One of the most popular communities provided by {{page_data.agentName}}

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

163

# of Listings

3

Avg # of Bedrooms

$492

Avg. $ / Sq.Ft.

$944,815

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

50 Properties Found. Page 1 of 4.

New on site 1 day ago

OPEN SATURDAY 2/21/26, 11AM TO 1PM! Come enjoy the Annapolis lifestyle in this three level, end unit townhouse in the centrally located Windgate community. A wide, inviting entryway welcomes you to an open floorplan on the main level with living area and dining area open to the kitchen. Crown moulding frame the first floor. The bright, kitchen features granite counters, stainless steel dishwasher, oven and and microwave plus an eat-in /coffee bar area. Natural light from side and rear windows make the kitchen a wonderful space. The dining area, with five light chandelier, has a sliding glass door to access the rear deck and yard. The upper level is home to the primary suite that was updated in 2024 and features a walk-in shower, marble dual sink vanity and updated floor. The primary bedroom features windows that overlook the rear yard, an oversized closet and engineered hardwood floor. A full bath and two additional bedrooms round out the upper level. The lower level is great for watching TV on the included video projector, and features a gas fireplace. A craft area and utility room provide great storage space. The fully fenced back yard is great for grilling and entertaining. Other seller updates include HVAC in 2021, Roof in 2015 and new Smoke /Co2 alarms. This home is close to everything you could need, including shopping and dining downtown or at the Annapolis Mall and Annapolis Towne Centre. The Navy-Marine Corps Memorial Stadium is just minutes away, and Historic Annapolis is right nearby for you to explore and enjoy. Access to major commuter routes like Rt 50 (.5 mi), Rt 70 (.3 mi) make this the ideal location for those needing to travel to Ft Meade, Washington DC, or Baltimore. What a great place to call home!

ANNAPOLIS

758 HOWARDS LOOP

3 Beds

3 Baths

2,168 Sq.Ft.

$500,000

MLS#: MDAA2136734

#MDAA2134478

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 307

2 Beds

2 Baths

1,318 Sq.Ft.

$499,900

MLS#: MDAA2134478

Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been tastefully renovated and includes a tub/shower combo. The newly-carpeted basement offers flexible space for a home office, gym or recreation area plus dual closets for extra storage. Utilize the savings and comfort from the high-efficiency zoned dual heating/cooling system and heat pump. Outside, enjoy the fully-fenced backyard with vinyl privacy fencing and a hardscaped patio-ideal for entertaining-and a custom 16 x 12 storage shed for tools and gear. Nature & water lovers will appreciate the home's close proximity to Quiet Waters Park, where you can enjoy walking trails, a dock and boat/kayak access to scenic Back Creek. You're also just minutes from the Severn River, the Annapolis Maritime Museum, downtown Annapolis, the Eastern Shore and major commuter routes to Washington D.C., Baltimore and beyond. Don't miss this perfect blend of location, charm and convenience-your Annapolis lifestyle awaits!

ANNAPOLIS

1005 HYDE PARK DRIVE

2 Beds

1 Baths

1,190 Sq.Ft.

$499,000

MLS#: MDAA2130832

BY APPOINTMENT ONLY.
55+ Luxury 2 bedroom/den with patio in elevator condo building. THE ELEMEMT boasts a variety of amenities to satisfy an active adult community. Natural light floods into the modern kitchen with white cabinetry, tiled backsplash, SS appliances & quartz countertops. Enhanced lighting & recessed lights throughout. Upgraded closet design w/a huge Master closet! Beautiful, light colored LPV flooring (no carpeting). Custom bathroom design with upgraded tilework. Double vanity in the master bath. Private balcony for sipping your morning coffee. Beautifully landscaped perimeter with a walking trail/path. Elegant lobby with automated golf room & pool table. Enjoy pickleball, dog park, outdoor grills & workout equipment. Assigned parking & lower-level storage area included. Call today to see this great property with amenities galore! Quick drive to downtown Annapolis, waterfront dining, shopping & the Bay Bridge.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 209

2 Beds

2 Baths

1,210 Sq.Ft.

$498,000

MLS#: MDAA2136282

Plans and permits are ready and building can start right away! Conditional Grading Permit issued! This is a rare opportunity to build a home with water views in the exclusive water-privileged neighborhood of Beacon Hill. Buyers can design their own home or use one of two gorgeous current plans. A smart buyer would fit his plan within the footprint of the current 2500 sq ft, 4-bedroom building plan, with a wrap-around porch. NOTE- Any increase in footprint (surface area) would have a negative impact (increase) on storm water management, setbacks from the septic system, etc.

Beacon Hill was originally a community of only forty houses, with twenty lots directly on the Bay and the other twenty with water views. 1546 Shipsview is undoubtedly the best of the ‘ water view’ lots. Directly across the street from 1546 is one of the community's two public water access points. It is the perfect spot to wade into the Bay or sit with a morning coffee and watch the sunrise. 1546 is a rare gem in a highly sought-after community. DO NOT DELAY, or you will miss the opportunity to build in this very special neighborhood. Easy access/commuter routes to the Chesapeake Bay Bridge, the Eastern Shore , Washington and Baltimore.

ANNAPOLIS

1546 SHIPSVIEW ROAD

None Beds

None Baths

0.47 acres

$495,000

MLS#: MDAA2133158

Exceptionally beautiful 1 BR/1 Bath with stunning sunset views in like-new condition. The only unit available in this Luxurious Condo Building still priced below $500K.
Many upgrades: New Bosch HVAC Heat Pump costing $10K, New designer walk-in shower costing $12 K , New carpeting in Bedroom., Hardwood floors, granite counters. Many amenities : 24/7 live person at the Lobby Front Desk, very secure building, One owned/ assigned underground garage parking space with remote opener, Fitness Center, Outdoor Pool and Hot Tub, Two Outdoor Gourmet BBQ kitchens, Gardening Area, Library, Party Room , TV Lounge , Free Shuttle Service to downtown, just blocks to City Dock attractions: restaurants, entertainment venues, shopping. The most luxurious condo residence in this county.

ANNAPOLIS

5 PARK PLACE 431

1 Beds

1 Baths

839 Sq.Ft.

$489,900

MLS#: MDAA2121784

New on site 2 days ago

Perched on the top floor of The Tecumseh, Maryland’s first condominium building, this two-level loft offers beautiful water views and an exceptional Eastport lifestyle. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This 1-bedroom, 1-bath residence features an open-concept main level with living and dining areas, a well-equipped kitchen, mechanical room, and storage closet. The loft-style upper level showcases exposed beams, soaring ceilings, abundant natural light, and a spacious bedroom with two closets and a full bath. Recent updates include fresh paint, new carpet and bathroom flooring (2024), refrigerator (2022), HVAC (2018), and dishwasher (2017). A rare bonus: boat slip entitlement in the private marina. Community amenities include gated parking, waterfront pool and deck, private marina, kayak and bike storage, secure entry with elevator, on-site management, and laundry on each upper floor. Located in the heart of Eastport, just steps to restaurants, shops, and downtown Annapolis by foot, bike, or water taxi. This is your opportunity to own in one of Eastport’s most sought-after waterfront communities - schedule a showing today.

(The Tecumseh Condominium has a 15-day first right of refusal.)

ANNAPOLIS

312 SEVERN AVENUE W 401

1 Beds

1 Baths

660 Sq.Ft.

$485,000

MLS#: MDAA2137140

Prime Retail/Office Space in the Heart of Annapolis

Welcome to 141 West Street, Suite 103 – a versatile retail/office space perfectly positioned in the vibrant core of Annapolis. This ground-level suite offers an open layout that’s ready to be outfitted to match your vision. Whether you’re looking to expand your business, launch a new venture, or establish a professional office, this space gives you the flexibility to make it your own.

Situated in a highly visible and walkable area, you’ll benefit from steady foot traffic, nearby shops, dining, and cultural attractions. The suite also comes with the added convenience of one dedicated parking space, a rare find in downtown Annapolis.

Seize the opportunity to plant your business in one of the city’s most sought-after locations! Prime retail/office condo in the heart of downtown Annapolis. Ground-level suite ready to be customized for your business. High visibility, walkable location near shops and dining. Includes 1 dedicated parking space. Perfect for professional office, boutique retail, or creative workspace. Contact City of Annapolis Permitting office to verify your intended use. The Condo fee is estimated $591 monthly.

ANNAPOLIS

141 WEST STREET 103

None Beds

None Baths

1,009 Sq.Ft.

$469,000

MLS#: MDAA2125942

#MDAA2133612

ANNAPOLIS

402 CRANES ROOST COURT

None Beds

None Baths

1,662 Sq.Ft.

$460,000

MLS#: MDAA2133612

Sweet, cozy, and lovely home semi-detached house. 3 bedroom, 1 1/2 baths and semi finished basement, NEW ROOF 2023. Close to Truxtun Park and easy access to downtown Annapolis and US 50 HWY. GREAT OPPORTUNITY! Bring your best offer.

ANNAPOLIS

108 CONLEY DRIVE

3 Beds

1 Baths

1,880 Sq.Ft.

$450,000

MLS#: MDAA2133422

HERITAGE HARBOUR SPACIOUS VILLA - Welcome home to this beautifully renovated 2 BEDROOM plus BONUS ROOM (could be 3rd BEDROOM), 2 BATH VILLA with over 1440 square feet of living space. Located in the desirable HERITAGE HARBOUR 55+ Active Community, this villa offers one level living. Some of the recent updates include newly refinished Brazilian Cherry Solid Hardwood Floors, new LIGHT FIXTURES, updated kitchen with QUARTZ COUNTERTOPS, LARGE SINK and FAUCET, new BACKSPLASH and UNDERCABINET LIGHTING, STAINLESS STEEL APPLIANCES, Beautiful Cherry Cabinetry and large BREAKFAST ISLAND. The home is an OPEN CONCEPT FLOORPLAN -- perfect for entertaining. CUSTOM PLANTATION SHUTTERS on the front windows of the home and ROOF is only about 5 years old. There is a laundry/storage closet conveniently located off the kitchen and a large BONUS ROOM (could be a 3rd bedroom or home office) with a walk-in pantry/closet. Sliding glass doors off the second bedroom open to a large, private, PAVED PATIO with hardscape and gas grill (outdoor furniture and grill are included).
Heritage Harbour offers lots of amenities including an indoor and outdoor swimming pool, fitness center, tennis courts, pickleball courts and a community center with a variety of activities. A golf course is located within the community if homeowners would like to join. GREAT LOCATION - Only minutes to downtown Annapolis, major roads, shopping, restaurants and medical facilities. Buyer pays a one-time recreation fee of $2,075 at settlement.

ANNAPOLIS

2510 PAINTER COURT

2 Beds

2 Baths

1,440 Sq.Ft.

$449,900

MLS#: MDAA2133702

Enjoy the ease of single-level living with a functional layout, while also benefiting from exceptional expansion potential—build up, build out, or create the outdoor space of your dreams. The generous lot provides flexibility for future potential improvements, whether that’s additional living space, a garage, or enhanced outdoor entertaining.

Located just minutes from shops, restaurants, marinas, and waterfront amenities, and conveniently close to Downtown Annapolis, this home delivers the Eastport lifestyle buyers crave. A true opportunity for homeowners, investors, or anyone looking to secure a foothold in one of Annapolis’ most desirable neighborhoods.

ANNAPOLIS

1106 BRASHEARS STREET

3 Beds

1 Baths

1,008 Sq.Ft.

$449,900

MLS#: MDAA2133596

Heritage Harbour a 55 plus community. Welcome Home to 1955 Marconi Cir. This two bedroom two bath home with garage offers low maintenance one level living. As you enter from the covered front porch, you'll notice the high vaulted ceilings and lovely hardwood floors throughout. Custom shutters have been added on all windows and slider. Both bedrooms are generous in size. The primary bedroom includes an ensuite bathroom. The rear of the home includes a fenced in patio. Roof is approximately 2 years old and includes solar panels with a monthly fee of $99.00. Heritage Harbour offers lots of amenities including an indoor and outdoor pool, fitness facility, community center with a variety of activities. A golf course is located within the community if homeowners would like to join. Close proximity to Major Roads, Shopping and Restaurants. Historic Annapolis is approximately 20 minutes drive time.

ANNAPOLIS

1955 MARCONI CIRCLE

2 Beds

2 Baths

1,200 Sq.Ft.

$445,000

MLS#: MDAA2131974

Beautiful Split Foyer in Whispering Woods! Classic floorplan - Laminate Flooring with Oak Finish Throughout. Upper Level Living Room with Chair Rail, Eat-In Kitchen features Stainless Appliances, Double Oven, and Sliding Door access to Rear Deck overlooking Wooded Lot. Two Generously Sized Bedrooms and Updated Full Bath with Dual Entry from both Hall AND Primary Bedroom. Walkout Lower Level includes Third Bedroom, Updated Full Bath, Laundry Room, and Large Den with Woodburning Fireplace and Sliding Door to Rear Yard and Covered Patio. Roof replaced apx 2014, HVAC installed apx 2020, Fireplace Inspected 2020, Radon Testing 2020. Less than a quarter mile from neighborhood public park Whispering Woods Drive Playground) down the street and apx 1 mile located close to Broadneck Peninsula Trail. Easy access to both 50 and RItchie Hwy.

ANNAPOLIS

1525 HICKORY WOOD DRIVE

3 Beds

2 Baths

1,265 Sq.Ft.

$445,000

MLS#: MDAA2134526

Welcome to 206 Admiral Drive, a charming and cozy single-family home in the heart of Annapolis! This delightful residence offers 2 comfortable bedrooms and 1 full bathroom, a perfect blend of simplicity and warmth.

Step inside and imagine the possibilities in this inviting home filled with character and potential. Whether enjoying a quiet morning coffee or hosting friends and family, each space feels welcoming and full of promise. The manageable lot size provides just enough outdoor space to garden, relax, or sip lemonade.

Located in the historic Annapolis area, this home puts you close to local amenities, charming neighborhoods, and vibrant community life. This is an ideal opportunity to own a slice of Annapolis living .

ANNAPOLIS

206 ADMIRAL DRIVE

2 Beds

1 Baths

762 Sq.Ft.

$435,000

MLS#: MDAA2133450

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Buyers resources

7 Reasons to Work with a Realtor

7 Principles For Home Buying Success

Getting a Mortgage To Buy a Home

Home Hazards Awareness

Key Items For Home Inspection

Questions When Buying a Condo

Questions When Choosing a Realtor

Sellers resources

8 reasons to work with a realtor

Calculating Capital Gains

Checklist for Better Showing

Cleaning Home For Sale

Improving Odds Of an Offer

Preparing Home for photoshoot

Selling Your Home for More $$

Buyers resources

BUYERS RESOURCES

Sellers resources

SELLERS RESOURCES

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