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
274
# of Listings
3
Avg # of Bedrooms
$510
Avg. $ / Sq.Ft.
$1,357,507
Med. List Price

Browse Annapolis Real Estate Listings

All listings

Under $250,000

$250,000 - $500,000

$500,000 - $1M

$1M - $3M

$3M - $5M

Over $5M

54 Properties Found. Page 2 of 4.

MASSIVE PRICE DROP! PRICE NOW RELECTS NEED FOR UPDATES. THIS IS THEE LOWEST PRICED SEMI-DETACHED HOME WITH A GARAGE IN HERITAGE HARBOUR INTHE PAST YEAR! Popular, one level floor plan in the 55+ community of Heritage Harbour offering just the right amount of space to enjoy the next phase of your life. You will feel right at home when you turn into this lovely, cul de sac with mature trees and attractive, brick or stone front homes. Pull into your one car garage with automatic door opener & immediate access to the kitchen for easy unloading of groceries or leave the car in your dedicated driveway. There is also overflow parking just across the street. Step into a bright entry foyer and kick off your shoes. Light the fire in your Woodburning Fireplace with Mantle the large living room with gleaming hardwood floors and grab a hot or cold drink to relax with. Large eat-in kitchen with natural oak cabinets, ceramic tile floor & ceramic tile backsplash. Kitchen pantry with pull out drawers. The washer and dryer are tucked away on the main level near the kitchen, so if you have a few minutes while dinner is cooking you can fold a load of laundry. This home offers a sliders to the deck from the sunken Den off the Living Room which could be used for whatever your interests are: crafts, reading, music, or a spot for your family to call their own when visiting. There is a large, primary bedroom with it's own en suite private bathroom offering a convenient, walk-in shower and spacious vanity with a double sink as well as access to the covered & screened porch The architecturally shingle roof is only a few years old. Neutral carpet has been installed in the bedrooms hallway & den. There's also a huge (700 sq ft+)deck "L" shaped deck & covered & screened porch off the main level. Perfect for entertaining! The lower level boasts an enormous 25' x 16' Family Room with newer carpet as well as an office & Walk-in closet/storage room. The combination of the office + walk-in closet could constitute a 3rd Bedroom in the lower level. Sliders off the basement, so on temperate nights you can walk out the lower level Family Room to your private, rear yard and lower patio to enjoy the outdoors. There is a Carrier Weather Maker 9200 92% efficient gas furnace in the utility & newer water heater. Heritage Harbour has fabulous amenities that include access to boating on the South River, Indoor and Outdoor swimming, workouts in the fitness center, a private, Executive Golf Course, putting green and Pro Shop, tennis & pickleball courts, walking paths, classes, organized groups, activities and travel. You will never be bored here! Get your buyer's agent to arrange a private tour of the Community! HOA fee - $167/mo. Condo fee - $190/mo. Deferred Water & Sewer fee - will start in January 2027.Cost will be not exceed $2,400/year.
#MDAA2139960

ANNAPOLIS

2646 QUIET WATER COVE

3 Beds

2 Baths

2,354 Sq.Ft.

$450,000

MLS#: MDAA2139960

Better price! Welcome home to this charming and well-maintained 3-bedroom, 2-bath property offering comfort, flexibility, and convenience in a sought-after location. From the moment you arrive, you’ll fall in love with the adorable front porch—perfect for relaxing, enjoying your morning coffee, and connecting with the neighborhood. Inside, the home features a functional layout with comfortable living spaces and a finished basement that adds incredible versatility. Whether you’re looking for a second family room, home office, or the potential to create an additional bedroom, the lower level offers endless possibilities. There is also additional storage space to keep everything organized. Step outside to a fully fenced backyard designed for both relaxation and entertaining. The rear patio is ideal for gatherings, while the spacious yard provides room to play, garden, or unwind. A large shed offers excellent storage for tools, lawn equipment, and more. Conveniently located just minutes from Route 50 and Route 97, this home provides easy access to shopping, dining, the mall, and downtown Annapolis. Even better—this property is located outside the city limits, so you’ll enjoy all the benefits of the area while only paying Anne Arundel County taxes. A wonderful opportunity to own a home that combines charm, space, and location—don’t miss it!
#MDAA2141180

ANNAPOLIS

100 1ST STREET

3 Beds

2 Baths

1,537 Sq.Ft.

$449,900

MLS#: MDAA2141180

New on site today
This rare 3 bedroom, 2 bath condo offers a spacious, open feel thanks to its 9'‑foot ceilings and well‑designed layout. The large primary suite includes its own private bath, while two additional bedrooms and a full hall bath provide flexibility for guests, shared living, or continued use as a high‑demand rental. The property has a proven track record as locum tenens housing for medical professionals at Anne Arundel Medical Center, located only one mile away, making it an excellent option for both living and investment. The open living and dining area flows comfortably into a functional galley kitchen with newer appliances and a door leading to a private patio. A brand‑new washer and dryer and a recently installed HVAC system add value and peace of mind. The condo is well maintained, with ample parking and a quiet, tucked‑away setting that feels surprisingly cozy despite its central location. The lifestyle here is exceptional. Just one block from Route 50, you have instant access to Annapolis, the Eastern Shore, Washington, and major commuter routes, yet the community remains calm and insulated from traffic noise. Parks, walking paths, and green spaces are close by, offering room to unwind outdoors. Popular restaurants, cafés, and shopping centers are only minutes away, making everyday errands and dining out easy and convenient. For recreation lovers, the area offers quick access to pickleball and tennis courts, along with other athletic and community amenities. Whether you enjoy an active lifestyle or simply want options close at hand, this location delivers. This condo is also a smart choice for anyone exploring the Annapolis area before making a full move. Live comfortably now, then keep the property as a steady monthly return once you find your perfect long‑term home. With no city taxes, a quiet residential setting, and unbeatable proximity to everything Annapolis has to offer, this 3 bedroom condo stands out as a rare opportunity for both homeowners and investors. LIVE IN OR BUY FOR INVESTMENT
#MDAA2146150

ANNAPOLIS

45 HARBOUR HEIGHTS DRIVE

3 Beds

2 Baths

1,464 Sq.Ft.

$445,000

MLS#: MDAA2146150

FRESHLY PAINTED AND NEW CARPET THROUGHTOUT. WALKOUT BASEMENT. THANK YOU FOR SHOWING
#MDAA2140770

ANNAPOLIS

1531 HICKORY WOOD DRIVE

3 Beds

2 Baths

916 Sq.Ft.

$439,900

MLS#: MDAA2140770

. Extremely attractive 4 bedroom 3.5 bath townhouse. Located near major roads and amenities in Annapolis. The kitchen has all stainless steel appliances and quartz counter top. The entire house has been repainted and and also the deck . The deck can be accessed from the living room... The master bedroom has a private bathroom and is a good size... There is a powder room on the main level and the entry from the garage is conveniently located on this level also.... There is space in the back for a nice cookout gathering also...The home has laminate flooring and is very well maintained. This is a great property for any buyer.........
#MDAA2144288

ANNAPOLIS

126 BRIGHTWATER DRIVE, ANNAPOLIS, MD 21401

4 Beds

3 Baths

1,780 Sq.Ft.

$419,990

MLS#: MDAA2144288

Welcome Home to Eastport. Walk to the Eastport Shopping center for breakfast or to downtown Annapolis for lunch or dinner. This cute 4-bedroom (egress in basement)1.5 bath rancher with eat-in kitchen and traditional floor plan living and dining room is perfect for you and your family. Relax and entertain on the size able deck off the kitchen. Enjoy central air conditioning, oil heating, electric hot water heater. New AC 2023, sewage line updated to PVC in 2023. Dishwasher, washer dryer included and you get to choose your own oven range and refrigerator.
#MDAA2138538

ANNAPOLIS

1014 WELLS AVENUE

4 Beds

1 Baths

880 Sq.Ft.

$419,900

MLS#: MDAA2138538

Welcome to 86 Harbour Heights Dr, Annapolis! This bright, move-in ready, 3-bedroom, two-level condo, offers modern comfort and a peaceful wooded view. Freshly painted and fitted with brand-new carpet throughout, this home welcomes you with a clean, neutral palette ready for your personal touches. The generous back deck provides a private, elevated view of the community’s wooded green space, perfect for morning coffee or evening relaxation. Enjoy easy access to Annapolis’ premier shopping, dining, and amenities, plus quick connections to major commuter routes for an effortless commute. Well-maintained and ideally located, this condo blends convenience with everyday tranquility. Schedule your showing today.
#MDAA2140860

ANNAPOLIS

86 HARBOUR HEIGHTS DRIVE

3 Beds

2 Baths

1,524 Sq.Ft.

$414,900

MLS#: MDAA2140860

Welcome to 1019 President St in the heart of Eastport—where charm, space, and modern upgrades come together just minutes from the water and Historic Annapolis. This beautifully renovated 3-bedroom, 2-bath home offers a rare combination of cozy living and exceptional outdoor space. Situated on an oversized lot with a classic white picket fence, the property features a huge yard, private parking for 4+ vehicles (a true rarity here), a welcoming front porch, and a spacious back patio—perfect for entertaining, relaxing, or simply enjoying the space that sets this home apart. Inside, the home has been completely transformed with top-to-bottom upgrades, including brand new central HVAC system, complete electric upgrades, new flooring throughout, a stunning modern kitchen with high-end finishes and appliances, and beautifully designed bathrooms. Natural light pours in on every level, highlighting the clean, fresh finishes, generous closet space, and an easy, functional layout. Located just a short walk to the water, nearby parks, and everything Eastport is known for—and only minutes to downtown Annapolis—this home offers a lifestyle that’s hard to match, blending comfort, convenience, and a truly standout setting.
#MDAA2142548

ANNAPOLIS

1019 PRESIDENT STREET

3 Beds

2 Baths

1,350 Sq.Ft.

$410,000

MLS#: MDAA2142548

Nestled in the heart of Annapolis, this 3-bedroom, 1-bath home offers a fantastic opportunity for investors or buyers looking to add their personal touch. The property features a solid layout with great bones and includes an unfinished ±800 sq ft addition—providing ample space to expand and customize to your needs. With a little vision and renovation, this home has tremendous potential to shine. Whether you're looking to create your dream home or your next investment project, the possibilities here are endless. Conveniently located near local amenities, shopping, dining, and major commuter routes. Don’t miss this chance to unlock the value and make it your own!
#MDAA2140302

ANNAPOLIS

3 CYPRESS ROAD

3 Beds

1 Baths

1,206 Sq.Ft.

$399,999

MLS#: MDAA2140302

Waterfront Condo Community! This beautiful West Annapolis 2 Bedroom 2 Full Bath water privileged condo is coming to the market with fresh paint and tile, updated kitchen. Screened patio and absolute turn-key! Lobby just finished reno with fresh paint and flooring! Community Marina with slips available for lease! Walking distance to fantastic restaurants and shopping! Just across from the Navy Stadium and just a quick trip to downtown Annapolis! This location is ideal for any commuter with Route 50/97 just moments away! The amenities are wonderful with community waterfront pool and pier on Weems Creek.
#MDAA2139486

ANNAPOLIS

300 FORBES STREET J

2 Beds

2 Baths

844 Sq.Ft.

$399,000

MLS#: MDAA2139486

Owner is offering $ 5,000.00 for helping buyer with closings costs!! Great location! Sweet, cozy, and lovely semi-detached home. 3 bedroom, 1 1/2 baths and semi finished basement. The house is ready for your personal touch! NEW ROOF 2023. Close to Truxtun Park and easy access to downtown Annapolis and US 50 /97 HWY. GREAT OPPORTUNITY! Bring your best offer.
#MDAA2133422

ANNAPOLIS

108 CONLEY DRIVE

3 Beds

1 Baths

1,880 Sq.Ft.

$395,000

MLS#: MDAA2133422

Located at the corner of Spa Road and Boxwood Drive, this property offers an excellent Annapolis location with convenient access to downtown, shopping, dining, and major commuter routes. The home sits on a prominent corner lot and presents a great opportunity for investors, builders, or buyers looking to renovate and customize a home to their own vision. The property is in need of updating and is being sold as-is, making it ideal for those seeking a value-add project in a highly desirable area. A rare chance to create something special in an established neighborhood with strong long-term potential.
#MDAA2136208

ANNAPOLIS

4 BOXWOOD ROAD

3 Beds

2 Baths

1,152 Sq.Ft.

$389,900

MLS#: MDAA2136208

Welcome to 198 Clay Street in the heart of Annapolis! This charming row home offers water views of College Creek and a short stroll to downtown and West Annapolis, where shops, dining, entertainment, and the U.S. Naval Academy are right at your doorstep. The location also provides easy commuter access to Routes 50 and 97 for Washington, D.C., Baltimore, and BWI Airport. Thoughtfully updated in the past year, the home features new flooring and paint throughout, all new kitchen appliances, countertops, and sink, new siding, four mini-split units, and all new upstairs windows. Walls were opened between the kitchen, dining, and laundry areas to create a more open flow, and a new upper-deck door leads to an expanded rooftop deck with water views. Additional highlights include exposed brick and beamed ceilings, a fenced rear yard, private access to College Creek, and rare rear parking. With a proven rental history including $21,500 earned on Airbnb in 2024, this home is ideal as a primary residence or investment opportunity.
#MDAA2139810

ANNAPOLIS

198 CLAY STREET

2 Beds

1 Baths

902 Sq.Ft.

$389,000

MLS#: MDAA2139810

New on site 2 days ago
This well-maintained 3-level Whispering Woods townhome offers a long list of updates, including many completed in April 2026. Recent improvements include luxury vinyl plank flooring throughout the main and upper levels, freshly painted walls, ceilings, and trim, granite kitchen countertops with a stainless steel under-mount sink, and GE stainless steel appliances including a refrigerator with ice/water dispenser, electric range, and dishwasher. Additional notable updates include an electric fireplace insert added in February 2025, hot water heater replacement, updated PEX plumbing lines in the basement, and a new garbage disposal in October 2025, roof replacement in 2021, rear deck and staircase replacement in 2020, exterior vinyl siding replacement in 2020, and updated front and storm doors in 2019. The Trane heat pump system, including indoor air handler and exterior compressor, was replaced in 2008. The unfinished lower level provides excellent storage space and offers great potential for future finishing. Whispering Woods is a peaceful wooded community featuring open green space, playgrounds, and walking/biking paths, all while offering convenient access to Downtown Annapolis, City Dock, USNA, Baltimore, and Washington D.C. via major commuter routes.
#MDAA2145602

ANNAPOLIS

1608 WOODTREE COURT W

3 Beds

1 Baths

1,360 Sq.Ft.

$367,900

MLS#: MDAA2145602

Step into this beautifully maintained top-floor 3-bedroom, 2-bath condo in the desirable Scott’s Crossing Condominiums, offering over 1,320 square feet and a prime location just minutes from the vibrant charm of downtown Annapolis. As you enter, you're welcomed by fresh paint throughout (2026), a foyer with a convenient coat closet, and elegant column accents that open into a bright and airy main living space. The kitchen features warm wood cabinetry, granite countertops, a tiled backsplash, and stainless steel appliances, along with a cozy breakfast nook framed by a bay window overlooking peaceful wooded views. Entertain with ease or unwind at the end of the day in the well-appointed living and dining areas, complete with hardwood floors, 9+ ft ceilings, a cozy gas fireplace, and access to a private patio that offers a serene setting to relax and take in the views. The primary suite is a true retreat, showcasing a vaulted ceiling with a lighted fan and a charming bay window, perfect for a reading nook or sitting area with a tranquil backdrop. Two spacious closets and an ensuite bath with a dual sink vanity and tub/shower combo complete the space. Two secondary bedrooms, each with ample closet space, are thoughtfully positioned for added privacy and versatility, whether used as guest rooms or an in-home office, and share a full bath with a large walk-in shower. A dedicated laundry room with additional storage and a full-sized washer and dryer adds everyday convenience. Recent updates include a newer HVAC (2021), water heater (2022), and plush new carpet (2026). Parking is a breeze in the off-street parking lot. Beyond the community, enjoy the nearby Bestgate Park, Trader Joe’s and Annapolis Mall, plus easy access to major highways for a quick commute to Baltimore, DC, and more. Don’t miss this rare find!
#MDAA2140698

ANNAPOLIS

2161 SCOTTS CROSSING COURT 302

3 Beds

2 Baths

1,328 Sq.Ft.

$364,900

MLS#: MDAA2140698

1 2 3 4
Buyers resources
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Getting a Mortgage To Buy a Home
Home Hazards Awareness
Key Items For Home Inspection
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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 $$

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