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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
264
# of Listings
3
Avg # of Bedrooms
$482
Avg. $ / Sq.Ft.
$1,293,351
Med. List Price

Browse Annapolis Real Estate Listings

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Under $250,000

$250,000 - $500,000

$500,000 - $1M

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$3M - $5M

Over $5M

264 Properties Found. Page 16 of 18.

A rare opportunity to own a lovingly maintained home in a prime Annapolis location, just minutes from Downtown Annapolis, shopping, dining, waterfront attractions, and major commuter routes. This home has remained in the same family since it was originally built and is being offered to the market for the very first time, showcasing true pride of ownership throughout. Properties with this kind of history and care rarely become available. Inside, you’ll find a fully renovated interior featuring brand new luxury plank vinyl flooring, fresh paint throughout, an upgraded bathroom, and a bright, clean feel from top to bottom. The kitchen includes brand new appliances, including a refrigerator, oven/range, and microwave. A brand new washer and dryer are also included for added convenience. Major system updates provide peace of mind, including an upgraded furnace with an active service contract, replaced electrical panel, and a roof that is less than 10 years old. Outside, enjoy a large yard perfect for entertaining, gardening, or relaxing, complete with a brand new white fence surrounding the yard for added charm, privacy, and functionality. The home also offers a full unfinished basement, providing endless possibilities for storage, workshop space, or future finishing potential. A truly move-in-ready home with modern updates, and a fantastic location in the heart of Annapolis—this is one you won’t want to miss. ( Photos coming soon )
#MDAA2143398

ANNAPOLIS

114 ROSELAWN ROAD

3 Beds

1 Baths

1,200 Sq.Ft.

$395,000

MLS#: MDAA2143398

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

Make an offer!! Nestled in the charming Forest Villa neighborhood, this delightful ranch-style home offers a perfect blend of comfort and functionality. With 1,008 square feet of renovated and well-designed living space, this residence features three inviting bedrooms with new carpet flooring and an updated full bathroom with tub shower, ideal for both relaxation and everyday living. Step inside to discover an open floor plan that seamlessly connects the living and dining areas, creating a warm atmosphere for gatherings. The country-style kitchen, complete with new stainless-steel appliances, upgraded quartz countertops, white shaker soft-close cabinetry and ample table space, invites culinary creativity and casual dining. Built-ins add character and practicality, while the cozy carpet and new luxury vinyl plank flooring enhances the home's inviting ambiance. Outside, the property boasts a lovely front yard and a spacious rear yard, perfect for outdoor activities or serene moments in nature. Enjoy leisurely afternoons on the side porch, where you can unwind and soak in the neighborhood's tranquility. Sidewalks throughout the area encourage leisurely strolls and community engagement. This residence is not just a house; it's a place to create lasting memories. Experience the warmth and comfort of home in this inviting Forest Villa gem.
#MDAA2131008

ANNAPOLIS

1808 LINCOLN DRIVE

3 Beds

1 Baths

1,008 Sq.Ft.

$379,000

MLS#: MDAA2131008

This is not your typical HOA. The association fee includes roof repair and replacement, all exterior maintenance (painting and staining), landscaping, gutter cleaning, and parking lot maintenance. Welcome to 1014 Cedar Ridge Ct in beautiful Annapolis , a stylish 3-bedroom, 2 full bath, 1 half bath townhome designed for easy living in a prime location (21403). Inside, the home is completely carpet-free and thoughtfully updated throughout. The kitchen features stainless steel appliances, while new hardware throughout the home adds a fresh, cohesive feel. The first-floor half bath has been refreshed, and a brand-new 2025 heat pump. Upstairs, the spacious primary suite offers a standout feature — an amazing private balcony, perfect for morning coffee or unwinding in the evening. Step outside to enjoy the beautifully redone backyard with Nicolock pavers and new sod, creating a polished and functional outdoor space. The yard is fully enclosed and includes a convenient storage shed. Positioned at the front of the development, this unit offers easy access in and out, ideal for commuters and everyday convenience.
#MDAA2137612

ANNAPOLIS

1014 CEDAR RIDGE COURT

3 Beds

2 Baths

1,320 Sq.Ft.

$379,000

MLS#: MDAA2137612

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.

$370,000

MLS#: MDAA2140698

Updated, move-in ready end-unit townhome with abundant natural light, a fenced backyard, and added privacy. Ideally located near Downtown Annapolis, shopping, dining, and commuter routes. Motivated seller! $5000 in closing costs assistance!
#MDAA2132586

ANNAPOLIS

1041 CEDAR RIDGE COURT

3 Beds

2 Baths

1,320 Sq.Ft.

$368,000

MLS#: MDAA2132586

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. 🏡✨
#MDAA2134148

ANNAPOLIS

50 HEARTHSTONE COURT E

3 Beds

2 Baths

1,620 Sq.Ft.

$360,000

MLS#: MDAA2134148

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

New on site 2 days ago
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

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

Undoubtedly the best unit in the Heritage Harbour Community of Clipper Cay! Main level condo with BIG year-round views to the South River. Southern exposure guarantees excellent natural light, creating an inviting and welcoming space. Outstanding open floor plan with two en suite bedrooms. Large kitchen with table space and full-sized laundry conveniently located off the kitchen. Freshly painted, updated lighting, newer hot water heater! Large private waterside patio for gathering, relaxing and enjoying the endless parade of nature and wildlife. Excellent assigned parking space very close to the main entrance. Ready to move in! Keep your active lifestyle at Heritage Harbour with the best community amenities in Annapolis! The Heritage Harbour Website reports - "Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms.Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers!" Your new life awaits!
#MDAA2143410

ANNAPOLIS

2900 SHIPMASTER WAY 120

2 Beds

2 Baths

1,044 Sq.Ft.

$345,000

MLS#: MDAA2143410

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.

$340,000

MLS#: MDAA2136790

Welcome to this charming townhouse nestled in the heart of Annapolis! This well-maintained home offers a comfortable and functional layout, perfect for everyday living. Upstairs you’ll find three cozy bedrooms, all featuring wall-to-wall carpeting, along with a full bathroom conveniently located to serve the upper level. The main floor boasts a thoughtfully updated kitchen with modern touches, providing a great space for cooking and gathering. Just off the kitchen, step outside to enjoy a fully fenced backyard which is ideal for relaxing, entertaining, or creating your own outdoor retreat. Additional highlights include a convenient half bathroom on the main level and an in-unit washer and dryer, making daily chores a breeze. With its inviting layout and desirable features, this townhouse offers a wonderful opportunity to enjoy comfortable living in a sought-after Annapolis location.
#MDAA2140030

ANNAPOLIS

130 DUMBARTON DRIVE

3 Beds

1 Baths

1,152 Sq.Ft.

$327,500

MLS#: MDAA2140030

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