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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

$418

Avg. $ / Sq.Ft.

$854,290

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

264 Properties Found. Page 4 of 18.

New on site 4 days ago

This is a stunning home in one of Annapolis’s hottest in-town neighborhoods --- offering generous living spaces, an entertainer's kitchen, and the perfect layout to suit many lifestyles. Eateries, coffee shops, boutiques, breweries, schools, churches, a grocery store, pharmacy, veterinarian, and more are just minutes from the front door—creating an effortless, walkable way of living. Easy commute to USNA, Fort Meade, NASA Goddard, D.C., and Baltimore. An excellent opportunity to own in coveted West Annapolis.

ANNAPOLIS

112 MELVIN AVENUE

4 Beds

2 Baths

3,462 Sq.Ft.

$1,350,000

MLS#: MDAA2132602

Bring your personal touch to this waterfront get away and enjoy the waterfront lifestyle!

Waterfront Suisse Chalet on Mill Creek – Annapolis, MD

Experience the perfect blend of charm, comfort, and waterfront living in this spacious 3-bedroom, 2.5-bath Suisse Chalet nestled on scenic Mill Creek, just off the Chesapeake Bay and Severn River. Located on Mulberry Hill Road in Annapolis, this beautiful and secluded home offers stunning views, abundant natural light, and a peaceful setting just minutes from downtown.

This airy home features a bright open floor plan, a beautiful loft with plenty of room for guests. Enjoy year-round comfort—cozy up by the fireplace in winter, or take in the summer breeze and fall colors from the expansive deck overlooking the water.

The fully equipped kitchen boasts modern stainless-steel appliances and ample space for entertaining. The property includes docking for two boats and deep-water access, perfect for boating, crabbing, and fishing enthusiasts.

Conveniently located just five minutes from the U.S. Naval Academy, West Annapolis, and historic downtown Annapolis, this home provides easy access to shopping, dining, and entertainment. Washington, D.C. and Baltimore are each only 30 minutes away.

Local highlights include Cantler’s Riverside Restaurant, a renowned spot for seafood and steamed crabs right on the water, as well as the charming shops and cafés along Main Street and in nearby West Annapolis. Outdoor lovers will appreciate the close proximity to, Sandy Point State Park, and nearby golf courses and trails for year-round recreation.

Whether you’re looking for a primary residence, a vacation retreat, or an investment property, this waterside home offers a rare opportunity to enjoy the best of Annapolis living—tranquil, scenic, and perfectly situated.

SHOWINGS BY APPOINTMENT ONLY/LISTING AGENT MUST ACCOMPANY/DO NOT WALK PROPERTY WITHOUT AN APPOINTMENT/NO SIGN ON PROPERTY

ANNAPOLIS

2203 MULBERRY HILL ROAD

3 Beds

2 Baths

1,994 Sq.Ft.

$1,350,000

MLS#: MDAA2124204

OPEN HOUSE LOCATION on 11/23 is 9 Rusty Red Dr. in Annapolis. At our show home. Welcome to Towne Row - A community of 18 Luxury Townhomes in the Annapolis Town Center Corridor.
A Towne Row home is superior in every way. The craftsmanship and expansive spaces are apparent immediately. Notice the contemporary exterior, rooftop terrace for entertaining and stargazing, and two-car garage. Savor the spacious kitchen and luxurious owner's suite, privately situated on its own level, and the high-end materials and fixtures throughout. Live graciously and vertically on four generous levels, whisked up and down by your private elevator. This is Towne Row, your haven, your showplace, your new home. It's like none other in Annapolis. Features include: 3,100 Square Feet of Living Space, 3 Bedrooms + Den, 3 Full Baths, 2 Half Baths , Expansive Gourmet Kitchen With Walk-out Deck, Private Elevator, Elegant, Spacious Owner's Suite on Its Own Level, Quartz Countertops Throughout, Four Levels of Finished Living Space, Rooftop Deck With Space for Hot Tub, Two-car Garage, Energy Star & LEED Gold Certified

Location, location, location. Living at Towne Row puts you in the heart of the bustling Annapolis Town Center corridor. You have instant access to an array of upscale and casual restaurants, boutiques and shops, favorite grocery stores, sophisticated fashion and home goods retailers, fitness clubs, movie theaters, and essential services. Plus, you'll be minutes from the Annapolis historic district, endless waterways, nearby marinas, and a short drive to Baltimore and Washington, D.C. It's luxury living and convenience beyond compare.
A 5 % deposit reserves your new home! Sturbridge Homes is offering a generous pre-construction incentive package for early buyers, including: $40,000 in closing cost credit, $30,000 in options and upgrades, including a hot tub installed on the rooftop terrace, no upcharge for end units, a one-year membership to Lifetime Fitness. Get in on these specials now, lock in current pricing, and have the ability to customize your home! Conditions apply. Sales Center appointments are available now. A sample of the builder's work nearby is available to tour.
Lot dimensions, floor plans, and square footage figures are approximate. Architectural renderings are samples only and may not reflect the exact product. The Riva Road address is for reference/GPS ease only. Once the community road is constructed, it will be called "Sellew Rd."

ANNAPOLIS

2555 RIVA ROAD

3 Beds

3 Baths

3,100 Sq.Ft.

$1,350,000

MLS#: MDAA2113932

Welcome to your dream home nestled in the sought after water privileged community of Anchorage, where life meets comfort and recreation. This stunning 5 bedroom, 2.5 bath beauty is designed for both relaxation and entertainment, offering a perfect blend of modern updates and classic charm.
Step inside to discover a bright and airy open concept living space, enhanced by an updated kitchen featuring elegant quartz countertops and sleek stainless steel appliances, including a 6 Burner Wolf Cooktop. This professional-grade cooktop is perfect for those who love to cook and entertain. Whether you’re hosting a dinner party or enjoying a casual meal, this kitchen is sure to impress. The adjacent dining area flows seamlessly into the spacious living room, providing an inviting atmosphere for family gatherings. Extend your living space outdoors where a delightful screened-in porch awaits, perfect for sipping morning coffee or enjoying evening cocktails. The deck and patio area offer additional space for alfresco dining and entertaining, all overlooking a fully fenced-in backyard…ideal for children and pets to play freely. Enjoy the numerous community amenities that make Anchorage a true gem, including access to a marina and boat ramp for your boating adventures, a basketball court for some friendly competition, and a sparkling swimming pool to cool off during warm summer days. With downtown Annapolis just a short drive or boat ride away, you’ll have the best of both worlds. Don’t miss this opportunity to make this exquisite home your own and experience the vibrant coastal lifestyle that awaits you in Annapolis!

ANNAPOLIS

3130 STARBOARD DRIVE

5 Beds

2 Baths

2,727 Sq.Ft.

$1,350,000

MLS#: MDAA2128728

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15 right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!

ANNAPOLIS

1836 CHERRY ROAD

None Beds

None Baths

3.92 acres

$1,300,000

MLS#: MDAA2126556

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!

ANNAPOLIS

1814 PLEASANT PLAINS ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2126554

RANCHER & DETACHED APARTMENT DWELLING on 3.92 WOODED ACRES WITH ACCESS 15' RIGHT OF WAY TO SCENIC BURLEY CREEK! PRIVACY & SERENITY mere minutes from Downtown City Dock Harbor and the Bay! Pier with 15’ right of way from Burley Lane to a 35' wide fee simple area along Burley Creek water frontage and Chesapeake boating access via Whitehall Bay. Sprawling stone Rancher boasting organic hardwoods, abundant windows framing verdant views, 4-season Sunroom, stone fireplace Living Room, updated Kitchen, 3 flexible-use Bedrooms, & 1 Bath. Unfinished basement for workshop/hobbyist and roomy 2-car garage. Rear fenced pool encircled by lush woodland and rambling lawns! Driveway meandering back to detached dwelling with lower 2-car garage and upper level 2BR/1BA apartment offering a screened porch treetop overlook to woodland hosting wildlife neighbors in their undisturbed habitats. Separate 2-car/RV vehicle/boat carport. Prime location minutes from historic Downtown, the USNA, Towne Centre & Westfield Malls, Chesapeake beaches & Bay Bridge, and commuter RTs 50/2/97. A RARE COMBINED LAND & HOME PARCEL TO CREATE YOUR OWN COMPOUND!!

ANNAPOLIS

1814 & 1836 PLEASANT PLAINS & CHERRY ROAD

5 Beds

2 Baths

1,919 Sq.Ft.

$1,300,000

MLS#: MDAA2124862

#MDAA2132396

ANNAPOLIS

45 E LAKE DRIVE

None Beds

None Baths

0.45 acres

$1,299,900

MLS#: MDAA2132396

Amazing NEW CONSTRUCTION is now complete! Experience luxury living in this beautifully crafted new home, located in the amenity-rich waterfront community of Arundel on the Bay. Enjoy some partial water views and exceptional design throughout. This quality-built residence features wide-plank hardwood floors, gorgeous, detailed trim work throughout and a thoughtfully designed open-concept layout. The gourmet kitchen boasts contemporary quartz countertops, GE Café appliances including a gas range, microwave drawer, stainless farm sink, center island,and stylish brushed bronze fixtures and lighting! A dedicated office on the main level provides the perfect work-from-home space or 4th bedroom area! The spacious owner's suite offers vaulted ceilings, a custom walk-in closet, and a spa-inspired bath. An additional ensuite bedroom provides comfort and privacy for guests or family. Main garage level has the opportunity for ANOTHER full bath (has rough in) and either another bedroom or large recreational room! Gorgeous TimberTech Decking w/contemporary rails runs entire length of home! Fall in love with everything it has to offer! Be sure to see the pier and playground area a few blocks down the road! Custom builder C.A.Desimone

ANNAPOLIS

3506 ROCKWAY AVENUE

4 Beds

3 Baths

2,875 Sq.Ft.

$1,299,000

MLS#: MDAA2117330

New on site 2 days ago

Foreclosure opportunity in sought-after Annapolis! Spacious 4BR/3.5BA Colonial with over 4,500 sq ft of living space. Features include multiple living areas, large kitchen footprint, finished lower level, and generous bedroom sizes. Private backyard with in-ground pool ready to be restored. Excellent potential for renovation or investment. Convenient to shopping, dining, major routes, and downtown Annapolis. Sold strictly AS-IS.

Schedule your showing now!

ANNAPOLIS

371 CARRIAGE PARK WAY

4 Beds

3 Baths

6,724 Sq.Ft.

$1,282,500

MLS#: MDAA2133126

Experience the Essence of Annapolis Charm at 179 Green Street

Nestled in the heart of historic downtown Annapolis, this beautifully updated home blends timeless character with modern comforts. Just steps from vibrant Main Street, the waterfront, boutique shopping, and Annapolis Elementary School, this location offers the very best of city living in one of the city's most coveted neighborhoods.

Inside on the main level, you'll find wide-board pine floors, a thoughtfully updated kitchen with new cabinetry and appliances, and inviting front and side porches perfect for morning coffee or evening relaxation. Rarely found in downtown Annapolis, two oversized off parking spaces add incredible convenience.

Upstairs, the home features two spacious bedrooms and a versatile third room—ideal for a home office, den, or oversized walk-in closet. The newly fenced backyard offers a private oasis for entertaining, dining al fresco, or simply enjoying the outdoors.

Living at 179 Green Street means immersing yourself in a lifestyle rich with history and culture. Stroll cobblestone streets to award-winning restaurants, art galleries, and the iconic City Dock. Enjoy sailing, community events, and the vibrant energy of downtown—right outside your door.

Don’t miss your chance to own a piece of Annapolis charm. Schedule your private tour today.

ANNAPOLIS

179 GREEN STREET

2 Beds

1 Baths

1,656 Sq.Ft.

$1,175,000

MLS#: MDAA2111662

Perfectly situated just minutes from the heart of Downtown Annapolis, yet tucked away for privacy, this 4 br, 3.5 bath NEW CONSTRUCTION coastal inspired home with a 2 car garage and optional detached guest cottage by Whitehall Building & Company offers the best of both worlds—convenience and tranquility. With over 3,400 square feet of finely crafted living space across three levels, every detail has been thoughtfully designed to deliver both comfort and sophistication. Step inside and be greeted by soaring 10-foot ceilings, expansive wide-plank flooring, and an open-concept layout ideal for both everyday living and elegant entertaining. The chef’s kitchen is the centerpiece of the home, featuring a grand center island, quartz countertops with matching backsplash, premium stainless steel appliances, and abundant storage. Flowing seamlessly into the breakfast area and spacious family room, this home is designed for hosting unforgettable gatherings. A versatile flex room offers the perfect space for a formal dining room, private home office, or cozy reading retreat. Additional main-level highlights include a custom mudroom, walk-in pantry, and stylish powder room. The upper level is a true sanctuary, boasting a luxurious primary suite with a generous walk-in closet and spa-inspired bath complete with dual vanities, a frameless glass shower, and a freestanding soaking tub. Two additional bedrooms share a beautifully appointed guest bath, while a convenient second-floor laundry room adds ease to daily living. The lower level provides endless possibilities, including a spacious recreation room, full bath and optional 5th bedroom—perfect for overnight guests or extended family. For those seeking even more flexibility, an optional detached guest house is available, offering a private one-bedroom suite with full bath, living room, and kitchenette—an ideal space for visitors, multigenerational living, or an au pair. All of this in an enviable location just minutes from the U.S. Naval Academy, fine dining, boutique shopping, waterfront attractions, and major commuter routes. Don’t miss the opportunity to personalize your finishes and create the luxury home of your dreams in the heart of Annapolis. Permits are almost fully approved and delivery of your new home is only 8 months away.

ANNAPOLIS

13 ELLIOTT ROAD

4 Beds

3 Baths

3,292 Sq.Ft.

$1,175,000

MLS#: MDAA2123968

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive water access community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,255 Sq.Ft.

$1,170,000

MLS#: MDAA2121748

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.

ANNAPOLIS

103 STILLY WAY

5 Beds

5 Baths

5,200 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!

ANNAPOLIS

1 TUCKER STREET

3 Beds

2 Baths

1,869 Sq.Ft.

$1,145,000

MLS#: MDAA2125152

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