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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

290

# of Listings

3

Avg # of Bedrooms

$449

Avg. $ / Sq.Ft.

$1,030,216

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

290 Properties Found. Page 6 of 20.

Welcome to 1141 Mainsail Drive, a beautifully updated colonial nestled on a desirable corner lot in Anchorage, one of Annapolis’ most coveted waterfront communities. This move-in-ready 4-bedroom, 2.5-bathroom home blends timeless colonial charm with thoughtful modern upgrades. Just one block from the community’s 49-slip marina, boat ramp, kayak and paddleboard racks, outdoor pool, and half basketball court, this property offers an exceptional lifestyle both inside and out.

Inside, you’ll find a traditional yet open layout floor plan with refinished hardwood floors on both the main and upper levels and tall windows that fill the home with natural light. The main level features a welcoming foyer, formal living and dining rooms, a powder room, and a family room with a freshly painted double-sided masonry wood-burning fireplace. The renovated eat-in kitchen boasts marble countertops, stainless steel appliances, and a gas line, seamlessly flowing into the casual dining area and family room—ideal for everyday living and entertaining. French doors lead to a charming brick patio, perfect for outdoor gatherings.

Upstairs, the primary suite with an en-suite bathroom and three (3) additional bedrooms are complemented by another bathroom and a versatile den/home office nook. The fully finished renovated basement, completed in July 2025, adds valuable living space with high-performance waterproof Pergo flooring, a recreation room, home gym or office area, and a renovated laundry/utility room with 2021 washer and dryer and ample storage.

Extensive updates include: roof, siding, gutters, and windows, new driveway and French drain system, new sump pump with backup battery system (July 2025), upgraded furnace, water heater, well pump, and sewer line.

The attached two-car garage provides convenient interior access, and the .34-acre lot features mature landscaping and a sense of privacy rare in Annapolis.

With only 106 homes, Anchorage is a close-knit, non-through-traffic community surrounded by wooded serenity and located just 3.5 miles to historic downtown Annapolis, 1 mile to Quiet Waters Park, and within 35 miles of D.C. and Baltimore.

Don’t miss this rare opportunity to own a thoughtfully renovated colonial in this hidden gem of a waterfront neighborhood—homes here rarely come to market at this price point.

ANNAPOLIS

1141 MAINSAIL DRIVE

4 Beds

2 Baths

3,264 Sq.Ft.

$949,000

MLS#: MDAA2108692

• Eclectic downtown location with 8 on-site parking spaces
• Unit has a reception/bullpen area, 5 offices, a kitchen that seats 4, copy/fax room and 2 restrooms (one with shower)
• Upgraded finishes and systems throughout
• Close proximity to Maryland State House, Circuit Court, State Office Buildings, United States Naval Academy, Annapolis City Dock, and St. John’s College
• Walking distance to Rams Head Bar & Grill, El Toro Bravo, Level, Tsunami, and various retail shops and services
• Taxes for the unit are $10,040 annually
• MX zoning, permitting uses of office, retail, restaurants, galleries, and laboratories.

ANNAPOLIS

79 WEST STREET 1

None Beds

None Baths

1,971 Sq.Ft.

$940,000

MLS#: MDAA2110468

An incredible opportunity with endless potential awaits! This 3-bedroom, 3-bath home sits on an elevated 3 acres, offering expansive views of Mill Creek and is surrounded by mature trees for a serene, private setting. Whether you're looking to enjoy the existing solidly built home, renovate, or expand - this property provides the space and flexibility to create your dream retreat. Take advantage of water views without the cost of waterfront taxes! Three marinas are just minutes from your doorstep, making this an ideal location for boating enthusiasts. Built by a member of the renowned Willard family, whose craftsmanship helped shape the Chesapeake Bay deadrise fishing boat, this property carries a rich history and offers a rare chance to create something truly special. The home itself features hardwood floors, beamed ceilings, and a screened-in porch - all positioned to capture the scenic surroundings. With a little thinning of the underbrush, you’ll have stunning water views from most rooms! Looking for even more potential? The adjoining lot (Lot #1) is 90% approved. Both properties have met all health department requirements, with the final piece being a public water extension along the existing house frontage. The subdivision is not at record plat and has been taken as far as the current owner is willing to go but all of the legwork to get it to this point will convey.
This is more than just a home—it’s a unique opportunity to craft your dream estate in a prime Annapolis location. Don’t miss out—schedule your showing today to explore the possibilities!

PLEASE NOTE: Documentation for the subdivision efforts can be emailed. The property does fall within the Chesapeake Bay critical area. Per the proposed subdivision plat a forest conservation easement would be imposed with the approval of the subvision. The home is being sold strictly as-is, where is. Any inspections for buyer's information only.

ANNAPOLIS

1634 ORCHARD BEACH ROAD

3 Beds

3 Baths

2,868 Sq.Ft.

$930,000

MLS#: MDAA2116058

This stunning log home on 2.48 scenic acres (with the potential to subdivide) offers the perfect blend of rustic elegance and thoughtful upgrades. Surrounded by lush landscaping, the property provides treetop views and a glimpse of the water during the winter months. The impressive two-story living room showcases a dramatic wood-burning fireplace and flows effortlessly into the dining area and the gourmet kitchen, which features granite countertops, a breakfast bar, ample cabinet space, and all major appliances.

Three generously sized bedrooms are located on the main level, each with gleaming hardwood floors. The primary suite includes a ceiling fan, walk-in closet, a spa-like bathroom with a soaking tub and separate shower, and private access to the deck.

Upstairs, a sunlit loft with oversized skylights offers flexible space for a home office, family room, or den and includes a full bathroom. The finished basement adds even more living space, with a spacious recreation room featuring wall-to-wall carpeting and recessed lighting, a fourth bedroom, a laundry area, and plenty of storage.

Outdoor living is just as inviting, with a large rear deck that backs to wooded privacy and a welcoming front paver walkway and deck. The driveway provides ample parking, and the home is just a short walk from community beach access.

Ideally located near major highways and downtown Annapolis, this home offers tranquil surroundings with convenient access to shopping, dining, and everyday necessities.

ANNAPOLIS

2977 SOUTHAVEN DRIVE

4 Beds

4 Baths

3,200 Sq.Ft.

$925,000

MLS#: MDAA2113476

OPEN THIS SATURDAY 11-1

Nestled in sought-after Kingsport, this impeccably maintained residence offers a rare combination of comfort, style, and convenience. Kingsport residents enjoy exclusive access to a private pool, community dock, and beautifully landscaped walking trails—perfect for morning jogs, evening strolls, or weekend paddle-boarding adventures.

This expansive home features five generously sized bedrooms and four and a half bathrooms, thoughtfully designed to accommodate both daily living and entertaining. The fully finished basement offers flexible space ideal for a media room, home gym, guest suite, or playroom. Inside, the open-concept floor plan flows effortlessly, enhanced by an abundance of natural light, high ceilings, and elegant architectural details.

At the heart of the home, the updated gourmet kitchen boasts modern appliances, ample counter space, and stylish finishes—making it a dream for both casual cooks and culinary enthusiasts. The adjoining living and dining areas create a welcoming space for gatherings of any size.

Step outside to a serene slate patio, perfectly positioned for outdoor dining, entertaining, or simply unwinding with a glass of wine as the sun sets. Eco-conscious buyers will appreciate the hidden rear solar panels, delivering significant energy savings while preserving the home’s clean exterior aesthetic.

With top-tier amenities just steps from your front door and community pride that’s second to none, 712 Pearson Point Place is more than a home—it’s a lifestyle. Don’t miss your chance to experience the very best of Kingsport living.

ANNAPOLIS

712 PEARSON POINT PLACE

5 Beds

4 Baths

6,870 Sq.Ft.

$925,000

MLS#: MDAA2113996

Stunning 5BR/4.5BA Luxury Home
Grand residence featuring hardwood foyer, formal oval dining room, living room, and main-level office. Gourmet kitchen with island cooktop, dual wall ovens, granite counters, and abundant cabinetry opens to the family room with vaulted ceilings, plantation shutters, and gas fireplace. The upper level includes a primary suite with spa bath and dual walk-in closets, en-suite second bedroom, plus two additional bedrooms with shared bath. The finished lower level offers a rec room with a wet bar, guest suite, and storage. Fully fenced yard with paver patio and raised garden bed. Property backs up to woods and walking paths. Close proximity to all commuter routes and minutes from downtown Annapolis

ANNAPOLIS

730 CRISFIELD WAY

5 Beds

4 Baths

5,151 Sq.Ft.

$899,000

MLS#: MDAA2120506

Nestled in one of Annapolis’s most sought-after and established neighborhoods, 309 McDonough Rd features modern upgrades in a flexible layout for everyday living. With major systems updated and stylish finishes throughout, this is a home you can move right into and enjoy for years to come.
The kitchen, updated in 2021, features butcher block counters, crisp white cabinetry, and modern appliances. Hardwood floors flow through the main and upper levels, while the family room and lower level offer the comfort and durability of luxury vinyl plank flooring (2025). Both the primary bath (2023) and hall bath (2025) shine with recent renovations, and the refreshed basement (2024) adds inviting bonus space. Key system upgrades include the roof and windows/doors (2017), siding (2020), HVAC (2016), and an electric car charger (2023) for convenient at-home charging. Step outside and enjoy peaceful summer evenings beneath the pergola on your private patio. The fully fenced backyard (2020) is a true retreat, with native plantings, an herb garden, and four storage sheds—ideal for gardening, hobbies, or extra storage. A two-car carport, side gravel pad, and driveway provide ample off-street parking. This location offers the best in Annapolis living—neighborhood waterfront parks and community docks for kayaking or canoeing, plus the option to join the Admiral Heights Swim Club or a private boat club. Just minutes from downtown Annapolis and City Dock, with quick access to US 50/301 and MD 2, you’ll enjoy an easy commute to D.C. or Baltimore while coming home to the quiet charm of a well-established neighborhood.

ANNAPOLIS

309 MCDONOUGH ROAD

4 Beds

2 Baths

3,040 Sq.Ft.

$890,000

MLS#: MDAA2122618

MAJOR PRICE IMPROVEMENT!!!
Welcome home to this gorgeous 4-bedroom, 3-bath home in the sought-after North River Forest neighborhood. Situated on over an acre, this property features a bright, open floor plan with two first-floor bedrooms and a full bath, plus a spacious family room with soaring ceilings, skylights, and beautiful hardwood floors. The home as been pointed up and painted, has a water filtration system and softener and a radon mitigation system.

The eat-in chef’s kitchen is a dream—complete with a gas cooktop, double ovens, island, quartz countertops, and a huge pantry that’s practically its own room. Perfect for hosting and everyday living!

Upstairs, the expansive primary suite includes room for a sitting area and a luxurious private bath with a soaking tub and walk-in shower. A charming loft area overlooks the family room below, adding even more versatility to the layout.

The lower level features a fourth bedroom, a full bath, a laundry room, and a flexible rec room or bonus space to use however you need.

The exterior is clad in high-end Hardie Plank fiber cement siding—a hallmark of quality construction - as well as a new roof. Outdoor living is just as impressive with a large Trex deck, partially covered and partially open. In the summer, you can cool off or get in a workout in the 15-foot swim spa, and in winter, enjoy the peaceful views of the South River. Backing to community open space, the property offers a rare sense of privacy and tranquility.

All this, just minutes from shopping, restaurants, and commuter routes. This is a truly special opportunity you won’t want to miss.

ANNAPOLIS

2020 JOHN HANSON OVERLOOK

4 Beds

3 Baths

4,592 Sq.Ft.

$875,000

MLS#: MDAA2103690

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful almost half acre lot with walkout basement condition in the well-established neighborhood of Rolling Knolls, in Annapolis. *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. Our exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite or quartz countertops in the kitchen, upgraded cabinets with soft close doors and drawers, ceramic-clad baths and laundry room floor, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. This location is a convenient commute to Baltimore and Washington DC and just minutes to historic Annapolis, Maryland. This is a rare opportunity for new construction in the Annapolis area. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features that are available. Prices, terms, conditions, and availability are subject to change without prior written notice. Other plans are available for this lot, including a rancher plan.

ANNAPOLIS

2175 GLENCREST CIRCLE - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$849,990

MLS#: MDAA2123152

Ameri-Star Homes is pleased to offer this incredible opportunity for a to-be-built, craftsman-style home situated on a beautiful 9,000 square foot lot in the sought-after waterfront community of Cape St. Clare in Annapolis. (There are two lots at this location). *Builder is paying $5,000 TOWARDS CLOSING COSTS with use of builders approved lender and title company. This exciting Taft model is appointed with an abundance of features that you deserve, 9-foot ceilings main level, engineered hardwood floors on the entire first floor, granite countertops, upgraded cabinets with soft close doors and drawers, ceramic-clad baths and laundry room, stainless appliances, washer and dryer package, stone accents on the exterior, architectural roof shingles, upgraded craftsman style moldings, craftsman newel posts with oak rails with black iron pickets, a garage door opener with wifi, a sodded lawn and generous landscaping package and so much more. ALL STANDARD! A home that you certainly will be proud to drive up to. There is 2,580 square feet of above grade living space to enjoy and plenty of room for expansion including adding an optional finished rec room, an optional basement bedroom and optional full bathroom in the basement at an additional cost. Come home and enjoy the exciting amenities that this incredible water privileged community has to offer. Just two and a half blocks from the water. Looking for Lifestyle? This water privileged community has all the lifestyle that you want, including 3 community beaches, access to community docks, fishing / crabbing pier, picnic area, boat launches, playgrounds, baseball fields, basketball courts, marinas, boat ramp and slips, community clubhouse and outdoor pool (with membership). All Boats, Kayaks, Canoes and all watercraft are welcome! This location is a convenient commute to Baltimore and Washington DC. This is a rare opportunity for new construction in the Cape St. Claire community. The images illustrated in this listing may be representative of the builder’s work in likeness and quality and may show optional features available. Prices, terms, conditions, and availability are subject to change without prior written notice. Existing home at this location will be demoed.

ANNAPOLIS

1094 LINDEN TREE DRIVE - TAFT MODEL

4 Beds

2 Baths

3,480 Sq.Ft.

$849,990

MLS#: MDAA2113422

#MDAA2119562

ANNAPOLIS

3447 ROCKWAY AVENUE

4 Beds

2 Baths

2,671 Sq.Ft.

$849,500

MLS#: MDAA2119562

Waterfront Living in Epping Forest with Stunning Views!

Nestled in the exclusive, gated community of Epping Forest, this beautifully maintained 2-bedroom, 2.5-bath home offers serene water views and a relaxed yet sophisticated lifestyle. Designed for effortless living, the open floor plan features 10-foot ceilings, gleaming hardwood floors, and a cozy fireplace in the Great Room. The expansive gourmet kitchen flows seamlessly into the all-season sunroom, complete with dedicated HVAC and stunning water vistas. A convenient half bath and laundry room complete the main level.

Upstairs, the grand owner’s suite boasts an oversized walk-in closet, a spa-like bathroom, and a private deck overlooking the water—perfect for morning coffee or evening sunsets. A spacious guest bedroom (or ideal office/den) with a charming full bath completes the upper level.

Outside, a fully fenced yard provides a secure space for furry friends to play freely. Off-street parking is plentiful, a rare and highly sought-after feature in this private enclave.

Epping Forest is more than a neighborhood—it’s a lifestyle. This vibrant waterfront community offers a marina with direct Severn River access, a private beach, clubhouse with a restaurant, boat club, fishing tournaments, tennis, volleyball, basketball, and year-round social events like oyster roasts, dock parties, summer camps, and holiday celebrations, including spectacular July 4th fireworks.

Located just minutes from major highways, shopping, and Historic Downtown Annapolis, this is a rare opportunity to experience the best of waterfront living. Come discover the charm of Epping Forest and make it your home!

ANNAPOLIS

336 SEVERN ROAD

2 Beds

2 Baths

1,708 Sq.Ft.

$849,000

MLS#: MDAA2110674

Rare Opportunity to Build Your Dream Home Near Historic Downtown Annapolis
3268 Kitty Duvall Drive | Offered at $875,000 |
Includes Lot, Site Work Budget & Customizable Chestnut Model by Timberlake Homes

Embrace the chance to create your dream home on a peaceful, build-ready .62-acre wooded lot just minutes from the charm and energy of downtown Annapolis. Nestled off a quiet, private gravel lane, this flat homesite offers public sewer access and the benefit of preliminary engineering already completed—making it easier and faster to build.

This exclusive opportunity includes Timberlake Homes’ highly flexible and elegant Chestnut floorplan, thoughtfully designed to combine comfort, functionality, and style. Enjoy the tranquility of a secluded setting with convenient access to vibrant shops, waterfront dining, cultural landmarks, and historic marinas.

Highlights of the “To Be Built” Chestnut Model:
2,251–2,498 sq. ft. | 4 Bedrooms | 2.5+ Bathrooms

Welcoming open foyer with tucked staircase and central powder room
Spacious family room with optional 4' extension and fireplace
Gourmet eat-in kitchen with 42” maple cabinetry, granite countertops, walk-in pantry, breakfast island, and Samsung appliances (including a double wall oven)
Mudroom entry from a 2-car garage
Elegant oak stairs from main to upper level
Hardwood, LVP, or laminate flooring throughout main level
9’ ceilings on main level with 9’ foundation walls for added volume
Ceramic tile in all bathrooms
Stylish brushed nickel hardware and Moen® fixtures throughout
Optional features: deluxe primary bath, third full bath, sunroom, and lower-level recreation room

Chestnut Floorplan Overview:
The Chestnut offers timeless appeal with a flexible layout. A bright foyer opens to a versatile flex room, while the central staircase leads to four generously sized bedrooms upstairs, a full hall bath, and a convenient second-floor laundry room. Enhance your living space with thoughtful options like a sunroom, extended family room, or finished basement recreation area.

Additional Notes:
Timberlake Homes makes no representations regarding the lot or its sale. Please contact the listing agent to connect directly with the builder. Photos and floor plans may show upgraded features not included in the base price. Final pricing may vary depending on selected options and builder allowances.

ANNAPOLIS

3268 KITTY DUVALL DRIVE

None Beds

None Baths

N/A

$849,000

MLS#: MDAA2117802

#MDAA2123444

ANNAPOLIS

701 SONNE DRIVE

4 Beds

3 Baths

2,704 Sq.Ft.

$829,900

MLS#: MDAA2123444

Open House Saturday 11 am - 1 pm. Great Opportunity to own this Amazing 4 Bedroom, 3.5 Bathroom 2 Car Garage, Single Family Home w/ over 5,000 Total Sq Ft in the Kingsport Subdivision of Annapolis, MD. (Sellers has a 2.375% VA Assumable Loan) As soon as you walk thru the door you will fall in love with the Grand Entrance, there are 9 Foot Ceilings throughout w/ Columned Entry to a Formal Living and Dining Room w/ Crown Molding and Chair Rail Detailing. The Main Level features Beautiful Hardwood Floors that flow into your Oversized Eat-In Gourmet Kitchen w/ Double Oven, Center Island w/ Gas Cooktop, New Stainless Steel Refrigerator and Stainless Steel Dishwasher installed 1 year ago, Granite Counter Tops, Walk-In Pantry. The Kitchen is Open to a Two-Story Family Room w/ Gas Fireplace. Off the Foyer you will find the Half Bathroom and near the Pantry is a Large Laundry Room and door that leads to the 2 Car Garage. Just off the Family/Living Room is a First Floor Office. Upstairs you will find all 4 Bedrooms including a Bonus Loft Area that Overlooks the Family Room. You will be very pleased when you see the size of the Primary Bedroom Oasis includes: Tray Ceiling up to 10 Feet, Sitting Area, Double Walk-In Closet and an En-suite w/ Luxury Bathroom that includes a soaking Tub, Separate Shower and Double Sinks. Second Bedroom also have an En-suite and walk-in Closet. Bedrooms 3-4 Share the 3rd Full Bathroom in the Hallway, Bedroom 3 has a Walk-In Closet, Bedroom 4 has Dual Closets. The unfinished 1,609 Sqft Basement offers a full bath rough-in, Radon Remediation System and Plenty of Storage Room plus additional Living Space and an Egress Window, so an extra Bedroom and Full Bathroom can easily be added. The Outside Features a stunning Stamped Concert Patio w/ an area to add Table and Chairs and even a Fire-Pit. Backyard is Fully Fenced for Privacy and home has an Asphalt Driveway. The Home is located in one of the prime spots in the neighborhood just across from the community pool and bathhouse. HOA Amenities include a community pool with terrace, spa pool, and grilling area; fishing; two playground areas; hiking and biking trails, kayak and canoe storage racks and kayak/canoe loading bar. Additional Items to Note: 1 year ago the Roof was replaced and a New Washer and Dryer were installed, New Carpet just installed up the stairs and in all the Bedrooms, Ceiling Fan prewire in Great Room, Exterior Trim was repainted just last week and any damaged trim was replaced and lastly 1 of the 2 HVAC Systems was replaced in 2021. Home is less than 5 miles from the Naval Academy and Downtown Annapolis. Conveniently located off Forest Drive and easy assess to Rt 2, 50 and 97 if commuting to DC, NSA or Fort Meade or Baltimore. Close to shopping, entertainment and restaurants. Don't miss out on seeing this one ASAP it will move quickly.

ANNAPOLIS

702 BANNEKER LANE

4 Beds

3 Baths

5,303 Sq.Ft.

$825,000

MLS#: MDAA2122726

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