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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

282

# of Listings

3

Avg # of Bedrooms

$504

Avg. $ / Sq.Ft.

$1,381,763

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

282 Properties Found. Page 13 of 19.

Amazing opportunity! Situated in one of Annapolis’ most desirable waterfront communities, Oyster Harbor, 3328 Shore Drive offers a premier corner-lot location with beautiful second-floor water views. Enjoy the coastal lifestyle with easy access to marinas, parks, the community beach, local dining, and the charm of nearby historic Annapolis. This property presents an incredible opportunity for buyers looking to renovate, update, or create their dream home in a sought-after location. Don’t miss this rare chance to bring your vision to life!

ANNAPOLIS

3328 SHORE DRIVE

3 Beds

2 Baths

1,824 Sq.Ft.

$625,000

MLS#: MDAA2144406

848 Deerwood Court offers a wonderful opportunity to enjoy life in Heritage Harbour, one of Annapolis' most sought-after active adult communities. Situated on a desirable corner lot at the end of a quiet cul-de-sac, this well-designed ranch-style home features three bedrooms, two full bathrooms, a spacious side addition, and a two-car garage.

The home has been lovingly maintained over the years and offers a comfortable floor plan with generous living spaces, abundant natural light, and excellent flow for both everyday living and entertaining. The side addition provides valuable extra living space rarely found in many homes of this size, while the corner lot setting offers attractive curb appeal and additional privacy.

This property presents an excellent opportunity for buyers to personalize a home to their own tastes and style while enjoying all that Heritage Harbour has to offer. Whether you're looking to make updates immediately or over time, the solid layout and desirable location provide a strong foundation for future improvements.

Residents of Heritage Harbour enjoy an exceptional lifestyle with access to a community lodge, indoor and outdoor pools, fitness facilities, walking trails, waterfront amenities, clubs, activities, and countless opportunities to stay active and connected.

Conveniently located near shopping, dining, downtown Annapolis, medical facilities, and major commuter routes, this home combines comfort, convenience, and community in one of the area's most desirable neighborhoods.

Don't miss the opportunity to make this Heritage Harbour home your own and enjoy the active lifestyle that has made this community such a popular destination for buyers seeking the very best of Annapolis living.

ANNAPOLIS

848 DEERWOOD COURT

3 Beds

2 Baths

1,900 Sq.Ft.

$605,000

MLS#: MDAA2146412

#MDAA2136300

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 112

2 Beds

2 Baths

1,621 Sq.Ft.

$602,602

MLS#: MDAA2136300

Tucked away on a gorgeous, private lot in the highly sought-after Cape St. Claire community, this beautifully maintained home combines exceptional outdoor living with the unmatched lifestyle that makes this waterfront neighborhood one of Annapolis' most desirable places to call home. From the moment you arrive, you'll appreciate the outstanding curb appeal featuring professional landscaping, an impressive retaining wall system, mature trees, and expansive outdoor living spaces designed for relaxing. Multiple decks provide the perfect setting to enjoy the peaceful surroundings and natural beauty of the property. Inside, the updated kitchen serves as the heart of the home, offering modern finishes and functionality while flowing seamlessly into the living spaces. Additional details and professional photos will be available soon. Living in Cape St. Claire means more than just owning a home. Residents enjoy access to community beaches, parks, playgrounds, walking trails, marinas, boat ramps, fishing and crabbing areas, and a variety of community events throughout the year. Located along the Magothy River and just minutes from Annapolis, the community offers a unique blend of waterfront living, outdoor recreation, and everyday convenience. Conveniently located near shopping, dining, Broadneck schools, Route 50, the Chesapeake Bay Bridge, and all that Annapolis has to offer, this is a rare opportunity to enjoy the Cape lifestyle on a beautiful private homesite. More details coming soon.

ANNAPOLIS

1178 GLENWOOD DL

4 Beds

2 Baths

1,828 Sq.Ft.

$600,000

MLS#: MDAA2147922

Summer is here, and the time is right for moving into that new place to call your own!
Tucked away on a quiet cul-de-sac just minutes from downtown Annapolis, this 2,000± square foot home offers the rare combination of privacy, meaningful upgrades, and everyday convenience. The shaded backyard is a summer favorite spot for your hammock or fire pit with s'mores.

Since 2021, major improvements have already been handled for you, including a new roof, windows and sliders, vinyl siding with upgraded gutters, HVAC system, water heater, and fully updated kitchen and bathrooms... giving buyers confidence in both condition and long-term value.

The layout offers 4 bedrooms and 2.5 baths with a flow that allows you to live comfortably day-to-day while still having that work-from-home dedicated bonus space without sacrificing an entire bedroom.

Set on a manageable, low-maintenance lot with no HOA, this is an ideal fit for those who want space and freedom without added restrictions. Extend the driveway, add a garage, put in a swing set, or a tree-house. Heck, add both! This is a great place to make it exactly what you want it to be.

With its location just minutes from downtown Annapolis dining, boutique shopping, water access, and commuter routes, the home delivers both accessibility and a tucked-away feel.

This home is waiting for you! Turn key and ready to move in. Or consider it as an investment property and enjoy the fruits of the demand from the US Naval Academy, traveling nurses, or LTR.

ANNAPOLIS

2 SILOPANNA COURT

4 Beds

2 Baths

2,000 Sq.Ft.

$599,900

MLS#: MDAA2141372

BIG $50K PRICE REDUCTION ON THIS BEAUTIFUL 2 BR UNIT! Look no further! This Chesapeake Harbour marina view condo, is available immediately in one of Annapolis' most sought after waterfront communities. This beautifully renovated 2 BR | 2 BA | 1200 SF condo on the second level is truly turn key offering over $100K in high end improvements crafted with top of the line materials throughout. Enjoy stunning tranquil marina views from your deck and living space, creating a peaceful coastal retreat. The sumptuous Primary Suite features access to deck, a spa-inspired Bath with an impressive walk in shower and custom closet with built-ins. Recent updates include new carpet throughout and a new oversized water heater, ensuring comfort and peace of mind. Residents of Chesapeake Harbour enjoy an exceptional lifestyle with front entrance security , waterfront dining at the Beacon Waterfront Bar, marina access, waterfront pools, tennis, private beach and walking trails and just minutes to Downtown Annapolis.

ANNAPOLIS

7022 CHANNEL VILLAGE COURT 101

2 Beds

2 Baths

1,200 Sq.Ft.

$599,900

MLS#: MDAA2136184

3 Level Colonial Brimming with Classic Charm and Timeless Character. This Home Features a Welcoming Covered Front Porch, Perfect for Relaxing and Enjoying the Neighborhood Setting. Inside, you’ll Find Spacious Bedrooms and Hardwood Floors that Add Warmth and Potential Throughout.
This Property is Ready for a Full Renovation, Offering an Incredible Opportunity for Investors, Builders or Buyers Looking to Restore and Customize a Classic Colonial to its Former Glory. With Vision and Updates, this Home can be Transformed into a Stunning Showcase Property. Ideally Located in Annapolis, this Home Offers Convenient Access to Downtown Annapolis, United States Naval Academy, and the Scenic Chesapeake Bay. Enjoy Nearby Shopping, Dining, Parks, and Waterfront Activities, along with Easy Commuter Routes to Baltimore and DC. A Fantastic Location Combining Historic Charm, Coastal Lifestyle, and Everyday Convenience. Sold As-Is

ANNAPOLIS

40 MUNROE COURT

3 Beds

1 Baths

1,280 Sq.Ft.

$599,895

MLS#: MDAA2148248

Welcome to easy waterfront living in the heart of Eastport. Rarely available and beautifully renovated, this top-floor 2-bedroom, 2-bath condominium in the sought-after Severn House community offers direct views of Back Creek, turnkey interiors, and effortless access to the Annapolis waterfront lifestyle.

Inside, the residence has been thoughtfully updated with a clean, coastal feel and comfortable, move-in ready finishes throughout. The open-concept living spaces are bright, inviting, and designed for easy everyday living. The kitchen opens to the dining area and living room, creating a comfortable flow for entertaining, gathering, or simply enjoying the sense of space. From the main living area, sliding glass doors lead to a private balcony with direct views over Back Creek, adding a beautiful waterfront backdrop to the home.

The primary suite features an ensuite bathroom and walk-in closet, while the second bedroom offers a gracious closet and utilizes the full hall bath. A washer/dryer combo unit adds everyday convenience.

Severn House is one of Eastport’s most beloved waterfront communities, known for its relaxed atmosphere, mature landscaping, and exceptional amenities. Residents enjoy a waterfront pool with spacious patio and deck areas, an outdoor clubhouse pavilion, kayak, canoe, and paddleboard launch, bike storage, communal laundry, on-site management, and available water taxi access from the dock.

Please note that pets are not allowed in this community (exception for support animals that are approved). Gas and water are included in the condo fees.

Just minutes from downtown Annapolis, Eastport restaurants, shops, marinas, and local favorites, 774-F Fairview Avenue offers a rare turnkey opportunity in one of Annapolis’ most convenient waterfront communities.

30-foot boat slip being sold separately - reach out for details.

ANNAPOLIS

774 FAIRVIEW AVENUE F

2 Beds

2 Baths

1,060 Sq.Ft.

$595,000

MLS#: MDAA2145660

New on site 1 day ago

Welcome to 1016 Timber Creek Drive, a well maintained home nestled in the sought-after Timber Creek community of Annapolis. Featuring 3 bedrooms, 3 full baths, and three levels of living space, this home offers the perfect blend of comfort, functionality, and style. The main level showcases hardwood floors, a gas fireplace with marble surround, and an updated kitchen remodeled by Realistic Builders . Off the kitchen, a spacious side deck provides the perfect spot for grilling or enjoying your morning coffee, while the private, partially fenced backyard with brick patio creates an inviting outdoor gathering space ideal for summer barbecues.
Upstairs, the spacious primary suite is complemented by two additional bedrooms and a second full bath. The lower level offers a large family room, full bath, laundry area, and flexible space perfect for guests, a home office, or recreation room.

Extensively updated over the years, improvements include the kitchen remodel (2012), installation of a gas line, gas furnace, central air conditioning, and gas fireplace (2012), replacement windows (2016), partial roof replacement (2020), tankless hot water heater (2021), new dishwasher and dryer (2023), new washer and dryer (2024), and fresh interior paint (2026).

Conveniently located just minutes from Quiet Waters Park, Eastport, and historic downtown Annapolis, as well as shopping, dining, and commuter routes, this move-in-ready home offers easy access to everything Annapolis has to offer.

ANNAPOLIS

1016 TIMBER CREEK DRIVE

3 Beds

3 Baths

1,730 Sq.Ft.

$589,000

MLS#: MDAA2148944

Motivated Sellers!! Price Just Improved!!

Rare Opportunity in an Amazing Annapolis Neighborhood!

Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring, fresh paint interior and exterior, a new refrigerator, and a new dishwasher, making it move-in ready.

The home features a fully finished basement, providing plenty of additional living or entertainment space, along with the convenience of a garage.

Enjoy the Chesapeake lifestyle with a private neighborhood marina just a short walk away, perfect for kayaking and paddleboarding. Outdoor lovers will also appreciate being less than 2 miles from Quiet Waters Park, offering trails, waterfront views, and year-round recreation.

Ideally located near the U.S. Naval Academy and just 3 miles from Historic Downtown Annapolis, you’ll have easy access to waterfront dining, shopping, and local events.

Professional landscaping is already scheduled and fully paid for, with improvements to be completed in April, adding even more curb appeal to this wonderful property.

Don’t miss this rare opportunity to own in an exceptional Annapolis location!

ANNAPOLIS

79 WINDWHISPER LANE

4 Beds

3 Baths

2,560 Sq.Ft.

$584,000

MLS#: MDAA2138392

Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting, with seamless flow from the cozy living room to the dining area and updated kitchen. You'll love the thoughtful details, including hardwood floors, a fireplace for those cooler evenings, and scenic views that bring the outdoors in. This home is ideally located to enjoy watching the sunrise over Chase Pond and the Bay with your morning coffee or tea. Later in the day the oversized wrap-around deck invites you to relax, entertain, or simply soak in the tranquil surroundings and watch the sunset over the Marina. Chesapeake Harbour is a vibrant, amenity-rich community with access to 2 pools, 2 tennis and pickle ball courts, kayaking, walking trails and a marina, all just minutes from downtown Annapolis. Whether you're a boating enthusiast or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience Chesapeake Harbour living at its finest!

ANNAPOLIS

2110 CHESAPEAKE HARBOUR DRIVE 101

2 Beds

2 Baths

1,237 Sq.Ft.

$579,900

MLS#: MDAA2138114

***Major Price Reduction***Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming hardwood floors, spacious and bright layout, and a stylish kitchen, this residence combines comfort and convenience. Park Place offers exceptional amenities including 24/7 concierge service, a pool, fitness center, meeting and party rooms, library, and a rear outdoor patio with a kitchen and grilling area—perfect for entertaining. The unit comes with a storage space as well as parking. Additional perks include a dog park and easy access to restaurants and shopping. A fabulous in-town location you won’t want to miss. Welcome home!

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$575,000

MLS#: MDAA2138356

Options for VA buyers. 5% 30 year fix mortgage. Large, beautifully maintained contemporary home in the sought-after Stone Creek community of Annapolis. Professional photos of this bright and airy property are coming soon.
Features of this 4-bedroom, 3.5-bathroom home include:
Renovated Interior: Recently painted throughout with an open-concept layout, remodeled kitchen and bathrooms, and vinyl plank flooring in the living and dining rooms.
Chef’s Kitchen: Features granite countertops, extensive cabinet space, and a breakfast bar that opens to a great room with a fireplace.
Primary Suite: Includes double closets and a recently remodeled primary bath.
Upgraded Systems: Newer roof and windows, with an HVAC unit installed in 2018.
Outdoor Living: A sliding door leads to a gorgeous new deck and mature landscaping, perfect for entertaining.
Lower Level: The basement includes a large laundry room, a full bath, and two rooms; the main family room area is framed and ready for completion.
Community Amenities: Access to a community center, in-ground pool, and tennis courts.
The property is conveniently located near major highways and downtown Annapolis, offering an easy commute to Washington D.C., Baltimore, and Fort Meade.

ANNAPOLIS

15 LANDINGS COURT

4 Beds

3 Baths

1,736 Sq.Ft.

$575,000

MLS#: MDAA2145304

Don’t miss this beautifully updated, move-in-ready condo in the highly sought-after, amenity-rich community of Chesapeake Harbour, offering serene marina views and the perfect backdrop to relax and watch the boats drift by. This inviting home is bright and cheery and features neutral paint and carpeting. There are two spacious bedrooms with two full baths. The open-concept living and dining areas create an effortless flow for both everyday living and entertaining and opens up to a deck that overlooks the marina. The updated kitchen showcases granite countertops and ample cabinetry, while the cozy wood-burning fireplace adds warmth and charm to the living space. Chesapeake Harbour offers resort-style living with 24/7 gated security, two pools, tennis courts, a private sandy beach, and scenic walking paths. Enjoy the convenience of a water taxi to Historic Annapolis or dine waterside at The Beacon, located right within the community. Experience low-maintenance coastal living at its finest, this is the one you’ve been waiting for.

ANNAPOLIS

7004 CHANNEL VILLAGE COURT 102

2 Beds

2 Baths

N/A

$575,000

MLS#: MDAA2143832

WELCOME HOME!This beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip A 54 & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage.A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit.Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading.Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops.This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.

ANNAPOLIS

755 FAIRVIEW AVENUE 755 D

3 Beds

2 Baths

1,295 Sq.Ft.

$574,999

MLS#: MDAA2148018

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