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1701 Delage Ln, Annapolis
$520,000
4 Beds ⋅ 2 Baths
1701 Delage Lane presents an exceptional opportunity for investors, contractors, or buyers ready to renovate and build instant equity. This large four-bedroom home with one and a half baths is full of potential, making it ideal for those with vision and creativity seeking to transform a property into something truly special. Situated on a generously sized lot in an established neighborhood, the home offers a solid foundation for a complete renovation or reimagining. Whether you're looking to customize your next residence or take on your next investment project, the possibilities here are abundant. Enjoy a prime location just minutes from historic downtown Annapolis, the United States Naval Academy, area marinas, waterfront attractions, shopping, and dining. Commuters will appreciate convenient access to major routes connecting to Baltimore, Washington, D.C., and Fort Meade. Bring your contractor and imagination—this is a rare chance to create value in one of Annapolis’s most desirable locations. Property is being sold strictly as-is.

1701 Delage Ln, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: New Western.

809 Midship Ct, Annapolis
$515,500
2 Beds ⋅ 2 Baths
Welcome to one of the most sought-after homes in Heritage Harbour! This beautifully maintained all-brick end-unit villa offers 2 bedrooms, 2 full bathrooms, and a 1-car garage—combining comfort, quality, and low-maintenance living. Inside, you’ll find gleaming hardwood floors, a spacious layout, and a well-appointed kitchen featuring stainless steel appliances. Enjoy the efficiency of gas heat and gas hot water, adding to the home’s overall value and convenience. End-unit villas like this are highly desirable for their added privacy, natural light, and classic brick construction—making them some of the most coveted homes in the community. For those new to Heritage Harbour, you’re in for a treat. This premier 55+ community offers an unmatched lifestyle with amenities that truly set it apart—golf course, tennis courts, indoor pickleball courts, both indoor and outdoor pools, hot tub, sauna, and a fully equipped fitness center with all new equipment. There’s even a woodworking shop for hobbyists and the popular Wilder Fresh Kitchen restaurant right within the community. Quite simply, no other 55+ community in the area compares to what Heritage Harbour has to offer. Don’t miss this incredible opportunity—homes like this do not last long!

809 Midship Ct, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: Douglas Realty LLC.

784 Fairviw Av Unit E, Annapolis
$515,000
2 Beds ⋅ 1 Baths
Rare Opportunity in Eastport's Desirable Severn House Community! Experience breathtaking, unobstructed views of Back Creek from this exceptional 2-bedroom, 1-bath condo, complete with a 30-foot boat slip included in the sale! Perfectly positioned to capture sweeping water views, this one-of-a-kind residence offers an incredible opportunity to enjoy the best of Annapolis living. Inside, you'll find beautiful white oak hardwood floors throughout, an updated kitchen, and an inviting open-concept living and dining area designed to maximize the stunning views. Both spacious bedrooms feature generous walk-in closets with custom built-in shelving, offering exceptional storage. Step outside onto your expansive private deck, perfect for relaxing, entertaining, or watching the boats cruise along Back Creek. Enjoy direct views of your very own 30-foot boat slip, conveniently located at Dock B, Slip B-1. Residents of Severn House enjoy an impressive collection of amenities, including an outdoor swimming pool, private marina, scenic promenade, kayak and paddleboard launch and storage, community pavilion, picnic areas, and beautifully maintained grounds. Nestled in the heart of Eastport, just minutes from downtown Annapolis, this exceptional condo combines effortless coastal living, boating convenience, and an unbeatable location. With its extraordinary views, boat slip, and coveted setting, this is a truly rare opportunity you won't want to miss!

784 Fairviw Av Unit E, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Unrepresented.

19 Dorset Ct, Annapolis
$515,000
2 Beds ⋅ 3 Baths
Welcome to 19 Dorset Court. This is a rare opportunity to own an updated, end unit with the primary suite on the main level. This home offers the perfect blend of privacy, convenience, amenities and low maintenance living at a price that is hard to find in Annapolis. Tucked away at the back of the cul de sac this home is surrounded by open green space and woods. The thoughtfully designed floor plan features everything you need on one floor plus a full, finished basement! The main level has hardwood floors, vaulted ceilings, and a cozy gas fireplace. The large, updated kitchen features a comfortable design with a sunny eating nook, loads of cabinetry & stainless appliances. The primary suite is extra large with high ceilings and a tastefully updated bathroom with a walk-in shower. Double doors from the living room can be opened to the second bedroom which could also be used as a sitting room, office or den. Step outside the french doors to a spacious, low maintenance deck - perfect for entertaining or simply relaxing and enjoying the wooded views. The finished lower level offers flexible living space dependent on your needs and lifestyle. In addition to a large recreation/family room it offers another full bath, a second finished room to use as you please, plus lots of storage. Hunt Meadow offers outstanding amenities includinag a community pool with a swim team, tennis and pickleball courts, a basketball court and wooded, walking trails. Residents also enjoy pedestrian access to Quiet Waters Park . Historic downtown Annapolis and Eastport are less than 3 miles away and offer exceptional dining, shopping, waterfront attractions and entertainment. It is rare to find a home that combines this much natural beauty, amenities and unbeatable convenience at this price point in Annapolis. Don't miss your chance to make this exceptional property your next home! Hunt Meadow has an active homeowner's association and is professionally managed.

19 Dorset Ct, Annapolis

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

Selling Office: Academy Realty Inc..

2802 Mockingbird Ct, Annapolis
$515,000
2 Beds ⋅ 3 Baths
What if touring a home could help an animal find one, too? Welcome to 2802 Mockingbird Court, where purchasing a home does more than begin your next chapter. The proceeds from this sale will help provide food, medical care, and shelter for animals at the SPCA as they wait for their forever homes. Completely renovated from top to bottom, this turnkey home features a stunning new kitchen, beautifully updated bathrooms, new flooring, fresh paint, a new HVAC system, and a finished basement offering flexible space for a recreation room, home office, gym, or guest suite. Step outside onto the spacious deck overlooking the woods, the perfect place to enjoy your morning coffee before an early paddle on Gingerville Creek, host friends for a summer cookout, or unwind at the end of the day surrounded by the sights and sounds of nature. Located in the highly sought after, water oriented community of Riva Trace, residents enjoy exceptional amenities including a community pier, kayak and paddleboard launch, extensive kayak storage racks, tennis and pickleball courts, basketball court, playground, gazebo, scenic walking trails, and beautifully maintained park like open spaces that make it easy to enjoy the outdoors and connect with neighbors. Just minutes from Riva Festival, Annapolis Town Center, the Annapolis Farmers Market, the Arundel Olympic Swim Center, Historic Downtown Annapolis, and major commuter routes including Route 50, I-97, and the nearby Park & Ride, this home offers the perfect combination of modern updates, an active outdoor lifestyle, and an unbeatable location. Find your forever home while helping homeless animals find theirs!

2802 Mockingbird Ct, Annapolis

Listing courtesy of EXP Realty, LLC. Contact:

Selling Office: Long & Foster Real Estate, Inc..

7024 Channel Village Ct Unit T2, Annapolis
$515,000
2 Beds ⋅ 2 Baths
Waterfront luxury meets resort-style living! Nestled in the gated community of The Village of Chesapeake Harbour, this stunning 2BR/2BA ground-floor condo offers views of the marina and open water. Welcome inside to an open-concept layout featuring gorgeous wood-look porcelain tile, custom electric shades, crown molding, and a cozy fireplace. The kitchen shines with an antiqued glass tile backsplash, pantry, and newer SS appliances. Relax in the primary suite boasting an en-suite bath with a granite double vanity, custom walk-in closet, and direct patio access. Step out onto the oversized patio—larger than most in the community—perfect for soaking in the views. Major updates include a brand-new HVAC & air purifier (2025), fresh paint (2022), and upgraded closets. Enjoy community amenities: private beach, 2 pools, tennis courts, kayak launch, walking trails, on-site dining, and an 81-slip marina. Minutes to Historic Annapolis with easy commutes to Baltimore & D.C.! Ask about the assumable VA loan!

7024 Channel Village Ct Unit T2, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Long & Foster Real Estate, Inc..

2178 Glenfield Rd, Annapolis
$515,000
4 Beds ⋅ 3 Baths
Welcome to Rolling Knolls! This spacious single-family home offers an attached two-car garage and a desirable floor plan with a substantial addition, providing plenty of room for everyday living and entertaining. Featuring 4 bedrooms and 3 full bathrooms, the home offers flexible living spaces to accommodate a variety of needs. The generous addition expands the home's footprint and creates endless possibilities for customization. While the property could benefit from some cosmetic updating, it presents an excellent opportunity to add your personal touches and build equity in a sought-after neighborhood. Conveniently located near shopping, dining, commuter routes, and local amenities, this home is ready for its next chapter.

2178 Glenfield Rd, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: United Real Estate Premier.

1052 Lido Dr, Annapolis
$515,000
4 Beds ⋅ 2 Baths
Welcome to 1052 Lido Drive! This charming 4-bedroom, 1.5-bath home offers comfortable living spaces filled with natural light and a layout designed for everyday living and entertaining alike. The main level features an open-concept living and dining area, where large windows create a bright and inviting atmosphere throughout the space. Just beyond, the kitchen continues the airy feel with ample cabinet storage, sleek stainless steel appliances, and easy access to the rear deck through sliding glass doors — perfect for indoor-outdoor entertaining or relaxing evenings outdoors. On the main level, you will find three bedrooms down the hall. The primary bedroom offers a spacious retreat with an attached half bath for added privacy and convenience. Two additional bedrooms provide plenty of flexibility for family, guests, or a home office setup. A full hall bath serves the floor with ease. The lower level offers a large family room centered around a cozy fireplace, creating the perfect gathering space for movie nights or relaxing weekends at home. Sliding glass doors provide direct access to the backyard, bringing in additional natural light and extending the living space outdoors. The fourth bedroom is tucked just off the family room, offering a private area ideal for guests, extended family, or a flexible workspace to fit your needs. Conveniently located in the desirable Cape St. Claire area of Annapolis, this home offers easy access to a variety of local amenities and waterfront attractions. Enjoy nearby outdoor recreation at Sandy Point State Park, featuring beaches, picnic areas, fishing, and scenic views of the Chesapeake Bay. Downtown Annapolis is just a short drive away, offering waterfront restaurants, boutique shopping, historic charm, and attractions like the United States Naval Academy and City Dock. Commuters will appreciate quick access to Route 50 for travel to both Baltimore and Washington. With bright living spaces, a versatile layout, and inviting indoor and outdoor areas, 1052 Lido Drive is ready to welcome you home.

1052 Lido Dr, Annapolis

Listing courtesy of Keller Williams Realty Centre. Contact:

Selling Office: Realty Navigator.

588 Wild Flower Glade, Annapolis
$515,000
4 Beds ⋅ 4 Baths
$10,000 seller credit toward renovations or closing costs! ** Being Sold AS-IS** WATER-privileged Woods Landing! Spacious 4BR, 3.5BA townhouse with serene wooded views, soaring ceilings, and abundant natural light. Open living/dining areas, eat-in kitchen with breakfast bar, plus main-level powder room. Upper-level primary suite features vaulted ceilings, en-suite bath, and private deck access on every level. Finished lower level offers family room, 4th bedroom, full bath, and walk-out patio. Roof & skylight replaced (2024), primary bath shower & toilet updated (2022), and Cat6/Cat8 wiring (2022). Community amenities include waterfront pier, kayak/canoe launch, tennis courts, dog park, and more—minutes to Downtown Annapolis, Eastport, and major commuter routes.

588 Wild Flower Glade, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: RE/MAX Advantage Realty.

113 Legion Ave, Annapolis
$515,000
6 Beds ⋅ 3 Baths
Tucked just off West Street in Annapolis, this well-maintained split foyer blends space and flexibility. Freshly painted with new flooring throughout, the home offers a bright, refreshed feel from the moment you step inside. With 6 bedrooms and 3 full baths—3 bedrooms on each level—the layout is ideal for multi-generational living, guests, or work-from-home needs. The main level bath was renovated in 2023 with age-in-place design, while the primary bath was updated in 2018. The stainless steel refrigerator with ice maker was installed in 2023 as was the gas stove. Enjoy everyday comfort with ceiling fans in many rooms and relax or entertain in the enclosed rear porch or on the back deck. Basement features a French drain waterproofing system, providing added protection and peace of mind. A carport, paved driveway, and off-street parking add convenience, while the location puts you close to everything Annapolis has to offer—shopping, schools, and the library just minutes away. Although many upgrades have been completed, property is selling As Is and is an ideal opportunity to design and personalize your dream home. Make 113 Legion Ave. your Home Sweet Home.

113 Legion Ave, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Compass.

530 Samuel Chase Way, Annapolis
$512,000
3 Beds ⋅ 4 Baths
Welcome home to 530 Samuel Chase Way — a fantastic end-unit townhome in the heart of Tidewater Colony! This home was designed for today's lifestyle, the flexible entry level features a private bedroom, full bath, and family room with wet bar— both rooms ideal for hosting guests, creating a dedicated home office, or enjoying additional living and recreation space. Upstairs, the open-concept main level is equally suited for everyday living and entertaining, showcasing a kitchen with quartz countertops, stainless steel appliances, and abundant natural light. The adjoining dining area and spacious living room create an inviting gathering space, while the large deck extends the living area outdoors for dining, relaxing, or entertaining. Oversized windows on three sides fill this level with natural light and creates an airy, welcoming feeling throughout. The upper level offers two generously sized bedrooms, including a private owner's suite, an additional full bath, and conveniently located laundry. Perfectly positioned just outside Annapolis city limits with direct access to US-50, you're minutes from Downtown Annapolis, the waterfront, Annapolis Mall, and Parole Town Center. Community amenities include walking trails, tennis courts, an outdoor pool, fitness center, clubhouse, and playgrounds. Seller is purchasing a buyer home warranty through CINCH Home Services. Schedule your tour today and come experience living in Tidewater Colony!

530 Samuel Chase Way, Annapolis

Listing courtesy of Jason Mitchell Group. Contact:

Selling Office: Douglas Realty LLC.

2023 Compton Ct, Annapolis
$510,000
3 Beds ⋅ 4 Baths
Tucked into the sought-after Windgate community, this end-unit townhome has it all—just minutes from downtown Annapolis, premier shopping and dining, and major commuter routes, just steps from the community playground and walking trails. With over 2,000 finished square feet across three thoughtfully designed levels, this home has been extensively updated with custom details that set it apart. The main level welcomes you with rich Brazilian cherry hardwood flooring, fresh designer neutral paint, and an abundance of natural light offering a bright, open layout designed for both everyday living and entertaining. The kitchen features newly installed tile flooring, newer appliances, and seamless flow to the surrounding living spaces. Throughout the home, custom built-ins offer both function and character, while sleek glass railings add a modern architectural touch. Upstairs, three generous bedrooms and two bathrooms provide comfortable accommodations, including a private primary suite complete with private ensuite bathroom, walk in closet, vaulted ceilings and bonus storage. The fully finished walk-out lower level expands your living space with luxury vinyl plank flooring, a stunning stone fireplace, built in shelving, an additional full bath, and private exterior access—ideal for guests, a home office, or recreation. Outside, extensive hardscaping creates inviting outdoor spaces with minimal maintenance, extending your living area beyond the home's walls. The end unit offers additional greenspace for entertaining or play, and the4 deck overlooks the community playground. New roof in 2022, Hot Water Heater 2025, HVAC 2017 Schedule your private tour today!

2023 Compton Ct, Annapolis

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

Selling Office: Coldwell Banker Realty.

21 Chelsea Ct, Annapolis
$510,000
3 Beds ⋅ 3 Baths
Tucked away on a quiet cul-de-sac in the sought-after Hunt Meadow community, this stylish 3-bedroom, 2.5-bath contemporary townhome offers warmth and versatility throughout. The main level features a spacious living room with a cozy fireplace, a separate dining room, and a convenient half bath—perfect for everyday living and entertaining. The kitchen is equipped with stainless steel appliances, a center island, and ample storage, and opens to a deck overlooking a private patio with a shed for added storage. Vaulted ceilings and sun-filled spaces enhance the primary suite, while the updated primary bath features a skylight, creating a bright, spa-like retreat. The flexible upper-level loft—converted to a bedroom or home office—adds functionality to fit your lifestyle. A finished lower level with rec room, full bath, and additional storage expands your living space. Enjoy serene views from this cul-de-sac lot backing to open common area. Hunt Meadow in Annapolis, MD, is a wonderful community featuring a neighborhood pool with swim team, separate baby pool, tennis and pickleball courts, basketball court, and picnic pavilion. Residents enjoy extensive walking paths and sidewalks with direct access to the 340-acre Quiet Waters Park, offering scenic, wooded surroundings and exceptional outdoor recreation. Assigned parking and a prime location close to schools, shopping, and commuter routes—all with low HOA fees. Extensive updates and thoughtful improvements throughout add both style and peace of mind, including a new architectural shingle roof (2024) and HVAC system (2022). The renovated kitchen (2019) features updated cabinetry, granite countertops, flooring, and appliances, along with new main-level flooring and carpet. The lower level was extensively renovated in 2021 with new flooring, reconfigured multi-use space, updated storage areas, two sump pumps with battery backup, and improved drainage with a French drain and updated downspouts. Additional improvements include a gas fireplace replacement (2019), custom closet system (2020), deck and exterior updates (2021), exterior painting with replaced clapboards (2025), and freshly painted lower level (2026).

21 Chelsea Ct, Annapolis

Listing courtesy of Redfin Corp. Contact:

Selling Office: Long & Foster Real Estate, Inc..

706 Howards Loop, Annapolis
$500,000
3 Beds ⋅ 4 Baths
Welcome to this beautiful and thoughtfully updated townhome in the sought-after community of Windgate! Offering 3 spacious bedrooms, 2 full and 2 half baths, a 1-car garage, three finished levels, and a desirable bump-out, this home combines comfort, style, and convenience. The remodeled eat-in kitchen features crisp white cabinetry, granite countertops, stainless steel appliances, gas cooking, and a bright breakfast area. The adjoining dining area opens to a large rear deck—perfect for grilling, entertaining, or simply relaxing. Plantation shutters, numerous built-ins, and beautifully upgraded flooring throughout add even more character and appeal, including engineered hardwood, luxury vinyl tile, ceramic tile, and carpet. Upstairs you'll find three generously sized bedrooms, including a spacious primary suite featuring vaulted ceilings and a large walk-in closet. The finished lower level provides even more living space with a large recreation room, half bath, and walk-out access to the patio and fully fenced backyard. This Townhome has been exceptionally well maintained with numerous recent improvements, including a NEW HVAC system, hot water heater, kitchen appliances, and flooring in 2023; NEW garage door and openers in 2025; plus a roof installed in 2019 with 50-year shingles—providing added peace of mind for the next owner. Location is another standout! Enjoy convenient access to Downtown Annapolis, the U.S. Naval Academy, Annapolis Mall, Anne Arundel Medical Center, and an incredible selection of restaurants, shopping, entertainment, and everyday conveniences. Commuters will appreciate the easy access to major routes connecting Annapolis, the Eastern Shore, Washington, D.C., and Baltimore. Beautifully updated, spacious, and ideally located—this wonderful Windgate townhome is ready to welcome its next owner!

706 Howards Loop, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Compass.

8 Spa Creek Lndg Unit 8A2, Annapolis
$500,000
1 Beds ⋅ 2 Baths
Come enjoy the ease of single-level living, secure community, and the unmatched lifestyle of waterfront. The warm and inviting living room opens to sweeping Spa Creek Views, while a dazzling kitchen with a picturesque window makes creating a meal a delight...with a wood-buring fireplace and engineered hardwoods. Step outside through sliding doors to a relaxing deck enjoying the sunsets. Extra storage on the deck and in the basement for all your needs. There are boat slips available, depending on size and water depth. Shearwater is one of Annapolis's most coveted gated communities know for its lush landscaping, amenities, and easy access to downtown. Here, you enjoy the best of both worlds-resort-style living while being minutes away from restaurants, shops, and the charm of Historic Annapolis. Enjoy an abundance of nature, blue herons, osprey, and wild fowl. The Shearwater community offers a private waterfront pool with sun deck, pickleball, regulation racketball court, tennis, kayak and dinghy rack/storage, a deep water marina, walking paths-all within a gated community. Enjoy a nice walk, bike, ride, or the water taxi will pick you up at the marina dock and take you downtown. All the fun activities in Eastport are right at your back yard. The Eastport Yacht Club parade of lights in December makes it's final turn right in front of Shearwater. Rare opportunity to combine waterfront access and the timeless Annapolis Lifestyle.

8 Spa Creek Lndg Unit 8A2, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Coldwell Banker Realty.

1427 Anna Marie Ct, Annapolis
$499,550
4 Beds ⋅ 4 Baths
Beautifully presented home at 1427 Anna Marie Ct in Annapolis, offering a comfortable blend of style, function, and everyday livability. Thoughtfully designed interior spaces create an easy flow for both quiet evenings at home and gathering with friends and family. Enjoy the feeling of coming home to inviting interiors, natural light, and well-planned living areas that support the way you live today. Open floor plan on main level flows to the deck, perfect for a bbq. Upstairs features a spacious primary suite, 2 guest bedrooms and a guest bath. Downstairs has a second living space, 4th bedroom, full bath, laundry room and tons of storage. It also provides access to the fenced yard and a gate to the community wooded area. This is a well maintained community with sidewalks, shade trees and paths for our canine friends. 2 assigned parking spaces plus visitor parking. Set in an Annapolis location with easy access to the area's coastal charm, trails, parks, shopping, dining, and commuter routes, this property offers a wonderful opportunity to enjoy convenience and community in one place. Whether you're relaxing at the end of the day or hosting weekend get-togethers, this home provides a welcoming backdrop for it all. Schedule your showing today and see all that 1427 Anna Marie Ct has to offer.

1427 Anna Marie Ct, Annapolis

Listing courtesy of Compass. Contact:

Selling Office: Coldwell Banker Realty.

2608 Quiet Water Cv Unit 26, Annapolis
$499,000
2 Beds ⋅ 2 Baths
JUST HIT THE MARKET! Don't miss this rare opportunity to own a beautifully maintained one-level, brick villa in the highly sought-after 55+ community of Heritage Harbour! Offering the perfect blend of comfort, convenience, and low-maintenance living, this 2-bedroom, 2-bath home features an attached one-car garage and a peaceful setting surrounded by mature trees. Inside, you'll appreciate the ease of single-level living and the confidence of knowing the home's major systems have already been updated, allowing you to move in and simply enjoy your new lifestyle. Step outside and discover why Heritage Harbour is one of Annapolis' most desirable active adult communities. Residents enjoy an incredible array of amenities including a championship golf course, fitness center, clubhouse, indoor and outdoor pools, tennis and pickleball courts, walking trails, boating opportunities with water access, and a vibrant calendar filled with clubs, classes, social events, concerts, and activities designed to keep you as active and engaged as you choose. Whether you're looking to relax in a tranquil setting, spend your days on the golf course or the water, or connect with friends and neighbors through an unmatched social lifestyle, this home offers it all. Opportunities like this don't come along often—schedule your showing today before this just-listed gem is gone!

2608 Quiet Water Cv Unit 26, Annapolis

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

Selling Office: EXP Realty, LLC.

102 Oak Dr, Annapolis
$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:

Selling Office: Long & Foster Real Estate, Inc..

543 Francis Nicholson Way, Annapolis
$492,500
4 Beds ⋅ 4 Baths
Move in ready Tidewater Colony townhome. Just completely painted throughout, complete new deck, recent carpeting and new architectural roof. This home shows beautifully! Hardwood flooring throughout the main level with updated kitchen. Living room with gas fireplace, newer slider that leads to a spacious deck. Upstairs features three generous size bedrooms, two full baths, lots of closet space and a large primary bathroom, soaking tub and walk in shower. The lower level has a bedroom/family room with full bath. New Maytag washer and dryer on the lower level. Community offers amazing amenities, including pool, tennis, clubhouse, exercise room, playgrounds, walking paths and all very convenient for commuting routes, shopping, dining and downtown Annapolis.

543 Francis Nicholson Way, Annapolis

Listing courtesy of TTR Sotheby's International Realty. Contact:

Selling Office: Real Broker, LLC - Annapolis.

648 Howards Loop, Unit 19, Annapolis
$490,000
3 Beds ⋅ 4 Baths
Welcome to this charming end unit TH near Annapolis! Just a 5 minute drive and you are in downtown Annapolis ! Also 3 minutes to Annapolis Mall and the Annapolis Medical Center and convenient access to Rt 50 ! Enjoy this end unit with a more private outdoor view with greenery. Recently stained deck awaits you for lovely evenings outside enjoying a more wooded view. Make the downstairs area under the deck your private oasis ! Serene master bedroom has vaulted ceilings w/ walk-closet & a master bathroom with skylight to brighten up your mornings. 2 other bedrooms on the same floor with another full bath round out the cozy living quarters . There is a half baths on each of the other 2 levels. Enjoy the bright & cheerful kitchen with granite countertops & opening to a big family room with lots of windows adding a comfortable bright & airy feel along with a separate dining area for ease of mingling. Step out to the outdoors on the freshly painted deck for some grilling or nature. Downstairs -make it another cozy retreat with fireplace for TV viewing, gaming, work, playroom, gym -Make it your own ! -along with a serene private back yard ready for you to put your final touches on. Community playground and dog park are available with walking paths which round out this neighborhood for community socializing ! Updates to include newer roof and paved driveway along with outside trim & stained deck and fencing. Seller also offering 6 months of paid BG&E coverage for systems and appliances. You don't wanna miss this opportunity !

648 Howards Loop, Unit 19, Annapolis

Listing courtesy of Douglas Realty LLC. Contact:

Selling Office: Providence Realty.

213 Georgetown, Annapolis
$485,000
3 Beds ⋅ 3 Baths
Meticulously maintained and move-in ready, this spacious sweet duplex offers an exceptional combination of comfort, charm, and convenience in a highly desirable Annapolis location. Featuring beautiful wood floors, fresh paint throughout, 3 bedrooms, and 2.5 updated baths, this home has been thoughtfully upgraded and lovingly cared for. The remodeled kitchen (2010) serves as the heart of the home, and the bright sunroom addition (2006) provides the perfect space to relax year-round. A brand-new slider installed in 2025 opens to the sunroom, while below, a stamped concrete patio is surrounded by beautifully landscaped gardens and lovely fencing, creating a private outdoor retreat. The finished basement offers additional living space and features a cozy wood stove, perfect for warming up on cool winter evenings. You'll also appreciate the abundant storage throughout the home. Recent updates include: New slider to sunroom (2025) New oven (2025) Water heater (2018) Remodeled kitchen (2010) Remodeled bathrooms The community amenities are equally impressive, with a pool, community center, sidewalks, and wonderful walking areas, all complemented by minimal HOA fees. Ideally situated just minutes from restaurants, grocery stores, banks, pharmacies, and downtown Eastport. Quiet Waters Park is even closer, offering easy access to trails, recreation, and waterfront beauty. There is simply too much to list. Come see this wonderful home for yourself and discover all it has to offer!

213 Georgetown, Annapolis

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

1516 Enyart Way Unit 304, Annapolis
$485,000
2 Beds ⋅ 2 Baths
Welcome to Four Seasons at St. Margarets, Annapolis' premier 55+ active adult community! This beautifully maintained, elevator-accessible third-floor condominium offers over 1,500 square feet of comfortable, low-maintenance living. The open floor plan features a kitchen with new appliances and adjacent dining and living room spaces, perfect for entertaining and everyday living. A relaxing covered outdoor terrace is an extension of the unit with morning and afternoon sun. The generous primary suite includes a private bath and walk-in closet. Off the living room, the hallway leads to the second bedroom, full bath, laundry room, and extra closets with plenty of storage. Bonus loft space can be used as an office, den and overflow for guests. Garage provides easy access to the building, extra storage space and separate closet, and close proximity to elevator. Residents enjoy exceptional resort-style amenities including a clubhouse, fitness center, outdoor pool, billiards and card room, gathering spaces, walking paths, and beautifully landscaped common areas. Clubhouse and pool are across the street from the building/unit. Ideally located just minutes from downtown Annapolis, the U.S. Naval Academy, St. John's College, shopping, restaurants, medical facilities, and major commuter routes, this condo offers the perfect combination of comfort, convenience, and an active lifestyle. NEW UPGRATES in 2026: stainless steel appliances - refrigerator, oven range, microwave and dishwasher, as well as paint throughout unit and new carpeting in the 2 bedrooms.

1516 Enyart Way Unit 304, Annapolis

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

Selling Office: EXP Realty, LLC.

2729 Yeomans Lantern Ct, Annapolis
$485,000
2 Beds ⋅ 2 Baths
Welcome to effortless living in the highly sought-after 55+ community of Heritage Harbour! This exceptional 2-bedroom, 2-bath villa has been completely renovated with quality craftsmanship and attention to detail throughout. Every major component has been thoughtfully updated, making this a truly move-in-ready home where you can simply unpack and begin enjoying the Heritage Harbour lifestyle. The beautifully redesigned kitchen features custom cabinetry, quartz countertops, updated flooring, modern lighting, designer tile backsplash, and a full suite of new stainless steel appliances. Both bathrooms have been completely renovated with stylish finishes, new vanities, upgraded fixtures, ceramic tile, and comfort-height toilets. Throughout the home, you'll find new carpeting, fresh paint, updated lighting, new door hardware, upgraded electrical switches and outlets, and numerous other improvements. The exterior has also been refreshed with updated lighting, new door hardware and weatherstripping, a tiled front entry, and a rebuilt and sealed rear deck—perfect for relaxing or entertaining. The bright, open floor plan is filled with natural light and offers comfortable everyday living with inviting spaces for gathering with family and friends. Every renovation was completed with an emphasis on quality, comfort, and low-maintenance living. Beyond your front door, Heritage Harbour offers one of the area's premier active adult lifestyles. Residents enjoy a 9-hole executive golf course, indoor and outdoor pools, tennis and pickleball courts, a fitness center, walking and biking trails, a community lodge overlooking the South River, a restaurant, kayak launch, boat slips, woodworking shop, library, billiards room, and more than 90 clubs, organizations, and social activities. This is a rare opportunity to own a beautifully renovated villa in one of Annapolis' most desirable 55+ communities. Schedule your private showing today and discover everything Heritage Harbour has to offer.

2729 Yeomans Lantern Ct, Annapolis

Listing courtesy of Academy Realty Inc.. Contact:

Selling Office: Berkshire Hathaway HomeServices PenFed Realty.

3 Kirkley Rd, Annapolis
$485,000
3 Beds ⋅ 2 Baths
WE HAVE RECEIVED AN OFFER. SELLER IS ASKING FOR HIGHEST AND BEST OFFER BY 5PM TUESDAY JUNE 2ND. Charming bungalow literally steps to West Annapolis. This cozy cottage features 3 bedrooms and 2 full baths with the potential to add another bath in the unfinished basement. There is a large rec room that could also be used as a 4th bedroom. The kitchen opens to the dining area. There is a large family room with fireplace. The two guest bedrooms share a hall bath. The primary suite features a separate office, large bedroom and full bath. The large unfinished basement has so much potential. Enjoy your morning coffee in the front screened in porch. The locals favorite, Hero's Pub, is just a short walk down the street. You can't beat this location at this price! The entire home was just painted and most of the windows have been replaced!

3 Kirkley Rd, Annapolis

Listing courtesy of Compass. Contact:

Selling Office: Taylor Properties.

1122 Crestview Dr, Annapolis
$485,000
4 Beds ⋅ 2 Baths
Welcome to 1122 Crestview Drive in the sought-after Cape Saint Claire community of Annapolis! This split foyer home offers a fantastic opportunity to create your dream space while enjoying an established neighborhood known for its access to water privileges and community charm. The home features a bright and airy great room enhanced by brand-new skylights, filling the space with natural light and creating an inviting atmosphere for everyday living and entertaining. A newly installed roof (2026) provides added peace of mind for years to come. With solid bones and great potential, this property is ideal for buyers looking to add their personal touch. The kitchen and bathrooms are ready for updates, allowing you to customize finishes and design to your taste. The home does not feature central heating or air conditioning, however, wall units are installed to provide year-round comfort and individual, area-by-area, temperature control. Whether you're an investor or a homeowner with vision, this is a rare chance to own in Cape Saint Claire and build equity in a prime Annapolis location. Enjoy nearby water access, beaches, parks, and all that the Chesapeake Bay lifestyle has to offer! Schedule your showing today and imagine the possibilities!

1122 Crestview Dr, Annapolis

Listing courtesy of Weichert Realtors - Blue Ribbon. Contact:

Selling Office: Compass.

76 Summerfield Dr, Annapolis
$485,000
3 Beds ⋅ 2 Baths
Welcome to this charming Cape Cod just minutes from downtown Annapolis and Eastport, where classic 1950s character meets thoughtful modern updates. Hardwood floors and original architectural details set the tone on the main level, with abundant natural light filling the living room and highlighting a cozy wood-burning fireplace. The updated eat-in kitchen features granite countertops, a peninsula for casual dining, and easy flow for everyday living and entertaining. Two spacious bedrooms and a full bath complete the main level, while upstairs the entire level is dedicated to a private primary retreat with a walk-in closet and a beautifully appointed ensuite bath featuring a soaking tub, walk-in shower, and dual vanity. The expansive, fully fenced backyard offers exceptional outdoor space with a deck and extensive hardscaping already in place, plus plenty of room to garden, entertain, or even design a future pool. The unfinished lower level provides great ceiling height, walk-out access to the yard, and excellent storage with potential to finish. With quick access to Forest Drive and Route 50, and just moments from Truxton Park, Pip Moyer Recreation Center, Spa Creek trails, tennis courts, and the public boat ramp, this location delivers some of the very best of Annapolis living.

76 Summerfield Dr, Annapolis

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: Berkshire Hathaway HomeServices Homesale Realty.

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