One of the most popular communities provided by {{page_data.agentName}}

Annapolis

One of the most popular communities provided by Maryland Sandbox

Annapolis

About Annapolis

Nestled on the shores of the Chesapeake Bay, Annapolis, Maryland, is a charming and historic community that seamlessly blends waterfront beauty with rich maritime heritage. As the state capital and home to the United States Naval Academy, Annapolis boasts a vibrant downtown area filled with unique shops, gourmet restaurants, and stunning colonial architecture. Residents and visitors alike can enjoy picturesque strolls along the scenic harbor, where sailboats and yachts bob in the water. With its engaging cultural scene, including art galleries, theaters, and annual festivals, Annapolis offers a lively atmosphere for all ages. The community takes pride in its top-rated schools, making it an ideal place for families. Outdoor enthusiasts can explore numerous parks, nature trails, and waterfront activities, while history buffs can immerse themselves in the city's storied past at landmarks such as the Maryland State House. Whether you're seeking a lively urban environment or a peaceful retreat by the bay, Annapolis is a vibrant community that truly has something for everyone.
One of the most popular communities provided by Maryland Sandbox
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

274 Properties Found. Page 17 of 19.

Owner is offering $ 5,000.00 for helping buyer with closings costs!! Great location! Sweet, cozy, and lovely semi-detached home. 3 bedroom, 1 1/2 baths and semi finished basement. The house is ready for your personal touch! NEW ROOF 2023. Close to Truxtun Park and easy access to downtown Annapolis and US 50 /97 HWY. GREAT OPPORTUNITY! Bring your best offer.
#MDAA2133422

ANNAPOLIS

108 CONLEY DRIVE

3 Beds

1 Baths

1,880 Sq.Ft.

$395,000

MLS#: MDAA2133422

Located at the corner of Spa Road and Boxwood Drive, this property offers an excellent Annapolis location with convenient access to downtown, shopping, dining, and major commuter routes. The home sits on a prominent corner lot and presents a great opportunity for investors, builders, or buyers looking to renovate and customize a home to their own vision. The property is in need of updating and is being sold as-is, making it ideal for those seeking a value-add project in a highly desirable area. A rare chance to create something special in an established neighborhood with strong long-term potential.
#MDAA2136208

ANNAPOLIS

4 BOXWOOD ROAD

3 Beds

2 Baths

1,152 Sq.Ft.

$389,900

MLS#: MDAA2136208

Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water views of College Creek and a short stroll to downtown and West Annapolis, where shops, dining, entertainment, and the U.S. Naval Academy are right at your doorstep. The location also provides easy commuter access to Routes 50 and 97 for Washington, D.C., Baltimore, and BWI Airport. Thoughtfully updated in the past year, the home features new flooring and paint throughout, all new kitchen appliances, countertops, and sink, new siding, four mini-split units, and all new upstairs windows. Walls were opened between the kitchen, dining, and laundry areas to create a more open flow, and a new upper-deck door leads to an expanded rooftop deck with water views. Additional highlights include exposed brick and beamed ceilings, a fenced rear yard, private access to College Creek, and rare rear parking. With a proven rental history including $21,500 earned on Airbnb in 2024, this home is ideal as a primary residence or investment opportunity.
#MDAA2139810

ANNAPOLIS

198 CLAY STREET

2 Beds

1 Baths

902 Sq.Ft.

$389,000

MLS#: MDAA2139810

New on site 2 days ago
This well-maintained 3-level Whispering Woods townhome offers a long list of updates, including many completed in April 2026. Recent improvements include luxury vinyl plank flooring throughout the main and upper levels, freshly painted walls, ceilings, and trim, granite kitchen countertops with a stainless steel under-mount sink, and GE stainless steel appliances including a refrigerator with ice/water dispenser, electric range, and dishwasher. Additional notable updates include an electric fireplace insert added in February 2025, hot water heater replacement, updated PEX plumbing lines in the basement, and a new garbage disposal in October 2025, roof replacement in 2021, rear deck and staircase replacement in 2020, exterior vinyl siding replacement in 2020, and updated front and storm doors in 2019. The Trane heat pump system, including indoor air handler and exterior compressor, was replaced in 2008. The unfinished lower level provides excellent storage space and offers great potential for future finishing. Whispering Woods is a peaceful wooded community featuring open green space, playgrounds, and walking/biking paths, all while offering convenient access to Downtown Annapolis, City Dock, USNA, Baltimore, and Washington D.C. via major commuter routes.
#MDAA2145602

ANNAPOLIS

1608 WOODTREE COURT W

3 Beds

1 Baths

1,360 Sq.Ft.

$367,900

MLS#: MDAA2145602

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime location just minutes from the vibrant charm of downtown Annapolis. As you enter, you're welcomed by fresh paint throughout (2026), a foyer with a convenient coat closet, and elegant column accents that open into a bright and airy main living space. The kitchen features warm wood cabinetry, granite countertops, a tiled backsplash, and stainless steel appliances, along with a cozy breakfast nook framed by a bay window overlooking peaceful wooded views. Entertain with ease or unwind at the end of the day in the well-appointed living and dining areas, complete with hardwood floors, 9+ ft ceilings, a cozy gas fireplace, and access to a private patio that offers a serene setting to relax and take in the views. The primary suite is a true retreat, showcasing a vaulted ceiling with a lighted fan and a charming bay window, perfect for a reading nook or sitting area with a tranquil backdrop. Two spacious closets and an ensuite bath with a dual sink vanity and tub/shower combo complete the space. Two secondary bedrooms, each with ample closet space, are thoughtfully positioned for added privacy and versatility, whether used as guest rooms or an in-home office, and share a full bath with a large walk-in shower. A dedicated laundry room with additional storage and a full-sized washer and dryer adds everyday convenience. Recent updates include a newer HVAC (2021), water heater (2022), and plush new carpet (2026). Parking is a breeze in the off-street parking lot. Beyond the community, enjoy the nearby Bestgate Park, Trader Joe’s and Annapolis Mall, plus easy access to major highways for a quick commute to Baltimore, DC, and more. Don’t miss this rare find!
#MDAA2140698

ANNAPOLIS

2161 SCOTTS CROSSING COURT 302

3 Beds

2 Baths

1,328 Sq.Ft.

$364,900

MLS#: MDAA2140698

Beautifully maintained 3-level townhome in the desirable Annapolis Overlook community in Annapolis! This spacious home offers approximately 1,680 sq ft with 3 bedrooms, 2.5 baths, and a functional layout designed for comfortable living. The main level features a bright living area, separate dining space, and an updated kitchen with ample cabinet storage and room for entertaining. Upstairs you’ll find generously sized bedrooms including a primary suite with private bath and great closet space. Enjoy low-maintenance living in a well-established community conveniently located near downtown Annapolis, the Naval Academy, shopping, restaurants, and major commuter routes. The 21403 area is known for its coastal lifestyle, outdoor recreation, and close proximity to the Chesapeake Bay.  Perfect for first-time buyers, investors, or anyone looking for easy living in a prime Annapolis location!
#MDAA2140034

ANNAPOLIS

40 IRONSTONE COURT J

3 Beds

2 Baths

1,680 Sq.Ft.

$359,999

MLS#: MDAA2140034

This colonial home, built in 1950, blends classic appeal with modern comfort. Spanning 1,584 square feet, this detached residence features four spacious bedrooms and two full bathrooms, making it an ideal retreat for those seeking both space and style. Venture inside to discover a warm and inviting interior adorned with carpet and hardwood floors. The eat-in kitchen, designed for both functionality and social gatherings, offers ample table space, perfect for casual dining or entertaining. The bathrooms feature a convenient tub-shower combination, providing a relaxing oasis after a long day. The unfinished full basement presents a blank canvas for customization, whether you envision a home gym, workshop, or additional storage. Outside, the property features a well-maintained front and rear yard, ideal for outdoor activities or serene relaxation. Parking is a breeze with off-street options or a driveway. This home is conveniently located with easy access to local dining, market and shopping. So, don't miss this opportunity to make his home your own
#MDAA2144184

ANNAPOLIS

7 CARVER STREET

4 Beds

2 Baths

1,584 Sq.Ft.

$350,000

MLS#: MDAA2144184

NEW KITCHEN just installed! The eat-in kitchen has been updated with NEW tall, white kitchen cabinetry w/brushed bronze handles, NEW upgraded quartz countertops,NEW lighting, freshly painted, and boasts all stainless steel appliances including a gas range, french door refrigerator, dishwasher, and microwave—all installed within the past year. Enjoy Annapolis living with a community pool and fitness center—right at home! This beautiful townhome-style condo features a sprawling top-floor Owner’s Suite with a private bath, soaking tub, separate shower, double vanity, and oversized walk-in closet. The second level offers two additional large bedrooms and a full bath, ideal for guests, family, roommates, or a home office. Recent upgrades include a brand-new roof, newer gas HVAC (approx. 1.5 yrs), full-size washer & dryer (approx. 2 yrs), and newer stain-resistant carpet with pad. The main level shines with luxury vinyl tile flooring for a modern, low-maintenance lifestyle. Convenient main-level half bath. Reasonable condo fees cover the pool, fitness center, roof, fencing, and lawn care—truly lock-and-leave living. Ideally located just minutes from downtown Annapolis, this home includes one reserved parking space plus one additional parking permit. Comfort, convenience, and carefree living—all in one place. 🏡✨
#MDAA2143694

ANNAPOLIS

50 HEARTHSTONE COURT E

3 Beds

2 Baths

1,620 Sq.Ft.

$350,000

MLS#: MDAA2143694

Just Reduced + $5000 closing cost credit towards this move-in ready condo in the sought-after Riva Trace community! Freshly painted with brand-new carpet throughout, this home features a bright solarium, a spacious primary bedroom with a walk-in closet, and a primary bath complete with a soaking tub and separate shower. All appliances convey, making this home truly turnkey. Step outside to enjoy your own private patio. The Riva Trace community offers an impressive array of amenities, including scenic walking paths, picnic areas, pickleball and tennis courts, a baseball field, basketball court, and a community pier—perfect for enjoying the outdoors and staying active. Conveniently located just minutes from downtown Annapolis, with quick access to major commuter routes.
#MDAA2136078

ANNAPOLIS

2702 SUMMERVIEW WAY 103

2 Beds

2 Baths

1,285 Sq.Ft.

$349,999

MLS#: MDAA2136078

Welcome to this beautiful 2-bedroom, 2-bath condo in the highly sought-after Tidewater Colony community of Annapolis. Inside, you’ll find 9-foot ceilings, luxury vinyl plank floors, custom blinds, and a modern kitchen with granite countertops, gas cooking, and a built-in microwave. The spacious primary suite features a double vanity and a luxurious bath with separate shower and soaking tub. Additional highlights include high-efficiency HVAC and a dedicated laundry room with full-size washer and dryer. Enjoy resort-style living with access to the clubhouse, fitness center, pool, tennis courts, playground, and walking trails. Perfectly positioned just minutes from downtown Annapolis and Anne Arundel Medical Center, with easy commuter access to Route 50 and Route 97. A prime location paired with comfort and convenience—this one checks all the boxes.
#MDAA2136790

ANNAPOLIS

2006 PEGGY STEWART WAY 204

2 Beds

2 Baths

1,046 Sq.Ft.

$335,000

MLS#: MDAA2136790

Welcome to this home nestled in the heart of Annapolis. Offering a blend of comfort, functionality, and convenience, this property features spacious living areas, abundant natural light, and a layout designed for everyday living and entertaining. Enjoy a generous backyard perfect for relaxing or hosting gatherings, along with easy access to local shopping, dining, marinas, parks, and major commuter routes. Located just minutes from downtown Annapolis and the Chesapeake Bay, this home provides the ideal balance of charm, accessibility, and lifestyle. Property is being sold as is. Don’t miss the opportunity to make this Annapolis gem your own.
#MDAA2144702

ANNAPOLIS

121 CONLEY DRIVE

3 Beds

1 Baths

1,280 Sq.Ft.

$330,000

MLS#: MDAA2144702

LOCATION, LOCATION, LOCATION!! Your Beautiful Home awaits in The Heart of Annapolis!! Brand New Carpet, New HVAC (2021) Inside and Outside Unit, Corian Counter's and even an Awesome Wooded View from your Private Balcony! Community Pool, Pickel Ball, Community Center, Exercise Room and so much more!!! Be in your new home in just 2 weeks, With preferred vendors!!
#MDAA2144778

ANNAPOLIS

631 ADMIRAL DRIVE 302

2 Beds

2 Baths

1,341 Sq.Ft.

$329,900

MLS#: MDAA2144778

0.65-acre corner lot along Bestgate Road in Annapolis with frontage on both Bestgate and Willey. Zoned R2, allowing for a single-family detached home. Public water and sewer connections are available through Anne Arundel County. Buyers will need to apply for service, obtain a connection permit, and pay the applicable capital facility charge along with any contractor installation costs. The existing well and septic are assumed to be nonfunctional. All site engineering, utility applications, and permitting will be the responsibility of the buyer. Convenient location near Route 50, downtown Annapolis, and area shopping. Excellent opportunity for a custom home project or long-term hold in a highly accessible central corridor.
#MDAA2129812

ANNAPOLIS

668 N BESTGATE ROAD

None Beds

None Baths

0.65 acres

$325,000

MLS#: MDAA2129812

1 Year home warranty offered by the seller (a $500 value)! Serenity Meets Convenience at The Reserve in Heritage Harbour, a premier 55+ community! What sets this unit apart from every other in the building is its unique relationship with the outdoors. As the only unit featuring a private brick patio with direct walk-out access to the parking lot and sidewalks, it bridges the gap between condo living and the autonomy of a villa. For the pet owner, it means no more navigating elevators or hallways at 6:00 AM; for the traveler, it means unloading luggage is a breeze. It is the gold standard for accessibility and ease, seamlessly blending indoor comfort with the outdoors. Inside, the home shines with fresh paint and gleaming hardwood floors. The open-concept living and dining areas flow naturally to the patio, creating an expansive feel for entertaining. The kitchen features 42-inch cabinetry, Corian countertops, and a four-burner gas stove with a grill insert, plus a sun-drenched bistro breakfast nook. The primary suite is a true sanctuary, featuring brand-new plush carpeting and a unique sunroom sitting area—ideal for a home office or reading nook. The spa-like ensuite boasts a new walk-in shower, granite counters, and a vessel sink. Practicality is built-in with a spacious walk-in closet, a dedicated laundry room with a new washer/dryer, and an extra storage cage in the building’s basement. Heritage Harbour Living: Living here grants access to The Lodge, the community’s social heartbeat. Enjoy world-class amenities including: indoor and outdoor pools & fitness center, tennis, pickleball, bocce, and a community golf course, woodworking shop, arts room, and a well-stocked library, private kayak launch on the South River. 90+ clubs and a robust social calendar. Located just minutes from Downtown Annapolis with easy access to Routes 50 and 97, this home offers the perfect balance of peaceful retreat and urban accessibility. Don’t miss this rare opportunity for true single-level living in a vibrant, amenity-rich enclave.
#MDAA2135514

ANNAPOLIS

940 ASTERN WAY 102A

1 Beds

1 Baths

1,073 Sq.Ft.

$318,000

MLS#: MDAA2135514

Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the **new price**Welcome to effortless living in one of Annapolis' most sought-after locations. With new systems like the efficient gas furnace and hot water heater, this well-maintained 2-bedroom, 2-bathroom condominium offers 1,065 square feet of comfortable living space with one standout feature that sets it apart: main-level access. In a building with no elevator, this ground-floor location means you'll never climb a single flight of stairs—ideal for those seeking accessibility and convenience. Step outside your front door onto a charming patio where you can enjoy your morning coffee or unwind after a day exploring everything Annapolis has to offer. This private outdoor space adds a welcoming touch to everyday living. The real magic lies in what's just beyond your doorstep. You're within walking distance or a short drive to the Annapolis Historic District, where cobblestone streets lead to the Maryland State House, boutique shops, and acclaimed restaurants. Stroll down to City Dock for waterfront dining and sailing culture, or catch a game at Navy-Marine Corps Memorial Stadium. The U.S. Naval Academy is practically in your backyard—making this an exceptional opportunity for parents of midshipmen seeking a convenient pied-à-terre during their student's four years at the Academy. Daily conveniences are equally close at hand: grocery stores, houses of worship, and easy transportation connections to Washington, D.C. for work or weekend adventures are here. With modest association fees and no-frills ownership, this condo delivers exceptional value in a location where proximity to history, culture, and community commands a premium. Whether you're downsizing, investing, or establishing a local home base, this main-level gem offers the freedom to live well in one of the Mid-Atlantic's most charming cities.
#MDAA2140882

ANNAPOLIS

2001 WARNERS TERRACE N 102

2 Beds

2 Baths

1,065 Sq.Ft.

$317,000

MLS#: MDAA2140882

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