$2,615,000 Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering. 6 Beds ⋅ 6 Baths Annapolis Stunning Coastal Colonial Waterfront Retreat where every day feels like a vacation. Perfectly positioned on the tranquil waters of the Chesapeake Bay tributaries, this extraordinary waterfront residence at 529 Lee Circle offers an exceptional blend of sophisticated coastal design and effortless indoor-outdoor living. Privately nestled among mature trees, the home enjoys a peaceful setting with panoramic water views, a private pier, a boat house and a floating dock, creating the ultimate Annapolis waterfront retreat. The impressive rear elevation is designed to embrace the waterfront lifestyle, featuring expansive walls of glass that flood the interiors with natural light while framing picturesque water views from nearly every level. Multiple outdoor living spaces—including a spacious waterside deck, an upper-level balcony, and an expansive lawn leading to the 114 feet shoreline—provide the perfect backdrop for entertaining or relaxing while enjoying spectacular sunsets. The boat house with lift, private pier, and protected water dockage offer immediate access to boating, paddleboarding, kayaking, and all the Chesapeake Bay has to offer. Whether departing for a day on the water or enjoying quiet evenings along the shoreline, this property delivers an unmatched waterfront experience. Architecturally, the home combines classic coastal elegance with contemporary comfort. Soft gray siding, crisp white trim, multiple gables, and oversized windows create a timeless façade that complements its natural surroundings. The residence offers approximately 6,000 square feet of living space with two owners suite (one on the main level), generous entertaining areas, multiple fireplaces, and luxurious accommodations designed for both everyday living and grand-scale gatherings. The home was originally built in 1965. In 2016 it went through a complete, down-to-the-studs renovation and expansion to the creation of stunning luxurious waterfront home. Custom-Built by Architect Teresa Todd and Timberlake Homes into a 6-bedroom and 5.5-bathroom residence. Located within the sought-after Hillsmere Shores community, residents enjoy a coveted Annapolis lifestyle with access to a private beach, marina, community pool, playgrounds, and convenient proximity to Historic Downtown Annapolis, waterfront dining, yacht clubs, and the U.S. Naval Academy. This is more than a waterfront home—it is a private Chesapeake Bay sanctuary where luxury, recreation, and timeless coastal beauty come together in one exceptional offering. 529 Lee Cir, Annapolis Listing courtesy of Coldwell Banker Realty. Contact: Selling Office: Compass.
$1,450,000 Sunsets, Water Views & Effortless Coastal Living in Hillsmere Perfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathtaking water views of Lake Hillsmere in the foreground and the South River beyond—without the expense of waterfront taxes. Designed to embrace its spectacular setting, the home is oriented to the west, delivering unforgettable sunsets from two expansive waterfront-facing decks and covered balconies. Set on a generously sized lot with ample setbacks, the property provides privacy, space, and a rare sense of tranquility. Best of all, the home is outside the floodplain, so flood insurance is not required, and an elevation certificate is available. Inside, over three finished levels, you'll find thoughtfully updated living spaces featuring hardwood floors, 9-foot ceilings, abundant natural light, and multiple indoor and outdoor areas designed for gathering and entertaining. The beautifully updated kitchen features granite countertops, stainless steel appliances, island seating, a pantry with built-in shelving, and sliding doors that open to the deck and water views beyond. The main-level primary suite is a true retreat, complete with private deck access, a custom walk-in closet by California Closets, and a renovated spa-inspired bath with a soaking tub, double vanity, and glass-enclosed shower. Additional bedrooms and flexible living spaces provide endless options for guests, recreation, a home office, or multigenerational living. The lower level offers a welcoming mudroom entry, family room with fireplace and wood stove insert, full bath, dedicated office or optional sixth bedroom, laundry room, and abundant storage. Outdoor living is equally impressive, featuring IPE decking, a rear deck, three-season room overlooking the backyard, kayak and paddleboard racks, two sheds, and a private driveway leading to the oversized two-car garage with additional storage. Meticulously maintained and exceptionally efficient, the home includes newer HVAC systems, a whole-house Generac generator, Cat 8 Ethernet throughout, closed-cell spray foam insulation, LED lighting, energy-efficient windows, and remarkably low utility costs for its size. Just three blocks away, enjoy the community beach for swimming, relaxing, or launching kayaks and paddleboards. Residents of Hillsmere enjoy an unparalleled waterfront lifestyle with a private marina, boat ramps, community pool, parks, playgrounds, waterfront pavilions, and direct access to the 340-acre Quiet Waters Park. This is a rare opportunity to enjoy panoramic water views, extraordinary sunsets, and an exceptional lifestyle—without waterfront taxes or flood insurance requirements. 5 Beds ⋅ 4 Baths Sunsets, Water Views & Effortless Coastal Living in Hillsmere Perfectly positioned on one of the quietest streets in Hillsmere, this exceptional residence offers breathtaking water views of Lake Hillsmere in the foreground and the South River beyond—without the expense of waterfront taxes. Designed to embrace its spectacular setting, the home is oriented to the west, delivering unforgettable sunsets from two expansive waterfront-facing decks and covered balconies. Set on a generously sized lot with ample setbacks, the property provides privacy, space, and a rare sense of tranquility. Best of all, the home is outside the floodplain, so flood insurance is not required, and an elevation certificate is available. Inside, over three finished levels, you'll find thoughtfully updated living spaces featuring hardwood floors, 9-foot ceilings, abundant natural light, and multiple indoor and outdoor areas designed for gathering and entertaining. The beautifully updated kitchen features granite countertops, stainless steel appliances, island seating, a pantry with built-in shelving, and sliding doors that open to the deck and water views beyond. The main-level primary suite is a true retreat, complete with private deck access, a custom walk-in closet by California Closets, and a renovated spa-inspired bath with a soaking tub, double vanity, and glass-enclosed shower. Additional bedrooms and flexible living spaces provide endless options for guests, recreation, a home office, or multigenerational living. The lower level offers a welcoming mudroom entry, family room with fireplace and wood stove insert, full bath, dedicated office or optional sixth bedroom, laundry room, and abundant storage. Outdoor living is equally impressive, featuring IPE decking, a rear deck, three-season room overlooking the backyard, kayak and paddleboard racks, two sheds, and a private driveway leading to the oversized two-car garage with additional storage. Meticulously maintained and exceptionally efficient, the home includes newer HVAC systems, a whole-house Generac generator, Cat 8 Ethernet throughout, closed-cell spray foam insulation, LED lighting, energy-efficient windows, and remarkably low utility costs for its size. Just three blocks away, enjoy the community beach for swimming, relaxing, or launching kayaks and paddleboards. Residents of Hillsmere enjoy an unparalleled waterfront lifestyle with a private marina, boat ramps, community pool, parks, playgrounds, waterfront pavilions, and direct access to the 340-acre Quiet Waters Park. This is a rare opportunity to enjoy panoramic water views, extraordinary sunsets, and an exceptional lifestyle—without waterfront taxes or flood insurance requirements. 621 Harbor Dr, Annapolis Listing courtesy of Long & Foster Real Estate, Inc.. Contact: Selling Office: TTR Sotheby's International Realty.
$1,030,000 Welcome to 122 E Bay View Drive in sought-after Hillsmere—where lifestyle and comfort come together just minutes from downtown Annapolis. Ideally located just steps from the community marina, this home also offers water peeks, bringing a touch of the Chesapeake Bay into your everyday living. This well-maintained home features generous living spaces, highlighted by hardwood floors and a thoughtfully updated kitchen designed for both everyday living and entertaining. The spacious room sizes provide flexibility for modern lifestyles, while the inviting wood stove adds warmth and character. Upstairs, the primary suite includes a private full bath, creating a comfortable retreat at the end of the day. Outside, enjoy your own backyard oasis with a fully fenced yard and an in-ground pool—perfect for summer gatherings, relaxing weekends, and entertaining guests. A two-car garage adds convenience and additional storage. Community amenities include beaches, boat ramps, marinas, community pool and playgrounds. Residents also enjoy close proximity to Quiet Waters Park, local dining, and all that historic Annapolis has to offer. This is a rare opportunity to enjoy space, location, and a vibrant waterfront lifestyle in one of Annapolis’ most desirable neighborhoods. Updates: Roof (2008), Heat pump (2020), Windows (2018), Appliances (2018) 3 Beds ⋅ 3 Baths Welcome to 122 E Bay View Drive in sought-after Hillsmere—where lifestyle and comfort come together just minutes from downtown Annapolis. Ideally located just steps from the community marina, this home also offers water peeks, bringing a touch of the Chesapeake Bay into your everyday living. This well-maintained home features generous living spaces, highlighted by hardwood floors and a thoughtfully updated kitchen designed for both everyday living and entertaining. The spacious room sizes provide flexibility for modern lifestyles, while the inviting wood stove adds warmth and character. Upstairs, the primary suite includes a private full bath, creating a comfortable retreat at the end of the day. Outside, enjoy your own backyard oasis with a fully fenced yard and an in-ground pool—perfect for summer gatherings, relaxing weekends, and entertaining guests. A two-car garage adds convenience and additional storage. Community amenities include beaches, boat ramps, marinas, community pool and playgrounds. Residents also enjoy close proximity to Quiet Waters Park, local dining, and all that historic Annapolis has to offer. This is a rare opportunity to enjoy space, location, and a vibrant waterfront lifestyle in one of Annapolis’ most desirable neighborhoods. Updates: Roof (2008), Heat pump (2020), Windows (2018), Appliances (2018) 122 E Bay View Dr, Annapolis Listing courtesy of EXP Realty, LLC. Contact: Selling Office: Fathom Realty MD, LLC.
$885,000 Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility, and everyday comfort. The bright, open main level is designed for gathering, featuring a beautifully updated white kitchen with quartz countertops, stainless appliances, custom backsplash, generous workspace, and seamless flow into a dining and seating area accented by shiplap details and French doors opening to an expansive entertaining deck overlooking the oversized, fully fenced backyard. The spacious primary suite includes a sitting area, custom California Closets walk-in, and a bathroom with 4' vanity, an extra large Smart Mirror/Medicine Cabinet and marble shower. The walkout lower level offers exceptional flexibility with a large room currently enjoyed as a family room but could easily serve as a fourth bedroom, complete with fireplace, closet, full egress, and direct access to a private covered deck with hot tub. Two additional bedrooms, both with California Closet systems, a beautifully renovated full bath with double vanity, extended tub and an updated laundry room complete this level. A bonus feature of this house is the separate, flex space adjacent to the garage with its own beautifully renovated powder room, mini-split HVAC, large deck, with endless possibilities as a home office, fitness studio, media room, teen hangout, creative workspace, or guest overflow. Outside, the oversized fenced-in back yard provides rare privacy and room to play, entertain, or garden, complemented by multiple outdoor living areas and a detached shed/workshop with power and air conditioning. The large two car garage features Flow Wall storage system, epoxy floor coating, and an EV charging plug as well as direct access to the rear yard. Extensive renovations throughout include the kitchen, baths, roof, siding, windows, HVAC, flooring, lighting, garage, landscaping, and countless custom details, creating a truly move-in-ready home. Enjoy one of Annapolis' most beloved waterfront communities with a voluntary HOA, private beach on the South River, marina, community pool, playgrounds, and year-round neighborhood events—all just minutes from Downtown Annapolis. 3 Beds ⋅ 3 Baths Experience the best of the Annapolis maritime lifestyle in this beautifully renovated coastal-inspired home, ideally located in the sought-after Hillsmere Shores community one block from the marina, private beach, waterfront playground/parks, community pool, and boat ramp. Thoughtfully redesigned with high-end finishes throughout, this turnkey home offers the perfect blend of style, flexibility, and everyday comfort. The bright, open main level is designed for gathering, featuring a beautifully updated white kitchen with quartz countertops, stainless appliances, custom backsplash, generous workspace, and seamless flow into a dining and seating area accented by shiplap details and French doors opening to an expansive entertaining deck overlooking the oversized, fully fenced backyard. The spacious primary suite includes a sitting area, custom California Closets walk-in, and a bathroom with 4' vanity, an extra large Smart Mirror/Medicine Cabinet and marble shower. The walkout lower level offers exceptional flexibility with a large room currently enjoyed as a family room but could easily serve as a fourth bedroom, complete with fireplace, closet, full egress, and direct access to a private covered deck with hot tub. Two additional bedrooms, both with California Closet systems, a beautifully renovated full bath with double vanity, extended tub and an updated laundry room complete this level. A bonus feature of this house is the separate, flex space adjacent to the garage with its own beautifully renovated powder room, mini-split HVAC, large deck, with endless possibilities as a home office, fitness studio, media room, teen hangout, creative workspace, or guest overflow. Outside, the oversized fenced-in back yard provides rare privacy and room to play, entertain, or garden, complemented by multiple outdoor living areas and a detached shed/workshop with power and air conditioning. The large two car garage features Flow Wall storage system, epoxy floor coating, and an EV charging plug as well as direct access to the rear yard. Extensive renovations throughout include the kitchen, baths, roof, siding, windows, HVAC, flooring, lighting, garage, landscaping, and countless custom details, creating a truly move-in-ready home. Enjoy one of Annapolis' most beloved waterfront communities with a voluntary HOA, private beach on the South River, marina, community pool, playgrounds, and year-round neighborhood events—all just minutes from Downtown Annapolis. 117 Sunset Dr, Annapolis Listing courtesy of Coldwell Banker Realty. Contact: Selling Office: Douglas Realty LLC.
$689,900 An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh paint throughout, new carpet, new fixtures, new appliances more. Home features two bedrooms upstairs to include a primary with his and hers walk in closets and a spa like primary bath. The second floor boasts two additional bedrooms. One being a second primary with an en suite and fireplace. The home includes a large deck outback and completely fenced back yard. This property is available for immediate occupancy. Come check it out. Seller will provide home warranty with full price offer. 4 Beds ⋅ 4 Baths An absolute must see! Stunning 4 bed 3 1/2 bath updated home in sought after Hillsmere Shores. This home just had cosmetic upgrades including but not limited to fresh paint throughout, new carpet, new fixtures, new appliances more. Home features two bedrooms upstairs to include a primary with his and hers walk in closets and a spa like primary bath. The second floor boasts two additional bedrooms. One being a second primary with an en suite and fireplace. The home includes a large deck outback and completely fenced back yard. This property is available for immediate occupancy. Come check it out. Seller will provide home warranty with full price offer. 110 Kuethe Dr, Annapolis Listing courtesy of JAK Real Estate. Contact: Selling Office: Park Modern Realty.
$625,000 Open House on 5/31/26 has been cancelled. Multiple offers received. Charming two-bedroom rancher with all the right updates! Remodeled kitchen (2020) features a pantry and opens to comfortable living spaces with LVP flooring throughout. Fireplace included. Bedrooms are nicely sized with generous closet storage. A light-filled breezeway connecting the one-car garage to the home and rear deck round out this move-in ready gem. Nestled on .41 acres, there's plenty of room to breathe and enjoy the outdoors. And the best is yet to come — an unfinished basement offers an additional 1,200 sq ft of potential, ready to be transformed into the space you've always wanted. All this plus the incredible Hillsmere community amenities just a short walk away — pool, marina, beach, and kayak and small boat storage. Easy, comfortable living with room to grow! 2 Beds ⋅ 1 Baths Open House on 5/31/26 has been cancelled. Multiple offers received. Charming two-bedroom rancher with all the right updates! Remodeled kitchen (2020) features a pantry and opens to comfortable living spaces with LVP flooring throughout. Fireplace included. Bedrooms are nicely sized with generous closet storage. A light-filled breezeway connecting the one-car garage to the home and rear deck round out this move-in ready gem. Nestled on .41 acres, there's plenty of room to breathe and enjoy the outdoors. And the best is yet to come — an unfinished basement offers an additional 1,200 sq ft of potential, ready to be transformed into the space you've always wanted. All this plus the incredible Hillsmere community amenities just a short walk away — pool, marina, beach, and kayak and small boat storage. Easy, comfortable living with room to grow! 105 Mansion Dr, Annapolis Listing courtesy of EXP Realty, LLC. Contact: Selling Office: Anne Arundel Properties, Inc..
$585,000 OPEN SATURDAY, 6/6, 10AM-12PM and SUNDAY, 6/7, 12-2PM Nestled in one of Annapolis's most beloved water-oriented communities, this 4-bedroom, 2 full bath home offers the space, updates, and lifestyle you've been waiting for. The spacious kitchen is perfect for entertaining with a passthrough window to make serving an ease. Unwind on the screened porch or take full advantage of the large fenced yard — perfect for garden parties or simply enjoying the outdoors. The finished basement offers a large family room with a cozy fireplace, full bath and 4th bedroom. Hillsmere Shores amenities include a private deep-water marina with direct access to the South River, sandy beaches, designated swim area, playgrounds, community pool, boat ramps, and waterfront pavilions. The neighborhood sits between Duvall Creek and Quiet Waters Park — 340 acres of trails, open space, and South River waterfront right outside your door. Downtown Annapolis, City Dock, and the Naval Academy are just minutes away. Roof (2024). Make your appointment today to view this wonderful home! 4 Beds ⋅ 2 Baths OPEN SATURDAY, 6/6, 10AM-12PM and SUNDAY, 6/7, 12-2PM Nestled in one of Annapolis's most beloved water-oriented communities, this 4-bedroom, 2 full bath home offers the space, updates, and lifestyle you've been waiting for. The spacious kitchen is perfect for entertaining with a passthrough window to make serving an ease. Unwind on the screened porch or take full advantage of the large fenced yard — perfect for garden parties or simply enjoying the outdoors. The finished basement offers a large family room with a cozy fireplace, full bath and 4th bedroom. Hillsmere Shores amenities include a private deep-water marina with direct access to the South River, sandy beaches, designated swim area, playgrounds, community pool, boat ramps, and waterfront pavilions. The neighborhood sits between Duvall Creek and Quiet Waters Park — 340 acres of trails, open space, and South River waterfront right outside your door. Downtown Annapolis, City Dock, and the Naval Academy are just minutes away. Roof (2024). Make your appointment today to view this wonderful home! 129 Meade Dr, Annapolis Listing courtesy of EXP Realty, LLC. Contact: Selling Office: EXP Realty, LLC.
$531,000 **OFFER DEADLINE MONDAY 8/10 @ 12 NOON** Welcome to 282 Cedar Lane, a beautifully updated rancher nestled in one of Annapolis' most sought-after waterfront communities. This move-in ready home blends timeless charm with thoughtful updates, beginning with a stunning magazine-worthy kitchen featuring nautical navy cabinetry, warm butcher block countertops, and stainless steel appliances—a space that's both stylish and functional. Beautiful oak hardwood floors flow throughout the main level, where you'll find three comfortable bedrooms and a full hall bath. The finished lower level provides additional living space perfect for a family room, home office, gym, or playroom and includes a half bath, the laundry room and additional unfinished storage space. Major updates provide peace of mind, including a new roof (2017) and hot water heater (2019). Life in Hillsmere Shores is about so much more than the home itself. This beloved waterfront community offers a private marina with direct access to the South River, a community pool, sandy beach, waterfront pavilions, and multiple playgrounds. Residents also enjoy walking access to Quiet Waters Park, Hillsmere Elementary School, the Eastport-Annapolis Library, PAL Park, and Bay Ridge Plaza shopping and dining. Just 3 miles from Historic Downtown Annapolis, Hillsmere Shores combines the charm of an established neighborhood with the convenience of nearby restaurants, boutiques, marinas, and waterfront attractions. PLEASE NOTE: Hillsmere is part of a Special Community Benefit District with the annual fee built into the annual property tax bill. 3 Beds ⋅ 2 Baths **OFFER DEADLINE MONDAY 8/10 @ 12 NOON** Welcome to 282 Cedar Lane, a beautifully updated rancher nestled in one of Annapolis' most sought-after waterfront communities. This move-in ready home blends timeless charm with thoughtful updates, beginning with a stunning magazine-worthy kitchen featuring nautical navy cabinetry, warm butcher block countertops, and stainless steel appliances—a space that's both stylish and functional. Beautiful oak hardwood floors flow throughout the main level, where you'll find three comfortable bedrooms and a full hall bath. The finished lower level provides additional living space perfect for a family room, home office, gym, or playroom and includes a half bath, the laundry room and additional unfinished storage space. Major updates provide peace of mind, including a new roof (2017) and hot water heater (2019). Life in Hillsmere Shores is about so much more than the home itself. This beloved waterfront community offers a private marina with direct access to the South River, a community pool, sandy beach, waterfront pavilions, and multiple playgrounds. Residents also enjoy walking access to Quiet Waters Park, Hillsmere Elementary School, the Eastport-Annapolis Library, PAL Park, and Bay Ridge Plaza shopping and dining. Just 3 miles from Historic Downtown Annapolis, Hillsmere Shores combines the charm of an established neighborhood with the convenience of nearby restaurants, boutiques, marinas, and waterfront attractions. PLEASE NOTE: Hillsmere is part of a Special Community Benefit District with the annual fee built into the annual property tax bill. 282 Cedar Ln, Annapolis Listing courtesy of RE/MAX Leading Edge. Contact: Selling Office: Paul Wesley Real Estate.
$420,000 Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities. 3 Beds ⋅ 2 Baths Nestled in the highly sought-after Hillsmere community—one of Annapolis' premier waterfront neighborhoods—this charming home offers access to an exceptional array of amenities, including a private beach, boat ramp, community pool, playground, and more. This 3-bedroom, 1.5-bath residence features a full, partially finished basement, a spacious screened porch perfect for relaxing or entertaining, ample off-street parking, and a beautifully landscaped, fenced yard with mature trees and plantings. Enjoy the best of coastal living in one of the area's most desirable communities. 406 Holly Dr, Annapolis Listing courtesy of RE/MAX Executive. Contact: Selling Office: Coldwell Banker Realty.