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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

275

# of Listings

3

Avg # of Bedrooms

$515

Avg. $ / Sq.Ft.

$1,436,939

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

126 Properties Found. Page 1 of 9.

Rare waterfront redevelopment opportunity in Annapolis. The existing structure is a complete shell and requires a full renovation or rebuild. Ideal for investors, builders, or buyers looking to design and construct a custom waterfront home from the ground up.

Located along the protected waters of Oyster Cove, the property includes a deep-water pier and boat house. The existing footprint and favorable waterside placement offer strong potential to maximize views and overall design.

Convenient access to the Chesapeake Bay and close proximity to Historic Downtown Annapolis by both land and water. Enjoy boating, sailing, and easy access to surrounding waterfront destinations throughout the region.

Property is being sold strictly as-is. A unique opportunity for those ready to take on a full redevelopment project in a prime waterfront setting.

ANNAPOLIS

1254 WASHINGTON DRIVE

5 Beds

4 Baths

9,960 Sq.Ft.

$1,000,000

MLS#: MDAA2143700

New on site today

A rare opportunity for the true history enthusiast, this stunning Keith Anthony reproduction of the iconic Noah Webster Home, originally built in New England circa 1758, masterfully blends authentic colonial architecture with the comforts of modern living. Situated on a premium corner lot in the water-privileged community of Broadview Estates, just off Riva Road, this one-of-a-kind residence offers timeless character and exceptional craftsmanship throughout.

Inside, authentic random-width pine flooring, exposed brick accents, and traditional plaster walls create a warm and inviting atmosphere. The main level features spacious living areas with two gas-burning fireplaces, a charming kitchen complete with a gas fireplace as well as a convenient first-floor bedroom and hallway half bath. French-inspired details and period-correct architectural elements make this home truly distinctive while seamlessly accommodating today's lifestyle.

Upstairs, the primary suite offers a private retreat with its own woodburning fireplace and en suite bath, accompanied by 2 additional bedrooms and a full bathroom. In total, the home features four bedrooms and 2.5 baths, providing flexibility for family, guests, or remote work.

The lower level offers additional living space and abundant storage, while the oversized two-car garage and expansive driveway provide ample parking. Outside, enjoy the large corner lot and fenced in brick patio, perfect for entertaining or relaxing on warm Maryland evenings with state of the art low voltage lighting that auto turns on around the exterior of the home for a stunning presentation at night.

If you're searching for a home with character, history, and charm that stands apart from today's cookie-cutter designs, this extraordinary property is truly one of a kind.

ANNAPOLIS

355 BROADVIEW LANE

4 Beds

2 Baths

2,786 Sq.Ft.

$999,999

MLS#: MDAA2148762

Why wait months for new construction when you can move into a fully upgraded, nearly new home today? Welcome to 141 Stilly Way in Parkside Preserve, one of Annapolis' most desirable newer communities. Less than two years old and meticulously maintained, this exceptional residence offers over 4,400 square feet of finished living space with every major upgrade already completed. Unlike a builder base model, this home is move-in ready and loaded with premium finishes including wide-plank flooring, designer lighting, quartz countertops, upgraded cabinetry, double wall ovens, gas cooktop, stainless hood, tiled backsplash, under-cabinet lighting, gas fireplace, and a fully finished lower level. Every detail has already been selected, installed, and perfected, allowing the next owner to simply unpack and enjoy. The heart of the home is the stunning open-concept kitchen and family room designed for both everyday living and entertaining. An oversized center island anchors the space while expansive windows frame peaceful wooded views and fill the home with natural light. The main level also offers flexible living and gathering spaces that easily adapt to today's lifestyle. Upstairs, the spacious primary suite serves as a private retreat featuring a spa-inspired bath and oversized walk-in closet. Generously sized secondary bedrooms provide flexibility for family, guests, home offices, or multigenerational living. The finished lower level creates exceptional additional living space perfect for recreation, fitness, media, gaming, guests, or entertaining. What truly sets this home apart is its location. Residents enjoy sidewalks, walking paths, community green space, and playground amenities while remaining just minutes from everything that makes Annapolis special. Walk or bike to Quiet Waters Park and enjoy miles of trails, waterfront views, kayaking, concerts, dog parks, and year-round events. Downtown Annapolis, marinas, waterfront dining, shopping, commuter routes, and the Chesapeake Bay lifestyle are all just moments away. For buyers seeking the benefits of newer construction without the wait, uncertainty, upgrade costs, or construction process, 141 Stilly Way represents a rare opportunity to own a beautifully finished home in a location that perfectly blends neighborhood living with the best of Annapolis.

ANNAPOLIS

141 STILLY WAY

5 Beds

4 Baths

5,140 Sq.Ft.

$999,000

MLS#: MDAA2139818

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

Tax records are incorrect the house has over 4000 square feet of living space.
English Tudor featuring large slate patio, flagstone retaining wall and small covered front porch, surrounded by mature trees and extensive landscaping. HVAC 2 zone system replaced with high efficiency units in 2021 & 2022. Driveway repaved and expanded in 2020. Great room with cathedral beamed ceiling, wide blank redwood walls, floor to ceiling brick fireplace, and Andersen slider to deck. Oversized 2 car garage with floored attic above for future expansion. Drywell was replaced and expanded in 2015. Exterior trim boards replaced in 2024. Rear deck is 45ft.x16ft. built to hold a large hot tub and perfect for large gathering. Back yard is level with ample play area and room for a pool, overlooks wooded community open space.
Spacious living room with hardwood floors and brick fireplace. Gourmet kitchen features solid cherry cabinets, stainless steel upgraded appliance package and large kitchen island with quartz top.
First floor guest room with wood floors and large closet with shelving.Three of the four bathrooms have been renovated. Lower level has large clubroom, office/study and full bath with walk-in shower. Large storage room with built-in storage. Community has water access to Saltworks Creek with fishing pier & dock for canoes and Kayaks. Convenient location for community to DC or Baltimore, 20 minutes to BWI Airport and five miles to Annapolis historic District and Naval Academy.

ANNAPOLIS

553 CHOPTANK COVE COURT

4 Beds

4 Baths

3,759 Sq.Ft.

$995,995

MLS#: MDAA2148078

704 Caleb Lane 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 and oversized two-car garage provide ample parking and 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.

$995,000

MLS#: MDAA2145044

#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)

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.

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

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

#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.

ANNAPOLIS

3249 ARUNDEL ON THE BAY ROAD

4 Beds

3 Baths

2,800 Sq.Ft.

$940,000

MLS#: MDAA2139224

Lovely, well maintained marina front townhouse with great views of the Bay. Chesapeake Harbour offers a unique lifestyle that these owners have enjoyed for many years. Now it's your chance to experience it, to relax by one of the two pools, play tennis or pickleball, fish off the docks and watch spectacluar moon and sun rises and the Blue Angels from your new home. This is the only village that has it's own gym and natural gas to heat and cook with. Meet neighbors as you and your pooch walk the paths around the community or join friends for a meal at The Beacon restaurant as you watch the boats enter and depart the marina.
Chesapeake Harbour may be the perfect place for you so make an appointment to see this home soon.

ANNAPOLIS

7001 CLINTON COURT 7B

3 Beds

3 Baths

2,085 Sq.Ft.

$900,000

MLS#: MDAA2139894

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

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