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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
282
# of Listings
3
Avg # of Bedrooms
$504
Avg. $ / Sq.Ft.
$1,381,763
Med. List Price

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282 Properties Found. Page 8 of 19.

Welcome to Eastport Estates at Griscom Square, a brand-new construction community of just 11 luxury single-family homes, located within one mile of downtown Eastport! Each residence showcases high-end finishes, spacious open-concept layouts, 9-foot ceilings, 4-5 Bedrooms, gourmet kitchen, modern baths, 2-car garages with private parking, and quality craftsmanship throughout, creating a truly well-built home. Inspired by its coastal setting, each home incorporates light-filled spaces and design elements that reflect Eastport’s nautical character. Enjoy effortless access to Eastport’s vibrant waterfront dining, live music, local marinas, yacht clubs, and scenic sunset views - or bike to or take the water taxi to City Dock, downtown Annapolis, and the United States Naval Academy. Luxury, lifestyle, and location - together in one place. This is a rare opportunity to build your own home this close to town. Lot and model options available!
#MDAA2134724

ANNAPOLIS

105 GRISCOM SQUARE WAY

4 Beds

3 Baths

2,850 Sq.Ft.

$995,000

MLS#: MDAA2134724

Rarely does a home combine over half an acre of privacy, neighborhood beach access, a heated 3-car garage, and Broadneck schools—all just minutes from downtown Annapolis and the Chesapeake Bay." Passing scenic, conservation-protected farmland before arriving in the highly sought-after Pleasant Plains neighborhood. Step inside through the welcoming foyer to a recently updated kitchen and dining area filled with beautiful natural light—an ideal space for everyday living and entertaining. Just off the main living area, a massive family room provides the perfect setting to gather with friends and family or enjoy the big game. Open the double sliding doors to a spacious deck overlooking a fully fenced 0.5+ acre lot, offering a blend of open lawn and mature trees—perfect for BBQs, outdoor games, a swing set, or simply relaxing in your private backyard retreat. Upstairs, you’ll find four generously sized bedrooms and two full baths, along with the convenience of a second-floor washer and dryer. The expansive primary suite features vaulted ceilings and a well-appointed en-suite bath with a soaking tub, stand-up shower, dual vanities, and a walk-in closet. The lower level includes two large, encapsulated dehumidfied crawlspaces with a dehumidification system installed in 2020—ideal for clean, dry storage. Additional highlights include an heated/cooled epoxied 3-car garage with ample storage space. Directly across the street, a picturesque sod farm enhances the open, rural feel. The quiet streets are perfect for walking, and neighborhood beach access is just a short stroll away—ideal for launching a kayak and simply enjoying sunsets and watching boats pass along the Chesapeake Bay. Don’t miss the opportunity to make this exceptional property your home in 2026. Recent upgrades include: • Roof (2020) • Kitchen appliances (2020) • 2 Encapsulated crawlspace with dehumidification (2020) • Sidewalk/driveway leveling (2021) • Ductless mini-split HVAC system (2022) • Freshly painted (2026) • Refurbished hardwood floors (2026)
#MDAA2145978

ANNAPOLIS

1469 PLEASANT LAKE ROAD

4 Beds

2 Baths

2,542 Sq.Ft.

$990,000

MLS#: MDAA2145978

One of Homewood’s most distinctive homes, this 8-bedroom, 4-bath residence offers over 3,100 square feet and a truly unique story. Once known as the “Gables Tourist Home” Bed & Breakfast, the property (built in 1938) still carries subtle nods to its past—including the numbered bedroom doors—while the current owners have thoughtfully updated the interiors and major systems for comfortable modern living. Inside, the home blends historic character with fresh, eclectic design—full of personality, flexibility, and space to live, work, and host. With eight bedrooms, the layout offers exceptional versatility for multi-generational living, guest suites, or creative uses. The fully renovated walkout basement (2021–2022) adds significant finished living space and includes a kitchenette and full bath—ideal for guests, recreation, or extended living arrangements. Recent improvements include basement waterproofing, new HVAC, boiler, water heater, roof, and the addition of a natural gas line—offering peace of mind alongside style and character. Out front, a classic covered porch and carport embrace true “porch life”—a welcoming spot to relax, gather, and enjoy the neighborhood (and a top notch, very sweet lemonade stand location). The location is equally compelling. Set in the heart of the Homewood neighborhood, the home sits next door to the beautiful Busch Library and is a stone’s throw to the Poplar Trail. Enjoy easy access to neighborhood favorites including Ceremony Coffee, Black Market Bakers, and Carlson’s Donuts, along with the convenience of downtown Annapolis, West Street shops, and commuter routes just minutes away. With parking for approximately 8+ cars, the property offers exceptional flexibility and convenience and a great spot to gather before Navy / Blues games. There is no HOA/Dues but residents are eligible to join the Admiral Heights pool. This is a rare opportunity to own a piece of Annapolis history in one of its most charming and connected neighborhoods.
#MDAA2146038

ANNAPOLIS

1422 WEST STREET

8 Beds

4 Baths

3,108 Sq.Ft.

$989,000

MLS#: MDAA2146038

Eastport Waterfront Condo – 2BR/2BA – 1250 sq ft. 2 outdoor decks – 1 deck with amazing full city and waterfront view. Open Concept Living Room with cooks kitchen. Living Room has hardwood floors and fireplace. Newer windows and sliding doors with blinds. Full size front loader washer/dryer. Designer style Bathrooms. Community has pool, pier and tennis courts. Walk to town and live the life.
#MDAA2145720

ANNAPOLIS

15 PRESIDENT POINT DRIVE B2

2 Beds

2 Baths

1,260 Sq.Ft.

$975,000

MLS#: MDAA2145720

Just across the street from the water in Southaven, this Annapolis home offers the kind of space and flexibility that’s increasingly hard to find. Recently updated, the main level includes a renovated kitchen with quartz countertops, dual ovens, gas cooking, stainless steel appliances, and modern cabinetry. The main level also features a living room with built-in speakers, a dining room, an optional sitting room, a half bath, garage access, and a coat closet at the front entry. Upstairs are four well-sized bedrooms, two thoughtfully updated full baths designed with a clean, timeless aesthetic, and a laundry room. The walkout lower level remains unfinished and offers excellent storage, along with a bathroom rough-in for those who may wish to explore future expansion. Exterior updates include a newer roof and a recently paved driveway. The attached two-car garage supports everyday needs, while the detached three-car garage offers access to an unfinished upper-level space that provides additional room to tailor to personal needs. A back deck extends off the main level, with a second deck accessible from the unfinished space above the three-car garage. Community water access is located across the street. The Southaven community also offers a community pier and a kayak/paddleboard launch area. Set on a generous lot with ample storage and water access, 2942 Southaven Drive combines usability with the relaxed coastal character that makes this part of Annapolis so appealing.
#MDAA2131620

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

Welcome to 909 White Marlin Way, an elegant brick-front Colonial ideally positioned on a quiet cul-de-sac in the highly sought-after Chesapeake Preserve community on the Broadneck Peninsula. Built in 1999 and set on a beautifully sized .49-acre lot within the desirable Broadneck School District, this meticulously maintained home offers over 4,200 square feet of finished living space, thoughtfully designed for both everyday living and effortless entertaining. Inside, you’ll find 5 bedrooms and 3.5 baths, complemented by a spacious, well-appointed layout. The main level showcases hardwood flooring, a private office with custom built-ins and crown molding, and a warm, inviting family room anchored by a wood-burning brick fireplace with a decorative mantel. The kitchen seamlessly blends function and style, featuring white cabinetry, granite countertops, a contrasting cherry island, stainless steel appliances, a walk-in pantry, and a built-in desk flowing naturally into the heart of the home. Upstairs, the expansive primary suite offers a true retreat, complete with a tray ceiling, two walk-in closets, and a well-appointed en-suite bath with a jetted tub. Brand new carpet (2026) throughout the upper level and stairs adds a fresh, modern touch. The finished lower level provides exceptional flexibility to suit a variety of lifestyles, offering a full bath, wet bar, and versatile spaces ideal for a home theater, gym, or potential sixth bedroom, along with abundant storage and a convenient walk-up exit to the backyard. Outdoor living is equally impressive. A large screened-in porch opens to a beautifully designed paver patio with firepit, perfect for relaxing evenings or hosting gatherings, surrounded by extensive hardscaping and a spacious, usable yard. Additional highlights include a two-car side-load garage, low HOA fees, and numerous updates: new patio and firepit (2024), screened-in porch was rescreened (2025), new carpet (2026), washer and dryer (2024), window screens (2021), large-capacity water heater (2020), and updated kitchen chandelier (2026), Roof replacement with 30 year architectural shingles (2014) . Ideally located just minutes from downtown Annapolis, top-rated restaurants, shopping, and major commuter routes to Baltimore, Washington, D.C., and the Eastern Shore. Enjoy convenient access to the new Broadneck walking trail, just a short distance from your front door. This is the perfect blend of space, style, and location, offering the lifestyle today’s buyers are looking for. Contact me to book your tour today.
#MDAA2140786

ANNAPOLIS

909 WHITE MARLIN WAY

5 Beds

3 Baths

4,170 Sq.Ft.

$949,900

MLS#: MDAA2140786

VIRTUAL TOUR: https://my.matterport.com/show/?m=FRKRayZVZEv&mls= ***PRICE DROPPED TO SELL, seller is moving away and just wants the home sold. Property appraised for $1,049,000 January 2026 so this is a great chance to walk into equity! Buyer may keep all furnishings if desired, all items in garage will be removed prior to sale. Welcome to 3249 Arundel on the Bay Road — where coastal charm meets timeless character in one of Annapolis’ most sought-after waterfront communities. Nestled in the heart of Arundel on the Bay, this beautifully positioned home offers the rare opportunity to enjoy true Chesapeake Bay living with a blend of tranquility, charm, and convenience. Surrounded by water and embraced by a tight-knit community known for its private beaches, boat ramps, and breathtaking sunsets, this property delivers a lifestyle—not just a home. Step inside to discover a residence filled with natural light, warm finishes, and an inviting layout designed for both everyday living and effortless entertaining. The home features spacious living areas, well-appointed bedrooms, and thoughtful touches throughout that create a sense of comfort and functionality. Outside, enjoy serene outdoor living with space to relax, entertain, or simply take in the coastal breeze via backyard and 2nd floor deck. Whether you’re hosting gatherings, unwinding after a long day, or heading out for a walk along the water, this home offers the perfect backdrop. Living in Arundel on the Bay means access to exclusive community amenities, including private beaches, a boat ramp, fishing piers, playgrounds, and kayak storage—making it a dream for water enthusiasts and nature lovers alike. All of this, just minutes from historic downtown Annapolis, dining, shopping, and major commuter routes. Whether you’re seeking a full-time residence, a weekend retreat, or an investment opportunity in a highly desirable waterfront enclave, 3249 Arundel on the Bay Road is a rare find that captures the essence of coastal Maryland living. Don’t miss your chance to own a piece of the Bay lifestyle.
#MDAA2139224

ANNAPOLIS

3249 ARUNDEL ON THE BAY ROAD

4 Beds

3 Baths

2,800 Sq.Ft.

$940,000

MLS#: MDAA2139224

GREAT OPPORTUNITY! Huge building offers two levels with office on main level (currently rented @$4500 a month and office on upper level is vacant and ready for you to run your business as the other is rented or just have them both rented. Close to Annapolis Mall, Route 50 and much more!
#MDAA2135848

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

Welcome home to 2906 Boyds Cove Drive, a stunning stone-front Colonial nestled in the highly sought-after, upscale enclave of Boyds Ridge. This home offers over 3,800 square feet of elegant above-grade living space, perfectly blending sophisticated design with everyday comfort. Step inside to an open flowing layout with gleaming hardwood floors, crown molding, and classic chair railings. The gourmet eat-in kitchen features granite countertops, cherry cabinetry, a gas cooktop, and a center island, flowing seamlessly into a breakfast nook and sunken family room anchored by a stone-front, wood burning fireplace, perfect for gathering with family and friends. A formal dining room rounds out the first floor, which also boasts an additional living room and library upon entrance to the house. Upstairs, the luxurious primary suite serves as a true private retreat. It boasts soaring cathedral ceilings, a gas fireplace, and expansive his-and-hers walk-in closets. The en-suite spa bath features a relaxing soaking tub and double vanities. Three additional generously sized bedrooms complete the upper level. The full walkout basement offers expansive unfinished space—a blank canvas ready to be transformed into a home theater, gym, or in-law suite. It already includes rough-in plumbing for a potential full bathroom, adding even more flexibility. Outside, enjoy a spacious rear deck overlooking a private lot, all tucked away on a quiet cul-de-sac. Located just minutes from Historic Downtown Annapolis, the Parole town center, and major commuter routes, this home offers the ultimate combination of luxury, space, and convenience. Don't miss your opportunity to own in Boyds Cove!
#MDAA2143826

ANNAPOLIS

2906 BOYDS COVE DRIVE

4 Beds

3 Baths

3,770 Sq.Ft.

$899,900

MLS#: MDAA2143826

Welcome to 220 West Street in Annapolis, Maryland. A rare, fully gut-renovated detached property located in the heart of the Downtown Arts District at a row home's price, offering exceptional flexibility with mixed-use zoning that allows for both residential and commercial use. Completed in 2024, this property has been completely transformed from top to bottom. Every major system and finish has been replaced, delivering a true turnkey opportunity for buyers seeking lifestyle, investment potential, or business use in one of the most walkable and desirable areas in Annapolis. Unlike the majority of Downtown Annapolis properties, this is a fully detached home, not a rowhome or townhouse, providing enhanced privacy, natural light, and a more versatile footprint. The extensive renovation includes a brand new roof, all new electrical and plumbing systems, a new high-efficiency mini-split HVAC system, redesigned floor plan, new flooring throughout, updated lighting, and fully rebuilt kitchen and bathrooms. The outdoor spaces have been completely upgraded with a new deck, new brick patio pavers, new fencing, and ambient lighting that creates a warm and inviting atmosphere for evening entertaining. Inside, the home features a bright two-story entry foyer and a professionally curated interior design that blends modern comfort with intentional functionality. With three bedrooms and two full bathrooms, the layout is flexible enough to support full-time living, guest accommodations, workspace needs, or commercial adaptation. The main-level primary suite opens directly to a private brick patio, while the second bedroom features access to a rear deck overlooking the fully fenced yard. These indoor-outdoor connections are rarely found in Downtown Annapolis and significantly enhance livability. The kitchen has been completely reimagined with new cabinetry, countertops, and appliances, designed to support both daily living and entertaining. The open dining area comfortably accommodates gatherings, reinforcing the home’s versatility. Adding even more value, this property is being sold fully furnished. Every piece has been professionally selected, allowing the next owner to move in immediately, operate as a short-term rental, or transition into a commercial or mixed-use setup with minimal effort. Historically, this property has served multiple purposes, including a furniture store, office space, and duplex residence, highlighting the true flexibility and long-term value of its mixed-use zoning designation. Step outside into a fully fenced private yard featuring a brick patio, outdoor dining area, lounge seating, and ambient lighting, creating a unique urban retreat just steps from the energy of Downtown Annapolis. Located just moments from restaurants, shops, nightlife, City Dock, the Maryland State House, and the U.S. Naval Academy, this property offers unmatched walkability and access. With convenient proximity to Baltimore, Washington D.C., and BWI Airport, it is equally appealing for commuters, investors, and second-home buyers. This is more than a home. It is a rare, fully renovated, detached mixed-use opportunity in Downtown Annapolis where lifestyle, flexibility, and long-term value align.
#MDAA2140068

ANNAPOLIS

220 WEST STREET

3 Beds

2 Baths

1,540 Sq.Ft.

$899,899

MLS#: MDAA2140068

Open House SUNDAY 11/31 11AM-1PM. Please join us!Adorable bungalow coming soon in sought-after West Annapolis! Super fun, walkable location—catch Navy Midshipmen football games or stroll to Chessie’s Wharf, Positano’s, Bean Rush Cafe , Always Ice Cream Company & more! Just a short distance to Downtown Annapolis for waterfront dining, shopping, and historic charm. Easy one-level living with a great fenced-in yard and a large detached garage. Professional interior photos coming soon—stay tuned!
#MDAA2136076

ANNAPOLIS

607 MELVIN AVENUE

2 Beds

2 Baths

1,102 Sq.Ft.

$899,000

MLS#: MDAA2136076

Prime West Annapolis Opportunity | B-1 Zoning | 13 Annapolis Street. Positioned in the heart of high-demand West Annapolis, 13 Annapolis Street presents an exceptionally rare opportunity to acquire a property with B-1 zoning flexibility in one of Annapolis’ most dynamic commercial districts. This is the kind of location where vision, creativity, and smart planning can translate into long-term value. B-1 zoning opens the door to a variety of potential uses such as boutique retail, professional offices, wellness studios, salons, galleries, cafés, creative workspaces, or thoughtfully designed mixed-use concepts (buyer to verify specific uses with the City). Whether you’re an entrepreneur looking to establish a flagship presence, a business owner seeking visibility, or an investor with a redevelopment vision, this property offers the versatility to bring those plans to life. Adding to its appeal is a feature rarely found in West Annapolis: a private driveway with abundant off-street parking, a significant advantage for clients, customers, or tenants and a true differentiator in this walkable corridor. Surrounded by beloved local restaurants, shops, and everyday conveniences, the property benefits from strong foot traffic, excellent visibility, and the vibrant energy that defines West Annapolis. Opportunities with this combination of location, zoning, and parking simply do not come along often.
#MDAA2135402

ANNAPOLIS

13 ANNAPOLIS STREET

None Beds

None Baths

2,240 Sq.Ft.

$899,000

MLS#: MDAA2135402

New Construction in Cape St. Claire. Home construction has now started. Delivery date will be end of August or beginning of September. Days on the market began when lot was purchased. Please look at the documents section of the listing to see all standard features included with this home and all floor plans and site plan. Pictures shown in this listing are of the home now framed and a previous completed home built at 1216 Ramblewood Drive Annapolis, Md. also located in Cape St. Claire during the construction of that home. This same floor plan will be constructed on this site. Please contact listing agent with any questions.
#MDAA2130056

ANNAPOLIS

1217 HAMPTON ROAD

4 Beds

2 Baths

2,700 Sq.Ft.

$896,000

MLS#: MDAA2130056

Some addresses just make life better. This one is tucked back in Beechwood on the Burley — a sought-after water-privileged community in St. Margarets, with private access to Burley Creek for kayaking, canoeing, and boating, plus a community pier, dock slips, and picnic area steps from your door. Downtown Annapolis is less than 2 miles away, yet the setting feels genuinely private, sheltered under a canopy of mature trees on a generous 0.7-acre lot. The house itself offers a rare combination: five bedrooms a, an open kitchen-to-family-room layout, a potential main-level bedroom and full bath ideal for guests or multigenerational living, a kitchen island, and built-in Bose surround sound with TV that conveys. A dedicated main-floor den gives you the flexibility to work from home without sacrificing living space. The two-car attached garage with four additional driveway spaces means there is always room for boats, bikes, kayaks, and company. Launch your boat from the private community ramp with quick access to Burley Creek and the Severn River, enjoy the community pier and waterfront playground, and experience the Annapolis lifestyle at its finest with easy access to restaurants, shopping, and marinas by both boat and car. Whether you are upsizing into a home that finally fits the whole family, seeking a place to launch a kayak on a Tuesday morning before work, or looking for a Chesapeake Bay-area property that gives you space without sacrificing proximity to Annapolis, this home delivers on all counts. Come see it before summer is in full swing!
#MDAA2144280

ANNAPOLIS

1848 CHERRY ROAD

6 Beds

3 Baths

3,150 Sq.Ft.

$895,000

MLS#: MDAA2144280

Tucked away on a private cul-de-sac in one of Annapolis's most coveted enclaves, this exceptional residence offers the refined living the Chesapeake Bay region is celebrated for. From the moment you arrive, beautifully manicured landscaping and an elegant facade set the tone for what awaits inside. Hardwood floors flow throughout the main level, anchoring an open floor plan where formal and informal living spaces are thoughtfully balanced. A gracious formal living room with a fireplace provides an elegant setting for entertaining, while the informal living room, anchored by a second fireplace, offers the kind of relaxed comfort that makes a house feel like a home. The heart of it all is a stunning two-story great room off the kitchen, where soaring ceilings soar overhead and natural light pours in from every angle; a breathtaking space that never loses its ability to impress. The chef-inspired eat-in kitchen is equally spectacular, appointed with a large center island, Corian countertops, gas cooktop, and dual wall ovens. Whether hosting an intimate dinner party or a festive gathering, this kitchen performs flawlessly. Recessed lighting throughout the main level lends a polished, gallery-like ambiance at every turn. The coveted first-floor primary suite is a true sanctuary, offering a generous walk-in closet and the ease of single-level living at its finest. First-floor laundry adds an everyday luxury that discerning buyers will immediately appreciate. Upstairs, two spacious bedrooms share a well-appointed full bath, while a versatile loft overlooks the living spaces below, equally suited as a private home office, library, or lounge. The finished lower level is nothing short of spectacular. Custom built-in bookcases, a third fireplace, a full bath, and a wet bar make this space ideal for entertaining, relaxing, or hosting overnight guests in style. A whole-home generator ensures uninterrupted comfort in every season. Outside, a paver patio and deck extend your living and entertaining space into the serene, landscaped backyard; the perfect backdrop for al fresco dining, morning coffee, or simply savoring the beauty of an Annapolis evening. A two-car garage completes this picture of thoughtful convenience. This is Annapolis living at its finest; where classic elegance, modern comfort, and Chesapeake Bay charm converge into something truly special.
#MDAA2143576

ANNAPOLIS

1604 TRAWLER LANE

3 Beds

3 Baths

4,295 Sq.Ft.

$889,000

MLS#: MDAA2143576

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