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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
305
# of Listings
3
Avg # of Bedrooms
$474
Avg. $ / Sq.Ft.
$1,088,507
Med. List Price

Browse Annapolis Real Estate Listings

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Over $5M

305 Properties Found. Page 15 of 21.

Recently adjusted price offers a great opportunity to own this charming 2-bedroom, 2-bathroom condo located in the amenity rich, Heritage Harbour 55+ community. With fresh updates and a coveted assigned parking spot in the garage, this home offers comfort, convenience, and an active lifestyle all in one place. Plenty of natural light and a comfortable, easy-going layout makes this a perfect place to call home. Newly installed carpet throughout, fresh paint, and brand-new windows in the guest bedroom. The kitchen is equipped with a brand-new double oven and microwave, perfect for preparing meals for family or entertaining friends. The primary suite features its own en-suite bathroom for privacy, while the second bedroom is perfect for guests, an office, or additional space for hobbies. The RARE assigned parking spot in the garage offers convenience and peace of mind. Heritage Harbour creates a vibrant, active environment for residents including indoor/outdoor pools, fully equipped fitness center and a spacious party room where you can host gatherings or enjoy community events. The Lodge, is also a central gathering space in Heritage Harbour and is packed with additional amenities, including additional pools, a game room and meeting rooms. Additional highlights are the tennis courts, walking trails and an ideal location close to Annapolis and all it has to offer!
#MDAA2115076

ANNAPOLIS

930 ASTERN WAY 502

2 Beds

2 Baths

1,477 Sq.Ft.

$399,999

MLS#: MDAA2115076

Welcome to your next home! Located in Annapolis, this townhouse at 93 Clay St offers spacious living with its four bedrooms and three bathrooms. Designed in the stylish End Unit Attach/Row House architecture, this residence provides a blend of modern comforts and classic appeal. Inside, you're greeted with a seamless flow of carpet and laminate floors, providing a cozy yet elegant atmosphere throughout the home. The central air conditioning ensures year-round comfort, complemented by efficient electric heating. This home is perfectly equipped for modern living, featuring a convenient in-unit washer and dryer, making laundry days a breeze. The layout promotes both privacy and open living, ideal for entertaining guests or enjoying quiet family evenings. Each bedroom offers ample space, ensuring everyone has their own retreat. The bathrooms are designed with functionality in mind, providing a perfect start to your day or a relaxing end. 93 Clay St is ready to welcome you home. Don't miss the opportunity to make this delightful townhouse your own!
#MDAA2117410

ANNAPOLIS

93 CLAY STREET

4 Beds

2 Baths

2,022 Sq.Ft.

$399,999

MLS#: MDAA2117410

Heritage Harbour community offers it all for its residents. Move into the convenience of one level living here. Home is also partially fenced for some added privacy. Subject is sold in as is condition, seller nor buyer can make any repairs prior to closing. Property is owned by the US Dept. of HUD, HUD Case #241-916291. Insurability Code: ie. Seller makes no representations or warranties as to property condition and HUD Homes are sold “AS-IS” only. Seller may contribute up to 3% for buyer’s closing costs, upon buyer request. EHO. SELLER DOES NOT ALLOW ASSIGNED CONTRACTS.
#MDAA2119170

ANNAPOLIS

1945 MARCONI CIRCLE

2 Beds

2 Baths

1,200 Sq.Ft.

$397,000

MLS#: MDAA2119170

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community .Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. Buyer responsible for all due diligence on condition of home. So much potential! Make this your today!!
#MDAA2121666

ANNAPOLIS

40 OAK COURT

2 Beds

2 Baths

1,061 Sq.Ft.

$389,900

MLS#: MDAA2121666

Don’t miss this updated 2-bedroom, 2-bath condo tucked into the treetops of sought-after Heritage Harbour. Freshly painted with new flooring throughout the main living areas, this home also features a remodeled kitchen with modern counters, sleek cabinetry, and newer appliances. Major upgrades already done for you: HVAC, water heater, washer, and dryer have all been replaced. Step out onto your private balcony and enjoy peaceful, elevated views. A dedicated storage unit is included, and the building features an elevator, game room, and indoor/outdoor pools. Heritage Harbour is known for its unmatched amenities: a community lodge with fitness rooms, a library, gathering spaces, and access to golf, shops, restaurants, medical offices, and water activities.
#MDAA2122918

ANNAPOLIS

930 ASTERN WAY 405

2 Beds

2 Baths

1,464 Sq.Ft.

$389,900

MLS#: MDAA2122918

Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two bedrooms/offices, two full bathrooms, and robust hardwood flooring throughout, presenting a promising canvas for renovation. Strategically located, this property is in close proximity to essential amenities and community features. Public transportation is conveniently accessible with the Riva Road & Forest Drive bus station less than 700 meters away, enhancing the location's connectivity. Additional features include a rear deck perfect for relaxation or casual gatherings, a useful rear shed for extra storage, and a generous off-street parking area that can accommodate up to 12 vehicles. Despite being sold as-is, with no repairs from the seller, the property's inherent potential and dual-use capability as both a residential and commercial space make it a lucrative deal. Capitalize on the chance to customize this space into a thriving business venture or a mixed-use development that promises both rental income and renovation possibilities. Dive into this project and shape it into your vision of success! Property is being sold AS-IS, Seller will make no repairs. All offers must have $1000 deposit and proof of deposit. So much potential! Make this your today!!
#MDAA2121664

ANNAPOLIS

40 OAK COURT

None Beds

None Baths

1,061 Sq.Ft.

$389,900

MLS#: MDAA2121664

Welcome to this spacious 3-bedroom, 2.5-bath townhome offering brand new paint and flooring. The open floor plan provides great flow and plenty of natural light, while the eat-in kitchen is the perfect place to gather. The primary suite includes a private bath, and two additional bedrooms offer flexibility for family, guests, or a home office. Enjoy the convenience of two assigned parking spots, plus community amenities including a clubhouse and private pool. The location can’t be beat—just minutes from downtown Annapolis, Quiet Waters Park, shopping, dining, and commuter routes. Move right in and add your personal touches to make this home truly yours!
#MDAA2123536

ANNAPOLIS

988 BREAKWATER DRIVE

3 Beds

2 Baths

1,373 Sq.Ft.

$389,000

MLS#: MDAA2123536

Beautifully renovated Townhome in the desirable** WHISPERING WOODS** neighborhood! This 3 Bedroom 1.5 Bathroom Interior Townhome is full of new renovations. Renovations include new Architectural shingled roof, attic insulation, windows, PVC Bay window, storm door, totally remodeled Kitchen and bathrooms. Flooring on the main level has been redone with Luxury Vinyl Planking, while the upper level has new carpet throughout. All new interior doors and trim. New recessed lights in kitchen, living room and master suite. New rear fenced-in backyard that includes a raised garden for that person with a Green thumb!! Even the grass is new!!! Community Amenities include a playground, picnic area, and walking/ jogging paths. Conveniently located near parks, shopping, and dining. Easy access to A.A. Community college and major transportation routes. Ten minutes to Historic Annapolis District and the Naval Academy. Don't miss out on this charming retreat,
#MDAA2122858

ANNAPOLIS

1584 LODGE POLE COURT

3 Beds

1 Baths

1,129 Sq.Ft.

$383,000

MLS#: MDAA2122858

Tucked in a quiet cul-de-sac, this home offers more than just a place to live. It provides a lifestyle shaped by comfort, convenience, and community. Inside, you will notice thoughtful updates throughout, from refreshed bathrooms and flooring to new lighting and fixtures completed in 2024. An office space and generous storage make it easy to balance work and home life, while the spacious owner's suite with a walk-in closet creates a private retreat at the end of the day. Life here extends beyond the walls of the home. In Whispering Woods, you will find tree-lined sidewalks that wind through the entire neighborhood, along with multiple playgrounds and open spaces that invite outdoor activity and connection. Nearby, Bay Hills Plaza makes everyday errands effortless with grocery shopping, coffee, dining, and more just minutes away. Outdoor enthusiasts can tee off at Bay Hills Golf Course, relax by the water at Sandy Point State Park, or take a short drive to enjoy the charm and culture of downtown Annapolis. With convenient access to Route 50, commuting and weekend getaways are always within easy reach. This is where everyday living meets the best of Annapolis, quiet, connected, and perfectly placed.
#MDAA2124252

ANNAPOLIS

1542 STAR PINE DRIVE

3 Beds

2 Baths

1,508 Sq.Ft.

$379,900

MLS#: MDAA2124252

Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and unmatched amenities. This 2-bedroom, 2-bath condo is priced to sell and provides a wonderful opportunity to make it your own. Inside, the unit offers a bright and spacious layout filled with natural light. The living room and both bedrooms open onto a private balcony with serene views of trees and woods—the perfect spot for morning coffee or evening relaxation. The condo needs a bit of TLC, but it has great bones and is priced accordingly. Features of Unit #203: Open floor plan with excellent natural light Balcony access from both bedrooms and living room Convenient parking space in the secured garage Large private storage unit located right in front of your parking space Easy in-and-out access within the garage Community Amenities at Heritage Harbour: 9-hole golf course & pro shop Indoor & outdoor swimming pools Fitness center with aerobics & exercise classes Tennis courts, pickleball, and bocce ball Community lodge with auditorium, dining room, billiards, and library Walking and biking trails throughout the neighborhood Dock & waterfront access on the South River Kayak/canoe racks and launch areas Woodworking shop & craft rooms On-site security & professional management Social clubs, classes, and community events year-round This is a chance to enjoy all the benefits of Heritage Harbour’s lifestyle at a fantastic value. With a little updating, this condo could be the perfect home for your next chapter. Don’t miss out—schedule your showing today!
#MDAA2121676

ANNAPOLIS

803 COXSWAIN WAY 203

2 Beds

2 Baths

1,190 Sq.Ft.

$379,900

MLS#: MDAA2121676

Open House Sunday, Aug 31, 1-3 PM! Welcome to the serene, water-privileged community of Riva Trace in Annapolis, a sought-after haven established in 1985 with 543 homes, blending single-family residences, townhomes, and stylish garden-style condos. This spacious second-floor condo offers tranquil wooded views, two full bathrooms, and a versatile layout currently designed as a chic one-bedroom with an expansive living area, easily convertible to a two-bedroom with the simple addition of doors. The sleek kitchen features modern finishes, ideal for hosting gatherings, while the sun-filled solarium and private balcony create inviting spaces to unwind amid lush greenery. A separate dining area is perfect for dinner parties or casual entertaining, and a private 3' x 9' secure storage unit in the lower level of the building adds effortless convenience. Riva Trace is renowned for its natural beauty, abundant birdlife, and resort-style amenities tailored for an active lifestyle. Enjoy private water access to Gingerville Creek and the South River via a 100+ foot pier with a floating dock, perfect for stunning sunsets or kayaking adventures with 90 storage spots for kayaks and canoes, plus a dedicated crabbing pier. Stay active with scenic fitness trails featuring 12 activity stations for cardio, strength, and endurance, two tennis courts (one lined for pickleball), and a basketball court. The dog-friendly, walkable neighborhood includes a children’s playground and picnic areas nestled among mature trees, fostering a welcoming community atmosphere. Residents praise the safety and serenity, all just minutes from downtown Annapolis’s vibrant restaurants, Annapolis Town Center’s trendy shops, and easy commuter routes to Washington, Baltimore, and Fort Meade. Embrace a low-maintenance lifestyle with urban excitement at your doorstep. Schedule your private tour today to discover your perfect Annapolis retreat in Riva Trace!
#MDAA2124118

ANNAPOLIS

2709 SUMMERVIEW WAY 201

2 Beds

2 Baths

1,266 Sq.Ft.

$375,000

MLS#: MDAA2124118

Step into this beautifully updated home at 23 Janwall Court, where style meets comfort. Freshly painted and carpeted, this 2-bedroom, 2.5-bath beauty is ready for new owners. The open floor plan and natural light create a welcoming atmosphere. Enjoy cozy evenings by the fireplace or stargaze from your private deck. The generous primary suite boasts vaulted ceilings, while the second bedroom offers its own private bath. You'll love the convenience of being close to shopping, Route 50 and 97, and just a short drive to downtown Annapolis. Don't miss this opportunity to own a piece of Annapolis charm.
#MDAA2119554

ANNAPOLIS

23 JANWALL COURT

2 Beds

2 Baths

1,968 Sq.Ft.

$375,000

MLS#: MDAA2119554

***Bundled service pricing available for buyers. Connect with the listing agent for details.*** Charming Townhome Near Downtown Annapolis & the U.S. Naval Academy Welcome to 1007 Madison Ct, a well-maintained 3-bedroom, 2-bathroom townhome ideally situated just minutes from historic downtown Annapolis and the U.S. Naval Academy. This versatile layout offers comfortable living across three levels. Upstairs, you’ll find two spacious bedrooms with plush carpeting and a full bathroom, providing a quiet retreat. The finished basement adds flexibility with a third bedroom, a second full bath, and additional living or guest space and laundry. Enjoy the convenience of being close to vibrant shops, waterfront dining, and cultural landmarks, all while tucked into a quiet, established community. Whether you're looking for a full-time residence or an investment property, this home offers location, comfort, and potential. Don’t miss this opportunity to own a home in one of Annapolis’s most desirable areas! Seller's current home warranty will transfer. Bundled service pricing available for buyers. Connect with the listing agent for details
#MDAA2112930

ANNAPOLIS

1007 MADISON COURT

3 Beds

2 Baths

1,350 Sq.Ft.

$374,900

MLS#: MDAA2112930

Love where you live! Located off of Hilltop Lane, with easy access to Forest Dr, West St, Eastport and Downtown Annapolis. This three-level end unit townhome has an updated kitchen, bathrooms and has been professionally painted. Outdoor amenities include a fully fenced yard, a second level deck and ground level brick patio. The community offers multiple swimming pools and is located near Truxton Park with multiple walking trails and water access to Spa Creek.
#MDAA2122820

ANNAPOLIS

23 COPLEY COURT

2 Beds

2 Baths

2,072 Sq.Ft.

$374,500

MLS#: MDAA2122820

Check the photos - Beautiful * Immediate possession * Amazing opportunity to own a detached home at a condominium price * NO HOA or condo fees * Large yard * Remodeled / upgraded * Cutest cape cod with hardwood floors * screened in front porch * updated kitchen and baths * New stainless steel appliances * All solid wood cabinets with granite countertop * Freshly painted * Deep lot with plenty of privacy * Brand new roof * New siding * New windows * New gutters * Convenient Location * $6,000 closing help
#MDAA2120816

ANNAPOLIS

16 PAROLE STREET

2 Beds

2 Baths

800 Sq.Ft.

$369,950

MLS#: MDAA2120816

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