pella windows, 2017 – Lower-level powder room remodel; new refrigerator and dishwasher, 2019 – Hall bath remodel; new washer and dryer, 2021 – Primary bath remodel; new indoor heating unit, front door, and gutters, 2022 – New roof; new smoke detectors (batteries good through 2032); deck painted, 2023 – New well pump; chimney cleaned, 2024 – New lower-level wiring; exterior drainage repairs, 2025 – New water softener

4 Beds ⋅ 3 Baths

Character, comfort, and versatility come together in this beautifully appointed Hillsmere home. Set among large, mature trees within an established waterfront community, the main level offers an open, airy feel with vaulted ceilings, attractive flooring, and a kitchen with stainless steel appliances. Every bathroom has been remodeled, including the primary suite's bath with a spacious shower, tile flooring, and custom shelving. The finished lower level adds a bedroom, an updated half bath, and a rec room wood stove, while a bonus room with its own private entrance offers flexible space for an office, studio, or additional living area and could potentially be converted back to a one-car garage. Outside, an expansive private yard bordered by a creek provides a serene backdrop, along with a spacious deck. Hillsmere is adjacent to Quiet Waters Park, and community amenities include an outdoor pool, marinas, beaches, playgrounds, a boat ramp, and boat storage with downtown Annapolis just minutes away. Updates: 2015 - Pella windows, 2017 – Lower-level powder room remodel; new refrigerator and dishwasher, 2019 – Hall bath remodel; new washer and dryer, 2021 – Primary bath remodel; new indoor heating unit, front door, and gutters, 2022 – New roof; new smoke detectors (batteries good through 2032); deck painted, 2023 – New well pump; chimney cleaned, 2024 – New lower-level wiring; exterior drainage repairs, 2025 – New water softener

456 Poplar Ln, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

$600,000

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.

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:

$590,000

PRICE DROP! ** OPEN HOUSE ON SATURDAY OCTOBER 10TH AND SUNDAY OCTOBER 11TH FROM 11 AM UNTIL 2 PM EACH DAY. ** 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!

4 Beds ⋅ 3 Baths

PRICE DROP! ** OPEN HOUSE ON SATURDAY OCTOBER 10TH AND SUNDAY OCTOBER 11TH FROM 11 AM UNTIL 2 PM EACH DAY. ** 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

Listing courtesy of ExecuHome Realty. Contact:

$699,990

THIS is Hillsmere living. Beautifully updated, incredibly versatile, and set on a fantastic level, fenced lot, 104 Groh Lane offers approximately 2,300 square feet of finished living space, four bedrooms, three full baths, and the space to live, work, entertain, and grow—all in one of Annapolis’ most loved waterfront communities. The main level features three bedrooms and two full baths, including the primary suite, along with light-filled living and dining spaces, a fireplace, and a beautifully renovated kitchen that brings everyone together. Downstairs, the walk-out lower level adds nearly 1,000 square feet of finished space with a fourth bedroom, full bath, recreation area, and laundry—ideal for guests, a private home office, gym, playroom, or separate living space. Step outside and the backyard may seal the deal: level, expansive, fully fenced, framed by mature trees, and overlooked by a spacious deck ready for grilling, entertaining, pets, play, or quiet evenings at home. And then there is Hillsmere. This is a neighborhood people move to for the amenities and stay in for the community—where neighbors walk and bike to the water, kids grow up with beach days and holiday traditions, and there is always something happening. Enjoy the sandy community beach overlooking the Chesapeake Bay, marina and boat ramps, waterfront pavilions, playgrounds, community pool, and year-round neighborhood events, from summer gatherings and live music to the oyster roast, holiday celebrations, and beloved bike parades. Quiet Waters Park, with miles of trails and a dog park, is practically next door, while Eastport, Historic Annapolis, City Dock, restaurants, shopping, and everything Annapolis are just minutes away. Updated, move-in ready, wonderfully flexible, and surrounded by the lifestyle that makes Hillsmere so special—104 Groh Lane isn't simply a house to see. It may be exactly the home you've been waiting for.

4 Beds ⋅ 3 Baths

THIS is Hillsmere living. Beautifully updated, incredibly versatile, and set on a fantastic level, fenced lot, 104 Groh Lane offers approximately 2,300 square feet of finished living space, four bedrooms, three full baths, and the space to live, work, entertain, and grow—all in one of Annapolis’ most loved waterfront communities. The main level features three bedrooms and two full baths, including the primary suite, along with light-filled living and dining spaces, a fireplace, and a beautifully renovated kitchen that brings everyone together. Downstairs, the walk-out lower level adds nearly 1,000 square feet of finished space with a fourth bedroom, full bath, recreation area, and laundry—ideal for guests, a private home office, gym, playroom, or separate living space. Step outside and the backyard may seal the deal: level, expansive, fully fenced, framed by mature trees, and overlooked by a spacious deck ready for grilling, entertaining, pets, play, or quiet evenings at home. And then there is Hillsmere. This is a neighborhood people move to for the amenities and stay in for the community—where neighbors walk and bike to the water, kids grow up with beach days and holiday traditions, and there is always something happening. Enjoy the sandy community beach overlooking the Chesapeake Bay, marina and boat ramps, waterfront pavilions, playgrounds, community pool, and year-round neighborhood events, from summer gatherings and live music to the oyster roast, holiday celebrations, and beloved bike parades. Quiet Waters Park, with miles of trails and a dog park, is practically next door, while Eastport, Historic Annapolis, City Dock, restaurants, shopping, and everything Annapolis are just minutes away. Updated, move-in ready, wonderfully flexible, and surrounded by the lifestyle that makes Hillsmere so special—104 Groh Lane isn't simply a house to see. It may be exactly the home you've been waiting for.

104 Groh Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

$669,999

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.

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: