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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

391

# of Listings

3

Avg # of Bedrooms

$455

Avg. $ / Sq.Ft.

$1,131,506

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

391 Properties Found. Page 4 of 27.

Incredible opportunity to own this once in a lifetime property in the heart of Downtown Annapolis! Wonderful and extensive updates including a new grease trap, new grease lines, new sanitary lines, new counter tops, freshly renovated bathrooms and more! The listing is for the building only but the seller is willing to consider all offers!

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$2,450,000

MLS#: MDAA2105176

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$2,390,000

MLS#: MDAA2113706

Turnkey opportunity in the heart of historic Downtown Annapolis! Located on bustling Main Street just steps from City Dock, this beautifully renovated restaurant space offers prime visibility and unbeatable foot traffic. The interior features seating for 89 guests, with additional outdoor dining for 12, and all major updates completed 2022 - 2024, including a new grease interceptor, updated sanitary lines, and remodeled restrooms. Views of the harbor from all three levels.

The bar area is the perfect setting to make locals feel at home and have visitors wishing they were locals!

This versatile space is ready for your vision. Zoned C2 and surrounded by local shops, restaurants, and waterfront views, it’s the perfect spot to bring your concept to life in one of Maryland’s most charming and visited destinations.

Seller will negotiate the purchase of all furnishings and equipment, will also consider long term lease.

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$2,350,000

MLS#: MDAA2118114

Turnkey opportunity in the heart of historic Downtown Annapolis! Located on bustling Main Street just steps from City Dock, this beautifully renovated restaurant space offers prime visibility and unbeatable foot traffic. The interior features seating for 89 guests, with additional outdoor dining for 12, and all major updates completed 2022 - 2024, including a new grease interceptor, updated sanitary lines, and remodeled restrooms. Views of the harbor from all three levels.

The bar area is the perfect setting to make locals feel at home and have visitors wishing they were locals!

This versatile space is ready for your vision. Zoned C2 and surrounded by local shops, restaurants, and waterfront views, it’s the perfect spot to bring your concept to life in one of Maryland’s most charming and visited destinations.

Seller will negotiate the purchase of all furnishings and equipment, will also consider long term lease.

ANNAPOLIS

81 MAIN STREET

None Beds

None Baths

N/A

$2,350,000

MLS#: MDAA2117302

**TEAR DOWN/NEW BUILD PACKAGE** The homesite sits on an elevated 3 acres offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. The proposed Luxury Wye Mills model features an open concept with the convenience of single level living as the primary suite and an additional bedroom with ensuite full bath along with laundry are all on the main level! The gourmet kitchen with an oversized island adjoins the dining room and overlooks a large family room with access via French sliders to a covered porch --- perfect for hosting family and friends! A huge walk-in pantry with coffee bar and a mudroom/powder room off of the garage complete the main level. The upper level features 2 additional bedrooms with ensuite bathrooms and walk-in closets. The basement offers a finished rec area with the option of adding 2 additional bedrooms and a full bathroom and/or finishing additional living space to create the theater room/home gym, etc of your dreams. The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department
requirements, with the final piece being a public water extension along the existing house frontage. The
subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the
legwork to get it to this point will convey. PLEASE NOTE: The existing home does have a moisture issue, and the HVAC system is not currently functioning. Call agent for more info. Documentation for the subdivision
efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed
subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The
home is being sold strictly as-is, where is. Any inspections for buyer's information only. Existing home without new build package listed under MLS#: MDAA2103336.

Builder is offering $10,000 towards options with use of preferred lender and title companies. HARDI-PLANK SIDING IS STANDARD! CO-PERM FINANCING REQUIRED - 100% VA CO-PERM OPTIONS AVAILABLE - BUILDER'S PREFERRED LENDER HAS GREAT RATES & A SPECIAL 5% DOWN NO PMI LOAN PROGRAM FOR BUYERS IN CERTAIN MEDICAL & PROFESSIONAL FIELDS! PLEASE NOTE: Photos are representative of builder's work and show previously completed custom homes with options/upgrades. Buyer must be pre approved for construction to permanent financing before meeting with builder and touring homes that are under construction. Please visit Whitehall Building website for more info. **PLEASE DO NOT SHOW WITHOUT AN APPOINTMENT**

ANNAPOLIS

1634 ORCHARD BEACH ROAD P 269

4 Beds

4 Baths

3,803 Sq.Ft.

$2,350,000

MLS#: MDAA2113364

Built by Captain Beriah Maybury in 1772 and known as the Kings' Arms Tavern, this Historically designated property is a MUST SEE! This Five-Bay wide brick Single Family Home sits on top of a high scored stone foundation. 9.5 foot ceilings illuminated by nearly floor to ceiling windows showcase a lovely Library with built-In Bookcases and a wood burning Fireplace; a Two Room Parlor, also with a wood burning Fireplace; an addition erected possibly as early as the 1830's includes a large Dining Room with high domed ceiling, a kitchen and a small porch. The upstairs 4 Bedrooms, 3 with their own wood burning Fireplace, wood floors, 2 full Baths and laundry provide plenty of room! The partially finished basement, most recently used as a woodworking shop, has a separate street entrance and could possibly be reimagined as additional living space. The long, gated driveway leads to 2 garage spaces and parking for an additional 6 cars and a charming English garden and patio area. Furnace chimney recently relined. This home is being sold AS IS, but has great bones. Bring your own TLC. Call Listing Agent with questions.

ANNAPOLIS

41 CORNHILL STREET

4 Beds

2 Baths

4,404 Sq.Ft.

$2,300,000

MLS#: MDAA2109384

Fabulous waterfront "Deck Home" with heated saltwater pool and unprecedented views across Broad Creek out to the South River. This special residence located in the Southwater Point enclave of waterfront homes offers the perfect elevation to oversee the stunning sunset and water views. The layout of the home is perfectly designed to enjoy the ever changing scenery from almost every room in the home. The well appointed interior boasts painted wood vaulted ceilings, exposed beams and gleaming hardwood floors throughout the main level. The gourmet Kitchen with island flows into the spacious Living room and Dining room with the floor to ceiling brick fireplace as the focal point. A cozy place to gather on a cool winter night! The expansive rear deck or the sun room off the kitchen are ideal for entertaining or relaxing all year long. The Primary bedroom suite on the main level exudes a true sense of peace and serenity with the panoramic water views, access to rear deck and a luxurious spa like bath featuring, double vanities, heated floors, soaking tub, huge walk-in shower and enviable custom closet. Head down the stairs to the lower level walkout with walls of glass and heated floors to enjoy the Family room with additional fireplace, 2 spacious and light-filled bedrooms with shared bath and a fully equipped bar area that is perfect for hosting all the friends and family that are sure to visit! Let the party flow out to the lower level patio and to the refreshing pool with expansive deck or head to the water's edge with easy access via the tram or stairs to the private pier with 2 boat lifts; perfect for the boating enthusiast. The detached 2 car garage completes this amazing property and the ideal location for quickly accessing the South River or Chesapeake Bay by boat, heading by car to Historic Annapolis or hopping on Rt. 50 to get back to Washington, DC., makes this property a must see. Welcome Home!

ANNAPOLIS

2908 SOUTHWATER POINT DRIVE

3 Beds

2 Baths

3,243 Sq.Ft.

$2,245,000

MLS#: MDAA2100378

The One That Outshines Them All—Near Downtown Annapolis

This stunning newly built colonial home is a true showcase of thoughtful design and refined craftsmanship, beautifully situated on 1.34 acres with no association fees to limit your lifestyle. From the rich French white oak flooring and custom stair railings to the intricate glass doorknobs and solid wood doors, every detail has been lovingly chosen. The chef’s kitchen is both stylish and functional, featuring white cabinetry with distinctive hardware, whimsical lighting, and a walk-in pantry complete with a sink and illuminated shelving. Spanning four thoughtfully planned levels, the third floor hosts five bedrooms, including a serene primary suite with an attached bath, as well as an oversized laundry room with custom cabinetry, work space, and a utility sink. The top level offers flexible space ideal for an au pair suite, while the fully finished lower level includes a rec room, full bath, bedroom, and walk-up access to the backyard. Car lovers and tinkerers alike will appreciate the three-car finished attached garage with soaring two-level ceilings, offering space for vehicles, hobbies, and storage galore. Located just minutes from downtown Annapolis—Maryland’s capital filled with charm, history, waterfront dining, and the U.S. Naval Academy—and with easy access to Routes 50 and 97, this home delivers elegance, space, and freedom in one exceptional package.

ANNAPOLIS

934 CHESTERFIELD ROAD

6 Beds

5 Baths

5,636 Sq.Ft.

$2,190,000

MLS#: MDAA2116832

Once-in-a-Lifetime Opportunity to Build Your Dream Waterfront Home in Bay Ridge. See potential plans in the pictures and meet the builder to discuss your dream home or bring your own builder. Don't miss your chance to own the last remaining waterfront lot in the prestigious and highly sought-after Bay Ridge community. This is a rare opportunity to design and build your dream home on a premium lot offering 57 feet of serene waterfront on protected Lake Ogleton. Enjoy breathtaking, unobstructed views and the peaceful lifestyle that only true waterfront living can offer. Whether you're envisioning a luxurious modern retreat or a timeless coastal home, this lot is the perfect canvas. Contact the listing agent for insight and inspiration on potential home designs tailored to this exceptional property. Bay Ridge is renowned for its rich history, vibrant community, and unmatched amenities, including a bayfront community pool and newly renovated clubhouse, sandy beaches and scenic waterfront , a large community marina, basketball and pickleball courts, a children's playground, and year-round community events. Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the charm of a tight-knit neighborhood with the convenience of city access. Experience the perfect blend of tranquility and community in one of the most desirable waterfront enclaves on the Chesapeake Bay. This is more than just a lot—it's the beginning of your dream lifestyle.

ANNAPOLIS

48 E LAKE DRIVE

None Beds

None Baths

0.22 acres

$2,150,000

MLS#: MDAA2118680

Wonderful waterfront home located on deep Oyster Creek with direct access to the Chesapeake Bay! Sprawling three levels of waterfront views fronted by large screened in porches, the home provides great areas for entertaining with a blend of coastal living. Custom-built in 2004 by a former midshipman, this energy efficient property is equipped with two separate Geo Thermal HVAC systems that keep the home comfortable year-round with fractional energy costs compared to comparable and even smaller homes on standard systems. Inside, the home boasts hardwood flooring, 9-foot ceilings, and large Anderson windows with views overlooking the water and private pier, which is equipped with water and electricity. Natural light beams into the living areas of the home, which feature wood burning-fireplaces located on two of the three levels. Crown and wall moldings throughout emphasize the custom craftsmanship that was put into the home when built. A modern kitchen with a cooktop and double wall oven are paired with granite countertops. The kitchen leads to the main eating and living area overlooking Oyster Creek with the Chesapeake Bay in the distance. A large master bedroom with a tray ceiling sits atop the third level with two individual decks perfect for enjoying a morning beverage. Two separate walk-in closets in the master provide ample space for all wardrobe needs. Master bath includes a jetted tub, walk in shower and double vanity. Main entrance level is highlighted by a beautiful cherry wood bar complete with accompaniments including a wine fridge, mini fridge, kegerator and highlighted by built in shelving. This area sets the tone for entertaining as guests can walk out onto the two-level screened in porch connected by a spiral staircase. The exterior lawn area is complete with hardscapes, lighting and irrigation systems. The rear patio and large yard along Oyster Creek provides plenty of space for outdoor gatherings, badminton, and volleyball. The waters edge is solidified by rip rap leading to the private pier, with a mean low water depth of 4 feet, ready for your boat. Of note, this home is also NOT in a flood plain, and does NOT require flood insurance.
This incredible home is located just minutes away from downtown Annapolis and Eastport. The Community provides a gated private beach on the Chesapeake Bay complete with a new playground within walking distance, along with community piers for boating and fishing.
Interior pictures COMING SOON!

ANNAPOLIS

1242 WASHINGTON DRIVE

5 Beds

4 Baths

3,687 Sq.Ft.

$2,100,000

MLS#: MDAA2105588

#MDAA2117576

ANNAPOLIS

1090 RIVER BAY ROAD

4 Beds

3 Baths

2,476 Sq.Ft.

$2,050,000

MLS#: MDAA2117576

PRICE REDUCTION - Exciting Opportunity in Sherwood Forest – Enjoy breathtaking panoramic water vistas of Brewers Pond and Round Bay on the Severn River. Observe Bald Eagles, Herons, and Osprey soaring amidst the stunning backdrop from your water view deck or spacious living room adorned with floor-to-ceiling windows. This elegantly designed home, nestled in the hillside, seamlessly blends modern amenities with the charm of a traditional cottage. Situated on one of the most secluded homesites in Sherwood Forest, ample parking is available for entertaining family and friends. Sherwood Forest is a prestigious gated community comprising 341 residences. Residents enjoy access to a plethora of amenities including a spacious multi-purpose Club House, General Store, 9-Hole Golf Course, 6 Tennis Courts, Marina, Beaches, Swimming Pool, Basketball Court, Bowling Alley, Pickle Ball Courts, Archery Pit, Nature Lab, and a renowned Children’s Summer Camp Program. Numerous fields throughout the neighborhood cater to various sports such as Lacrosse, Soccer, Football, Softball, Volleyball, and Badminton. The surrounding forest boasts over 5 miles of scenic walking and mountain biking trails, with a picturesque 2-mile waterfront loop offering captivating views of the Severn River and Brewers Pond. Golf carts are the preferred mode of transportation within the community. The vibrant social calendar is filled with events including the 3rd of July Fireworks, 4th of July Parade, Summer Dances, 5K Race, Corn Roast, Clam Bake, Tennis and Golf Tournaments, and much more. Holiday festivities cater to both adults and children alike. A one-time $20,000 membership fee to join the Sherwood Forest Club is required as part of your Real Estate Transaction.

ANNAPOLIS

201 NOTTINGHAM HILL

5 Beds

3 Baths

2,353 Sq.Ft.

$1,980,000

MLS#: MDAA2115758

Perched above a quiet cove just minutes from downtown Annapolis, this refined Southern Colonial offers a rare combination of privacy, flexibility, and water views that will never be obstructed. With the Chesapeake Bay Foundation Nature Sanctuary directly across the creek, the setting is defined by light, sky, and uninterrupted natural beauty.\n\n

Graciously scaled living and entertaining spaces open to multiple covered porches and terraced gardens, all oriented toward the water. Inside, natural light fills the home through French doors and oversized windows, while detailed millwork, wide-plank hardwoods, and coffered ceilings create a sense of quiet sophistication. The kitchen is a true chef’s space — outfitted with custom cabinetry, a commercial-grade range, and generous work surfaces for hosting or day-to-day living.\n\n

Beyond the main residence, two fully finished private living quarters are seamlessly integrated into the home’s layout — one tucked on its own wing with separate entry and kitchenette, the other on the walkout level with its own full kitchen, bath, living room, and water-facing porch. Whether used for extended family, guests, or professional hosting, these suites add rare versatility while preserving the elegance of the whole.\n\n

The landscaped half-acre lot leads gently to a private dock and natural shoreline ideal for paddleboarding, kayaking, or simply enjoying the quiet.\n\n

3209 Henson is a property that lives beautifully in all seasons — offering timeless design, flexible spaces, and a lifestyle rooted in privacy, nature, and proximity to the best of Annapolis.

ANNAPOLIS

3209 HENSON AVENUE

5 Beds

5 Baths

4,348 Sq.Ft.

$1,950,000

MLS#: MDAA2117340

Welcome to 21 Chesapeake Landing, the epitome of Eastport’s waterfront lifestyle. Nestled at the tip of the Eastport Peninsula in a premier gated community, this exceptional four-level townhome with amazing water views offers luxury living in one of Annapolis’s most sought-after enclaves. This lovingly-maintained home has been thoughtfully designed with meticulous, craftsman-level upgrades. The result is a seamless blend of elegance, comfort, and timeless design. At the heart of the home is a spectacular chef’s kitchen: A generous center island invites casual gatherings, while warm-toned custom cabinetry, complete with artful display nooks, add depth and functionality. Sleek stainless-steel appliances pair beautifully with the honed-granite countertops, to provide ample prep space for the most discerning gourmet. A private deck just off the kitchen is perfectly positioned for effortless outdoor grilling. The open-concept layout is both flexible and inviting. Island seating flows naturally into the adjacent dining area, which overlooks the living room and captures water views beyond. Rich, gleaming hardwood floors span the main, bedroom, and loft levels, adding warmth and sophistication throughout. On the ground level, beautifully finished neutral tile flooring provides a clean and durable foundation for everyday living. The living room is a true retreat, enhanced by 9-foot ceilings and a gas fireplace that adds instant ambiance with the flip of a switch. Expansive sliding glass doors open onto a newly expanded deck; an ideal setting for savoring water views, or simply relaxing with evening libations. It’s also a front-row seat for the 4th of July, New Year’s Eve fireworks displays and the annual Blue Angels Airshow; a spectacular bonus that makes this home truly unique. Upstairs, the graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. Glass doors provide yet another opportunity to connect with the view. The recently renovated spa-inspired ensuite bath is a sanctuary in itself, featuring a glass-enclosed shower and soaking tub that doubles as a steam room complete with folding chairs to relax and reap the therapeutic benefits a sauna provides. Dual vanities, high-end fixtures, and generous storage, all finished in calming, modern tones complete the experience. Two additional bedrooms offer versatility and comfort; ideal for guests, family, or as a dedicated art studio, home gym, or private home office. The ground-level living space adds even more flexibility. Outfitted with a full bath and a custom kitchenette—including a refrigerator, sink, microwave, and built-in storage. This area can be completely closed off from the rest of the home, making it a perfect in-law suite or private guest quarters. Additional amenities include a one-car garage, an extra driveway parking space, a large paver patio, and the freedom to lock, leave, and travel with peace of mind. Outside your front door, the Eastport lifestyle unfolds. Take a leisurely stroll to local waterfront restaurants, pubs, and boutique shops. Catch a water taxi to historic downtown Annapolis, or launch your kayak or paddleboard from nearby Horn Point Beach Park. Eastport offers the charm of a coastal village with the energy of a thriving maritime hub, just across Spa Creek from the U.S. Naval Academy and all the culture, history, and amenities of downtown Annapolis. As a resident of Chesapeake Landing, you also have the option to join, for a fee, the private Annapolis Maryland Yacht Club, located within the gates of the community, featuring a pool, marina, and clubhouse. 21 Chesapeake Landing is more than a home, it’s a lifestyle. This is a rare opportunity to experience the best of Annapolis in a setting that’s both refined and relaxed. Don’t miss this opportunity to make it yours!

ANNAPOLIS

21 CHESAPEAKE LANDING

4 Beds

3 Baths

2,232 Sq.Ft.

$1,885,000

MLS#: MDAA2117644

Gorgeous, One-of-a-Kind Luxury Penthouse in Downtown Annapolis!
Welcome to this stunning 3-bedroom, 3.5-bathroom penthouse condo in the exclusive Acton’s Landing community—offering an unparalleled blend of historic charm and sophisticated modern living. With private elevator access, deeded use of two garage parking spaces, and two expansive balconies with breathtaking skyline views, this residence is truly exceptional.
Thoughtfully designed to capture natural light from sunrise to sunset, the open floor plan features a gourmet kitchen boasting Silestone countertops, custom tile backsplash, custom cabinetry, new refrigerator, new dishwasher, gas cooking, wine fridge, under cabinet lighting, and updated fixtures.
Recent upgrades include new HVAC system, new hardwood flooring, and new high-end wall to wall carpet in the 3 bedrooms, new dining room chandelier. The powder room and main level ensuite bath has been updated. The laundry room has custom built-in cabinetry, new flooring, new washer, dryer, and 2 refrigerated beverage drawers. Entire unit freshly painted for a crisp, modern feel.
Residents of Acton’s Landing enjoy first-class amenities: secure entry, on-site property management and assistant, a fitness center, recreation and meeting rooms, library, and a beautifully landscaped courtyard with a central fountain.
Steps from Acton’s Cove waterfront park, boutique shopping, fine dining, the U.S. Naval Academy, Maryland State House, and the Governor’s Mansion—this is the perfect fusion of urban convenience and tranquil retreat.
Don’t miss this rare opportunity to live in one of Annapolis’ most coveted locations!

ANNAPOLIS

66 FRANKLIN STREET 509

3 Beds

3 Baths

2,477 Sq.Ft.

$1,850,000

MLS#: MDAA2116316

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