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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
268
# of Listings
3
Avg # of Bedrooms
$429
Avg. $ / Sq.Ft.
$928,196
Med. List Price

Browse Annapolis Real Estate Listings

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268 Properties Found. Page 5 of 18.

This expansive two-story home is designed for both everyday comfort and unforgettable entertaining. It opens with a formal dining room off the foyer, leading into a gourmet kitchen that flows effortlessly into the breakfast nook, morning room, and a cozy sitting area—perfect for lingering conversations or quiet mornings. The Great Room, complete with a charming fireplace, anchors the main level and overlooks a serene backdrop of mature woods for added privacy and relaxation. Upstairs, a spacious loft is surrounded by three secondary bedrooms and a luxurious owner’s suite with a spa-inspired bathroom. The lower-level recreation room adds even more room to grow, offering endless possibilities for work, play, or hosting.
#MDAA2131540

ANNAPOLIS

103 STILLY WAY

5 Beds

5 Baths

10,400 Sq.Ft.

$1,161,840

MLS#: MDAA2131540

30K Price Improvement! Seller motivated! Incredible West Annapolis home that has been renovated from top to bottom with high end finishes,, and reconfigured interior that includes a primary bedroom on the main level. Lovely fenced yard, new roof, new everything! Main Level Master Suit with walk in closets! Buyer agents warmly welcome and appreciated!
#MDAA2125152

ANNAPOLIS

1 TUCKER STREET

3 Beds

2 Baths

2,571 Sq.Ft.

$1,145,000

MLS#: MDAA2125152

“A rare price improvement now makes this park-like, 1+ acre estate an even more exceptional opportunity. Discover the privacy, beauty, and craftsmanship of this custom home before it quietly slips off the market.” A Rare Exceptional Retreat in Winchester Estates — Annapolis, MD Welcome to an extraordinary custom-built residence where timeless elegance meets unparalleled serenity. Set on a magnificently landscaped, park-like acre, this 5-bedroom, 4-bath estate offers a level of privacy and tranquility seldom found so close to the heart of downtown Annapolis. Nestled within the prestigious Winchester Estates, this property grants private water-access creating a lifestyle that blends luxury living with the best Annapolis has to offer. Inside, unique design and exceptional craftsmanship define every space. The chef’s kitchen, outfitted for the culinary enthusiast, anchors the main level and opens seamlessly to a grand, light-filled living area—an ideal setting for refined entertaining or intimate gatherings. Expansive windows invite the lush landscape indoors, enhancing the home’s natural harmony and sense of calm. The elegant lower level offers a rare level of versatility, featuring a full private suite with its own bedroom, bathroom, kitchen, dining room, and living room—perfect for multigenerational living, distinguished guest accommodations, or an au pair residence. Outside, the estate’s grounds unfold like a private sanctuary. Mature trees, newly developing gardens, and verdant open spaces create an atmosphere of effortless peace—a truly restorative environment just minutes from world-class dining, boutique shopping, and the historic charm of Annapolis. Highlights Include: * Custom-built architecture on a serene 1+ acre park-like lot * Exclusive neighborhood water-access privileges * Right next door to the beautiful Baltimore Annapolis Trail Park * Gourmet chef’s kitchen with Blue Star 8 Burner Stove and expansive entertaining areas * Full private lower-level suite with separate living quarters * A Total of Five spacious bedrooms and four well-appointed bathrooms * Two upper level bedrooms have self-contained climate control * Exceptional privacy in one of Annapolis’ most coveted communities * Full Premium Warranty Offered This is more than a home—it is a private retreat offering refined luxury, natural beauty, and an unmatched Annapolis lifestyle.
#MDAA2130382

ANNAPOLIS

1635 WINCHESTER ROAD

5 Beds

4 Baths

3,660 Sq.Ft.

$1,139,400

MLS#: MDAA2130382

Walk in and be amazed with a beautiful and luxurious remodeled open floor concept. Open the front door and look to the gorgeous living room with electric fire place that produces up to 5,000 BTU of heat for the comfort on cold and snowy days. Living room flows into your brand new gourmet style kitchen set up for fabulous days of entertaining friends and family. Main floor offers a spectacular primary bedroom with a personal home office and access to a private deck to enjoy the outdoors along with a private laundry room for your convenience not to mention a large room ready to be made into the closet of your dreams, even better a bathroom with a spa like atmosphere , In addition the main floor has an in law suit with a private bathroom and access to a covered deck area. Lets walk to the second floor where you will be amazed with a spectacular second living room/game room/ study area/ etc. make this room as you wish for any entertainment. Three great bedrooms, 2 share a large bath and one with a private in suit bath, all three with walk in closets. All new floors throughout the home along with all new lighting The expansive basement with over 2,700 SQ.FT has an open concept where you can let your imagination take over along with a second home office and full bathroom. This house is conveniently located off Riva rd, just a few minutes from Downtown Annapolis, plenty of near by shopping including Annapolis Mall and a multitude of restaurants. DON’T LET THIS ONE PASS YOU BY !
#MDAA2127360

ANNAPOLIS

301 UNITY LANE

5 Beds

5 Baths

7,616 Sq.Ft.

$1,127,000

MLS#: MDAA2127360

Price Reduction: Motivated Seller BRING ALL OFFERS! Get ready to fall in love with this Annapolis gem Nestled in the sought-after Captain Cove neighborhood on a 1.21-acre wooded lot, this beautifully maintained home is minutes from downtown Annapolis. Unique features include a rooftop deck, expansive back decking, and a bonus treehouse that doubles as a fun space for children or a peaceful retreat for adults—perfect as a she shed or man cave. This is a cozy place to call home, look no further . Don’t miss your chance to own a piece of Annapolis charm. Professional photos to follow!
#MDAA2115552

ANNAPOLIS

15 E NAP LANE

5 Beds

3 Baths

6,525 Sq.Ft.

$1,100,000

MLS#: MDAA2115552

Comfy coastal cottage just a few blocks from Lake Ogleton and Chesapeake Bay in the coveted Bay Ridge community. The interior impresses with vaulted ceilings, exposed beams, charming built-ins, and stylish finishes throughout. The floor plan features a galley Kitchen with classic finishes and upgraded appliances with convenient pass thru to the spacious living area. The Living room with cozy wood burning stove and dining room create a wonderful space to gather and the expansive screened porch ensures there is plenty of room for alfresco dining and enjoying the outdoors. Relax on the screened porch and take in the peaceful sounds of the pond and waterfall. 2 spacious bedrooms on the main level share a well appointed bathroom. Completing this level is the mudroom/laundry room that leads out to the expansive backyard. Head upstairs to enjoy the 2 additional bedrooms with spacious closets and shared hall bath. The charming sitting nook is the perfect place to curl up with a book. The detached garage at the rear of the 0.42 acre lot provides plenty of storage area for cars or water toys. Enjoy fishing, swimming, kayaking and heading out on the water from the community access just a block from the home or the community marina. Enjoy the waterfront lifestyle and feel like you are on vacation every day! The sought-after Bay Ridge Community features a community pool with a clubhouse that overlooks the beautiful waters of the Bay, community beaches on both the River and the Bay and a community Marina with a newly renovated clubhouse. Off-the-water activities include enjoying the basketball court, playground, ball fields, pickleball courts, common areas and year-round community activities. Walk or ride your bike for miles along the water and enjoy all the benefits of the Bay Ridge lifestyle, there is no other place like it! Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Don't let this one slip away. Welcome Home!
#MDAA2129496

ANNAPOLIS

30 DECATUR AVENUE

4 Beds

2 Baths

1,477 Sq.Ft.

$1,100,000

MLS#: MDAA2129496

English Tudor featuring a stone front patio, covered front porch for nature lovers and bird watchers. Driveway paved and widened in 2021, extensive gardens and plantings. House surrounded by mature trees for tons of shade and privacy. Rear deck is 45 feet long and was constructed in 2017 for entertaining and large gatherings. Backing to community open space the rear lawn has level play areas and room for a pool. Drywell was replaced and expanded in 2016. Two Zone HVAC systems were replaced with high efficiency systems in 2021 and 2022. Three of the four full baths were renovated in 2021. Over 4000 square feet of living space plus an oversized garage 24x25 with a floored attic space above for expansion or storage. Spacious kitchen with two Andersen French sliders to rear deck, solid cherry cabinets, quartz island with smooth cooktop and built-in exhaust fan, stainless steel appliances. The great room has cathedral ceilings, wood beams and wide plank redwood siding, floor to ceiling brick fireplace and Andersen French slider to rear deck. First floor guest room features wood flooring and access to full bath and walk-in shower. Laundry room with generous built-in shelving. Upstairs features high end neutral carpet, 3 bedrooms, 2 full baths and generous closet space. Finished Lower Level has clubroom, full bath with walk-in shower, office/5th bedroom potential (needs larger window for egress) large storage room with built-in shelving. The community has water privileges with fishing pier and canoe storage and sidewalks for dog walking or strolling the neighborhood. Convenient location for commuting to Baltimore or D.C. and 20 minutes to BWI Airport. Five miles to Downtown Annapolis for great shopping, restaurants, Naval Academy and Historic District..
#MDAA2117832

ANNAPOLIS

553 CHOPTANK COVE COURT

5 Beds

4 Baths

4,438 Sq.Ft.

$1,077,000

MLS#: MDAA2117832

Experience the Eastport Lifestyle in a Stunning Rebuilt Home Enjoy coastal living in this beautifully rebuilt Eastport residence. Completely gutted and expanded in 2023, this home combines modern luxury with timeless charm. The chef’s kitchen is a showstopper, featuring a 36-inch Bertazzoni range with gas burners and electric oven, hood, built-in refrigerator and dishwasher with cabinetry overlays, and a wine refrigerator — creating a sleek, seamless design that’s every cook’s dream. The main level offers a spacious family room and dining area with access to the rear deck and yard, perfect for entertaining. The first-floor primary suite includes a luxurious bath with a stand-up shower for your comfort and convenience. Upstairs, you’ll find two generous bedrooms and a stylish full bath with a stand-up shower. The lower level adds versatility with a cozy wood-burning fireplace, workshop area, abundant storage, an additional refrigerator, and a triple-safe sump pump system. The property features a large yard with access from both the front and rear streets, including off-street parking at the back. Plans are already drawn for a two-car garage or an optional garage with an accessory dwelling unit above. Additional highlights include an underground irrigation system for the front yard and flower beds and a fully encapsulated crawl space for enhanced comfort and efficiency. With everything — from the roof and appliances to the HVAC, bathrooms, and flooring — replaced in 2023, this home is truly move-in ready. Enjoy the best of Eastport living, just moments from restaurants, shops, and downtown Annapolis.
#MDAA2130292

ANNAPOLIS

1007 PARK AVENUE

3 Beds

2 Baths

2,677 Sq.Ft.

$1,075,000

MLS#: MDAA2130292

Development opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.). Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Assemblage possible with adjacent buildings at 2 & 4 Annapolis Street grossing rent from 6 retail & 2 residential tenants totaling $20,700/Mo.
#MDAA2127368

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

2,064 Sq.Ft.

$975,000

MLS#: MDAA2127368

Redevelopment opportunity in an established boutique shopping & business district. Value is in the land (approximately 15,000 sq. ft.) Being offered "as is - where is". Former location of Tara's Gifts at the gateway to West Annapolis. B1 zoning permits retail, office & residential use. Easy access to/from Rt. 50. Walkable to offices, restaurants, shopping, downtown Annapolis, USNA & Navy/Marine Corp. Memorial Stadium. Possible assemblage with adjacent 2 buildings at 2-4 Annapolis Street...gross rents totaling $20,700/Mo. from 6 retail & 2 residential tenants. Total land area for 2, 4 & 10 Annapolis Street is approximately 37,500 sq. ft. (0.86 acres).
#MDAA2127370

ANNAPOLIS

10 ANNAPOLIS STREET

None Beds

None Baths

0.34 acres

$975,000

MLS#: MDAA2127370

Time to Make a Lifestyle Change – Stunning & Fabulous at The GrandView! Welcome to The Flagship, a unique and highly sought-after corner unit in the premier GrandView community. Perfectly positioned for the best location, views, and luxury, this residence offers an unmatched lifestyle in the heart of Annapolis Town Center. Step inside and be captivated by the wall of windows that flood the space with natural light and showcase panoramic views of Annapolis Town Center’s vibrant activity. Enjoy morning coffee or evening cocktails from your private, covered corner balcony. This 2-bedroom, 2-bath home is beautifully appointed with granite countertops, 10-foot coffered ceilings, hardwood floors, and custom window treatments. Recent upgrades include: New HVAC system, New stainless steel appliances, New bedroom carpeting, Updated lighting and black hardware through out. Additional features include an assigned storage unit and two reserved garage parking spaces. Residents of The GrandView enjoy luxury amenities such as: Concierge services, Fitness center, and Rooftop pool with stunning city views. Live the walkable lifestyle! Stroll to Whole Foods Market, Target, fine dining, cafés, banking, and boutique shopping—all just steps from your door. You’re minutes from Historic Downtown Annapolis, Annapolis Mall, Anne Arundel Medical Center, and with easy access to Route 50 and I-97 for effortless commuting. This is truly a must-see residence—a perfect blend of comfort, convenience, and modern elegance in one of Annapolis’ most desirable addresses.
#MDAA2127946

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1004

2 Beds

2 Baths

1,794 Sq.Ft.

$975,000

MLS#: MDAA2127946

This stunning home is move-in ready and boasts high-end upgrades throughout. It features a first-floor owner's suite, plus three additional bedrooms on the second level, along with two full bathrooms and a spacious loft. The gourmet kitchen is a chef’s dream, complete with custom cabinetry and an open-concept design. The impressive two-story family room with soaring ceilings creates a dramatic focal point, while the finished basement rec room, featuring a wet bar with a refrigerator and sink, is perfect for entertaining. Experience luxury living at its finest—schedule your tour today! Photos for illustration purposes only. Agent must attend first visit.
#MDAA2125928

ANNAPOLIS

106 STILLY WAY

4 Beds

4 Baths

4,594 Sq.Ft.

$974,990

MLS#: MDAA2125928

Nestled in the serene Dellwood community, this contemporary gem offers an exclusive lifestyle defined by luxury and comfort. Perfect location leaves you minutes from downtown Annapolis, Luminus Health Hospital as well as all the charm Annapolis proper (Parole) has to offer. Step inside to discover an inviting open floor plan adorned with rich hardwood and ceramic tile flooring, seamlessly blending elegance with warmth. The heart of the home features a country-style kitchen equipped with stainless steel appliances, including a six-burner stove and double ovens, perfect for culinary enthusiasts. Main level bedroom if needed with full bath attached. Currently being used as the office. Unwind in the spacious living area, complete with a cozy wood stove or wood burning fireplace and built-in sound system, or retreat to the inviting screened in porch to take in the natural setting of this large corner lot. Enjoy outdoor living with multiple decks and porches, a personal lap pool, ideal for exercise or relaxation. The property also includes water access to the Severn River with boat slip included if that fits your needs , enhancing your lifestyle with boating and fishing opportunities. With an attached garage and additional storage, this home is designed for effortless living.
#MDAA2131896

ANNAPOLIS

1800 SEVERN GROVE ROAD

3 Beds

3 Baths

2,281 Sq.Ft.

$967,000

MLS#: MDAA2131896

Welcome to 1909 Eleanor Ct, a stunning colonial featuring five bedrooms and three and a half bathrooms. You’ll fall in love the moment you walk in! Highlights include a large eat-in kitchen that opens to the family room, perfect for gatherings, plus a mudroom with ample storage. There’s even a cozy area off the kitchen ideal for a home office or homework station. The oversized owner’s suite boasts a custom walk-in closet and a spacious bathroom for the ultimate retreat. The fully finished basement includes a full bathroom, and the three-car garage provides plenty of space for vehicles and storage. All of this sits on a flat lot in a quiet cul-de-sac, offering both privacy and convenience.
#MDAA2127206

ANNAPOLIS

1909 ELEANOR COURT

5 Beds

3 Baths

5,124 Sq.Ft.

$950,000

MLS#: MDAA2127206

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131620

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

3,078 Sq.Ft.

$949,900

MLS#: MDAA2131620

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