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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

300

# of Listings

3

Avg # of Bedrooms

$467

Avg. $ / Sq.Ft.

$1,062,130

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

300 Properties Found. Page 3 of 20.

#MDAA2103110

ANNAPOLIS

2175 CHESAPEAKE HARBOUR DRIVE

4 Beds

4 Baths

2,513 Sq.Ft.

$2,595,000

MLS#: MDAA2103110

Don’t miss the rare chance to create your waterfront dream lifestyle in the highly sought-after Bay Ridge community. This premium lot offers sweeping views of the Chesapeake Bay from the rear and serene lake views from the front—an unparalleled setting for your custom-designed home. This stunning 4-bedroom, 3.5-bathroom residence has been thoughtfully designed to maximize the views, featuring expansive front and rear porches perfect for enjoying breathtaking sunrises and sunsets. The home showcases exceptional craftsmanship and luxury finishes throughout, including Hardiplank siding, wide-plank luxury vinyl flooring, a gourmet kitchen with quartz countertops and backsplash, upgraded stainless steel appliances, a spacious island, soaring 10-foot main level ceilings, and spa-inspired ceramic and porcelain baths. Bay Ridge is a community unlike any other, steeped in history and cherished for its vibrant spirit and unmatched amenities. Residents enjoy a bayfront pool and newly renovated clubhouse, sandy beaches, scenic waterfront areas, a large community marina, basketball and pickleball courts, a children’s playground, and year-round events that bring neighbors together. Ideally located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the rare combination of a private, resort-style lifestyle within easy reach of city conveniences.
This is more than just a homesite—it’s an invitation to design and build the perfect retreat, where every day feels like a vacation and every view inspires.(This property is also listed as a lot with the existing home which can be remodeled or torn down)

ANNAPOLIS

45A E LAKE DRIVE

4 Beds

3 Baths

3,824 Sq.Ft.

$2,375,000

MLS#: MDAA2124836

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

2,550 Sq.Ft.

$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

5,484 Sq.Ft.

$2,350,000

MLS#: MDAA2113364

Iconic Views | 90 River Drive, Bay Ridge!
Wonderful opportunity to create your own waterfront oasis in the heart of Bay Ridge, Annapolis. Enjoy breathtaking views of the Bay Bridge and direct access to one of the area’s most spectacular private beaches. Nestled in a vibrant coastal community known for its sailing, beach walks, and friendly charm, this property offers a rare blend of lifestyle, location, and flexibility. The highly sought-after Bay Ridge community in Annapolis offers a rare blend of resort-style amenities and vibrant coastal charm. Residents enjoy a scenic community pool and clubhouse overlooking the sparkling waters of the Chesapeake Bay, as well as private community beaches on both the Bay and the River. Boating enthusiasts will appreciate the community marina, complete with a newly renovated clubhouse.

For those who prefer land-based recreation, Bay Ridge features basketball courts, ball fields, pickleball courts, playgrounds, and open green spaces, along with a year-round calendar of community events. Whether you’re walking or biking along miles of waterfront paths, the Bay Ridge lifestyle is truly one-of-a-kind.

Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the perfect balance of small-town charm and big-city access. Commuting is easy with nearby access to Routes 50 and 97, connecting you directly to Baltimore, BWI Airport, Fort Meade/NSA, and Washington, DC. And when it’s time for a getaway, the Eastern Shore and ocean beaches are just a short drive across the Bay Bridge.

Non-riparian water front. 1 ft of water front added for marketing purposes only.

ANNAPOLIS

90 RIVER DRIVE

None Beds

None Baths

0.19 acres

$2,300,000

MLS#: MDAA2120966

Coastal Charm with Iconic Views | 90 River Drive, Bay Ridge!
Experience timeless waterfront living at 90 River Drive in the heart of Bay Ridge, Annapolis. This beautifully appointed 3–4 bedroom, 4-bath home features a detached guest house, ideal for guests, a home office, or a studio space. Enjoy breathtaking views of the Bay Bridge and direct access to one of the area’s most spectacular private beaches. Nestled in a vibrant coastal community known for its sailing, beach walks, and friendly charm, this property offers a rare blend of lifestyle, location, and flexibility.
The highly sought-after Bay Ridge community in Annapolis offers a rare blend of resort-style amenities and vibrant coastal charm. Residents enjoy a scenic community pool and clubhouse overlooking the sparkling waters of the Chesapeake Bay, as well as private community beaches on both the Bay and the River. Boating enthusiasts will appreciate the community marina, complete with a newly renovated clubhouse.

For those who prefer land-based recreation, Bay Ridge features basketball courts, ball fields, pickleball courts, playgrounds, and open green spaces, along with a year-round calendar of community events. Whether you’re walking or biking along miles of waterfront paths, the Bay Ridge lifestyle is truly one-of-a-kind.

Located just minutes from downtown Annapolis and Eastport, Bay Ridge offers the perfect balance of small-town charm and big-city access. Commuting is easy with nearby access to Routes 50 and 97, connecting you directly to Baltimore, BWI Airport, Fort Meade/NSA, and Washington, DC. And when it’s time for a getaway, the Eastern Shore and ocean beaches are just a short drive across the Bay Bridge.

ANNAPOLIS

90 RIVER DRIVE

3 Beds

4 Baths

1,830 Sq.Ft.

$2,300,000

MLS#: MDAA2116342

Welcome to the Thomas Hyde House – a rare opportunity to own a piece of Annapolis history in the heart of downtown. Built in 1769, this impeccably restored Federal- style property blends 18th-century charm with modern luxury. Perfectly situated on sought- after Duke of Gloucester Street, this vibrant and colorful home offers stunning views of the Maryland State House and extremely rare off-street parking for nine vehicles.

Originally configured as office space, the residence has been reimagined into six spacious bedrooms and four full baths across two beautifully remodeled levels, with the potential for third floor updating plus a large basement with ample storage and updating space. The first floor offers true single level living with a primary suite and second bedroom, while the second level features four additional bedrooms and a convenient laundry area.

No detail has been overlooked – from new appliances, countertops, and cabinetry to frameless glass showers, ceramics, extensive trim and molding, recessed lighting, fresh interior and exterior paint, updated flooring throughout and more. The result is a turnkey home where historic character meets modern sophistication & luxury.

The property is offered with negotiable furnishings, electronics and art, The Thomas Hyde House is as versatile as it is fun and captivating. Just steps from downtown Annapolis shopping, dining, yacht clubs, local marinas & major commuter routes. Whether as a primary residence, investment property, or distinctive downtown retreat, this is an Annapolis treasure ready for its next chapter.

ANNAPOLIS

192 DUKE OF GLOUCESTER

6 Beds

4 Baths

3,415 Sq.Ft.

$2,200,000

MLS#: MDAA2122834

This waterfront Annapolis retreat in the sought-after Fishing Creek Farm community is one you don't want to miss! Perfectly sited on a quiet cul-de-sac, this home is ready to move into and elegantly designed for both everyday living and entertaining. Extensively renovated with over $500,000 in architectural and interior upgrades, the residence offers almost 3,700 square feet of thoughtfully designed space. The bright, open chef’s kitchen boasts custom cabinetry, marble countertops, designer backsplash, and top-of-the-line appliances—perfect for preparing intimate family meals or hosting large gatherings.
Step outside to the expansive deck, and enjoy waterfront views and breathtaking sunsets over Fishing Creek. The first floor includes a guest bedroom with full bath and an extra half bath, while the serene primary suite upstairs features water views and a beautifully renovated bathroom. Two additional en suite bedrooms complete the second level, complemented by updated baths, and fresh carpeting. Pull down stairs lead to additional attice storage as well as under the stairwell, and the eaves in the loft.
Don't miss the versatile loft above the garage that provides the perfect space for a home office, gym, or recreation room and lots of storage accessed off the back deck. Pull down attic stairs for additional storage
Living in Fishing Creek Farm offers more than a home—it’s a lifestyle. Residents enjoy resort-style amenities, including a private community beach with fire pit, pool, tennis and pickle ball courts, walking trails, and an active marina.

ANNAPOLIS

1307 BEACHVIEW ROAD

4 Beds

4 Baths

3,690 Sq.Ft.

$2,198,000

MLS#: MDAA2123232

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

$1,999,900

MLS#: MDAA2124832

23-acre parcel zoned primarily R-1, with some O-S. Preliminary engineering work indicates the property can be subdivided and coul support multiple residential lots. The concept drawing attached.

ANNAPOLIS

1016 E COLLEGE PARKWAY

None Beds

None Baths

23.33 acres

$1,995,000

MLS#: MDAA2123584

A rare opportunity for a well located worship facility on 23 acres in Cape St. Claire with exceptional frontage on Rt 50. This large complex with extensive acreage allows a congregation an unusual and great opportunity to grow or fund itself. Existing complex can be restored and used with a great opportunity for later expansion for a larger facility on the additional acreage. Selling addition acres for subdivision may be possible. Available preliminary engineering supports subdivision possibilities. This facility's main room is big enough for 175 and building boasts over 4600 total sq ft, includes a kitchen with serving bar, study, multipurpose room, foyer and reception desk, offices, and classrooms. Noteworthy architectural features include palladium windows, exposed brick, beamed ceilings and a custom staircase. The main building will require less updating and the parsonage, once used as offices, will require significant renovation. Property sold as-is, where-is. Zoning is residential and supports some commercial uses. See attached zoning table for R1 uses. All uses will require certificate of use and occupancy.

ANNAPOLIS

1016-1024 E COLLEGE PARKWAY

None Beds

None Baths

4,473 Sq.Ft.

$1,995,000

MLS#: MDAA2123582

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

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

6,957 Sq.Ft.

$1,895,000

MLS#: MDAA2116832

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

Location, location, location! INVESTOR alert for an apartment unit building that can be converted to a single family home in historic Annapolis! This property is steps away from city dock and all that downtown Annapolis has to offer! Enjoy incredible views of historic Annapolis & Spa Creek. The Red Brick Inn is currently being used as a full time Airbnb, but it can easily be converted to a single family home. There are a total of three separate apartments that have all been updated in 2014 and are all separately metered. Floor plans and additional information available upon request! Don’t miss out on this one!

ANNAPOLIS

15 NEWMAN STREET

7 Beds

None Baths

3,509 Sq.Ft.

$1,799,999

MLS#: MDAA2016852

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