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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

316

# of Listings

3

Avg # of Bedrooms

$463

Avg. $ / Sq.Ft.

$1,071,137

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

316 Properties Found. Page 17 of 22.

#MDAA2125874

ANNAPOLIS

1004 PRIMROSE ROAD 203

2 Beds

2 Baths

1,020 Sq.Ft.

$305,000

MLS#: MDAA2125874

Welcome to 26 Pleasant Street: a charming 2-bedroom, 1-bath home in the heart of Annapolis, just steps from West Street’s restaurants, shops, and nightlife.

Whether you’re looking for a primary residence, weekend getaway, or investment, this home offers incredible flexibility. This turnkey property is not only move-in ready but also a proven licensed Airbnb performer, with nearly $40,000 in earnings in 2024 and over $22,000 already booked through August 2025.

Inside, the main level features a spacious family room, dining area, and kitchen that opens to a deck and fenced backyard, perfect for entertaining. Upstairs, you’ll find two bedrooms, a full bath, and a bonus loft area for an office or guest space.

Don’t miss your chance to own an Annapolis gem with walkable lifestyle perks and a track record of short-term rental success.

ANNAPOLIS

26 PLEASANT STREET

2 Beds

1 Baths

972 Sq.Ft.

$299,900

MLS#: MDAA2125926

**LISTING DESCRIPTION UPDATED 10/3/2025**
This top-floor penthouse condo has been extensively renovated from top to bottom, offering modern finishes, durable materials, and functional design updates. Every major system and space has been improved.
LAYOUT IMPROVEMENTS:
Walls were reconfigured to expand the footprint and create a more open flow. A dedicated laundry closet was added for convenience, featuring an oversized Maytag washer and dryer.
BATHROOMS:
The original 1.5 baths were converted into 2 full baths. Both include new tile, new toilets, and stone-top vanities with Delta faucets. Showers were rebuilt with concrete board and green board for long-lasting durability. The primary bath includes a new tub surround and exhaust fan. The hall bath features a raised ceiling, full tiled walk-in shower, and a new exhaust fan with LED light. Mold and mildew-resistant PVC baseboards were installed in both bathrooms.
PLUMBING:
All water shut-off valves, sinks, and fixtures were replaced throughout the unit, ensuring updated and reliable plumbing.
FLOORING AND FINISHES:
All previous carpet was removed, subfloor leveled, and commercial-grade waterproof luxury vinyl plank installed throughout. New 5” decorative baseboard trim was added, and the entire condo has been freshly painted with accent walls for a modern finish.
WINDOWS & DOORS:
All windows and the sliding glass door were replaced with energy-efficient, noise-reduced models. Bedroom windows tilt inward for easy cleaning.
LIGHTING & ELECTRICAL:
Significant electrical upgrades were completed, including a new electrical panel and replacement of all switches/outlets. Lutron Alexa-ready dimmers were installed, with 3- and 4-way wireless switching and remote controls. Downlighting and/or ceiling fans were added in every room. Commercial-grade dim to warm 3000k-1700k fixtures are indirect in living room & dining area and direct lighting in hallways & kitchen. Built-in GFI night lights were installed in the kitchen and baths. The kitchen features commercial-grade dimmable downlights at 4,000k for task lighting, eliminating shadows in prep areas. Surround sound and ethernet wiring were run through the living room walls. Modern light fixtures were added in the bathrooms and over the primary bedroom vanity.
HVAC:
Gas furnace and HVAC were replaced 2.5 years ago, including updated breaker, gas shut-off valve, and insulated ducts. A WiFi-enabled thermostat was added in the living room.
KITCHEN:
The kitchen was fully remodeled. Bulkheads were removed to allow for a full-size refrigerator. Cabinets were updated with pull-out drawers for additional storage. Dark granite countertops with a 4” backsplash complement an oversized stainless steel sink, Kohler pull-down faucet, and new garbage disposal. Ventilation was upgraded with a larger, quieter exhaust fan. Appliances include dark stainless steel Whirlpool refrigerator, dishwasher, and gas oven.
ADDITIONAL UPGRADES:
New closet doors were installed, and the primary bedroom was redesigned with updated finishes. A TV wall mount with in-wall hidden cable pass-through was added, complete with pull string for future wiring.
BUILDING UPDATES:
The roof was replaced five years ago, and tuckpointing completed one year ago, both handled by the condo association.
EFFICIENCY & COSTS:
Gas and water are included in the condo association fees, covering furnace operation.

ANNAPOLIS

10 SILVERWOOD CIRCLE 10

2 Beds

2 Baths

1,164 Sq.Ft.

$299,900

MLS#: MDAA2122610

#MDAA2126114

ANNAPOLIS

300 HILLTOP LANE 300I

2 Beds

2 Baths

1,321 Sq.Ft.

$290,000

MLS#: MDAA2126114

MOTIVATED SELLER, JUST REDUCED ANOTHER $10,000!! It's a life of luxury amid the Annapolis waterfront shores of the Chesapeake Bay. You've earned this! Sit back, relax and take in the incredible views while someone else takes care of the cooking and cleaning... Nothing to do but live your best life! Immense social opportunities await: meet your friends on the putting green or have cocktails on the waterfront deck, walk the shores of the Chesapeake and never leave your home. Monthly Co-op fees covers all utilities, taxes, insurance, multiple dining options, weekly house cleaning, maintenance/replacement of appliances, including HVAC, local transportation, a wide variety of fitness/social functions. Not to mention, on-site banking, convenience store and beauty/barber shop. Baywoods of Annapolis is a premier retirement community offering all the perks of being a homeowner, with the peace of mind that help is immediately available. It's your New Waterfront Home and you'll never want to leave!

ANNAPOLIS

7101 BAY FRONT DRIVE 400

1 Beds

1 Baths

1,000 Sq.Ft.

$265,000

MLS#: MDAA2116362

MAJOR PRICE ADJUSTMENT on this lovely flat lot in a private, convenient neighborhood.
This lot was subdivided many years ago and used by the present owners for picnics and famly gatherings.
Please contact the listing agent with any questions. And drive by but do not walk the lot without prior authorization.
Please contact the listing agent regarding the potential availability of the house next door.

ANNAPOLIS

29 COLLISON ROAD

None Beds

None Baths

0.29 acres

$250,000

MLS#: MDAA2116978

Open Sunday, Oct 19th, 11-1 pm. Updated. Previously listed tenant occupied. Now vacant, new paint, carpet and full bath. Please take a second look. First floor has an open living / dining room combo with wood fireplace and patio door to a nice deck. Upstairs has two bedrooms with lots of closets and new bath. Well priced in an excellent location near many popular community amenities for purchasers seeking an active lifestyle. Home is a great first home, or rental in an investor friendly community. For purchasers seeking to rent, lister willing to provide rental and management services free for the first year. Call for more information.

Across the street from Truxton Park with includes "The Pip Moyer Recreation Center, ball fields, tennis and pickleball courts, a skateboard park, swim center and boat ramp are spread across the park. But what is often overlooked are the trails that wind through the park. To walk a two mile loop through the woods and along the creek, park behind the rec center near a fun new playground and look for a wooded trail head that is closer to the Salvation Army side. The trail is easy to follow. The path goes through the woods and down a slope until you see a pump station. The new pool is in the woods to your right. Continue on until you reach a driveable path coming from the direction of the pool. If you turn left you can cross a wooden bridge and walk on Silopanna until it reaches the Spa Creek Trail which passes the Chesapeake Children’s Museum and ultimately the trail that surrounds Bates Middle School. Following this trail can add significantly to your walk."

ANNAPOLIS

290 HILLTOP LANE M

2 Beds

1 Baths

1,024 Sq.Ft.

$244,950

MLS#: MDAA2128836

***Opportunity to build in Annapolis***
Grading permit was approved by the City of Annapolis, but expired December 2024 during the building permit review. The Seller has filed a request for renewal of the grading permit and awaits approval. Once the grading permit is approved the building permit will follow. House to be built is the Wexford (84 Lumber). Choose your builder, exterior/interior materials and finishes. Contact the agent with questions.

ANNAPOLIS

216 GROSS AVENUE

None Beds

None Baths

0.14 acres

$225,000

MLS#: MDAA2118590

Welcome to the sought-after community of Cape St. Claire! This lot is being offered as an addition to a home for sale. Please contact the county for possible development.

ANNAPOLIS

1167 GREEN HOLLY DRIVE

None Beds

None Baths

0.21 acres

$160,000

MLS#: MDAA2116560

Seize the opportunity to own a cleared, water-view lot in the community of Highland Beach, an incorporated municipality, Located just minutes from Downtown Annapolis, this lot provides easy access to schools, shopping, and dining. The community beach is only steps away, offering picturesque water views. Sewer hook-up is available at the street.

ANNAPOLIS

3210 BRUCE

None Beds

None Baths

0.14 acres

$159,000

MLS#: MDAA2114238

BUSINESS SALE ONLY- Fantastic opportunity to own this turnkey and well established restaurant in the heart of downtown Annapolis. Approximately 1500SF with 20 dine-in seat capacity. Fully equipped kitchen ready for any menu. Downtown Annapolis boasts a vibrant and diverse restaurant scene, seamlessly blending historic charm with modern culinary offerings. This location has excellent visibility on the popular Main St. Beer & Wine license available. Landlord approval of new tenant is required. Showings by appointment only.

ANNAPOLIS

138 MAIN STREET

None Beds

None Baths

N/A

$150,000

MLS#: MDAA2105548

Discover a Rare Opportunity in the Heart of Annapolis! Build your dream home or investment property on this prime, in fill buildable lot ideally located at 8 Dorsey Avenue. Enjoy a walkable lifestyle just minutes drive to Downtown Annapolis, with its charming shops, dining, and the scenic City Dock. Commuters will appreciate easy access to major routes connecting to Washington, D.C., Baltimore, and surrounding areas.

Land only — no existing structure, approved plans, or permits convey.

ANNAPOLIS

8 DORSEY AVENUE

None Beds

None Baths

0.12 acres

$125,000

MLS#: MDAA2128632

Level lot, 2017 perc evaluation indicated a possible home up to a 2,500 sq ft . Buyer to verify all information.

ANNAPOLIS

1012 CARRS ROAD

None Beds

None Baths

0.16 acres

$98,000

MLS#: MDAA455886

Excellent opportunity to fulfill your dream of constructing your own dream custom home. This lot is located in a beach community with lots of creeks. Enjoy the lazy days on or by the water with lots of activities. Make this a second home to just relax and enjoy being away from the hustle and bustle of city life. The property is currently not connected to public water or sewer but are slated for future development making this a great piece of property to buy and hold or start your planning with the utility option for a future date.

ANNAPOLIS

1221 CREEK DRIVE

None Beds

None Baths

0.26 acres

$55,000

MLS#: MDAA2111916

Welcome to 1848 Milvale located in the Saint Margarets area of Annapolis. As you enter the home you are struck by the beautiful wide views of Mill Creek, the open floor plan, and architectural details. The dining room and living room have gorgeous coffered ceilings, cherry hardwood floors, extensive millwork, floor-to-ceiling windows, and French doors that overlook the saltwater pool, spa, and creek. The kitchen offers a huge central island, wolf range, and custom cabinetry. Off the kitchen is the family room... it's striking with its vaulted barrel ceiling, custom built-ins, bar area, gas fireplace, and curved bank of windows centering again on the views of Mill Creek. The home has 2 main-floor bedroom suites with attached baths. The waterside bedroom has a poolside door and views of the creek while the front bedroom has serene views of the cornfields across the road facing East. One of the architectural highlights of the home is the stairwell tower with its impressive wide girth access to two distinct upper-level areas. Flooded with light, the high ceiling with clerestory windows first lands at the hall library-study. This cozy nook opens to a multi-purpose suite that can be used as a 3rd bedroom, a nursery, a 2nd family room, or an often-needed teen hangout area. The tower takes a turn to the left and accesses the primary bedroom and adjoining waterside office. The primary bedroom provides his and her walk-in closets, a huge spa bath with a soaking tub, heated floors, a walk-in shower, and laundry. Off of the primary bedroom is a handsome office with custom cabinets, a gas fireplace, and a deck to enjoy your morning coffee or a sunset cocktail. The lower level is the fifth-bedroom suite. This room is both the seller's workout room and wine cellar. The utility room has a wash sink, great for gardening, and houses the water treatment systems and 2 Geo-Thermal systems. The home has beautiful hardscaping with irrigation, and a rock garden water feature in the front of the home, and in the back, there is 148 ft of water frontage with a handsome Belgium stone seawall. The pier is "like new" with 2 slips, a 15,000 lb. boat lift, and 8 MLW. The pier is in a NO WAKE ZONE on weekends .. Located on one of the most sought-after roads in Annapolis and known for its privacy and country-like living, Milvale Road winds along the banks of Mill Creek in Saint Margarets surrounded by farmland and corn fields. A perfect place to unwind and enjoy the best sunsets around! Available from December 1, 2024-June 1, 2025

ANNAPOLIS

1848 MILVALE ROAD

5 Beds

5 Baths

5,855 Sq.Ft.

$25,000

MLS#: MDAA2074056

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