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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

190

# of Listings

3

Avg # of Bedrooms

$518

Avg. $ / Sq.Ft.

$1,053,520

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

75 Properties Found. Page 1 of 5.

Prime West Annapolis Opportunity | B-1 Zoning | 13 Annapolis Street. Positioned in the heart of high-demand West Annapolis, 13 Annapolis Street presents an exceptionally rare opportunity to acquire a property with B-1 zoning flexibility in one of Annapolis’ most dynamic commercial districts. This is the kind of location where vision, creativity, and smart planning can translate into long-term value. B-1 zoning opens the door to a variety of potential uses such as boutique retail, professional offices, wellness studios, salons, galleries, cafés, creative workspaces, or thoughtfully designed mixed-use concepts (buyer to verify specific uses with the City). Whether you’re an entrepreneur looking to establish a flagship presence, a business owner seeking visibility, or an investor with a redevelopment vision, this property offers the versatility to bring those plans to life. Adding to its appeal is a feature rarely found in West Annapolis: a private driveway with abundant off-street parking, a significant advantage for clients, customers, or tenants and a true differentiator in this walkable corridor. Surrounded by beloved local restaurants, shops, and everyday conveniences, the property benefits from strong foot traffic, excellent visibility, and the vibrant energy that defines West Annapolis. Opportunities with this combination of location, zoning, and parking simply do not come along often.

ANNAPOLIS

13 ANNAPOLIS STREET

None Beds

None Baths

2,240 Sq.Ft.

$1,000,000

MLS#: MDAA2135402

Welcome to the heart of downtown Annapolis at 179 Green Street. This charming home blends timeless character with modern comfort, this is just a block from Main Street and City Dock, few block from the Naval Academy, State Capitol building, boutique shopping, and Annapolis Elementary School. Located in one of the city’s most desirable neighborhoods, it offers exceptional walkability and vibrant city living. Move in ready with a new roof, new updated kitchen, new full bathroom on main floor, new plumbing, new electrical, new basement ceiling, new fenced in yard, The main level features inviting front and enclosed side porches—perfect for morning coffee or unwinding with a glass of wine in the evening. Inside, wide-board pine floors lead to an updated L-shaped kitchen with bright white cabinetry, stainless steel appliances, and a convenient stackable washer and dryer nearby. The living room showcases rich wood wainscoting, detailed wood trim, custom built-in bookcases, and a rustic fireplace accent, creating a warm and cozy atmosphere. A dedicated dining room completes the main level, ideal for everyday living and entertaining. Upstairs, the home offers two spacious bedrooms and there is an extra versatile space featuring an exposed beam ceiling, curved built-in arch shelving, and custom cabinetry—ideal for a home office, or a den. A large bathroom showcases a Victorian-style Van Buren clawfoot tub, new LVP flooring adding timeless historic character. Outdoors, the fenced backyard provides a private retreat for entertaining or relaxing. The property also includes two oversized off-street parking spaces, offering exceptional convenience. Step into a lifestyle steeped in history and culture. Wander charming cobblestone streets to acclaimed dining, embrace sailing and local events, and enjoy the dynamic rhythm of downtown living just beyond your doorstep. This is a rare opportunity to own a true piece of Annapolis charm—schedule your private showing today. Fireplace non operational.

ANNAPOLIS

179 GREEN STREET

2 Beds

2 Baths

1,656 Sq.Ft.

$999,999

MLS#: MDAA2135874

*** A must-see opportunity in the desirable Eastport Peninsula! This unique property features two attached dwellings in one, offering exceptional flexibility and income potential. The original dwelling, once a charming church, has been thoughtfully converted into a 2-bedroom, 1.5-bath home with an open-concept main level full of character and charm.
The second dwelling, located at the rear, is a cozy cottage complete with 1 bedroom, loft, and kitchen —perfect for rental income, guests, or extended family. A truly special property with endless possibilities—don’t miss it!

ANNAPOLIS

200 CHESAPEAKE AVENUE

2 Beds

1 Baths

2,942 Sq.Ft.

$999,900

MLS#: MDAA2131796

#MDAA2134724

ANNAPOLIS

105 GRISCOM SQUARE WAY

4 Beds

3 Baths

2,850 Sq.Ft.

$995,000

MLS#: MDAA2134724

New on site today

Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this Home Your Own! USE YOUR IMAGINATION! UPGRADES/IMPROVEMENTS: New Roof 2022, New Exterior Custom Stairs 2022, Man Level Bamboo Flooring 2019, Kitchen Re-model 2013 Sub Zero Fridge, Induction Cooktop etc., HVAC 2013, Pella Windows 2002, Master Bathroom 2002. THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! SUPERIOR WATER ACCESS, STEPS TO COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE COMMUNITY BEACHES! & THE BIG WOODS "BAY RIDGE CONSERVATION AREA” W/TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! WALK TO COMMUNITY MARINA, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS , KASS PARK w/ BASEBALL/SOCCER, LACROSSE FIELD!! WHETHER YOU'RE A BOATER, SUP ENTHUSIAST, DOG WALKER, HIKER (PRIVATE TRAILS IN THE BIG WOODS), RUNNER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. SOLD AS IS

ANNAPOLIS

143 E LAKE DRIVE A

3 Beds

2 Baths

1,952 Sq.Ft.

$979,000

MLS#: MDAA2135146

To be built! Two outstanding plans ready for new owner to make their choice and selections! Builder is ready to go! Plans and permits in hand and building can start right away! Extraordinary opportunity to tailor a home to fit your lifestyle and needs. Excellent open floor plans. Great flexible spaces with floor plans to meet your needs. Options include a main level primary suite, larger 2nd floor primary or extra baths. Construction to perm loans are easier and better than you think. A truly rare chance to build a home with water views in the exclusive water-privileged neighborhood of Beacon Hill. Construction to perm loans are easier and better than you think and can be adapted to fit your financial situation. Contact the listing agent for details.

Beacon Hill was originally a community of only forty houses, with twenty lots directly on the Bay and the other twenty with water views. 1546 Shipsview is undoubtedly the best of the ‘ water view’ lots. Directly across the street from 1546 is one of the community's two public water access points. It is the perfect spot to wade into the Bay or sit with a morning coffee and watch the sunrise. 1546 is a rare gem in a highly sought-after community. DO NOT DELAY, or you will miss the opportunity to build in this very special neighborhood. Easy access/commuter routes to the Chesapeake Bay Bridge, the Eastern Shore , Washington and Baltimore.

ANNAPOLIS

1546 SHIPSVIEW ROAD

4 Beds

3 Baths

2,449 Sq.Ft.

$969,000

MLS#: MDAA2136356

Architecturally distinctive and thoughtfully designed, this three-level contemporary residence offers 4 bedrooms, 2 full baths, and 2 half baths, all set on a corner lot in the established South Haven community. The home combines a flexible floor plan with curated custom details and multiple living spaces that adapt effortlessly to modern lifestyles. The entry level features a versatile bonus room that currently serves as a stylish home bar, complete with built-in elements and a nearby half bath. This space could easily transition into a private office, studio, fitness area, or guest suite depending on the next owner’s needs. The main living level is open and light-filled, anchored by a spacious kitchen with an oversized island, professional-grade gas cooking, and distinctive custom finishes. The kitchen flows seamlessly into the dining and living areas, creating an inviting environment for entertaining and everyday living. One standout feature of this home is the built-in dumbwaiter, offering effortless convenience for transporting groceries, firewood, and other essentials between levels. Upstairs, the primary suite offers a peaceful retreat with a private coffee bar, walk-in closet, and spa-inspired bath. Two additional bedrooms, a full hall bath, and an upper-level laundry area complete the sleeping level. A ladder-access rooftop lookout provides a unique bonus space and elevated 365 degree view of the South River / Broad Creek and the Southaven Community. Outdoors, mature landscaping and wooded surroundings offer privacy while maintaining proximity to community amenities. Extensive hardscaping, a detached storage shed, and pre-installed hot tub wiring enhance the backyard’s potential. Located just steps from the neighborhood park with convenient access to major commuter routes, this home delivers design-forward living paired with everyday practicality. Don't miss your chance to make this your new home!

ANNAPOLIS

2941 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,390 Sq.Ft.

$949,999

MLS#: MDAA2134358

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.

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

Modern accents meet classic Georgian design in a downtown Annapolis private enclave of customized homes. Monthly neighborhood get togethers, progressive dinners, holiday celebrations and lovingly curated green spaces for outdoor living. Self managed HOA includes yard care and snow removal for lock and leave convenience.

If you’re looking for rolling acres with grass to cut weeds to pull beds to mulch and snow to shovel this is not the home for you. If you desire almost 4000 sq feet with a small carbon footprint energy efficient with Georgian timeless beauty turn key lock and leave where weekends are your own then this is the one for you. Add a close knit community of only 30 homes with holiday and social gatherings to attend (or not) walking biking distance to Historic Annapolis and Eastport and short DC Baltimore commute.
Two ensuites, office space, flex space and huge storage rooms. Private outdoor paved patio and 2 car garage with additional 2 driveway spaces along with extra guest parking, rare for in town Annapolis living.
Hardwoods on upper and lower levels with carpeted bonus room in fully finished basement offering its own full bath. Brick front and Hardiplank siding.

Gym, hiking trails, sports and pickle ball courts, and boat/ kayak/paddle launch across the street.

Urban vibe with suburban feel, premier coastal living, Restaurants shopping and conveniences within biking and walking distance.

Summer nights at Dining Under the Stars on West Street. Morning walks to the historic waterfront of City Dock
Kayaking on Spa Creek just across the street. Happy hours in Downtown Annapolis. Water taxi or bike ride to Eastport for dinner. Navy game days coming soon!

With nearby marinas for boating, waterfront parks, and recreation centers within walking distance everything you need to live and love Annapolis.

Primrose Hill is coastal living among an exceptional collection of homes where every day feels like a retreat in your luxury primary residence or weekend sanctuary.

Iconic craftmark design with model upgrades throughout create a luxury home with all the modern touches for easy living. Newly built to age gracefully with modern accents set against classic design.

Finished Lower level with family room, full bathroom, office, storage and additional room for wellness space, spa, music room or other flexible lifestyle area.

ANNAPOLIS

52 PRIMROSE HILL LANE

5 Beds

4 Baths

3,978 Sq.Ft.

$949,900

MLS#: MDAA2138534

#MDAA2136542

ANNAPOLIS

148 JEFFERSON STREET

5 Beds

3 Baths

2,330 Sq.Ft.

$925,000

MLS#: MDAA2136542

GREAT OPPORTUNITY! Huge building offers two levels with office on main level and office on upper level, both units are vacant and ready to run your business as you rent the other unit out or combine both. Close to Annapolis Mall, Route 50 and much more!

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

New Construction in Cape St. Claire. Home construction will start in March. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of a previous home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions. Home is scheduled to be completed by August/September of 2026.

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

Welcome to this beautifully maintained 5 bed, 4.5 bath, colonial home situated on almost a half of acre and only 2 blocks to the Chesapeake Bay where you can hear the sounds of the ships passing by in your backyard! Located in the very desirable and relaxed Oyster Harbor Community. This move-in ready home features: over 3,100 finished sqft, 2 primary suites with private full baths which makes it perfect for multigenerational living. The main level is filled with natural light, cathedral ceilings, and an open layout. The main level primary suite offers a spacious bedroom with costume shutters, a walk-in closet with extra room for storage, and a oversized walk-in shower with floor to ceiling tile, multiple shower heads, and a bench. The upper level features the second primary suite with a full bath, 2 additional bedrooms and another full bath. The huge lower level has multiple rooms including a large rec room that can fit a pool table, games and a bar area, plus a family room or theatre room, a 5th bedroom, and a full bath! There is even space for a kitchenette! The lower level has outside access which would make it perfect for an in-law suite. The backyard is fully fenced in and perfect for summertime entertaining! When spring hits you will be surrounded by green trees; the lot next to the home is a preserved lot. This home is nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay. Oyster Harbor offers the best of Coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. Quiet Waters Park is only minutes away with walking trails, dog park and beach, concerts, ice skating, and so much more! Walking distance to Thomas Pointe Park. The Coast Guard is just down the street. This home is MOVE-IN READY AND A MUST-SEE!

ANNAPOLIS

3280 ARUNDEL ON THE BAY ROAD

5 Beds

4 Baths

3,144 Sq.Ft.

$895,000

MLS#: MDAA2138708

New on site today

OPEN HOUSE Saturday 3/21 - 12:00 - 2:00
At last, the one you've been waiting for. A beautiful home in a waterfront community. Move right in and start enjoying the Annapolis lifestyle. Anchorage is an amenity filled waterfront community in which the yearly HOA fee includes the use of a boat slip, community pool and more.
This characterful 5 bedroom 2 1/2 bath home has approximately 2,354SF of living space and has been renovated within the last 4 years. Upgrades that include HVAC, tankless hot water heater, well pump, sewer line, roof, downspouts, gutters, soffit and windows make this home a low maintenance joy. A bespoke new sunroom addition off of the kitchen includes a wood burning stove. Simply delightful!
The sparkling kitchen with a new double oven and stainless appliances has an easy flow with classically beautiful cabinetry and quartz counters. Wood floors continue through the living room and down the hall to 3 bedrooms which include the primary with ensuite bath and an additional half bath.
Downstairs there are 2 bedrooms, a full bath, laundry room, storage room and family room with a fully lined fireplace and wood stove. Garage access is through this room. In the 2 car garage you'll find 2 EV chargers. The harmonious floor plan guides you from room to room with ease.
Sitting on nearly 1/2 acre, the outdoor space won't disappoint. Entertaining is a breeze here, enjoy the spacious deck which is adjacent to the sunroom and overlooks the level, lightly treed and fenced backyard. Landscaping which has matured with the years adds to the natural charm of the property.
Two storage sheds provide plenty of storage with one facing the driveway for easy bike storage access.
The community waterfront on Lake Ogleton includes 49 deep water slips in the marina, community pool, kayak storage, boat ramp and basketball court. The Chesapeake Bay is a quick motor away and historic downtown Annapolis is minutes by car underscoring the desirability of this home's locale.
Filled with amenities and coupled with location, Anchorage is a community that truly has it all.

ANNAPOLIS

1106 MAINSAIL DRIVE

5 Beds

2 Baths

2,059 Sq.Ft.

$895,000

MLS#: MDAA2139090

New on site today

Located on one of the most desirable streets in Homewood, this classic four-square home offers timeless character and an exceptional Annapolis lifestyle. Just a short walk to the library, the commuter bus to DC, ceremony coffee, Navy Stadium, neighborhood parks, and downtown Annapolis, the location is truly hard to beat.

Inside, you’ll find beautiful hardwood floors throughout and the traditional layout that makes four-square homes so beloved. A large main-level addition provides generous living space for everyday living and entertaining, while a dedicated home office offers the perfect work-from-home setup.

Upstairs, the home continues to deliver charm and functionality, and the attic presents exciting potential to be finished for additional living space, a studio, or guest suite.

Outside, enjoy a spacious backyard with plenty of room for entertaining, play, or gardening—an increasingly rare find this close to downtown. With classic architecture, flexible living spaces, and an unbeatable location on one of Homewood’s best streets, this home captures the very best of Annapolis living.

Professional Photos coming 3/18/2026. Showings to Start Friday 3/20/26

ANNAPOLIS

1309 POPLAR AVENUE

3 Beds

2 Baths

2,141 Sq.Ft.

$889,000

MLS#: MDAA2139062

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