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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

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

108 Properties Found. Page 1 of 8.

Welcome to 605 Lighthouse Landing Ln, located on a quiet corner lot. This home has 6 bedrooms, 4 ½ baths, designed with an open floor plan. The great room on the first level has a den with fireplace, breakfast nook, and kitchen. Also on the first floor is the living room, foyer, dining room, and a primary bedroom with shower and soak in tub also there are two large, his and hers walk in closets. On the second level there is a primary suite and three bedrooms. The lower level comes with a complete 900 sq ft in law apartment with a primary bedroom. The fenced in yard is great for kids and pets. The large composite deck provides a great place to relax. If the power fails the Generac generator kicks in within 30 seconds, providing power to the entire house. Two large unfinished storage rooms provide more than adequate space for storage or an exercise room. All comments, data is provided by seller or seller's representatives. Buyer to confirm all & hold all parties harmless from any discrepancy data in the mls and advertising. Limited Service–Data Entry Addendum signed by seller/s must be signed by buyer/s with Purchase Contract.

ANNAPOLIS

605 LIGHTHOUSE LANDING LANE

6 Beds

4 Baths

4,041 Sq.Ft.

$998,000

MLS#: MDAA2140662

#MDAA2134724

ANNAPOLIS

105 GRISCOM SQUARE WAY

4 Beds

3 Baths

2,850 Sq.Ft.

$995,000

MLS#: MDAA2134724

Experience the ultimate “lock & leave” lifestyle in the heart of downtown Annapolis in this rare, two-story Condo at Actons Landing with convenient elevator access to each floor. The main level is sun-drenched with banks of windows outfitted with plantation shutters, 9-foot ceilings, crown molding, custom built-ins, and a gourmet granite and stainless kitchen and half bath. The lower-level hosts two primary suites with walk-in showers and an abundance of storage space. Premium amenities elevate your comfort, an assigned garage parking space, a private fitness center, library, and concierge service. Step outside and find yourself just one block from Church Circle, Spa Creek, fine dining, boutique shopping, and the water taxi.

ANNAPOLIS

66 FRANKLIN STREET 418

2 Beds

2 Baths

1,800 Sq.Ft.

$995,000

MLS#: MDAA2148022

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.

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.

ANNAPOLIS

15 PRESIDENT POINT DRIVE B2

2 Beds

2 Baths

1,260 Sq.Ft.

$975,000

MLS#: MDAA2145720

Nestled in the highly sought-after, water-privileged community of Cape St. John, this exceptional 4-bedroom, 3.5-bath residence, beautifully renovated in 2017, offers an ideal blend of luxury, comfort, and the coveted Chesapeake Bay lifestyle. Residents enjoy exclusive access to the South River, including a private beach, boat ramp, docks, pavilion, and playground. Whether spending the day on the water, gathering with neighbors, or taking in breathtaking sunsets along the shoreline, life here is defined by effortless waterfront living. Perfectly positioned on the corner of Cape St. John Road and Valley View Road, this well appointed home is designed for both refined entertaining and effortless everyday living. The professionally landscaped, fully fenced backyard creates a private outdoor retreat, highlighted by an elegant stone patio ideal for al fresco dining, evening cocktails, or relaxing around the fire pit under the stars.
Inside, the open-concept living space is anchored by a dramatic six-foot fireplace, creating a sophisticated yet inviting atmosphere. The gourmet kitchen serves as the heart of the home, featuring a spacious quartz-topped island, soft-close cabinetry, and premium stainless steel appliances....perfect for casual gatherings and memorable celebrations alike. The main-level primary suite offers a luxurious private sanctuary, complete with a generous walk-in closet and spa-inspired en-suite bath. Upstairs three additional bedrooms and two-and-a-half baths provide ample space for family, guests, or dedicated office and flex spaces. The heated and air-conditioned garage adds exceptional versatility, ideal for a fitness studio, workshop, hobby space, or climate-controlled storage. Combining upscale finishes, thoughtfully designed living spaces, and access to one of Annapolis’ most desirable waterfront communities, this remarkable home offers a rare opportunity. to embrace the luxury lifestyle of Cape St. John! Located just minutes from
Annapolis Town Center, restaurants, shopping and easy access to major highways Cape St John is the perfect location!

ANNAPOLIS

2978 VALLEY VIEW ROAD

4 Beds

3 Baths

2,553 Sq.Ft.

$975,000

MLS#: MDAA2149336

Two houses for the price of one! 704 Caleb Lane includes an amazing garden apartment, perfect for an in-law or au pair! It is beautifully maintained and loaded with recent updates in the highly sought-after, amenity-rich Kingsport community of Annapolis. The spacious, open floor plan is enhanced by the many value-added updates in the home, including the renovated kitchen, roof (2022), HVAC systems (2025 and 2022), and water heater (2022). The light-filled walk-out lower level is a complete in-law/au pair suite that includes a kitchen, both a full AND a half bath, a 2nd laundry, and not one but two bedrooms! A huge bonus and sheer perfection for guests, multigenerational living, a theater room, or an extended entertaining space. The stunning main-level kitchen is designed to impress, featuring sparkling granite countertops, a massive center island, custom cabinetry, and convenient access via a fun and functional secondary staircase. The kitchen opens seamlessly to the dramatic two-story Great Room, highlighted by a cozy gas fireplace, soaring windows, and elegant custom wood blinds that run throughout the main level. Beautifully maintained hardwood floors run throughout the home, adding warmth and timeless appeal. Outside, the pristine driveway with ample parking and an oversized two-car garage with built-in cabinets and fantastic storage space for gardening, landscaping, and recreational needs.

Situated on nearly a quarter-acre lot, the property is the best location in the neighborhood, just two short blocks from the community pool, clubhouse, playgrounds, water access for kayaking and fishing, and scenic walking and biking trails. This exceptional property offers the perfect blend of comfort, elegance, and convenience. Located only 10 minutes from Downtown Annapolis, this home provides the tranquility of private community living without sacrificing easy access to shopping, dining, and waterfront attractions.

This elegant home truly checks every box — offering exceptional space, thoughtful upgrades, outstanding community amenities, and an unbeatable Annapolis location.

ANNAPOLIS

704 CALEB LANE

6 Beds

4 Baths

6,027 Sq.Ft.

$974,000

MLS#: MDAA2145044

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.

ANNAPOLIS

2942 SOUTHAVEN DRIVE

4 Beds

2 Baths

2,142 Sq.Ft.

$949,900

MLS#: MDAA2131620

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)

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.

ANNAPOLIS

3249 ARUNDEL ON THE BAY ROAD

4 Beds

3 Baths

2,800 Sq.Ft.

$940,000

MLS#: MDAA2139224

New on site 3 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.

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.

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!

ANNAPOLIS

2563 FOREST DRIVE

None Beds

None Baths

20,173 Sq.Ft.

$899,999

MLS#: MDAA2135848

#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!

ANNAPOLIS

2906 BOYDS COVE DRIVE

4 Beds

3 Baths

3,770 Sq.Ft.

$899,900

MLS#: MDAA2143826

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