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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

312

# of Listings

3

Avg # of Bedrooms

$468

Avg. $ / Sq.Ft.

$1,078,011

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

312 Properties Found. Page 3 of 21.

"NEW PRICE":SPECTACULAR WATER VIEWS OF THE THE CHESPEAKE BAY! LOCATION LOCATION! Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this your "NEW HOME"! SEE HOUSE LOCATION SURVEY WITH SITE TABULATIONS. AMAZING POTENTIAL! USE YOUR IMAGINATION! CONTACT YOUR ARCHITECT & BUILDER OF CHOICE NOW! .38 acre Lot size w/ 2502 SQFT total home currently & 2-Car Detached Garage. STEPS to EVERYTHING BAY RIDGE HAS TO OFFER! THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! PRIVATE COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE "SANDY" COMMUNITY BEACHES ALONG BAY & RIVER DRIVE! WALK OR GOLF CART TO COMMUNITY MARINA & CLUBHOUSE,W/BOAT RAMP, MOORING BALLS, SLIPS & Pump out station, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS ETC., ALSO "THE BIG WOODS BAY RIDGE CONSERVATION AREA” W/ PRIVATE TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! , AND DON'T FORGET ABOUT KASS PARK (ON WEST LAKE DR): BASEBALL/SOCCER, LACROSSE FIELD, OPEN SPACE!! WHETHER YOU'RE A BOATER, SWIMMER, SUP ENTHUSIAST, DOG WALKER, RUNNER, HIKER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. Current Home: Roof 2012 , HVAC 2011 , Hot water heater 2020, Sold AS-IS. SEE HOUSE LOCATION SURVEY WITH SITE TABULATIONS in MLS documents section.

ANNAPOLIS

93 BAY DRIVE

None Beds

None Baths

0.38 acres

$2,750,000

MLS#: MDAA2126142

"NEW PRICE": SPECTACULAR WATER VIEWS OF THE THE CHESPEAKE BAY! LOCATION LOCATION! Don't MISS this RARE OPPORTUNITY IN THE VERY POPULAR COMMUNITY OF BAY RIDGE. Make this your "NEW HOME"! SEE HOUSE LOCATION SURVEY WITH SITE TABULATIONS. AMAZING POTENTIAL! USE YOUR IMAGINATION! CONTACT YOUR ARCHITECT & BUILDER OF CHOICE NOW! .38 acre Lot size w/ 2502 SQFT total home currently & 2-Car Detached Garage. STEPS to EVERYTHING BAY RIDGE HAS TO OFFER! THE BAY RIDGE LIFESTYLE IS UNMATCHED IN ALL OF MARYLAND! PRIVATE COMMUNITY POOL/CLUBHOUSE W/ WATERCRAFT STORAGE RACKS , PRIVATE "SANDY" COMMUNITY BEACHES ALONG BAY & RIVER DRIVE! WALK OR GOLF CART TO COMMUNITY MARINA & CLUBHOUSE,W/BOAT RAMP, MOORING BALLS, SLIPS & Pump out station, PLAYGROUND, BASKETBALL/PICKEL BALL COURT, KAYAK RACKS ETC., ALSO "THE BIG WOODS BAY RIDGE CONSERVATION AREA” W/ PRIVATE TRAILS AND ACCESS TO BLACKWALNUT CREEK, A TRUE GEM! , AND DON'T FORGET ABOUT KASS PARK (ON WEST LAKE DR): BASEBALL/SOCCER, LACROSSE FIELD, OPEN SPACE!! WHETHER YOU'RE A BOATER, SWIMMER, SUP ENTHUSIAST, DOG WALKER, RUNNER, HIKER, THIS NEIGHBORHOOD HAS IT ALL! JOINING THE BAY RIDGE CIVIC ASSOCIATION IS VOLUNTARY. Current Home: Roof 2012 , HVAC 2011 , Hot water heater 2020, Sold AS-IS. SEE HOUSE LOCATION SURVEY WITH SITE TABULATIONS IN MLS DOCUMENTS SECTION.

ANNAPOLIS

93 BAY DRIVE

3 Beds

1 Baths

2,502 Sq.Ft.

$2,750,000

MLS#: MDAA2125108

Waterfront Luxury with Unmatched Views – 145 Spa Drive, Annapolis, MD
Nestled along the tranquil shores of Spa Creek, this exceptional residence offers a rare opportunity to own a slice of Annapolis waterfront paradise. With 87 feet of pristine water frontage and sweeping views that stretch across the creek, this 4-bedroom, 4-bathroom home is a masterclass in elegance, comfort, and coastal sophistication.
From the moment you arrive, the curb appeal is undeniable—classic architectural lines, mature landscaping, and a stately oversized two-car garage welcome you home. Step inside to discover a thoughtfully designed interior that blends timeless charm with modern luxury. The open-concept living spaces are bathed in natural light, with expansive windows framing the water like living art.
At the heart of the home lies a gourmet kitchen that will delight culinary enthusiasts and entertainers alike. Outfitted with high-end appliances (Wolf and Subzero), custom cabinetry, and sleek countertops (Calacatta Marble), it flows seamlessly into the dining and living areas, creating a perfect setting for intimate dinners or lively gatherings.
The primary suite is a sanctuary of serenity, featuring a spa-inspired steam bath, heated floors, soaking tub, a spacious layout, and a secure walk-in closet designed for both style and discretion. Additional bedrooms offer flexibility for guests, home offices, or creative spaces, with the potential for a fifth bedroom to suit your lifestyle needs.
Step outside to enjoy the true magic of this property. Whether you're sipping coffee on the deck, hosting sunset cocktails, or launching your boat from one of two private lifts, the waterfront lifestyle here is second to none. The property is equipped with an indoor sprinkler system, a backyard irrigation system ensuring lush greenery year-round, and the gentle lapping of Spa Creek provides a soothing soundtrack to daily life.
Located just minutes from downtown Annapolis, this home offers the perfect balance of privacy and proximity. Enjoy easy access to world-class dining, boutique shopping, historic charm, and vibrant maritime culture—all while retreating to your own peaceful haven at day’s end.
Key Features:
- 4–5 Bedrooms 4 Bathrooms
- 87 Feet of Spa Creek Waterfront
- Gourmet Kitchen with Premium Appliances
- Secure Primary Bedroom Closet
- Luxury Steam Bath, soaking tub and heated floors
- Oversized Two-Car Garage
- Two Private Boat Lifts 40,000 lb and 10,000 lb
- Indoor Sprinkler System
- Breathtaking Water Views from Multiple Rooms
This is more than a home—it’s a lifestyle. Schedule your private tour today and experience the unmatched beauty and tranquility of 145 Spa Drive.

ANNAPOLIS

145 SPA DRIVE

5 Beds

4 Baths

4,842 Sq.Ft.

$2,750,000

MLS#: MDAA2126922

Exquisite Savannah Style custom-built home in sought after, amenities-rich, Fishing Creek Farm community in Annapolis. This non-riparian waterfront home is nestled between 2 bodies of water providing endless water views from almost every room of the house. Wake up early to watch the wildlife and the sunrise over Cherry Tree Cove from the rear screened porch or enjoy peaceful water views and sunsets over Duvall Creek from the relaxing front porch. Upon entering the home the generous Foyer opens onto the formal Living Room with fireplace and custom built-ins and the spacious Dining Room which flows into the beautiful Gourmet Kitchen filled with high-end appliances and charm. The adjacent spacious Family Room and expansive 3 seasons porch overlooking the lush backyard and sparkling water of Cherry Tree Cove are perfect for entertaining. With 5 bedrooms and 5.5 baths including a private and conveniently located guest suite above the garage, there is plenty of space for a large family and the many guests that are sure to come visit in this stunning setting. The fully finished basement boasts an additional living space, game room, play area, full bath and wet bar. The free-standing Office/Studio area provides endless possibilities. The sought after community of Fishing Creek Farm offers a community pool, tennis courts, marina, beach and much more, all just a quick stroll from this amazing property. Located just minutes from downtown Annapolis and Eastport which offer the perfect balance of small-town charm and big world sophistication. Traveling or commuting is just as convenient by easily accessing Rt. 50 and 97 which provides direct access to Baltimore, BWI, Ft. Meade/NSA and Washington, DC., or head over the Bay Bridge to the Eastern Shore for a quick beach vacation. Welcome Home!

ANNAPOLIS

1241 CHERRY TREE LANE

5 Beds

5 Baths

6,428 Sq.Ft.

$2,675,000

MLS#: MDAA2115392

#MDAA2103110

ANNAPOLIS

2175 CHESAPEAKE HARBOUR DRIVE

4 Beds

4 Baths

2,513 Sq.Ft.

$2,595,000

MLS#: MDAA2103110

Most desirable Eastport location! Walking distance to everything Annapolis and a mere block away from marinas and restaurants. This home is in impeccable condition with amazing upgrades and designer finishes. Enjoy relaxing on your covered front porch greeting your neighbors or friends and family coming for a visit. The custom gourmet kitchen and high-end upgrades make it perfect for entertaining. The upper-level features spacious bedrooms and the owner's suite has 2 large walk-in closets and an amazing owner's bathroom. The recently completed lower level has an additional bedroom and full bath with steam shower. Additionally, there is an enormous family room with a butler's pantry, bar, multiple tv's and a bonus storage room. The fenced rear yard leads to beautiful hardscape, lawn and a screened gazebo with electric and a television. The temperature-controlled garage offers 2 large parking spaces, storage area and workshop and a great gym above in the upper level.

ANNAPOLIS

520 SECOND STREET

4 Beds

3 Baths

4,245 Sq.Ft.

$2,500,000

MLS#: MDAA2126872

There is nothing else in Eastport like this beautiful, one floor living, attached garage, home with 4 bedrooms, 3 baths, large finished lower level and separate guest house with a 5th bedroom, 4th full bath. Built in 2014 on two lots with 10 foot ceilings, 8 foot doors (18 inches taller than the standard door), in a Montecito west coast style with incredible proportions and finishes, this home's design makes a strong statement in addition to its unique combination of features for Eastport. The main living area is a great room with huge window in the front facing kitchen and 34 feet of glass doors opening to a 34-foot-long screen porch with vaulted ceiling, five skylights and a gas fireplace. The bedroom layout is for the sophisticated owner. There is a separate two bedroom guest suite with its own foyer off the entry hall, linens storage and full bath to the design standard of primary bath with walk-in shower, finishes and lighting. The large primary bath has an outer room with free standing tub and double sinks. This room has two tall thin windows framing the tub mosaic wall and two skylights. The second room of the primary bathroom has an oversized walk-in shower with rain shower and wall showerheads in addition to a third skylight. Both the tub and the shower walls have beautiful mosaic tile floor to ceiling back walls dramatically lit from above by recessed lights. The large walk-in closet is what you would expect in a home designed to this standard and there is a second closet in the primary suite. There is another bedroom or office on the opposite side of the great room, and like the primary bedroom, looks out on the large landscaped backyard mosaic tile wall. The windows are proportionally large for the 10-foot ceilings. The design of the kitchen reflects the space that a single floor, double lot home provides. Ample storage below counters in drawers with hidden utensil drawers and expansive counterspace in the kitchen, provide a clean, contemporary feel. The Melie separate refrigerator and freezer are completely hidden behind the cabinet doors completing the sophisticated contemporary design. A large square island with two ovens, seating for 6, and surface area is the center of this entertaining kitchen. The front hall leads to the living area that is centered on a long, glass sealed fireplace that is both practical and striking. The two-car garage is part of the home, directly entering on a side hallway. It is large enough for two of the largest SUVs and has a finished storage loft above. There is also a finished lower level with a gym, surround sound entertainment system, pool table, separate large workshop, and a 14x14 storage room, all with 9 foot ceilings. THE HVAC as well as hot water are all geothermal, cost effective with no noisy outside systems. The separate guest house has a cathedral ceiling and full bath. The HVAC in the guest house is a high efficiency Mitsubishi split system. The front landscaping includes stone wall and gardens as well as a pergola swing and small patio with Adirondak chairs for when you want outdoors to be social. Illuminated brick sidewalk and mahogany stairs lead to the large entry doors. Privacy is in the large backyard where landscaping accentuates the beauty and utility of an impressive entertaining space. Brick sidewalks and a large stone patio under the shade of 4 red bud trees with outdoor kitchen and firepit. Landscape lighting and irrigation complete and match the look.

ANNAPOLIS

1004 MOSS HAVEN COURT

4 Beds

3 Baths

4,972 Sq.Ft.

$2,450,000

MLS#: MDAA2128650

Stunning Waterfront New Construction 0n Back Creek in the Eastport area. Don't miss this rare opportunity to build your dream home in one of Annapolis’s most sought-after waterfront communities. Ideally located on a quiet, picturesque corner lot in Eastport, this beautifully designed custom home will offer expansive views of Back Creek and luxury finishes throughout. Enjoy wide plank floors, dramatic walls of glass to showcase the water views, custom built-in kitchen cabinetry, and a chef’s kitchen featuring high end appliances, quartz countertops, oversized island, and a full-height backsplash. Optional elevator can be added for additional convenience. Every detail has been thoughtfully selected to blend style, comfort, and function for modern coastal living. This home is conveniently located just close to the heart of Eastport—renowned for its strong sense of community, marinas, walkability, and vibrant dining scene. Enjoy morning strolls to your favorite coffee shop or evenings out at nearby waterfront restaurants. Located in the Parkwood Civic Association (PCA), a voluntary neighborhood group with $100 annual dues that support maintenance of local green spaces—including Hoffman Park and the community docks. PCA membership is also required to apply for a dock slip. Contact the listing agent today or check out Whitehall Building & Co's website to schedule a tour of the model home and start customizing your waterfront residence. With construction soon underway, you could be enjoying life on the water by next boating season.

ANNAPOLIS

703 A GLENDON AVENUE

4 Beds

4 Baths

4,800 Sq.Ft.

$2,375,000

MLS#: MDAA2119986

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

Price Reduction! Seller says to bring all offers! 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

4,974 Sq.Ft.

$2,100,000

MLS#: MDAA2109384

Price Improvement! 100k Reduction. 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 6+ 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, new plumbing/electric and sprinkler system, updated flooring, freshly painted standing seam roof/front dormers 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.

$2,100,000

MLS#: MDAA2122834

For sale , this is a huge opportunity 2 ASSETS FOR SALE , 1991-1993 West Street: 3000 sf retail building Lot Size.Discover an exceptional investment opportunity with this portfolio of two retail assets located at 1991 and 1993 West Street, Annapolis, MD.

- Property Overview:

- 1991 West St:

- Lot Size: 8,000 sq. ft.

- Zoning: BCE (Business Corridor Enhancement district)

- Features a retail building with high visibility and heavy traffic, ideal for attracting customers.

- The current tenant is willing to continue leasing or vacate if necessary, providing flexibility for potential buyers.

- 1993 West St:

- Lot Size: 4,800 sq. ft.

- This property is currently condemned, with value primarily in the land itself, offering a unique redevelopment opportunity.

Location Highlights:

- Situated in a bustling area with high foot traffic and direct proximity to Annapolis’ historic downtown, this location promises excellent visibility and accessibility for any retail business.

Important Note:

- Please do not visit the property without a scheduled appointment to ensure a smooth viewing experience.

Take advantage of this rare chance to invest in prime real estate in a thriving area. Contact us for more details or to schedule a viewing!

ANNAPOLIS

1991-1993 WEST STREET

None Beds

None Baths

3,000 Sq.Ft.

$2,099,000

MLS#: MDAA2128872

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

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

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

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