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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

272

# of Listings

3

Avg # of Bedrooms

$428

Avg. $ / Sq.Ft.

$925,284

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$1M - $3M

51 Properties Found. Page 1 of 4.

#MDAA2131890

ANNAPOLIS

703 GLENDON AVENUE

5 Beds

4 Baths

4,376 Sq.Ft.

$2,950,000

MLS#: MDAA2131890

Welcome to 139 Spa Drive – A Stunning Waterfront Craftsman Home on Spa Creek!
Update to public records - Use and Occupancy issued in 2025.

Experience the best of coastal-inspired living at this beautifully designed, single-family home located directly on Spa Creek. This exquisite residence offers three fully finished levels, each with expansive walls of windows that flood the home with natural light and showcase breathtaking water views.

The open-concept layout is ideal for both entertaining and everyday living. A gourmet kitchen sits at the heart of the home, complete with custom shaker cabinetry, quartz countertops, a stylish tile backsplash, premium Bosch appliances, and an oversized center island that offers ample seating and storage. The adjacent Great Room features a cozy gas fireplace and opens to a large waterside deck—perfect for enjoying the serene surroundings year-round.

Upstairs, the luxurious primary suite offers a tranquil escape with its own private balcony overlooking Spa Creek, a second gas fireplace, and a spa-like bathroom featuring a double vanity, freestanding soaking tub, frameless glass walk-in shower, and a linen closet. The expansive, under-finished walk-in closet is a blank canvas offering endless potential to perfectly reflect your personal style and become a dream space. Two additional generously sized bedrooms each have their own beautifully appointed en suite bathrooms, and a convenient second-floor laundry room adds everyday ease.

The lower level offers approximately 1,300 square feet of finished living space, including a bright and spacious walk-out family room plumbed for a future wet bar, a full bath, an egress fourth bedroom, and two storage areas. The recreation space opens to a stone patio and professionally landscaped yard—ideal for hosting or relaxing in style.

Built with lasting quality and exceptional craftsmanship, this home features 2x6 framing, Hardie Plank siding with stone accents, and Anderson high-efficiency windows. Inside, you’ll find 9-foot ceilings throughout, solid wood interior doors, engineered hardwood floors, and detailed architectural millwork. Outdoor features include a bluestone front porch and rear patio, a paver driveway, and professionally designed landscaping. The home is equipped with three heating and cooling zones, a propane tank servicing both fireplaces and the kitchen range, and a full-house sprinkler system with recessed heads.

Whether you’re an avid boater or simply cherish the tranquility of waterfront living, this home delivers a rare combination of elegance, comfort, and direct water access. Enjoy your private, fully outfitted 90-foot slip with a 16-foot width, 54-foot finger pier, and 220-foot platform, and a mean low water depth of 4.5 feet—making this an unparalleled waterfront offering.

ANNAPOLIS

139 SPA DRIVE

4 Beds

4 Baths

4,885 Sq.Ft.

$2,850,000

MLS#: MDAA2115180

#MDAA2123548

ANNAPOLIS

778 BON HAVEN DRIVE

6 Beds

4 Baths

5,094 Sq.Ft.

$2,800,000

MLS#: MDAA2123548

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 4 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

4 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

New on site 4 days ago

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#: MDAA2132402

To Be Built by Whitehall Building & Co. | Over 5,800+ Sq. Ft. Total

New home to be built by Whitehall Building & Company, offering the perfect blend of luxury, craftsmanship, and personalization. Almost 8 beautiful rural-like acres located in the heart of everything but tucked away leaving a feeling of being in the country. Conveniently located in the highly sought-after Broadneck School District of Arnold, Maryland. This property presents an exceptional opportunity to select from the builder’s models (shown or others) and customize the home to your lifestyle. Superior finishes throughout including tech package, Bosch stainless steel appliances, Kohler faucets, stand alone tub with stand faucets, tile on bathroom walls and Primary shower floors, etc...Customizable floor plan and finishes allowing buyers flexibility and lots of options to choose from while benefiting from Whitehall’s exceptional construction quality.

Featuring over 5,800 sq. ft. of total living space, this home showcases superior architectural detail, including beamed ceilings in the main living area, spacious room layouts, and an open-concept flow that supports modern living.

This thoughtfully planned home includes 5 total bedrooms, featuring two primary suites—one on the main level and one upstairs—ideal for multi-generational living or long-term flexibility. With 4 full baths and 1 half bath, the layout provides comfort and convenience for family and guests.

The main level offers 9' ceilings, a gourmet kitchen flowing into a large dining area and family room, a private library/office, first-floor bedroom suite, mudroom, powder room, and access to the standard 2-car garage. Buyers may also choose an optional second 2-car garage for additional vehicles, storage, hobbies, or workshop space.

The second floor includes a spacious loft, upper-level laundry room, three additional bedrooms, and a luxurious primary suite with two walk-in closets and a spa-inspired bath.

The expansive lower level offers incredible potential with a large recreation room, options include: gym, 6th bedroom, billiards room, and storage... Possibilities are endless!

Perfectly positioned in central Anne Arundel County, this home offers convenient commutes to BWI Airport, Annapolis, Baltimore, Washington D.C., Fort Meade, Sandy Point State Park Beach Area, nearby parks, marinas, fine dining and shopping.

Builder incentives are available when using the preferred lender and title company.

A rare opportunity to build a high-quality, customizable home in one of Anne Arundel County's most desirable areas.

ANNAPOLIS

P. 317 SHOT TOWN ROAD

5 Beds

4 Baths

5,862 Sq.Ft.

$2,195,000

MLS#: MDAA2131672

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

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

New on site 4 days ago

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#: MDAA2132404

TO-BE-BUILT. Construction has not started. Photos are of a previously built home by Builder. Choose your options and finishes. Located in picturesque Annapolis, MD this one-of-a-kind property will sit on just shy of 1 acre and will feature a main level owner's suite and high end finishes throughout. Optional features include a gourmet kitchen with quartz countertops, large center island, Z-Line or Monogram chef-grade appliances including 6 burner dual-fuel range and stylish soft-close cabinets. Additional main level amenities include a spacious office, two story family room, formal dining area, morning room, laundry and an owner's suite with dual walk-in closets, large spa-like shower and soaking tub. The upper level features 2-4 additional bedrooms and 2-3 full baths. Standard features include 30 year architectural singles, two zone 92% efficient Carrier HVAC, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, 400A electric service, EV charging prewire and much more. Excellent connectivity via Rt 50 and 97 ensures effortless commuting to Washington, DC, Ft. Meade, and Baltimore. Successful percolation tests have been completed by Seller. Contact listing agent with questions.

ANNAPOLIS

341 DUBOIS ROAD

4 Beds

3 Baths

3,716 Sq.Ft.

$1,999,000

MLS#: MDAA2129980

Arts & Crafts–inspired residence built in 2012 by Gate One Builders and designed by Fred Sieracki with exceptional materials and craftsmanship. Set on an elevated and private 5.46-acre wooded property, this home offers Broad Creek/ South River views, a deep-water, 100 ft private pier with boat lift, floating dock for kayaks, a living shoreline, and a fully fenced property with deer fencing. Exterior highlights include HardiePlank siding, custom stonework, curated landscaping, an outdoor shower, and a firepit.
Inside, the first floor is reminiscent of a lodge-style retreat with vaulted ceilings and blue knotty pine wood floors reclaimed from a 1900s South Carolina mill. The open floor plan features a masonry stone fireplace, a gourmet kitchen with marble countertops, and a spacious screened porch for entertaining with big vistas across the property. The en-suite primary spa bath includes porcelain tile floors and marble countertops. Two primary suites plus a third bedroom/office are located on the main level.
The walkout lower level provides flexible living space with a potential bedroom/sitting room, full bath, concrete flooring, and abundant storage. Enjoy spectacular sunsets, a gravel driveway with ample parking, and the feeling of being worlds away—yet just minutes from Whole Foods, Starbucks, and everyday conveniences. Seller prefers a 60 day close and all prefers to sell 95% of all furniture.

ANNAPOLIS

397 FORELANDS ROAD

3 Beds

3 Baths

4,120 Sq.Ft.

$1,998,000

MLS#: MDAA2131394

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

Elegant charm meets modern convenience in this one-of-a-kind residence located in the heart of Murray Hill. Offering the very best of the downtown lifestyle, this remarkable property boasts a chef’s kitchen with custom cabinetry, granite counters, and high-end appliances and soaring ceilings. The stunning Living room with gas fireplace and light filled dining area flows seamlessly to the picturesque gardens in the front yard to the elegant fountain in the back. Elevator service to all levels provides ease, while the spacious primary retreat encompassing the entire top floor includes a sitting room/office, private covered porch, and breathtaking views of Spa Creek and the iconic Annapolis skyline.

Unmatched in both location and amenities, this residence includes a rare downtown garage, plenty of parking, multiple guest suites for friends and family, and elegant details throughout—from granite foyer floors to a library and breakfast room filled with light and curated finishes. Whether entertaining in style or enjoying a quiet evening watching the boats glide by, this home represents the finest package in the city: an extraordinary blend of history, luxury, and walkable convenience just steps from everything downtown Annapolis has to offer. Welcome Home!

ANNAPOLIS

2 SOUTHGATE AVENUE 10

3 Beds

2 Baths

3,884 Sq.Ft.

$1,975,000

MLS#: MDAA2129932

1 2 3 4

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