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** Rare Mid-Century Modern Waterfront Sanctuary on Bay View Drive ** Welcome to 129 E Bay View Drive, an authentic 1954 mid-century modern masterpiece offering a rare combination of 2,852 square feet of seamless, single-level living and an elite 102 feet of premium shoreline. Perched safely outside the high-risk flood plain, this property delivers a rare blend of elevated peace of mind and significant annual insurance savings not shared by many neighboring waterfront properties. ** The 102 feet of bulkheaded shoreline features a pristine water entry point, perfectly suited for launching kayaks, paddleboards, or rowing shells directly into the scenic waterways. ** Designed for the design purist and luxury downsizer alike, the home flows effortlessly across an expansive one-level footprint. At the heart of the residence is a masterfully restored 1954 kitchen featuring iconic, authentic Geneva steel cabinetry, a celebrated testament to mid-century industrial design. ** In place of a standard garage, the home boasts a spectacular, museum-grade botanical conservatory flooded with natural light from specialized skylights. This architectural feature transforms the traditional parking footprint into a world-class, climate-controlled indoor oasis, perfect for the avid collector, artist, or green thumb. ** Floor-to-ceiling vistas frame the sweeping water views, leading out to a beautifully manicured lot. Positioned perfectly for DC and Northern Virginia professionals seeking a sophisticated weekend retreat, or locals looking to "right-size" without sacrificing premium water access. Complete with floor plans and site surveys ready for your review. Schedule your private tour today. Welcome!

129 E Bay View Dr, Annapolis

Listing courtesy of RE/MAX Allegiance. Contact:

Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along picturesque East Bay View Drive with water views, this thoughtfully updated home is just one block from the neighborhood beach with stunning water views, around the corner from the community marina, and a block away from the boat ramp and kayak racks, offering an easy connection to the South River lifestyle. Inside, a welcoming two-story foyer introduces the home’s fresh, elevated feel, highlighted by a remodeled staircase with wrought iron balusters, maple railing and treads, and fresh neutral interior paint throughout. The main level offers an open and airy floor plan with recessed lighting, large picture windows, and a wood-burning fireplace with a white brick surround. The living area flows seamlessly through glass sliding doors to the wraparound covered deck, creating a wonderful setting for outdoor dining, relaxing, entertaining, or simply enjoying the peaceful surroundings. From the main level living area, 180-degree views capture both Duvall Creek and the Chesapeake Bay, offering a rare setting to enjoy beautiful sunrise and sunset views. The spacious kitchen features abundant maple cabinetry, stainless steel appliances, a center island with bar seating, and a walk-in pantry. The main level also includes three bedrooms with new luxury wool carpeting, including a spacious primary suite with multiple closets and a beautiful en suite bath. The stunningly remodeled primary bath features a high-end double vanity, luxurious polished nickel fixtures, elegant medicine cabinets, alabaster sconces, a freestanding soaking tub, an oversized glass-enclosed curbless shower with a rain showerhead, custom niches, a custom double window, and a touchless toilet. The second full hall bathroom has also been recently remodeled and offers designer finishes, a new skylight, and a tub/shower combination. The lower level provides exceptional flexibility with a large second living area featuring new maple hardwood flooring throughout, a new sliding glass door, a coat closet, under-stair storage, a spacious fourth bedroom, and a fully remodeled bathroom with a glass-enclosed shower and designer finishes. A laundry/mudroom with additional storage connects to the oversized two-car garage, which includes a large attached separate storage room or exercise room. Outdoors, the newly fenced backyard with horizontal cedar plank fencing enhances privacy and creates a comfortable space for pets, play, gardening, or entertaining. With refreshed interiors, renovated bathrooms, updated flooring, improved lighting, generous indoor and outdoor living spaces, and a prime Hillsmere Shores location, 124 E Bay View Drive is ready to welcome you home. Hillsmere Shores offers a true Annapolis waterfront lifestyle, ideally located approximately three miles from historic Downtown Annapolis and adjacent to Quiet Waters Park, with a convenient neighborhood entrance located within Hillsmere Shores. The community offers residents access to a private marina with direct South River access, a sandy beach with stunning water views, a community pool, multiple playgrounds, waterfront pavilions, boat ramp, and kayak/dinghy storage. The neighborhood is also close to The Key School, the Eastport-Annapolis Neck Library, Hillsmere Elementary, and all the shops, restaurants, and waterfront charm of Downtown Annapolis.

$1,025,000

Welcome to 124 E Bay View Drive, beautifully remodeled and ideally located in Hillsmere Shores, one of Annapolis’ most beloved water-oriented communities. Set along picturesque East Bay View Drive with water views, this thoughtfully updated home is just one block from the neighborhood beach with stunning water views, around the corner from the community marina, and a block away from the boat ramp and kayak racks, offering an easy connection to the South River lifestyle. Inside, a welcoming two-story foyer introduces the home’s fresh, elevated feel, highlighted by a remodeled staircase with wrought iron balusters, maple railing and treads, and fresh neutral interior paint throughout. The main level offers an open and airy floor plan with recessed lighting, large picture windows, and a wood-burning fireplace with a white brick surround. The living area flows seamlessly through glass sliding doors to the wraparound covered deck, creating a wonderful setting for outdoor dining, relaxing, entertaining, or simply enjoying the peaceful surroundings. From the main level living area, 180-degree views capture both Duvall Creek and the Chesapeake Bay, offering a rare setting to enjoy beautiful sunrise and sunset views. The spacious kitchen features abundant maple cabinetry, stainless steel appliances, a center island with bar seating, and a walk-in pantry. The main level also includes three bedrooms with new luxury wool carpeting, including a spacious primary suite with multiple closets and a beautiful en suite bath. The stunningly remodeled primary bath features a high-end double vanity, luxurious polished nickel fixtures, elegant medicine cabinets, alabaster sconces, a freestanding soaking tub, an oversized glass-enclosed curbless shower with a rain showerhead, custom niches, a custom double window, and a touchless toilet. The second full hall bathroom has also been recently remodeled and offers designer finishes, a new skylight, and a tub/shower combination. The lower level provides exceptional flexibility with a large second living area featuring new maple hardwood flooring throughout, a new sliding glass door, a coat closet, under-stair storage, a spacious fourth bedroom, and a fully remodeled bathroom with a glass-enclosed shower and designer finishes. A laundry/mudroom with additional storage connects to the oversized two-car garage, which includes a large attached separate storage room or exercise room. Outdoors, the newly fenced backyard with horizontal cedar plank fencing enhances privacy and creates a comfortable space for pets, play, gardening, or entertaining. With refreshed interiors, renovated bathrooms, updated flooring, improved lighting, generous indoor and outdoor living spaces, and a prime Hillsmere Shores location, 124 E Bay View Drive is ready to welcome you home. Hillsmere Shores offers a true Annapolis waterfront lifestyle, ideally located approximately three miles from historic Downtown Annapolis and adjacent to Quiet Waters Park, with a convenient neighborhood entrance located within Hillsmere Shores. The community offers residents access to a private marina with direct South River access, a sandy beach with stunning water views, a community pool, multiple playgrounds, waterfront pavilions, boat ramp, and kayak/dinghy storage. The neighborhood is also close to The Key School, the Eastport-Annapolis Neck Library, Hillsmere Elementary, and all the shops, restaurants, and waterfront charm of Downtown Annapolis.

124 E Bay View Dr, Annapolis

Listing courtesy of Washington Fine Properties. Contact:

Welcome to 117 Gardner Drive, a beautifully renovated home nestled in the coveted water-privileged community of Hillsmere Shores. Situated on an exceptional lot, this turnkey property offers the perfect blend of amazing updates and great space for everyday living and effortless entertaining. At the heart of the home, the brand-new and thoughtfully designed eat-in kitchen is designed to gather, cook, and connect. Just off the kitchen, the inviting family room flows seamlessly into the large screened porch with built-in heaters creating a cozy, year-round outdoor living space ideal for relaxing evenings, morning coffee, or hosting friends and family in every season. Main level bedroom/home office/playroom and spacious mudroom with great storage just off the garage. Throughout the home, you’ll find fresh paint, brand-new flooring, and meticulous care that reflects true pride of ownership. The upper level features four bedrooms and two newly renovated full bathrooms featuring modern aesthetics, allowing the next owner to simply move in and enjoy. The exterior has been updated with durable Hardi Plank siding and paver driveway, providing both timeless curb appeal and long-term peace of mind. The spacious lower level features a ton of storage and an opportunity for a future recreation room or home gym. Living in Hillsmere Shores means embracing the Chesapeake Bay lifestyle. Residents enjoy access to a private beach, playground, marinas with boat launches, boat slips (availability varies), kayak racks and launches, and a community pool (membership subject to availability). Outdoor lovers will appreciate being just a few blocks from the entrance to Quiet Waters Park, featuring miles of scenic trails, a dog park, gardens, and waterfront views. Downtown Annapolis, with a great dining scene, boutique shopping, and historic waterfront charm, is only minutes away. Don't wait - this home is special and ready for you to enjoy!

$935,000

Welcome to 117 Gardner Drive, a beautifully renovated home nestled in the coveted water-privileged community of Hillsmere Shores. Situated on an exceptional lot, this turnkey property offers the perfect blend of amazing updates and great space for everyday living and effortless entertaining. At the heart of the home, the brand-new and thoughtfully designed eat-in kitchen is designed to gather, cook, and connect. Just off the kitchen, the inviting family room flows seamlessly into the large screened porch with built-in heaters creating a cozy, year-round outdoor living space ideal for relaxing evenings, morning coffee, or hosting friends and family in every season. Main level bedroom/home office/playroom and spacious mudroom with great storage just off the garage. Throughout the home, you’ll find fresh paint, brand-new flooring, and meticulous care that reflects true pride of ownership. The upper level features four bedrooms and two newly renovated full bathrooms featuring modern aesthetics, allowing the next owner to simply move in and enjoy. The exterior has been updated with durable Hardi Plank siding and paver driveway, providing both timeless curb appeal and long-term peace of mind. The spacious lower level features a ton of storage and an opportunity for a future recreation room or home gym. Living in Hillsmere Shores means embracing the Chesapeake Bay lifestyle. Residents enjoy access to a private beach, playground, marinas with boat launches, boat slips (availability varies), kayak racks and launches, and a community pool (membership subject to availability). Outdoor lovers will appreciate being just a few blocks from the entrance to Quiet Waters Park, featuring miles of scenic trails, a dog park, gardens, and waterfront views. Downtown Annapolis, with a great dining scene, boutique shopping, and historic waterfront charm, is only minutes away. Don't wait - this home is special and ready for you to enjoy!

117 Gardner Dr, Annapolis

Listing courtesy of Compass. Contact:

Welcome to this amazing home in sought after Hillsmere Estates, where you will always have a beautiful water view of the Chesapeake Bay! The owners have spared no expense in maximizing the water view with large sliders to a private deck off of the living room. The large, open kitchen with breakfast bar walks out to the large back deck and private yard with beautiful, mature trees. The primary suite has a nice attached bathroom and access to the deck. Two more bedrooms and a full bath complete the main level. The lower level has a large family room with wood stove, fourth bedroom option, full bathroom, laundry, and a large custom built mudroom. The carport has been converted to a bonus three seasons room perfect for a gym, office, playroom and more! Hillsmere is known for the access to the waterfront with playgrounds, parks, a boat ramp, marina, and community pool (extra fee). This is a special tax district neighborhood where the fees are included in the property taxes and there is a voluntary HOA. Don’t miss this rare opportunity to own a well-appointed property with a beautiful view in a sought-after location. Located only minutes to Downtown Annapolis, Eastport, shopping and dining. Don't miss this one!

$903,500

Welcome to this amazing home in sought after Hillsmere Estates, where you will always have a beautiful water view of the Chesapeake Bay! The owners have spared no expense in maximizing the water view with large sliders to a private deck off of the living room. The large, open kitchen with breakfast bar walks out to the large back deck and private yard with beautiful, mature trees. The primary suite has a nice attached bathroom and access to the deck. Two more bedrooms and a full bath complete the main level. The lower level has a large family room with wood stove, fourth bedroom option, full bathroom, laundry, and a large custom built mudroom. The carport has been converted to a bonus three seasons room perfect for a gym, office, playroom and more! Hillsmere is known for the access to the waterfront with playgrounds, parks, a boat ramp, marina, and community pool (extra fee). This is a special tax district neighborhood where the fees are included in the property taxes and there is a voluntary HOA. Don’t miss this rare opportunity to own a well-appointed property with a beautiful view in a sought-after location. Located only minutes to Downtown Annapolis, Eastport, shopping and dining. Don't miss this one!

102 Green Spring Dr, Annapolis

Listing courtesy of Compass. Contact:

121 Spruce Ln, Annapolis

Listing courtesy of Non Subscribing Office. Contact:

Welcome to 600 Tayman Drive, where timeless Colonial charm meets the easy, coastal lifestyle that defines this sought-after Annapolis waterfront community. From the moment you arrive, the inviting front porch sets the tone — a place for morning coffee, evening wine, and neighbors who still wave as they pass by. Inside, the home opens effortlessly with a bright, flowing floor plan anchored by rich wood floors and a kitchen designed for real life — complete with stainless steel appliances and seamless connection to everyday living and entertaining spaces. Upstairs, every bedroom is thoughtfully placed on the second level, including a spacious primary suite that feels like a true retreat, featuring a tray ceiling and an updated spa-inspired bath that brings a sense of calm at the end of the day. Step outside to a private back deck perfect for grilling, gathering, or simply unwinding, while the low-maintenance yard still offers room for play, pets, or a future outdoor vision. And in a community where parking can be a premium, the attached garage is a rare and valuable bonus. The full unfinished basement offers incredible upside — a blank canvas ready to become whatever you need next: home gym, media room, guest suite, or additional living space. But what truly sets this home apart is the lifestyle. Just a short walk away, Hillsmere residents enjoy one of the largest private community beaches on the Chesapeake Bay, along with a marina, boat ramps, pool, playgrounds, and year-round neighborhood events. Here, days are spent on the water, evenings bring unforgettable sunsets over the South River, and weekends feel like a permanent vacation. All of this, just minutes from downtown Historic Annapolis, with its restaurants, shops, and waterfront charm. If you’ve been waiting for the right home in Hillsmere — don’t blink.

$895,000

Welcome to 600 Tayman Drive, where timeless Colonial charm meets the easy, coastal lifestyle that defines this sought-after Annapolis waterfront community. From the moment you arrive, the inviting front porch sets the tone — a place for morning coffee, evening wine, and neighbors who still wave as they pass by. Inside, the home opens effortlessly with a bright, flowing floor plan anchored by rich wood floors and a kitchen designed for real life — complete with stainless steel appliances and seamless connection to everyday living and entertaining spaces. Upstairs, every bedroom is thoughtfully placed on the second level, including a spacious primary suite that feels like a true retreat, featuring a tray ceiling and an updated spa-inspired bath that brings a sense of calm at the end of the day. Step outside to a private back deck perfect for grilling, gathering, or simply unwinding, while the low-maintenance yard still offers room for play, pets, or a future outdoor vision. And in a community where parking can be a premium, the attached garage is a rare and valuable bonus. The full unfinished basement offers incredible upside — a blank canvas ready to become whatever you need next: home gym, media room, guest suite, or additional living space. But what truly sets this home apart is the lifestyle. Just a short walk away, Hillsmere residents enjoy one of the largest private community beaches on the Chesapeake Bay, along with a marina, boat ramps, pool, playgrounds, and year-round neighborhood events. Here, days are spent on the water, evenings bring unforgettable sunsets over the South River, and weekends feel like a permanent vacation. All of this, just minutes from downtown Historic Annapolis, with its restaurants, shops, and waterfront charm. If you’ve been waiting for the right home in Hillsmere — don’t blink.

600 Tayman Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Welcome to Hillsmere Shores, one of Annapolis' premier waterfront communities, where coastal living meets convenience and an active lifestyle. This beautifully maintained all-brick, two-story Colonial offers a highly desirable open floor plan, hardwood floors, elevator access, and ADA-friendly design, providing comfort and accessibility for all stages of life. Enjoy seasonal water views from the main living areas and upper-level bedrooms, bringing the beauty of the Chesapeake lifestyle right into your home. Recent improvements include a new roof (2025) and new appliances (2026), offering peace of mind for years to come. The floored attic presents exciting potential for future expansion and additional living space. Primary bedroom offers spacious deck for relaxing with morning coffee and evening conversation. Situated on an attractive lot, this home is located within the sought-after Hillsmere Shores community, known for its vibrant neighborhood spirit and year-round events and celebrations. Residents enjoy access to exceptional amenities including a waterfront playground, volleyball court, two marinas with individual slips available for lease, and a community beach. The community swimming pool is available through a separate membership. Just minutes from historic Downtown Annapolis, residents can take advantage of award-winning restaurants, boutique shopping, waterfront parks, sailing, cultural events, and endless outdoor recreation. Commuters will appreciate the convenient access to Routes 50 and 97, providing easy connections to Washington, DC, Baltimore, and BWI Airport. Whether you're seeking a primary residence, a retirement-friendly home with elevator access, or a place to embrace the Annapolis waterfront lifestyle, this exceptional property offers the perfect combination of location, community, and value.

$890,000

Welcome to Hillsmere Shores, one of Annapolis' premier waterfront communities, where coastal living meets convenience and an active lifestyle. This beautifully maintained all-brick, two-story Colonial offers a highly desirable open floor plan, hardwood floors, elevator access, and ADA-friendly design, providing comfort and accessibility for all stages of life. Enjoy seasonal water views from the main living areas and upper-level bedrooms, bringing the beauty of the Chesapeake lifestyle right into your home. Recent improvements include a new roof (2025) and new appliances (2026), offering peace of mind for years to come. The floored attic presents exciting potential for future expansion and additional living space. Primary bedroom offers spacious deck for relaxing with morning coffee and evening conversation. Situated on an attractive lot, this home is located within the sought-after Hillsmere Shores community, known for its vibrant neighborhood spirit and year-round events and celebrations. Residents enjoy access to exceptional amenities including a waterfront playground, volleyball court, two marinas with individual slips available for lease, and a community beach. The community swimming pool is available through a separate membership. Just minutes from historic Downtown Annapolis, residents can take advantage of award-winning restaurants, boutique shopping, waterfront parks, sailing, cultural events, and endless outdoor recreation. Commuters will appreciate the convenient access to Routes 50 and 97, providing easy connections to Washington, DC, Baltimore, and BWI Airport. Whether you're seeking a primary residence, a retirement-friendly home with elevator access, or a place to embrace the Annapolis waterfront lifestyle, this exceptional property offers the perfect combination of location, community, and value.

131 Kuethe Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: RE/MAX Distinctive Real Estate, Inc..

$850,000

Welcome to 123 Spruce Lane, a completely renovated home in the sought-after waterfront community of Hillsmere Shores—where every detail has been thoughtfully redesigned to offer the feel and function of new construction. This stunning home has been fully transformed from top to bottom. Everything has been replaced—including a brand-new roof, HVAC system, hot water heater, water conditioning system, radon mitigation system, windows, flooring, and more. Simply put, they didn’t miss a thing. The gourmet kitchen anchors the home with an open-concept design that flows seamlessly into the family and dining rooms—perfect for entertaining and everyday living. Walls were thoughtfully reconfigured to create a bright, open floor plan designed for today’s lifestyle. The main-level family room features a cozy fireplace and beautifully restored custom built-in bookcases, preserving the character of the home while blending modern style. The primary suite is a true retreat, featuring a newly added walk-in closet and a luxurious, fully renovated bath with double vanities. Two additional beautifully renovated full baths, including a guest bath with double sinks, offer both style and convenience. The lower level is now fully finished and ready to be enjoyed, offering a second fireplace, recreation room, bedroom, and a nicely renovated full bath—ideal for guests, extended family, or additional living space. An abundance of natural light fills the home, thanks to new windows throughout, a stunning bay window at the front, and a private rear-corner office surrounded by windows on all sides—an ideal work-from-home space. Outside, the lot has been professionally cleared and refreshed, with weeds and dying trees removed and new plantings added, leaving a clean slate for new owners to personalize the outdoor space to their liking. Additional features include a large two-car garage with new doors and openers, adding both convenience and storage. This exceptional renovation was designed and executed by Frame House, known for creating homes tailored to today’s busy, active lifestyles—perfect for entertaining, hosting, and everyday comfort. All of this is located within the waterfront community of Hillsmere Shores, offering a private beach and playground, two marinas with boat launches, over 100 boat slips, kayak racks and launches, and a community pool (membership subject to availability). The entrance to Quiet Waters Park is within walking distance, and Downtown Annapolis—with its dining, shopping, and waterfront charm—is just minutes away. This is a rare opportunity to own a fully renovated, move-in-ready home in one of Annapolis’ most beloved communities. A truly special property that will not last long.

4 Beds ⋅ 4 Baths

Welcome to 123 Spruce Lane, a completely renovated home in the sought-after waterfront community of Hillsmere Shores—where every detail has been thoughtfully redesigned to offer the feel and function of new construction. This stunning home has been fully transformed from top to bottom. Everything has been replaced—including a brand-new roof, HVAC system, hot water heater, water conditioning system, radon mitigation system, windows, flooring, and more. Simply put, they didn’t miss a thing. The gourmet kitchen anchors the home with an open-concept design that flows seamlessly into the family and dining rooms—perfect for entertaining and everyday living. Walls were thoughtfully reconfigured to create a bright, open floor plan designed for today’s lifestyle. The main-level family room features a cozy fireplace and beautifully restored custom built-in bookcases, preserving the character of the home while blending modern style. The primary suite is a true retreat, featuring a newly added walk-in closet and a luxurious, fully renovated bath with double vanities. Two additional beautifully renovated full baths, including a guest bath with double sinks, offer both style and convenience. The lower level is now fully finished and ready to be enjoyed, offering a second fireplace, recreation room, bedroom, and a nicely renovated full bath—ideal for guests, extended family, or additional living space. An abundance of natural light fills the home, thanks to new windows throughout, a stunning bay window at the front, and a private rear-corner office surrounded by windows on all sides—an ideal work-from-home space. Outside, the lot has been professionally cleared and refreshed, with weeds and dying trees removed and new plantings added, leaving a clean slate for new owners to personalize the outdoor space to their liking. Additional features include a large two-car garage with new doors and openers, adding both convenience and storage. This exceptional renovation was designed and executed by Frame House, known for creating homes tailored to today’s busy, active lifestyles—perfect for entertaining, hosting, and everyday comfort. All of this is located within the waterfront community of Hillsmere Shores, offering a private beach and playground, two marinas with boat launches, over 100 boat slips, kayak racks and launches, and a community pool (membership subject to availability). The entrance to Quiet Waters Park is within walking distance, and Downtown Annapolis—with its dining, shopping, and waterfront charm—is just minutes away. This is a rare opportunity to own a fully renovated, move-in-ready home in one of Annapolis’ most beloved communities. A truly special property that will not last long.

123 Spruce Ln, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: Anne Arundel Properties, Inc..

$849,990

Welcome to 116 Carroll Drive, a classic brick-front colonial set on a spacious corner lot in one of Annapolis’s most sought-after waterfront communities. Hillsmere Shores isn’t just a place to live — it’s a lifestyle. Here, neighbors gather for beach picnics at sunset, kids splash in the sparkling community pool, kayaks launch at sunrise from the private marina, and weekends are spent exploring the Chesapeake Bay from your community boat ramp. Just seconds from all these amenities, this warm and welcoming home offers the perfect backdrop for every season — from cozy holiday gatherings by the fire to summer crab feasts on the back deck. The inviting front porch sets the tone for this gracious home, where light-filled spaces and timeless charm combine for easy everyday living. The main level offers a formal foyer, a spacious living room with a wood-burning fireplace, a dedicated dining room perfect for hosting family dinners, and a large updated kitchen with a breakfast nook that opens to the backyard — ideal for indoor-outdoor entertaining. Upstairs, you’ll find four generous bedrooms including a primary suite with a walk-in closet and private bath, plus an updated hall bath for the additional bedrooms. The finished lower level expands your living space with a versatile bonus room — perfect as a 5th bedroom, home office, gym, or den — along with a large recreation room and convenient walk-out stairs to the fully fenced backyard. Outside, the large deck, storage shed, and flat yard offer endless possibilities for play, gardening, or outdoor gatherings. The side-load two-car garage adds curb appeal and convenience, while the corner lot location enhances privacy and space. With its classic design, spacious layout, and unbeatable location, 116 Carroll Drive is ready for its next chapter — and it won’t last long. Come experience the Hillsmere Shores lifestyle and make this exceptional home yours before it’s gone!

Welcome to 116 Carroll Drive, a classic brick-front colonial set on a spacious corner lot in one of Annapolis’s most sought-after waterfront communities. Hillsmere Shores isn’t just a place to live — it’s a lifestyle. Here, neighbors gather for beach picnics at sunset, kids splash in the sparkling community pool, kayaks launch at sunrise from the private marina, and weekends are spent exploring the Chesapeake Bay from your community boat ramp. Just seconds from all these amenities, this warm and welcoming home offers the perfect backdrop for every season — from cozy holiday gatherings by the fire to summer crab feasts on the back deck. The inviting front porch sets the tone for this gracious home, where light-filled spaces and timeless charm combine for easy everyday living. The main level offers a formal foyer, a spacious living room with a wood-burning fireplace, a dedicated dining room perfect for hosting family dinners, and a large updated kitchen with a breakfast nook that opens to the backyard — ideal for indoor-outdoor entertaining. Upstairs, you’ll find four generous bedrooms including a primary suite with a walk-in closet and private bath, plus an updated hall bath for the additional bedrooms. The finished lower level expands your living space with a versatile bonus room — perfect as a 5th bedroom, home office, gym, or den — along with a large recreation room and convenient walk-out stairs to the fully fenced backyard. Outside, the large deck, storage shed, and flat yard offer endless possibilities for play, gardening, or outdoor gatherings. The side-load two-car garage adds curb appeal and convenience, while the corner lot location enhances privacy and space. With its classic design, spacious layout, and unbeatable location, 116 Carroll Drive is ready for its next chapter — and it won’t last long. Come experience the Hillsmere Shores lifestyle and make this exceptional home yours before it’s gone!

116 Carroll Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Welcome home to Holly Drive and the quiet rhythms of coastal Annapolis living. Some homes are defined by their rooms. 403 Holly Drive is shaped by everyday beauty - soft morning light in the kitchen, afternoons drifting between indoors and out, and evenings softened by bay breezes and birdsong through the trees. Set within the beloved water-privileged Hillsmere Shores community, this updated Craftsman home, built in 2003, offers a rare balance of warmth, refinement, and an unmistakable connection to the water and the outdoors. From the moment you arrive, the covered front porch feels like an invitation to slow down, breathe deeply, and stay awhile. Inside, the home unfolds with ease and intention. Hardwood floors stretch across both the main and upper levels, grounding the spaces in timeless elegance. The heart of the home is an open, beautifully updated kitchen where crisp white cabinetry, gleaming quartz countertops, and stainless steel appliances come together tastefully. Just beyond is the breakfast room, with its vaulted ceiling and a wall of windows offering panoramic views of the meticulously manicured yard, which changes beautifully with the seasons. A spacious family room anchored by a gas fireplace, a convenient powder room, a formal dining room, and a living room off the foyer complete the main level, providing well-balanced flow for everyday living and entertaining. From both the kitchen and the family room, new doors open to the expansive deck. Outdoors, the fully fenced backyard is both beautiful and purposeful - designed to support the local environment while offering a serene setting for play, gardening, and gatherings. Whether hosting dinner with friends, lingering over a weekend brunch, gathering around the fire pit, or simply listening to the sounds of the bay carried on the breeze, this home makes outdoor living feel natural and elegant. Upstairs, four generously sized bedrooms provide comfort and privacy. The primary suite is a peaceful retreat, complete with a spacious walk-in closet and a newly updated en-suite bath featuring a standing shower, jacuzzi tub, and dual vanities. One additional full bath with a tub/shower combination in the hallway, along with a convenient upper-level laundry room, completes this level. The lower basement level, with a walk-up stairway to the backyard, offers a bright, renovated space that feels anything but secondary. Freshly carpeted, it provides a cozy spot for a playroom, media center, or office. A second, recently updated half bath and a spacious utility storage room complete this level. The bonus room, with double French doors facing the driveway and its own dedicated HVAC zone, could be converted back into a two-car garage or used as extra storage, a gym, workshop, or studio space. You’re not simply looking for a place to live - you’re searching for a new way of living. And at 403 Holly Drive, that way of life is truly special. Reach out to the listing agent Gloria Griner to schedule your private tour today! The Hillsmere Shores Lifestyle: *Voluntary HOA with exceptional community amenities for only $25/annually *Community beach and waterfront access *Main marina with boat slips and small craft launch *Multiple boat ramps and kayak launch points *Kayak racks and boat storage areas *Community pool with swim team and seasonal events *Playground, walking paths, and BBQ picnic areas *Minutes to Quiet Waters Park *Easy access to the Chesapeake Bay, South River, and Duvall Creek Recent Updates and Improvements: 2025: Basement Carpet Installed 2025: Basement Bathroom Updated 2025: Dishwasher replaced 2025: Garbage Disposal replaced 2024: Main and backup sump pumps replaced 2024: Water heater replaced 2023: First Floor HVAC replaced 2023: Driveway paved 2021: Washer and Dryer replaced

$825,000

4 Beds ⋅ 4 Baths

Welcome home to Holly Drive and the quiet rhythms of coastal Annapolis living. Some homes are defined by their rooms. 403 Holly Drive is shaped by everyday beauty - soft morning light in the kitchen, afternoons drifting between indoors and out, and evenings softened by bay breezes and birdsong through the trees. Set within the beloved water-privileged Hillsmere Shores community, this updated Craftsman home, built in 2003, offers a rare balance of warmth, refinement, and an unmistakable connection to the water and the outdoors. From the moment you arrive, the covered front porch feels like an invitation to slow down, breathe deeply, and stay awhile. Inside, the home unfolds with ease and intention. Hardwood floors stretch across both the main and upper levels, grounding the spaces in timeless elegance. The heart of the home is an open, beautifully updated kitchen where crisp white cabinetry, gleaming quartz countertops, and stainless steel appliances come together tastefully. Just beyond is the breakfast room, with its vaulted ceiling and a wall of windows offering panoramic views of the meticulously manicured yard, which changes beautifully with the seasons. A spacious family room anchored by a gas fireplace, a convenient powder room, a formal dining room, and a living room off the foyer complete the main level, providing well-balanced flow for everyday living and entertaining. From both the kitchen and the family room, new doors open to the expansive deck. Outdoors, the fully fenced backyard is both beautiful and purposeful - designed to support the local environment while offering a serene setting for play, gardening, and gatherings. Whether hosting dinner with friends, lingering over a weekend brunch, gathering around the fire pit, or simply listening to the sounds of the bay carried on the breeze, this home makes outdoor living feel natural and elegant. Upstairs, four generously sized bedrooms provide comfort and privacy. The primary suite is a peaceful retreat, complete with a spacious walk-in closet and a newly updated en-suite bath featuring a standing shower, jacuzzi tub, and dual vanities. One additional full bath with a tub/shower combination in the hallway, along with a convenient upper-level laundry room, completes this level. The lower basement level, with a walk-up stairway to the backyard, offers a bright, renovated space that feels anything but secondary. Freshly carpeted, it provides a cozy spot for a playroom, media center, or office. A second, recently updated half bath and a spacious utility storage room complete this level. The bonus room, with double French doors facing the driveway and its own dedicated HVAC zone, could be converted back into a two-car garage or used as extra storage, a gym, workshop, or studio space. You’re not simply looking for a place to live - you’re searching for a new way of living. And at 403 Holly Drive, that way of life is truly special. Reach out to the listing agent Gloria Griner to schedule your private tour today! The Hillsmere Shores Lifestyle: *Voluntary HOA with exceptional community amenities for only $25/annually *Community beach and waterfront access *Main marina with boat slips and small craft launch *Multiple boat ramps and kayak launch points *Kayak racks and boat storage areas *Community pool with swim team and seasonal events *Playground, walking paths, and BBQ picnic areas *Minutes to Quiet Waters Park *Easy access to the Chesapeake Bay, South River, and Duvall Creek Recent Updates and Improvements: 2025: Basement Carpet Installed 2025: Basement Bathroom Updated 2025: Dishwasher replaced 2025: Garbage Disposal replaced 2024: Main and backup sump pumps replaced 2024: Water heater replaced 2023: First Floor HVAC replaced 2023: Driveway paved 2021: Washer and Dryer replaced

403 Holly Dr, Annapolis

Listing courtesy of RLAH @properties. Contact:

Selling Office: Keller Williams Flagship.

$800,000

520 Harbor Drive isn’t simply another home hitting the market — it’s the opportunity buyers spend months waiting to find in Hillsmere and rarely secure. Perfectly positioned in the heart of one of Annapolis’ most loved waterfront communities, this home delivers the lifestyle that keeps people here for years: private beaches, marina access, boat ramps, a community pool, playgrounds, and effortless access to the South River and Chesapeake Bay. From the moment you arrive, the home feels polished, intentional, and completely move-in ready. This isn’t a cosmetic refresh — this home has been extensively renovated with permits and thoughtfully updated throughout, delivering the confidence and peace of mind buyers want. The work is already done with updated systems, quality finishes, and a level of care that is difficult to replicate. Inside, light-filled spaces and a flowing layout create the kind of everyday comfort buyers are searching for, anchored by a beautifully designed kitchen that opens seamlessly into generous living and gathering spaces built for both entertaining and real life. Step outside and the experience only gets better with a brand-new paver patio creating the perfect setting for summer gatherings, morning coffee, or evenings under the stars. The huge fully fenced backyard offers exceptional space and privacy, while the detached shed adds valuable storage and flexibility. And then there is Hillsmere itself — where life truly revolves around the water. Residents enjoy neighborhood traditions and waterfront gatherings throughout the year, from the annual Fourth of July bike parade to beach picnics and community events that bring neighbors together. The community beach features a playground overlooking the water, and many consider Hillsmere to offer one of the most desirable beach and pool lifestyles in Annapolis. This is more than a move-in ready home — it is a chance to become part of a community people fall in love with and rarely want to leave.

520 Harbor Drive isn’t simply another home hitting the market — it’s the opportunity buyers spend months waiting to find in Hillsmere and rarely secure. Perfectly positioned in the heart of one of Annapolis’ most loved waterfront communities, this home delivers the lifestyle that keeps people here for years: private beaches, marina access, boat ramps, a community pool, playgrounds, and effortless access to the South River and Chesapeake Bay. From the moment you arrive, the home feels polished, intentional, and completely move-in ready. This isn’t a cosmetic refresh — this home has been extensively renovated with permits and thoughtfully updated throughout, delivering the confidence and peace of mind buyers want. The work is already done with updated systems, quality finishes, and a level of care that is difficult to replicate. Inside, light-filled spaces and a flowing layout create the kind of everyday comfort buyers are searching for, anchored by a beautifully designed kitchen that opens seamlessly into generous living and gathering spaces built for both entertaining and real life. Step outside and the experience only gets better with a brand-new paver patio creating the perfect setting for summer gatherings, morning coffee, or evenings under the stars. The huge fully fenced backyard offers exceptional space and privacy, while the detached shed adds valuable storage and flexibility. And then there is Hillsmere itself — where life truly revolves around the water. Residents enjoy neighborhood traditions and waterfront gatherings throughout the year, from the annual Fourth of July bike parade to beach picnics and community events that bring neighbors together. The community beach features a playground overlooking the water, and many consider Hillsmere to offer one of the most desirable beach and pool lifestyles in Annapolis. This is more than a move-in ready home — it is a chance to become part of a community people fall in love with and rarely want to leave.

520 Harbor Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Non Subscribing Office.

$800,000

Life in Hillsmere revolves around the water — the Chesapeake Bay, the South River, and a lifestyle that most people only experience on vacation. Welcome to 298 Edgemere Drive, located in one of Annapolis’ most beloved waterfront communities, where the rhythm of everyday life is shaped by fresh air, sunset skies, and a neighborhood designed for living well. Hillsmere Shores offers an extraordinary collection of amenities rarely found in a private community. Residents enjoy access to one of the largest private beaches on the South River, where sandy shoreline, panoramic water views, and unforgettable sunsets become part of your daily routine. Just moments away, the marina and community boat ramp provide effortless access — making boating, sailing, fishing, jet skis, and paddleboarding feel like second nature. The lifestyle continues on land with a community pool, playgrounds, kayak storage, volleyball court, and vibrant neighborhood events that bring neighbors together all year long. It’s the kind of place where weekends are spent at the beach, kids ride bikes until sunset, and neighbors quickly become lifelong friends. Within this exceptional setting, is a fantastic property, offering five bedrooms, three full baths, and more than 2,600 square feet of living space — a size and layout that is increasingly rare in this coveted waterfront community. Inside, the home offers bright, welcoming living spaces designed for both everyday comfort and entertaining. Multiple living areas provide flexibility for modern lifestyles — whether hosting friends after a day on the water, creating private work-from-home space, or comfortably accommodating guests and family. But what truly sets this home apart is the lifestyle that surrounds it. Morning walks along the Bay. Launching the boat on the South River. Summer afternoons at the community beach. Evenings watching the sun melt into the Chesapeake. All of it just minutes from Historic Downtown Annapolis, world-class sailing, marinas, waterfront restaurants, and the charm of Maryland’s capital city. Homes offering this amount of space, flexibility, and access to the Hillsmere waterfront lifestyle rarely come to market. 298 Edgemere Drive is more than a home — it’s an invitation to live the Chesapeake Bay life Annapolis is famous for.

Life in Hillsmere revolves around the water — the Chesapeake Bay, the South River, and a lifestyle that most people only experience on vacation. Welcome to 298 Edgemere Drive, located in one of Annapolis’ most beloved waterfront communities, where the rhythm of everyday life is shaped by fresh air, sunset skies, and a neighborhood designed for living well. Hillsmere Shores offers an extraordinary collection of amenities rarely found in a private community. Residents enjoy access to one of the largest private beaches on the South River, where sandy shoreline, panoramic water views, and unforgettable sunsets become part of your daily routine. Just moments away, the marina and community boat ramp provide effortless access — making boating, sailing, fishing, jet skis, and paddleboarding feel like second nature. The lifestyle continues on land with a community pool, playgrounds, kayak storage, volleyball court, and vibrant neighborhood events that bring neighbors together all year long. It’s the kind of place where weekends are spent at the beach, kids ride bikes until sunset, and neighbors quickly become lifelong friends. Within this exceptional setting, is a fantastic property, offering five bedrooms, three full baths, and more than 2,600 square feet of living space — a size and layout that is increasingly rare in this coveted waterfront community. Inside, the home offers bright, welcoming living spaces designed for both everyday comfort and entertaining. Multiple living areas provide flexibility for modern lifestyles — whether hosting friends after a day on the water, creating private work-from-home space, or comfortably accommodating guests and family. But what truly sets this home apart is the lifestyle that surrounds it. Morning walks along the Bay. Launching the boat on the South River. Summer afternoons at the community beach. Evenings watching the sun melt into the Chesapeake. All of it just minutes from Historic Downtown Annapolis, world-class sailing, marinas, waterfront restaurants, and the charm of Maryland’s capital city. Homes offering this amount of space, flexibility, and access to the Hillsmere waterfront lifestyle rarely come to market. 298 Edgemere Drive is more than a home — it’s an invitation to live the Chesapeake Bay life Annapolis is famous for.

298 Edgemere Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Cummings & Co Realtors.

$800,000

OPEN HOUSE CANCELLED! UNDER CONTRACT! Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, one of Annapolis’ most coveted water-privileged communities. Completely renovated and impeccably maintained, this home offers approximately 4,000 finished square feet of beautifully designed living space where scale, comfort, and craftsmanship come together seamlessly. Walls of windows flood the open layout with natural light, highlighting rich hardwood floors, custom moldings, and timeless fixtures throughout. The gourmet kitchen is the true centerpiece of the home, featuring 42" cabinetry, stainless steel and chef-grade appliances, gleaming granite countertops, and an oversized center island—perfect for everyday living and effortless entertaining. A sunny morning room connects the kitchen and dining spaces, creating an inviting flow for gatherings large and small. The formal dining room is accented by a stunning tray ceiling, while the expansive living room offers an ideal setting for entertaining or relaxing. The primary suite is a showstopper, complete with vaulted ceilings, a sitting area, a custom walk-in closet, and a spa-inspired bath featuring a frameless glass walk-in shower with designer tile and a deep soaking tub. All additional bedrooms are generously sized with excellent closet space. The screened upper porch extends your living space outdoors—ideal for champagne sunsets, crab feasts, and relaxed evenings—finished with maintenance-free composite decking and vinyl posts. The lower level impresses with exposed brick walls, a large recreation room for movie nights and gatherings, and an open den with a cozy wood stove that works beautifully as a home office or study. A guest bedroom, full bath, oversized laundry room, and separate utility room provide flexibility, storage, and function. Outside, the fenced backyard is level, private, and surrounded by mature trees, offering endless possibilities for gardening, play, entertaining, or even adding a pool. A large paver patio is perfect for a fire pit and s’mores under the stars. Plenty of off-street parking completes the package. Hillsmere Shores delivers an unmatched lifestyle with two private beaches, beachfront playgrounds, a boat ramp, canoe and kayak storage, boat slips, beach pavilions, volleyball courts, and a community pool—all just moments away. Enjoy a vibrant calendar of neighborhood events including poolside movie nights, Food Truck Fridays, beach Easter egg hunts, Fourth of July bike parades, spring sock burning, and the annual pig roast. This is more than a home—it’s a community, a lifestyle, and an absolute 10.

OPEN HOUSE CANCELLED! UNDER CONTRACT! Welcome to 406 Harbor Drive, an exceptional residence in the heart of Hillsmere Shores, one of Annapolis’ most coveted water-privileged communities. Completely renovated and impeccably maintained, this home offers approximately 4,000 finished square feet of beautifully designed living space where scale, comfort, and craftsmanship come together seamlessly. Walls of windows flood the open layout with natural light, highlighting rich hardwood floors, custom moldings, and timeless fixtures throughout. The gourmet kitchen is the true centerpiece of the home, featuring 42" cabinetry, stainless steel and chef-grade appliances, gleaming granite countertops, and an oversized center island—perfect for everyday living and effortless entertaining. A sunny morning room connects the kitchen and dining spaces, creating an inviting flow for gatherings large and small. The formal dining room is accented by a stunning tray ceiling, while the expansive living room offers an ideal setting for entertaining or relaxing. The primary suite is a showstopper, complete with vaulted ceilings, a sitting area, a custom walk-in closet, and a spa-inspired bath featuring a frameless glass walk-in shower with designer tile and a deep soaking tub. All additional bedrooms are generously sized with excellent closet space. The screened upper porch extends your living space outdoors—ideal for champagne sunsets, crab feasts, and relaxed evenings—finished with maintenance-free composite decking and vinyl posts. The lower level impresses with exposed brick walls, a large recreation room for movie nights and gatherings, and an open den with a cozy wood stove that works beautifully as a home office or study. A guest bedroom, full bath, oversized laundry room, and separate utility room provide flexibility, storage, and function. Outside, the fenced backyard is level, private, and surrounded by mature trees, offering endless possibilities for gardening, play, entertaining, or even adding a pool. A large paver patio is perfect for a fire pit and s’mores under the stars. Plenty of off-street parking completes the package. Hillsmere Shores delivers an unmatched lifestyle with two private beaches, beachfront playgrounds, a boat ramp, canoe and kayak storage, boat slips, beach pavilions, volleyball courts, and a community pool—all just moments away. Enjoy a vibrant calendar of neighborhood events including poolside movie nights, Food Truck Fridays, beach Easter egg hunts, Fourth of July bike parades, spring sock burning, and the annual pig roast. This is more than a home—it’s a community, a lifestyle, and an absolute 10.

406 Harbor Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Keller Williams Flagship.

$785,000

YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the great room… this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just catching up at the end of the day, it’s easy, comfortable, and it works. And it flows right out to the deck—so your living space doesn’t stop at the back door. And then… the yard. Over 1/3 acre of flat, usable space—which in Hillsmere is a big deal. This isn’t a “look at it from the window” yard. This is a run around, roam around, throw a ball, set up a fire pit, bring all the toys (for kids and adults) kind of yard. The kind you actually use. There is plenty of storage space to store all those toys in your extra deep one car garage which is an added bonus. Back inside—everything’s been done. Hardwood floors throughout the upper level, freshly painted, and ready for you. Kitchen, baths, finishes—clean, updated, and done right. No projects. No guesswork. Just move in and start living. Upstairs offers three bedrooms and 1.5 baths. Downstairs? A private primary suite with a full bath, plus additional living space that flexes however you need it—guests, office, gym, or all three. And then there’s the lifestyle that makes Hillsmere what it is… Just a few blocks in any direction takes you to the best of Hillsmere—the beach, marina, boat launch, pool, playground, pavilion… and right across from Key School. Your Morning walks by the water, spontaneous sunset plans, weekends that don’t need planning—YES, YOU CAN HAVE IT ALL.

YES, YOU CAN HAVE IT ALL. Completely remodeled from top to bottom in one of the most sought-after neighborhoods around—this one checks ALL the boxes. The kitchen, the great room… this is the hub. The heart of the home. And the best part? You’re not dreaming about what it could be—the work is already done. Big island, open flow—everyone ends up here. Whether you’re cooking, hanging out, or just catching up at the end of the day, it’s easy, comfortable, and it works. And it flows right out to the deck—so your living space doesn’t stop at the back door. And then… the yard. Over 1/3 acre of flat, usable space—which in Hillsmere is a big deal. This isn’t a “look at it from the window” yard. This is a run around, roam around, throw a ball, set up a fire pit, bring all the toys (for kids and adults) kind of yard. The kind you actually use. There is plenty of storage space to store all those toys in your extra deep one car garage which is an added bonus. Back inside—everything’s been done. Hardwood floors throughout the upper level, freshly painted, and ready for you. Kitchen, baths, finishes—clean, updated, and done right. No projects. No guesswork. Just move in and start living. Upstairs offers three bedrooms and 1.5 baths. Downstairs? A private primary suite with a full bath, plus additional living space that flexes however you need it—guests, office, gym, or all three. And then there’s the lifestyle that makes Hillsmere what it is… Just a few blocks in any direction takes you to the best of Hillsmere—the beach, marina, boat launch, pool, playground, pavilion… and right across from Key School. Your Morning walks by the water, spontaneous sunset plans, weekends that don’t need planning—YES, YOU CAN HAVE IT ALL.

101 Huse Dr, Annapolis

Listing courtesy of RE/MAX One. Contact:

Welcome to 107 Lake View Drive — a stunning, fully renovated retreat tucked inside one of Annapolis's most coveted waterfront neighborhoods. Nestled in the heart of Hillsmere Shores, just steps from the Chesapeake Bay near the mouth of the South River, this 4-bedroom, 3.5-bath home is a rare opportunity to live the quintessential bay lifestyle! The open layout immediately draws you in — a spacious bump-out family room, beautifully updated kitchen, and natural light throughout. Step outside to a private fenced backyard perfect for entertaining or unwinding after a day on the water. Updated top to bottom: brand new HVAC, electrical, and plumbing. Nothing overlooked. Truly move-in ready. Blocks from a private beach, marina, boat slips, community pool, and playground. Minutes from downtown Annapolis, Quiet Waters Park, and Key School. Whether you're planting roots or chasing that Chesapeake dream — 107 Lake View Drive is ready for you!

$780,000

4 Beds ⋅ 4 Baths

Welcome to 107 Lake View Drive — a stunning, fully renovated retreat tucked inside one of Annapolis's most coveted waterfront neighborhoods. Nestled in the heart of Hillsmere Shores, just steps from the Chesapeake Bay near the mouth of the South River, this 4-bedroom, 3.5-bath home is a rare opportunity to live the quintessential bay lifestyle! The open layout immediately draws you in — a spacious bump-out family room, beautifully updated kitchen, and natural light throughout. Step outside to a private fenced backyard perfect for entertaining or unwinding after a day on the water. Updated top to bottom: brand new HVAC, electrical, and plumbing. Nothing overlooked. Truly move-in ready. Blocks from a private beach, marina, boat slips, community pool, and playground. Minutes from downtown Annapolis, Quiet Waters Park, and Key School. Whether you're planting roots or chasing that Chesapeake dream — 107 Lake View Drive is ready for you!

107 Lake View Dr, Annapolis

Listing courtesy of Jason Mitchell Group. Contact:

Selling Office: Non Subscribing Office.

$780,000

Almost new 5 bedroom, 3 full bath home in the amenity filled neighborhood of Hillsmere Estates.

Almost new 5 bedroom, 3 full bath home in the amenity filled neighborhood of Hillsmere Estates.

106 Pinecrest Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: EXP Realty, LLC.

$700,000

Turn-key and beautifully appointed, this 5-bedroom, 3 full bath home sits on a generous 0.27-acre lot in the highly sought-after Hillsmere Estates community. A long driveway offers ample parking and leads to a spacious 2-car garage. The main level features a warm and inviting family room with a wood-burning stove and a dining room with hardwood floors. The gourmet kitchen is a standout, complete with granite countertops, GE Monogram appliances, gas cooktop with hood and heat lamps, wall oven with warming drawer, and a center island with sink—all seamlessly flowing into a bright sunroom. From there, step out onto the custom, maintenance-free Trex deck overlooking the expansive backyard—perfect for entertaining. Enjoy luxury touches throughout, including Pella windows, heated floors in the kitchen and baths, and skylights with electric open/close and shades. The upper level offers four bedrooms and three full baths, including a spacious primary suite with walk-in closet and ensuite bath with jetted tub. The cozy lower level includes a family room with electric stove, brand-new LVP flooring, a 5th bedroom, laundry room, and has been fully waterproofed for peace of mind. Additional highlights include a 4-year-old roof, oversized gutters with guards, and a charming front walkway with a koi pond and waterfall (koi fish convey). 5 minute walk to Hillsmere Elementary and a 3 minute drive to Key School. Located in amenity-rich Hillsmere Estates—featuring a community pool, beach, boat ramp, volleyball court, frisbee golf, pavilion, and more—plus adjacent access to Quiet Waters Park. This home offers the perfect blend of comfort, upgrades, and lifestyle.

Turn-key and beautifully appointed, this 5-bedroom, 3 full bath home sits on a generous 0.27-acre lot in the highly sought-after Hillsmere Estates community. A long driveway offers ample parking and leads to a spacious 2-car garage. The main level features a warm and inviting family room with a wood-burning stove and a dining room with hardwood floors. The gourmet kitchen is a standout, complete with granite countertops, GE Monogram appliances, gas cooktop with hood and heat lamps, wall oven with warming drawer, and a center island with sink—all seamlessly flowing into a bright sunroom. From there, step out onto the custom, maintenance-free Trex deck overlooking the expansive backyard—perfect for entertaining. Enjoy luxury touches throughout, including Pella windows, heated floors in the kitchen and baths, and skylights with electric open/close and shades. The upper level offers four bedrooms and three full baths, including a spacious primary suite with walk-in closet and ensuite bath with jetted tub. The cozy lower level includes a family room with electric stove, brand-new LVP flooring, a 5th bedroom, laundry room, and has been fully waterproofed for peace of mind. Additional highlights include a 4-year-old roof, oversized gutters with guards, and a charming front walkway with a koi pond and waterfall (koi fish convey). 5 minute walk to Hillsmere Elementary and a 3 minute drive to Key School. Located in amenity-rich Hillsmere Estates—featuring a community pool, beach, boat ramp, volleyball court, frisbee golf, pavilion, and more—plus adjacent access to Quiet Waters Park. This home offers the perfect blend of comfort, upgrades, and lifestyle.

326 Cedar Ln, Annapolis

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

Welcome home to completely renovated 529 Tayman Drive, an impeccably renovated residence blending modern luxury with prime Hillsmere convenience. Situated on a large/spacious, fenced-in corner lot, this 3-bedroom 2.5-bathroom with a finished basement offers a lifestyle of comfort and ease. Step inside and be captivated by the two-story vaulted living room, a sun-drenched space designed for both relaxation and grand entertaining. The gourmet kitchen is a chef’s dream, featuring sleek quartz countertops and all-new appliances. The primary bedroom is a true retreat, offering a spa-like en-suite bathroom for ultimate relaxation. The finished basement provides ample flexible space for a media room, home gym, or play area. With no detail overlooked, this home is entirely move-in ready. Upgrades include a new roof, new siding, a new composite deck and porch, a new HVAC system, a new water heater, and a new French drain waterproofing system. The backyard has a pour concrete pad with electrical service for a large shed or hot tub! As if the home itself weren't enough, the location is unbeatable—just one block from the Key School and a short walk from the community beach. Discover the best of Hillsmere living.

$700,000

Welcome home to completely renovated 529 Tayman Drive, an impeccably renovated residence blending modern luxury with prime Hillsmere convenience. Situated on a large/spacious, fenced-in corner lot, this 3-bedroom 2.5-bathroom with a finished basement offers a lifestyle of comfort and ease. Step inside and be captivated by the two-story vaulted living room, a sun-drenched space designed for both relaxation and grand entertaining. The gourmet kitchen is a chef’s dream, featuring sleek quartz countertops and all-new appliances. The primary bedroom is a true retreat, offering a spa-like en-suite bathroom for ultimate relaxation. The finished basement provides ample flexible space for a media room, home gym, or play area. With no detail overlooked, this home is entirely move-in ready. Upgrades include a new roof, new siding, a new composite deck and porch, a new HVAC system, a new water heater, and a new French drain waterproofing system. The backyard has a pour concrete pad with electrical service for a large shed or hot tub! As if the home itself weren't enough, the location is unbeatable—just one block from the Key School and a short walk from the community beach. Discover the best of Hillsmere living.

529 Tayman Dr, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: EXP Realty, LLC.

$670,000

Multiple Offers – 101 Lake View (Deadline Sun 10/5 at 5pm) Welcome to 101 Lake View Drive, a charming 3-bedroom, 2-bath home tucked into the highly desirable waterfront community of Hillsmere Shores. Perfectly blending comfort, convenience, and lifestyle, this home has been thoughtfully updated and maintained. Inside, you’ll find an open and inviting layout with a spacious bump-out family room, an updated kitchen, and plenty of natural light throughout. The primary level also offers access to the fenced backyard—complete with a firepit overlooking water views making it the perfect spot for entertaining or unwinding after a long day. Additional highlights include: * 3 bedrooms, 2 full baths * Attached 2-car garage for parking and storage * Updated kitchen with modern finishes * Bump-out family room for extra living space * Fenced backyard with water views and firepit Hillsmere Shores offers an incredible lifestyle with water access, community beaches, a marina, playground, and pool, plus an unbeatable location just minutes from downtown Annapolis and Quiet Waters Park. Whether you’re looking for your first home, your next chapter, or a place to enjoy the Chesapeake Bay lifestyle, this one checks all the boxes.

3 Beds ⋅ 2 Baths

Multiple Offers – 101 Lake View (Deadline Sun 10/5 at 5pm) Welcome to 101 Lake View Drive, a charming 3-bedroom, 2-bath home tucked into the highly desirable waterfront community of Hillsmere Shores. Perfectly blending comfort, convenience, and lifestyle, this home has been thoughtfully updated and maintained. Inside, you’ll find an open and inviting layout with a spacious bump-out family room, an updated kitchen, and plenty of natural light throughout. The primary level also offers access to the fenced backyard—complete with a firepit overlooking water views making it the perfect spot for entertaining or unwinding after a long day. Additional highlights include: * 3 bedrooms, 2 full baths * Attached 2-car garage for parking and storage * Updated kitchen with modern finishes * Bump-out family room for extra living space * Fenced backyard with water views and firepit Hillsmere Shores offers an incredible lifestyle with water access, community beaches, a marina, playground, and pool, plus an unbeatable location just minutes from downtown Annapolis and Quiet Waters Park. Whether you’re looking for your first home, your next chapter, or a place to enjoy the Chesapeake Bay lifestyle, this one checks all the boxes.

101 Lake View Dr, Annapolis

Listing courtesy of Next Step Realty, LLC.. Contact:

This Hillsmere Shores residence is conveniently located within walking distance of South River and Key School. The property features a flexible interior layout, including a main-level suite with a full bathroom and sitting area, currently utilized as a family room with a home office. A rear staircase offers secondary access to the updated kitchen, which showcases stainless steel appliances and granite countertops. Hardwood floors extend throughout the living and dining areas, as well as three bedrooms. The living room includes a fireplace, with an electric insert, while the dining area, with cabinetry—opens to a climate-controlled four-season room Bedroom level has 3 bedrooms one bedroom has "ensuite" access to the hallway full bathroom. The fenced rear yard features a firepit area, patio, expansive green space, established gardens, and a potting shed. Ample driveway and off-street parking. Hillsmere community offers the residents a voluntary community association ; access to a beach, marina, boat ramp, as well as an optional community pool membership. The location is within walking distance to the library and Quiet Waters Park, and is convenient to shopping, restaurants, gas stations, Historic Annapolis, and the U.S. Naval Academy.

$645,000

This Hillsmere Shores residence is conveniently located within walking distance of South River and Key School. The property features a flexible interior layout, including a main-level suite with a full bathroom and sitting area, currently utilized as a family room with a home office. A rear staircase offers secondary access to the updated kitchen, which showcases stainless steel appliances and granite countertops. Hardwood floors extend throughout the living and dining areas, as well as three bedrooms. The living room includes a fireplace, with an electric insert, while the dining area, with cabinetry—opens to a climate-controlled four-season room Bedroom level has 3 bedrooms one bedroom has "ensuite" access to the hallway full bathroom. The fenced rear yard features a firepit area, patio, expansive green space, established gardens, and a potting shed. Ample driveway and off-street parking. Hillsmere community offers the residents a voluntary community association ; access to a beach, marina, boat ramp, as well as an optional community pool membership. The location is within walking distance to the library and Quiet Waters Park, and is convenient to shopping, restaurants, gas stations, Historic Annapolis, and the U.S. Naval Academy.

107 Spring Valley Dr, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.

$600,000

Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.

100 Carroll Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Unrepresented.

$599,900

This move-in-ready 4-bedroom home blends classic character with tasteful modern touches throughout. The kitchen features sleek surfaces and opens to a cozy dining area with a fireplace. Gleaming floors span the main level, including a versatile bonus room that could easily serve as a 5th bedroom. The main-level half bath has been updated and is prepped for an easy conversion to a full bath. Upstairs, the spacious primary suite offers ample room to add an additional bath if desired. Additional highlights include solid wood panel doors, custom trim work throughout, and a brand-new HVAC system complemented by newer mini-split units in the upstairs bedrooms for personalized comfort. The foundation has been recently waterproofed, offering peace of mind and a dry, well-maintained lower level. Outside, enjoy a freshly landscaped fenced yard and an oversized, fully refinished garage. The walk-up, unfinished basement includes a rough-in for another full bathroom—perfect for future expansion, recreation, or storage. All this, plus community water access, beach, and pier on the South River.

This move-in-ready 4-bedroom home blends classic character with tasteful modern touches throughout. The kitchen features sleek surfaces and opens to a cozy dining area with a fireplace. Gleaming floors span the main level, including a versatile bonus room that could easily serve as a 5th bedroom. The main-level half bath has been updated and is prepped for an easy conversion to a full bath. Upstairs, the spacious primary suite offers ample room to add an additional bath if desired. Additional highlights include solid wood panel doors, custom trim work throughout, and a brand-new HVAC system complemented by newer mini-split units in the upstairs bedrooms for personalized comfort. The foundation has been recently waterproofed, offering peace of mind and a dry, well-maintained lower level. Outside, enjoy a freshly landscaped fenced yard and an oversized, fully refinished garage. The walk-up, unfinished basement includes a rough-in for another full bathroom—perfect for future expansion, recreation, or storage. All this, plus community water access, beach, and pier on the South River.

508 Harbor Dr, Annapolis

Listing courtesy of Innovation Properties, LLC. Contact:

UNDER CONTRACT - ACCEPTING BACKUPS!!!! Nestled in the charming Hillsmere Estates, this home is on an oversize large corner lot. **BRAND NEW** Roof. Small storage/workshop shed. The partially finished basement provides additional space for recreation or relaxation. Enjoy private access for swimming, boating, kayaking, or simply soaking in the stunning waterfront views along the community beach. The community fosters a love for the outdoors, with nearby parks (Quiet Waters & others) offering trails, picnic areas, and playgrounds, perfect for leisurely weekends. Voluntary HOA! The association takes care of common area maintenance, ensuring that the neighborhood remains pristine and welcoming. Experience the joys of waterfront living in a community that values connection and nature. This home is not just a place to live; it's a place to thrive.

$529,000

UNDER CONTRACT - ACCEPTING BACKUPS!!!! Nestled in the charming Hillsmere Estates, this home is on an oversize large corner lot. **BRAND NEW** Roof. Small storage/workshop shed. The partially finished basement provides additional space for recreation or relaxation. Enjoy private access for swimming, boating, kayaking, or simply soaking in the stunning waterfront views along the community beach. The community fosters a love for the outdoors, with nearby parks (Quiet Waters & others) offering trails, picnic areas, and playgrounds, perfect for leisurely weekends. Voluntary HOA! The association takes care of common area maintenance, ensuring that the neighborhood remains pristine and welcoming. Experience the joys of waterfront living in a community that values connection and nature. This home is not just a place to live; it's a place to thrive.

503 Harbor Dr, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Heymann Realty, LLC.

$505,000

This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and partially finished walkout lower level. Additional features include a primary suite with a private bath and sitting area, a wood-burning fireplace, hardwood flooring, an asphalt driveway, and access to community beaches, picnic areas, a playground, boat ramp, and marina.

This 4-bedroom, 2.5-bath detached Colonial in Hillsmere Estates offers a spacious three-level layout with an eat-in kitchen, family room, sunroom, fenced backyard, and partially finished walkout lower level. Additional features include a primary suite with a private bath and sitting area, a wood-burning fireplace, hardwood flooring, an asphalt driveway, and access to community beaches, picnic areas, a playground, boat ramp, and marina.

318 Beach Dr, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy access to Quiet Waters Park, with miles of scenic walking and biking trails, dog parks, playgrounds, and year-round outdoor recreation. Inside, the home is filled with natural light, creating bright and inviting living spaces. Designed for both everyday living and entertaining, the layout offers flexibility to suit a variety of needs. The finished family room provides direct access to the backyard, where thoughtfully designed hardscaping with extensive brickwork creates multiple areas for outdoor dining, grilling, and gathering. A hot tub adds to the appeal, offering a perfect spot to relax and unwind. With its great neighborhood setting and convenient location, 102 Oak Drive presents an excellent opportunity to enjoy all that Annapolis has to offer.

$498,000

2 Beds

Located in the highly desirable Hillsmere Shores community, 102 Oak Drive offers a comfortable lifestyle in one of Annapolis’ most well-established neighborhoods. Conveniently located just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes, this home provides easy access to shopping, dining, and everyday essentials. Residents of Hillsmere Shores also enjoy easy access to Quiet Waters Park, with miles of scenic walking and biking trails, dog parks, playgrounds, and year-round outdoor recreation. Inside, the home is filled with natural light, creating bright and inviting living spaces. Designed for both everyday living and entertaining, the layout offers flexibility to suit a variety of needs. The finished family room provides direct access to the backyard, where thoughtfully designed hardscaping with extensive brickwork creates multiple areas for outdoor dining, grilling, and gathering. A hot tub adds to the appeal, offering a perfect spot to relax and unwind. With its great neighborhood setting and convenient location, 102 Oak Drive presents an excellent opportunity to enjoy all that Annapolis has to offer.

102 Oak Dr, Annapolis

Listing courtesy of Samson Properties. Contact:

SOLD AND SETTLED SITE UNSEEN WITH MULTIPLE OFFERS ... LISTED AND SOLD SIMLOUTANELOUSY ... GREAT BONES, FIXER UPPER

$490,000

SOLD AND SETTLED SITE UNSEEN WITH MULTIPLE OFFERS ... LISTED AND SOLD SIMLOUTANELOUSY ... GREAT BONES, FIXER UPPER

109 Sunset Dr, Annapolis

Listing courtesy of Winning Edge. Contact:

Selling Office: Winning Edge.

$445,000

Priced with opportunity in mind, this Hillsmere ranch offers a home with good bones and a flexible layout, presenting an excellent chance for buyers to build equity and make it their own. Set on a level .29-acre lot with a long driveway accommodating 4+ cars, the home features true one-level living with the added benefit of a lower level. The main level includes two bedrooms and a full bath, while the lower level offers a large recreation room, third bedroom, second full bath, laundry area, and utility/storage room—ideal for guests, a home office, or additional living space. With thoughtful updates over time, this home can compete favorably with higher-priced, renovated homes within the neighborhood. Key updates include a new roof (2022), Trane oil furnace, AO Smith electric water heater (2019), and a well water treatment system. A one-year home warranty is offered to buyers for added peace of mind. Located in the desirable Hillsmere community, residents enjoy access to a private marina and boat ramp with direct access to the South River, canoe and kayak storage, a sandy beach and swim area, waterfront playgrounds with pavilions and grills, and the option for membership to the community pool. Enjoy the feeling of “getting away from it all” while remaining just minutes from Historic Annapolis (within 3 miles), walking distance to Quiet Waters Park, the library, shopping and restaurants, and convenient access to DC, Baltimore, and BWI. An appealing opportunity to enter Hillsmere at a price point that reflects the work needed, with strong upside in a vibrant, waterfront-oriented community.

3 Beds ⋅ 2 Baths

Priced with opportunity in mind, this Hillsmere ranch offers a home with good bones and a flexible layout, presenting an excellent chance for buyers to build equity and make it their own. Set on a level .29-acre lot with a long driveway accommodating 4+ cars, the home features true one-level living with the added benefit of a lower level. The main level includes two bedrooms and a full bath, while the lower level offers a large recreation room, third bedroom, second full bath, laundry area, and utility/storage room—ideal for guests, a home office, or additional living space. With thoughtful updates over time, this home can compete favorably with higher-priced, renovated homes within the neighborhood. Key updates include a new roof (2022), Trane oil furnace, AO Smith electric water heater (2019), and a well water treatment system. A one-year home warranty is offered to buyers for added peace of mind. Located in the desirable Hillsmere community, residents enjoy access to a private marina and boat ramp with direct access to the South River, canoe and kayak storage, a sandy beach and swim area, waterfront playgrounds with pavilions and grills, and the option for membership to the community pool. Enjoy the feeling of “getting away from it all” while remaining just minutes from Historic Annapolis (within 3 miles), walking distance to Quiet Waters Park, the library, shopping and restaurants, and convenient access to DC, Baltimore, and BWI. An appealing opportunity to enter Hillsmere at a price point that reflects the work needed, with strong upside in a vibrant, waterfront-oriented community.

117 Pinecrest Dr, Annapolis

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