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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

290

# of Listings

3

Avg # of Bedrooms

$450

Avg. $ / Sq.Ft.

$1,031,642

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

290 Properties Found. Page 3 of 20.

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

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

Nestled at the end of a quiet cul-de-sac and set on over half an acre, this rare waterfront opportunity on Mill Creek offers stunning panoramic views, tranquil privacy, and a lifestyle centered around the water. With a deep-water pier, a dock with a single slip, and a mean low water depth of 8 feet, the property can comfortably accommodate 80 foot vessels making it a dream for serious boaters and waterfront enthusiasts alike. The home is filled with potential, waiting for your vision to make the most of its prime setting. Hardwood floors flow throughout the main level, which includes a spacious living room with a fireplace and a large dining room just off the kitchen. The kitchen enjoys its own water view and is enhanced by sliding glass doors that open to the expansive deck, perfect for morning coffee or entertaining against a backdrop of sunrise skies over the creek. One of the standout features is the sunroom, with floor-to-ceiling windows that flood the space with natural light and offer uninterrupted water views year-round. At the far end of the home, the primary suite addition is a retreat of its own, complete with an en-suite bath, walk-in closet, and a few steps down to a dramatic sitting room with a two-story ceiling and a second fireplace. Sliding glass doors in both the bedroom and sitting room provide easy access to the deck and backyard, creating a seamless indoor-outdoor connection.
The lower level includes three additional bedrooms and a full bath, along with a laundry room and utility space. Mature landscaping surrounds the home, and a backyard shed provides extra storage.
Located in a sought-after waterfront community, this home offers convenient access to shopping, dining, marinas, and recreation. Mill Creek flows into the Chesapeake Bay, offering easy access to the Severn River and Downtown Annapolis, delivering the quintessential Annapolis boating lifestyle. This is an estate sale with key documents already in hand and ready for review. Whether you’re an investor, renovator, or hoping to create your dream waterfront retreat, this is a rare chance to secure a prime piece of Mill Creek shoreline.

ANNAPOLIS

1924 HIDDEN POINT ROAD

4 Beds

2 Baths

2,606 Sq.Ft.

$1,875,000

MLS#: MDAA2114178

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

FABULOUS PENTHOUSE. Embrace a lifestyle of unparalleled luxury and breathtaking views with this rare opportunity to own an exquisite penthouse at the GrandView in Annapolis Town Center. Perched atop the prestigious 12th floor, this sprawling residence stands as one of the most coveted penthouses, offering panoramic views that stretch for miles, complemented by two expansive balconies that provide front-row seats to the vibrant holiday events and outdoor venues of the Town Center.

Step inside to discover a world of refined elegance, where light cascades through oversized windows, illuminating the dramatic 11-foot ceilings that stretch overhead, creating an atmosphere of open, airy sophistication. This penthouse boasts an expansive layout, featuring three private ensuite bedrooms, each a serene retreat of comfort and luxury. A large den offers flexibility for your lifestyle, whether as a home office, media room, or additional guest space, ensuring this home meets your every need. Newly installed 2-Zone HVAC system, new tankless water heater, and new washer and dryer.

The heart of this home is the open floor plan, seamlessly connecting living spaces with Brazilian cherry hardwood and ceramic tile floors underfoot, exuding warmth and timeless elegance. The gourmet kitchen is a chef's dream, outfitted with high-end appliances, sumptuous granite countertops, and a massive kitchen island, making it perfect for hosting gatherings or savoring quiet moments over coffee.

GrandView isn’t just a residence; it’s a community that offers a true sense of belonging. Residents enjoy exclusive access to a rooftop sky lounge and pool, an outdoor kitchen, a state-of-the-art fitness center, and a club/party room, all designed to foster a lifestyle not just of luxury, but of wellness and social connectivity. The addition of a professionally managed concierge staff ensures every day is lived with ease, convenience, and security.

Situated in the heart of Annapolis, GrandView places you just a stroll away from the finest dining, Whole Foods, Target, Life Time Fitness Club, banking, and boutique shopping. Historic downtown Annapolis, the US Naval Academy, Anne Arundel Medical Center, and Annapolis Mall are mere minutes away, making this a dream location for commuters with quick access to Route 50 and 97.

Seize this unmatched opportunity to indulge in refined urban living at its most sophisticated. Schedule your showing today and take the first step into a life filled with luxury, comfort, and breathtaking beauty in this unparalleled penthouse residence.

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 1210

3 Beds

3 Baths

3,520 Sq.Ft.

$1,750,000

MLS#: MDAA2103424

Custom coastal craftsman home is currently under construction in Eastport - Annapolis, Maryland. This home will feature a perfect blend of classic Eastport and luxury coastal craftsman design. Permitting is complete. This expansive 3600 +/- (approx. 850 unfinished) sq. foot home will offer 4 bedrooms and 3 baths with an open floor plan concept. Truly an entertainer’s dream with hardwood floors, high ceilings, impressive millwork and trim, walk-in closets, beautiful gourmet kitchen, large rooms with multiple dining and gathering areas, and a fully finished basement. The second level of the home offers three bedrooms including the owner’s suite. The suite features a fireplace and master bath with dual vanity, frameless glass shower and soaking tub. The builder did not leave anything out, by placing an office or bedroom on the main level and washer and dryer on the second floor for convenience. The exterior of the home will include a charming front porch, back deck for hosting seasonal barbecues, and ample green space in the rear. A landscaping package is included, as well as 3 off-street parking spaces. Walkability to downtown Annapolis including premier restaurants, shopping, yacht clubs, water activities, and more... Take advantage of this rare opportunity to purchase Eastport new construction. The delivery delivery is summer 2025.

ANNAPOLIS

400 JEFFERSON STREET

4 Beds

3 Baths

3,640 Sq.Ft.

$1,700,000

MLS#: MDAA2032362

Spectacular Water View Home nestled at the tip of Eastport Peninsula between Spa Creek, Back Creek and the Severn River in the premiere gated community of Chesapeake Landing, with onsite Yacht Club and pool memberships available. 21 Chesapeake Landing embodies the epitome of Eastport’s waterfront lifestyle. The Maritime Republic of Eastport is a vibrant waterfront community deeply rooted in both sailboat racing and pleasure boating traditions. Residents treasure the walkable lifestyle, with more than 50 restaurants, pubs, boutique shops, and historic City Dock and Downtown Annapolis just steps away. This immaculately-maintained home has been thoughtfully designed with meticulous, high-level upgrades, resulting in a seamless blend of elegance, comfort, and timeless design. A private in-law, guest suite or
entertainment room on the ground level adds to the homes versatility. On the main level, expansive sliding glass doors open onto one of three decks; 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. The daily parade of sail and power boats, regattas, navy vessels and pirate ships is a spectacular bonus that makes this home truly unique. At the heart of the home is a spectacular chef’s kitchen: An oversized center island invites casual gatherings, while 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. 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. Upstairs, wake up to enjoys water views of Annapolis Harbor and the Severn River. The graciously sized owner’s suite welcomes you with dramatic vaulted ceilings and abundant natural light. 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 for relaxation and the therapeutic benefits of a sauna. 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. Featuring its’ own paver patio and private entrance, a full bath and a custom kitchenette—including a refrigerator, sink, microwave, built-in storage and neutral tile flooring. This area can be completely closed off from the rest of the home, making it a perfect in-law suite, private guest quarters or family entertainment area. 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! Don't Miss The Opportunity to Make This Your Home!

ANNAPOLIS

21 CHESAPEAKE LANDING

4 Beds

3 Baths

2,232 Sq.Ft.

$1,695,000

MLS#: MDAA2117644

Stunning Waterfront Coastal Retreat on Oyster Creek with Breathtaking Sunsets! This exceptional 4-bedroom, 4-bathroom home is perfectly situated on the shores offering unique views of the Chesapeake Bay and Oyster Creek from nearly every room. Step inside to discover the open design, highlighting a gourmet kitchen designed for both beauty and function, featuring granite countertops, stainless steel appliances, and breakfast bar. The open-concept living and dining areas flow easily out to the multi-level waterfront decking, ideal for entertaining or simply enjoying the peaceful surroundings. The luxury primary suite is a true sanctuary, complete with a private waterfront deck, spa-like bathroom featuring a walk-in shower, soaking tub, and a generous walk-in closet. The third-level living space includes a full bath and offers endless possibilities—perfect as a media room, guest suite, or home office with elevated views.
Outside, a private pier with a 20,000 lb boat lift invites you to explore the water with ease. Whether you're boating, fishing, or just soaking in the serene creekfront setting, this property offers the ultimate coastal lifestyle. Don’t miss this rare opportunity to own a slice of waterfront paradise on Oyster Creek. Property is in a Special Tax District. - $2,274.75 annually.

ANNAPOLIS

3300 SHORE DRIVE

4 Beds

4 Baths

2,798 Sq.Ft.

$1,650,000

MLS#: MDAA2116986

#MDAA2120636

ANNAPOLIS

3126 PORT WAY

4 Beds

3 Baths

3,892 Sq.Ft.

$1,630,000

MLS#: MDAA2120636

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