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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
266
# of Listings
3
Avg # of Bedrooms
$529
Avg. $ / Sq.Ft.
$1,357,478
Med. List Price

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266 Properties Found. Page 8 of 18.

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.

$949,000

MLS#: MDAA2145978

***PRICE DROPPED TO SELL, seller is moving away and just wants the home sold. Property appraised for $1,097,000 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

New on site 4 days ago
Nestled in the highly sought‑after waterfront community of Hillsmere Shores, this residence offers an exceptional blend of coastal charm, modern comfort, and resort‑style outdoor living. The home features four spacious bedrooms and three full baths, all set within an open, airy floor plan designed to capture natural light and create an inviting sense of space. A generously sized kitchen serves as the heart of the home, offering abundant prep areas, modern appliances, and effortless flow into the main living spaces. The living room is anchored by a refined propane fireplace, adding warmth and ambiance throughout the seasons. The lower-level functions as an extension of the home, complete with a private bedroom and full bath—ideal for guests or multigenerational living. A sprawling great room provides endless possibilities for entertaining or relaxation, while a dedicated laundry space and two additional flex rooms offer versatility for a home gym, office, studio, or hobby space. Outdoor living is elevated to a new level with a massive, covered deck that spans the entire length of the home, creating a year‑round retreat for dining, lounging, and entertaining. The walkout lower level opens to a patio area with a bar area and fire pit, perfect for gatherings on warm summer nights or crisp fall evenings. The fully fenced, flat backyard is pool‑ready and offers ample room for recreation. A private gate leads directly into Quiet Waters Park, enhancing the home’s connection to nature and neighborhood amenities. A large barn‑style garage building, complete with heat and air conditioning, provides exceptional space for storage, creative pursuits, or workshop use. Ample off‑street parking accommodates residents and guests with ease. Residents of Hillsmere Shores enjoy access to some of the finest amenities in Annapolis, including a private community beach, a beautiful community pool with swim team, a marina, boat storage, and multiple launch points for kayaks, canoes, and paddleboards—creating a true Chesapeake Bay lifestyle. This property delivers a rare combination of space, style, and community in one of Annapolis’ most desirable waterfront neighborhoods.
#MDAA2149064

ANNAPOLIS

278 HILLSMERE DRIVE

4 Beds

3 Baths

1,506 Sq.Ft.

$935,000

MLS#: MDAA2149064

TIMELESS ARCHITECTURE & RESORT-STYLE LIVING IN KINGSPORT of ANNAPOLIS Nestled within the highly sought-after community of Kingsport of Annapolis, this exceptional Neo-Traditional residence offers timeless architecture, thoughtfully curated designer updates, and an idyllic setting backing to mature trees. With five bedrooms, FOUR full and one half baths, a finished walk-up lower level, and a side-entry two-car garage, the home blends elegant formal spaces with comfortable everyday living. A classic brick front, Hardi-Plank siding, covered front porch, manicured landscaping, custom Hardi-Plank storage shed, fenced rear yard, pergola entry, raised stone garden bed, and expansive stone patio create outstanding curb appeal and inviting outdoor living spaces. Inside, the entry foyer introduces beautifully proportioned living spaces filled with natural light and clad in hardwood floors. The formal living room is framed by architectural columns, multiple windows, and transoms, while the elegant dining room showcases a distinctive octagonal turret wrapped in plantation-shuttered windows. Privately tucked between the living room and great room, the study features French glass doors and tranquil views of the wooded rear landscape. The wrap-around kitchen is designed for both entertaining and everyday living, featuring crisp white cabinetry, brushed gold hardware, contrasting quartz on the center island with breakfast bar seating, gas cooktop, and designer nautical pendant lighting. The spacious breakfast area, highlighted by a striking Sputnik chandelier, flows effortlessly into the spectacular two-story great room where soaring windows and stacked clerestory windows frame peaceful tree views and flood the home with natural light. A cozy gas fireplace anchors the space, while an atrium door opens directly to the stone patio, gardens, and fenced backyard, seamlessly blending indoor and outdoor living. An upgraded main-level laundry room adds everyday convenience. Upstairs, an open loft provides the perfect work-from-home space overlooking the dramatic great room below. French doors welcome you into the luxurious primary suite featuring a tray ceiling, designer chandelier, sitting room, private balcony, and two spacious walk-in dressing closets. The renovated spa-inspired bath offers dual designer quartz vanities, custom feature walls, elegant sconces, a frameless glass shower, soaking tub, and plantation-shuttered windows. A generous ensuite bedroom with private bath and walk-in closet, plus two additional spacious bedrooms, complete the upper level. The finished walk-up lower level offers exceptional flexibility with a spacious recreation room opening directly to the backyard, an oversized guest suite with luxury vinyl plank flooring, walk-in closet and adjacent full bath, a versatile flex room ideal as a home office, gym or overflow guest space, plus abundant storage. Life in Kingsport is equally exceptional. Nestled along the scenic shores of Spa Creek and Back Creek, this award-winning planned community is known for its distinctive architecture, mature trees, village greens, pocket parks, sidewalks, tot lots, and beautifully landscaped common areas. Residents enjoy a resort-style pool and elegant brick pool house, signature stone monument entrance with fountain, walking and jogging trails, fishing dock, kayak launch, and water access. All this is located just minutes from Historic Downtown Annapolis, the U.S. Naval Academy, waterfront dining, shopping, marinas, and convenient commuter routes to Washington, D.C. and Baltimore. Come home to a coastal inspired lifestyle with a vibrant neighborhood feel.
#MDAA2149024

ANNAPOLIS

704 BRANNOCK TERRACE

5 Beds

4 Baths

5,036 Sq.Ft.

$900,000

MLS#: MDAA2149024

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 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.

$899,900

MLS#: MDAA2140068

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

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

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

Welcome to Kingsport—where timeless elegance meets waterfront living. Nestled within this coveted, water-privileged community, this exceptional 5-bedroom, 4.5-bath residence offers a seamless blend of sophistication, comfort, and everyday luxury. A grand entry welcomes you with rich hardwoods and graceful architectural details, leading to a formal oval dining room, refined living room, and a private main-level office—perfect for today’s lifestyle. The heart of the home is a beautifully appointed gourmet kitchen, featuring a custom center island with cooktop, dual wall ovens, gleaming granite countertops, and extensive cabinetry. The space flows effortlessly into a dramatic family room, highlighted by soaring vaulted ceilings, plantation shutters, and a warm gas fireplace. Upstairs, the primary suite is a true retreat, offering a spa-inspired bath and dual walk-in closets. An elegant en-suite bedroom and two additional bedrooms with a shared bath complete the upper level, offering both comfort and privacy. The fully finished lower level is designed for entertaining and relaxation, featuring a spacious recreation room with a wet bar, a private guest suite, a playroom, and abundant storage. Outdoors, a fully fenced backyard invites quiet moments and gatherings alike, with a paver patio, raised garden beds, and serene wooded views backing to scenic walking paths. Residents of Kingsport enjoy an exceptional lifestyle with resort-style amenities including a community pool, playgrounds, hiking and biking trails, kayak launch and storage, and a picturesque pier on Crab Creek—ideal for sunset views, fishing, or peaceful afternoons by the water. Perfectly positioned just minutes from downtown Annapolis and convenient to major commuter routes, this home offers the rare opportunity to live beautifully in one of the area’s most desirable communities.
#MDAA2143706

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

3,586 Sq.Ft.

$865,000

MLS#: MDAA2143706

Quintessential Eastport charm in this sought-after Lower Eastport location. A welcoming front porch invites you to enjoy the vibrant local lifestyle. Inside, the light-filled layout features a spacious kitchen with a breakfast bar, a dedicated dining area, a convenient mudroom side entrance, half bath, & first-floor laundry. The upper level offers two generously sized bedrooms and a full bath. Relax on the large, private screened-in back porch overlooking a huge, level backyard perfect for entertaining. A standout feature is the over-sized detached shed/barn equipped with mini split (Heat and AC), ideal for a workshop, home office, or studio. This move-in-ready home is steps away from marinas, street-end waterfront parks, shopping, dining, and downtown Annapolis.
#MDAA2147534

ANNAPOLIS

418 CHESAPEAKE AVENUE

2 Beds

1 Baths

1,128 Sq.Ft.

$850,000

MLS#: MDAA2147534

Our Adams model with a 2' extenstion will be built at this beautiful location near Duvall Creek. Home is priced at the base house only - act fast to choose the options and additions to make this home your own. Photos are of the model with optional In-Law Suite. Contact Listing Agent to schedule appointment.
#MDAA2147542

ANNAPOLIS

3268 KITTY DUVALL DRIVE

4 Beds

2 Baths

2,474 Sq.Ft.

$849,990

MLS#: MDAA2147542

Welcome to 1848 Carriage Road, a timeless gem that is beautifully situated in the highly sought-after Lindamoor community. Just a short stroll from the community beach and only a few streets from both neighborhood docks, this home offers the perfect blend of water accessibility, convenience, and undeniable charm. Step inside to discover a warm and inviting main level filled with large windows and natural light. The spacious living room flows seamlessly into the dining area and kitchen, creating an ideal layout. Designed for easy living, the home functions like a rancher, with three generous sized, sun-filled bedrooms, two bathrooms and everything you need on the main level. The kitchen opens onto a deck overlooking a spacious, wooded backyard — perfect for gardening, entertaining, pets, or play. The fully finished walk-out lower level significantly expands the living space and offers exceptional flexibility. With direct access from the garage and a large sliding door to the backyard, this level features a spacious family room, a separate sitting area perfect for a media room or home office, a large fourth bedroom, and a full bathroom. Abundant storage and versatile spaces provide endless possibilities for guests, fitness, recreation, or work-from-home needs. Ideally located just minutes from historic downtown Annapolis, you'll enjoy easy access to waterfront restaurants, boutique shopping, marinas, and year-round cultural events, along with convenient commuting routes to both Washington, D.C. and Baltimore. Offered at an attractive price and ready for its next owners, this is a rare opportunity to enjoy the lifestyle and amenities that make Lindamoor one of Annapolis’ desirable waterfront communities. Don't miss your chance to make this charming property your new home.
#MDAA2148380

ANNAPOLIS

1848 CARRIAGE DRIVE

4 Beds

3 Baths

2,622 Sq.Ft.

$849,000

MLS#: MDAA2148380

Experience the very best of downtown Annapolis living at Acton's Landing. Ideally located just a block from the waterfront and within easy walking distance of City Dock, Main Street, the Naval Academy, restaurants, shops, and marinas, this sought-after community offers an exceptional opportunity to enjoy a truly walkable Annapolis lifestyle. Acton's Landing is known for its distinctive residences, where no two floor plans are exactly alike. Residents enjoy secure entry, elevators, a fitness center, library, beautifully maintained common spaces, and inviting outdoor gathering areas. The building has also undergone significant recent improvements, including a full interior refresh and exterior rehabilitation. This light-filled residence offers over 1,400 square feet of comfortable one-level living. Large windows fill the home with natural light, while the open floor plan creates inviting spaces for both everyday living and entertaining. The updated kitchen features peninsula seating and opens seamlessly to the dining and living areas. Two private balconies provide additional outdoor living space. The thoughtfully designed floor plan includes two spacious bedroom suites, each with its own updated bathroom and generous closet space, along with a dedicated home office and an additional half bath for guests. The living area includes a custom built-in entertainment center and a 55-inch Samsung (2024) television. Recent owner improvements include fresh interior paint, a new HVAC system, new hot water heater, new dishwasher, and an under-sink water filtration system, allowing the next owner to move in and immediately enjoy the home. Whether you're enjoying waterfront strolls, dining al fresco, summer concerts, or the shops and restaurants that make Annapolis such a special place to live, Acton's Landing places it all just outside your door.
#MDAA2149170

ANNAPOLIS

66 FRANKLIN STREET 412

2 Beds

2 Baths

1,479 Sq.Ft.

$849,000

MLS#: MDAA2149170

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