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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

277

# of Listings

3

Avg # of Bedrooms

$506

Avg. $ / Sq.Ft.

$1,381,680

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

277 Properties Found. Page 7 of 19.

Tucked within the gated waterfront community of Epping Forest, this charming Craftsman bungalow captures the ease and appeal of Annapolis waterfront living with the rare advantage of true one-level living. Perfectly positioned on one of the community’s largest and flattest lots, the property offers a difficult-to-find combination of privacy, outdoor space, and low-maintenance comfort just moments from the Severn River and downtown Annapolis.

Inside, the three-bedroom, two-bath residence is filled with warmth and character. Heated floors provide year-round comfort, while dual fireplaces, including one gas and one wood-burning, create inviting gathering spaces throughout the home. The sun-filled great room features transom windows, abundant natural light, and French doors that open seamlessly to the outdoor living areas, creating an effortless connection between indoors and out.

The surrounding grounds have been thoughtfully designed to embrace every season of Chesapeake Bay living. Mature landscaping, a dedicated vegetable garden, outdoor fireplace, cedar outdoor shower, and expansive patio create a setting equally suited for quiet mornings or entertaining after a day on the water. Seasonal winter views of the Severn River further enhance the property’s appeal and reinforce its connection to the waterfront lifestyle that defines Annapolis and Anne Arundel County.

Life in Epping Forest extends far beyond the home itself. Residents enjoy access to one of Annapolis’ most established and sought-after waterfront communities, complete with a private clubhouse with waterfront dining, deep-water marina, sandy beach, boat ramp, tennis courts, scenic walking trails, and a vibrant calendar of neighborhood events and clubs. The location also offers convenient access to downtown Annapolis, the U.S. Naval Academy, Washington, D.C., Baltimore, and major commuter routes.

This is a rare opportunity to own a turnkey home in one of Annapolis’ premier gated waterfront communities, where the Chesapeake Bay lifestyle is part of everyday living.

Epping Forest is a Special Tax District. Annual tax: $1,583.64. Community is governed by binding Rules and Regulations.

ANNAPOLIS

310 EPPING WAY

3 Beds

2 Baths

2,036 Sq.Ft.

$1,100,000

MLS#: MDAA2145574

Discover luxurious living in this exceptional 5-bedroom, 4-bathroom home nestled on a full acre in an exclusive WATER ACCESS community. This meticulously crafted residence seamlessly blends elegant design with modern comfort, offering the perfect retreat for those seeking both tranquility and sophistication. The expansive one-acre lot offers endless possibilities for outdoor enjoyment, including gardening, relaxing on the rooftop deck, or sitting under the ceiling fans on the large front porch. Each of the five spacious bedrooms offers comfort and style, while four full bathrooms feature premium tile work, modern vanities, and spa-like amenities. All the while, enjoying the water access community amenities that offer boating, fishing, and waterfront recreation just moments from your doorstep. Easy access to local restaurants, shopping, and major roadways.

ANNAPOLIS

767 BON HAVEN DRIVE

5 Beds

4 Baths

3,255 Sq.Ft.

$1,100,000

MLS#: MDAA2140440

Stately brick traditional in sought-after Bowen Manor community. - Turn key,move- in ready just minutes from Historic Annapolis, major commuter routes, and marinas. Offering spacious, bright living throughout. Built with numerous custom upgrades and additions by the original owner, this beautifully maintained residence combines timeless elegance with thoughtful design and very low maintenance From the moment you open the handsome front doors, you'll appreciate the rich Brazilian cherry hardwood floors,elegant crown molding and timeless architectural details throughout this beautiful home. A private first-floor office with French doors and a sunny window provides the perfect space for working from home, reading or a quiet retreat. Designed for both comfortable living and entertaining, the chef's kitchen features gas cooking, center island, and generous gathering space flowing seamlessly into the inviting family room with a cozy gas fireplace. The luxurious primary suite offers a private sitting room, tray ceilings, and an generous walk- in closet. Four spacious bedrooms provide room for family and guests alike. Bedroom level laundry room. The walkout lower level is ideal fro expansive family room, second gas fireplace, and access to a wonderful brick patio area - perfectly suited for a future hot tub installation. Generous amounts of storage, the insulated under- deck drainage system helps keep the patio protected from rain. Additional highlights include all TVs convey, security system, and electric air filtration system. Perfectly located with convenient access to BWI Airport and just 15 minutes to the Beltway, this exceptional property offers comfort, convenience, and enduring quality. A warm and welcoming home you'll proudly call "Home Sweet Home"

ANNAPOLIS

216 BOWEN COURT

4 Beds

4 Baths

4,032 Sq.Ft.

$1,100,000

MLS#: MDAA2145756

Backs to Quiet Waters Park! This spacious and elegant home offers 4 bedrooms, 3.5 bathrooms and approximately 4,400 sq. ft. of living space, with the option to expand to 5,300 sq. ft. by adding a fourth level. The gourmet kitchen features double wall ovens (with the upper oven including an air-fry option), a 36-inch gas cooktop and the choice of a cabinetry hood or stainless-steel chimney hood. Additional highlights include a sunroom. These are to-be-built homes, allowing buyers to make all selections and personalize their finishes.

ANNAPOLIS

116 STILLY WAY

4 Beds

3 Baths

4,400 Sq.Ft.

$1,099,990

MLS#: MDAA2138688

Waterfront home nestled in the serene enclave of Kitty Creek; located right off the South River with easy access to the Chesapeake Bay. This recently updated home offers the perfect blend of luxury, comfort, and waterfront living. Inside, you’re welcomed by refinished hardwood floors and abundant natural light. The updated kitchen features new GE stainless steel appliances and opens to a cozy living room with a wood-burning fireplace and direct access to the deck; ideal for dining under the stars overlooking the peaceful backyard and creek. A main-level laundry/mudroom with side entrance and ramp adds everyday convenience.The primary suite is a true retreat, featuring a waterfront-facing design with a private balcony and updated en-suite bath. Three additional bedrooms with new carpet offer flexibility for guests, a home office, or growing needs. The fully finished walkout lower level provides a private in-law suite with its own entrance, full kitchen, large updated bath, and laundry hookup; perfect for extended stays or entertaining. Outside, enjoy 50 feet of waterfront with a private dock slip, kayak rack, and a spacious .41-acre lot offering plenty of room to relax, garden, or play. Ideally located with easy access to Annapolis, BWI, and DC, this home offers the best of peaceful waterfront living in Annapolis and everyday convenience.

ANNAPOLIS

996 HEADWATER ROAD

4 Beds

3 Baths

2,288 Sq.Ft.

$1,099,500

MLS#: MDAA2143898

New on site 4 days ago

Don’t miss this rarely available 4-bedroom, 2.5-bath Colonial in the highly sought-after, water-privileged community of Amberley. Fresh paint and abundant natural light create a warm and inviting atmosphere throughout. The kitchen is filled with natural light and offers gray-toned cabinetry, recessed lighting, a sunny breakfast area, and peaceful tree-lined views. Perfect for both everyday living and entertaining, the spacious family room offers a cozy gas fireplace with a charming brick surround, custom built-ins, and direct access to the rear covered porch. Overlooking picturesque Whitehall Creek, this tranquil outdoor retreat provides the perfect setting to gather with friends or unwind while taking in the serene waterfront scenery at any time of day. Just beyond is a versatile formal dining area framed by lovely front lawn views. Whether hosting memorable dinners, creating a cozy sitting room, or using the space as a private home office, this room offers flexibility while enjoying a peaceful scenery. A nearby powder room and laundry room add convenience and functionality. Retreat upstairs to the spacious primary suite, where large windows adorned with plantation shutters fill the room with natural light. The walk-in closet is thoughtfully outfitted with a custom organization system, while the en-suite bath offers a tiled walk-in shower, creating a comfortable and private retreat at the end of the day. Three additional bedrooms, each with ample closet space, share a well-appointed hall bath with a tub/shower combo, completing the upper level. The unfinished lower level provides abundant storage space and shelving with the possibility for future expansion if finished. An attached two-car garage, complete with a built-in workshop, is ideal for hobbyists, DIY enthusiasts, or extra storage needs. An extended driveway offers ample off-street parking for 4+ cars. With nature as your backdrop, this spectacular 29,500 sq ft lot is an entertainer's dream. Create your own private oasis with breathtaking riverfront views and a meandering pathway leading to your private boat slip. Enjoy endless opportunities to relax or entertain outdoors, from cozy evenings around the firepit on the brick patio to peaceful mornings surrounded by mature trees that provide beauty, privacy, and a serene setting year-round. Amberley's exceptional amenities further enhance this waterfront lifestyle. Residents enjoy access to three community piers with 45 boat slips, kayak and dinghy racks, a kayak launch pier, and a boat ramp. In addition, more than 15 acres of preserved forest and open fields offer walking trails and scenic vistas, making this a truly special place to call home.

ANNAPOLIS

700 N HOLLY DRIVE

4 Beds

2 Baths

2,072 Sq.Ft.

$1,099,000

MLS#: MDAA2141328

Spacious and elegant, this 4-bedroom, 4.5-bath home offers approximately 4,400 sq. ft., with the option to expand to 5,300 sq. ft. with a fourth level. The gourmet kitchen features double wall ovens (upper with air-fry), a 36" gas cooktop, and choice of cabinetry or stainless steel hood. Enjoy a sunroom, cozy fireplace, 9-foot ceilings on all levels, and a finished basement with full bath. Energy-efficient upgrades include a tankless water heater and two-zone HVAC. Private setting near Quiet Waters Park. Fully furnished model available. Estimated move-in July/August.

ANNAPOLIS

113 STILLY WAY

4 Beds

4 Baths

4,700 Sq.Ft.

$1,079,990

MLS#: MDAA2134880

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

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 approximately 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

New on site 2 days ago

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

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

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