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
388
# of Listings
3
Avg # of Bedrooms
$475
Avg. $ / Sq.Ft.
$1,078,329
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

388 Properties Found. Page 16 of 26.

Welcome to 316 Burnside Street, Unit #208 — a charming one-bedroom, one-bath condominium nestled in the heart of Annapolis. This inviting residence features beautiful luxury vinyl plank flooring, a recently installed water heater (2024), and central A/C for year-round comfort. This flexible layout offers additional sleeping accommodations with a Murphy bed in the dining area and a sleeper sofa. Residents will enjoy access to a rooftop pool with stunning water views, perfect for relaxing or entertaining. Ideally located near vibrant shops, restaurants, and waterfront attractions, this home offers the best of Annapolis living. Don't miss the opportunity to make it yours!
#MDAA2112714

ANNAPOLIS

316 BURNSIDE STREET 208

1 Beds

1 Baths

768 Sq.Ft.

$535,000

MLS#: MDAA2112714

NEW PRICE & OPEN Saturday, 5/31, 11-1! Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in one of Annapolis’s most amenity-rich waterfront communities. Nestled between Oyster Creek, Fishing Creek, and the Chesapeake Bay, Oyster Harbor offers the best of coastal Maryland living—just minutes from historic downtown Annapolis, top-rated restaurants, shopping, and commuter routes. This move-in ready home features a long list of updates, including a brand-new roof, new granite countertops, new dishwasher and recent mechanical improvements: a new heat pump and A/C compressor (2024), and new refrigerator, stove, washer, and dryer (2019). The fully fenced backyard boasts water peeks, a hot tub, and a spacious deck surrounded by beautiful landscaping—ideal for entertaining or quiet evening relaxation. Inside, the layout includes a welcoming living area, functional kitchen with plenty of cabinet space, and a light-filled dining area. Upstairs, the primary suite includes a private full bath, with two additional bedrooms and a full bath. But what truly sets this home apart are the amazing resort-style amenities: private community beach with swimming area and sea nettle nets, three marinas , fishing pier, boat ramp, kayak racks, beach volleyball, and playgrounds! Whether you’re looking for a full-time residence or a weekend retreat, this home and its community offer something truly special: a waterfront neighborhood that embraces recreation, relaxation, and the Chesapeake lifestyle.
#MDAA2114714

ANNAPOLIS

3331 ARUNDEL ON THE BAY ROAD

3 Beds

2 Baths

1,364 Sq.Ft.

$535,000

MLS#: MDAA2114714

WOW! Nestled along the Chesapeake Bay, this waterfront residence offers views of the community marina and the open water beyond. Situated in the sought-after gated community of The Village of Chesapeake Harbour, this beautifully updated two-bedroom, two-bath home combines modern elegance with coastal charm. Step into the welcoming foyer, where an open-concept design unfolds with a soothing color palette freshly painted in 2022. Custom shades, including select electric-controlled options, add both privacy and convenience. The living and dining area boasts striking wood-look porcelain tile flooring, seamlessly blending gray and blue hues that echo the shimmering waters just beyond. Crown molding adds a refined touch, while the living room’s fireplace creates a cozy retreat. A three-panel sliding glass door leads to the expansive patio—larger than others in the community—where you can unwind in a private setting while soaking in the serene water views. The well-appointed kitchen is both stylish and functional, featuring stainless steel appliances, including a recently replaced dishwasher, range, and microwave. An antiqued glass tile backsplash reflects natural light, creating a luminous atmosphere, while a pantry provides ample storage. Another triple-panel sliding glass door opens to a front patio, making this space feel bright and airy. The primary bedroom is a tranquil haven, offering direct patio access through yet another sliding glass door, providing serene water views. The en-suite bath is a luxurious retreat with a double vanity topped with granite, a water closet, and a floor-to-ceiling tiled shower. A spacious walk-in closet with a built-in organizational system completes this private sanctuary. Down the hall, the second bedroom is generously sized, accompanied by an updated full bath with a modern vanity. A sleek, stacked washer and dryer are tucked away in the laundry room, rounding out the home’s well-designed layout. Storage is plentiful, with custom-built closet systems enhancing organization throughout. For peace of mind, the brand-new HVAC system was upgraded in 2025, including an added air purifier. Ample space is available for residents and guests in the unassigned parking lot. The community offers resort-style living with premier water access and exceptional amenities. Enjoy dining at the on-site Beacon Waterfront Galley & Bar, take a dip in one of two pools with bay views, or relax on the private sandy beach. Outdoor enthusiasts will love the fishing piers, kayak launch, and scenic walking and biking trails. Tennis courts and a picnic area provide additional recreation options. Electric car charging stations offer convenience. Boaters will appreciate the Chesapeake Harbour Marina, featuring 81 wet slips with fresh water, electricity, and WiFi, as well as a full-service yacht facility. Ideally situated near Historic Downtown Annapolis, Chesapeake Harbour provides a peaceful retreat while remaining within commuting distance of Baltimore and Washington, D.C. Experience coastal living at its finest—where the water meets effortless luxury. Property Updates: Porcelain tile flooring, dishwasher, range and microwave, washer & dryer, blinds, kitchen faucet and disposal, kitchen backsplash, interior paint, full bath vanity, closet built-ins, HVAC updates, and more!
#MDAA2116088

ANNAPOLIS

7024 CHANNEL VILLAGE COURT T2

2 Beds

2 Baths

1,177 Sq.Ft.

$525,000

MLS#: MDAA2116088

Welcome Home to 901 Chesterfield Road!! This Beautifully updated Single family home located in Annapolis has the space you need to create a life you desire. Boasting an array of sleek finishes throughout this 5 Bedroom, 3 Bathroom home has so much to offer!! The main level offers an open concept layout featuring spacious living room, dining area, 3 entry level bedrooms, 2 full bathrooms, and sunroom. The kitchen boasts S/S appliances, white shaker cabinets, Quartz counters and MORE! All bathrooms have been updated with new ceramic tile, and all new bathroom fixtures! The basement has been fully finished to include 2 additional bedrooms, 3rd full bathroom, and utility room. Off street private parkin and SO MUCH MORE!! Book your private showing today before its gone!!
#MDAA2114934

ANNAPOLIS

901 CHESTERFIELD ROAD

5 Beds

3 Baths

2,457 Sq.Ft.

$524,900

MLS#: MDAA2114934

ANNAPOLIS lifestyle in this 3 Level Cape Cod, boasting 5 Bedrooms and 2 full Bathrooms. The Beautiful interior showcases contemporary finishes and a thoughtful layout that maximizes both style and functionality. The custom kitchen with quartz countertops, stainless-steel appliances and attractive cabinetry enhances your cooking and gathering experience. Complete with a traditional floor plan and modern finishes that will WOW you the moment you walk through the door. The bathrooms have been tastefully refreshed adding modern elegance to this classic home. Freshly painted, new carpet and laminate wood plank flooring throughout. The expansive yard provides the perfect setting for outdoor activities, entertainment, and a place for pets to play in the rear fenced yard. Conveniently located in ANNAPOLIS, close to Fine Dining, Fun Eateries, Nightlife Entertainment, Water Sports, Historic sites and major routes. Don't miss this opportunity to make this your lovely home.
#MDAA2116470

ANNAPOLIS

86 SUMMERFIELD DRIVE

5 Beds

2 Baths

2,340 Sq.Ft.

$524,900

MLS#: MDAA2116470

Welcome to 2004 Quay Village Court, Unit T2—a stunning 2-bedroom, 2-bath terrace-level condo nestled in the resort-style community of Chesapeake Harbour! With its prime location and newly updated kitchen, this home is move-in ready, offering the perfect gateway to luxurious coastal living. The spacious primary suite features an ensuite bath, a walk-in closet, and direct access to a private patio—your personal oasis for peaceful mornings or cozy evenings. The beautifully renovated kitchen, completed in 2023, boasts stainless steel appliances, quartz countertops, and a wine bar, with a slider leading to an additional patio area for seamless indoor-outdoor living. The foyer entry welcomes you to a sunken dining room that flows into a bright living room with a wood-burning fireplace. Step outside to the main patio and enjoy a view of the landscaped lawn and pool—a serene setting perfect for entertaining or unwinding. New HVAC installed in 2023. The second bedroom offers ample closet space and a large window, with a nearby full bath ideal for guests. Additional conveniences include an in-unit stacked washer and dryer, reserved parking for residents, and abundant visitor parking just steps away. As a resident of Chesapeake Harbour, you’ll enjoy a wealth of amenities, including a deep-water marina with direct Bay access, a private sandy beach, crabbing and fishing piers, two fenced outdoor pools (one heated), four tennis courts with pickleball, kayak rentals, walking paths, picnic areas and a waterfront bar/restaurant, Beacon. With 24-hour gated security and convenient access to Quiet Waters Park, local shopping, fine dining, and all that Annapolis has to offer, this is luxury living at its finest! Don’t miss your opportunity to call this extraordinary property home—schedule your showing today!
#MDAA2101798

ANNAPOLIS

2004 QUAY VILLAGE COURT T2

2 Beds

2 Baths

1,221 Sq.Ft.

$524,900

MLS#: MDAA2101798

Price Reduced! Welcome to 746 Warren Drive Annapolis, Maryland —nestled just a block and a half from Back Creek in the highly desirable Greenacres community of Eastport. This charming 5-bedroom, 1.5-bath home sits on a generous lot along a quiet street, offering both privacy and water access. Enjoy first-floor living with a freshly painted interior and exterior, brand new carpet throughout the finished basement and stairs, and abundant natural light pouring in from the beautiful bay window with newly installed side windows. A dedicated office space on the lower level makes working from home a breeze. Step outside to a spacious rear deck—perfect for entertaining—overlooking newly landscaped grounds with fresh sod and updated exterior lighting. The home also features solar panels, off-street parking, and multiple updates within the past couple of weeks. Located in a water-privileged community with access to a large waterfront green space, and close to local restaurants and marinas, this home delivers the ultimate Eastport lifestyle. Don’t miss your chance to live steps from the water in one of Eastport’s most sought-after neighborhoods.
#MDAA2109984

ANNAPOLIS

746 WARREN DRIVE

5 Beds

1 Baths

1,200 Sq.Ft.

$524,900

MLS#: MDAA2109984

Building One Nearly Sold Out - Model Home Now For Sale! Bright, spacious unit showcasing gorgeous design upgrades throughout. Start an exciting new chapter in this amenity-rich 55+ community conveniently located minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking space included. Turnkey luxury, private balcony... Tour this incredible Model Home today!
#MDAA2095514

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 207

2 Beds

2 Baths

1,318 Sq.Ft.

$523,655

MLS#: MDAA2095514

Stunning Penthouse in Four Seasons at St. Margaret’s – A Premier 55+ Community! Discover luxury and convenience in this beautifully maintained penthouse unit, nestled in the sought-after Four Seasons at St. Margaret’s. Designed for effortless living, this home features an elevator-equipped building, garage and an inviting open floor plan with soaring vaulted ceilings. Step inside to find gorgeous wood flooring extending through the foyer, living, dining, kitchen, and hallway areas. The updated kitchen boasts granite countertops, stainless steel appliances (2020), a stove with a convection oven option, pantry cabinets with roll-out shelving (2020), and under-cabinet lighting (2020)—perfect for both everyday cooking and entertaining. The spacious primary suite offers a walk-in closet with a built-in safe and a remodeled en-suite bath (2020) featuring a jetted soaking tub, new vanity, countertops, flooring, and a walk-in shower with seat & grab bars and a remote bidet. The hallway bath also includes a bidet and custom tilework. The second bedroom and loft provide flexible space, with carpeting replaced in 2020. Additional highlights include: ✅ Front-load washer/dryer (2020) in a dedicated laundry room with cabinetry ✅ New windows (2021) with a lifetime warranty ✅ Extra storage under the loft stairs ✅ Surge protector added to the main electrical panel ✅ One-car garage with shelving and interior access ✅ Brand-new furnace and A/C unit (2024) and water heater (2019) Enjoy resort-style amenities, including a swimming pool, fitness center, library, meeting/game room, billiard room, community kitchen, and spacious gathering areas. Relax outdoors on the main patio or upper deck overlooking the pool. This exceptional home blends modern upgrades with a vibrant, active lifestyle. Schedule your private tour today!
#MDAA2109724

ANNAPOLIS

903 NOAH WINFIELD TERRACE 303

2 Beds

2 Baths

1,516 Sq.Ft.

$520,000

MLS#: MDAA2109724

Experience the best of Heritage Harbour in this rarely available penthouse condo—one of the most spacious units in the building! This stunning two-story home is packed with premium features, offering 2 large bedrooms, each with a walk-in closet, 2.5 bathrooms, and ample storage space. Gleaming hardwood floors flow throughout the open floor plan, where the kitchen overlooks the family room, complete with a cozy wood-burning fireplace. Step outside onto your private balcony patio, the perfect retreat on beautiful days. Bonus: A reserved garage parking space conveys with the unit! This exceptional building includes indoor and outdoor pools and a fully equipped gym for your convenience. Plus, Heritage Harbour’s world-class amenities are second to none, featuring: ✅ Indoor & outdoor pools ✅ Hot tub & sauna ✅ Golf course ✅ Tennis & pickleball courts ✅ On-site restaurant ✅ Boat slips & kayak racks ✅ RV/boat storage ✅ The Lodge/Community Center—offering endless social and recreational activities Don’t miss this opportunity to enjoy luxury, space, and an unbeatable 55+ lifestyle in Heritage Harbour!
#MDAA2109828

ANNAPOLIS

930 ASTERN WAY 609

2 Beds

2 Baths

1,926 Sq.Ft.

$519,900

MLS#: MDAA2109828

Move-In Ready! This beautifully updated home features an updated kitchen with modern appliances, a fully renovated bathroom, new washer & dryer, new hot water heater, new HVAC system, refinished hardwood floors, and a new roof. Additional highlights include a wood-burning fireplace, a spacious screened-in rear porch, and a one-car garage that is currently in the process of being converted back into a functional garage. The entire house will also be fully repainted prior to settlement. Located within walking distance to Truxton Park and Annapolis public transit, this home offers convenience, comfort, and charm.
#MDAA2108848

ANNAPOLIS

9 EDELMAR DRIVE

4 Beds

2 Baths

936 Sq.Ft.

$519,900

MLS#: MDAA2108848

Bright, spacious unit at second floor elevation showcases stylish design upgrades throughout! Start an exciting new chapter in this amenity-rich 55+ community conveniently located mere minutes to downtown Annapolis, retail shopping, waterfront dining and Bay Bridge. Reserved parking space included. Turnkey luxury includes window treatments, full-size washer/dryer and more! Building One nearly sold out - tour this stunning new home today!! Virtual staging used to demonstrate the space & layout.
#MDAA2110762

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 107

2 Beds

2 Baths

1,318 Sq.Ft.

$519,090

MLS#: MDAA2110762

Welcome to this Wonderful home very close to Annapolis & the properties to be in a private area but close proximity to be in the City of Annapolis! Located in close proximity to restaurants , shopping, and entertainmemt . You will enjoy summer evenings dining - out in the over large deck out back! The Home offers an open floor plan that leads you to entertaining with a spacious living room, Dining Room & Remodeled Kitchen with Granite counter tops and New stainless steel Appliances. The dining & Living room boasts beautiful refinished hardwood flooring and Open to a Kitchen . The primary bedroom offers private Full remodeled bath with access to shower In addition to 2 others great size bedrooms and a Full renovated bathroom! Relax in the finished basement that offers large rec room, Additional bedroom/office/playroom and full renovated 3rd bath! You will love this home! Ready for your buyer to move-in!!
#MDAA2101268

ANNAPOLIS

1971 DOMINOE ROAD

4 Beds

3 Baths

2,160 Sq.Ft.

$519,000

MLS#: MDAA2101268

New on site 2 days ago
Picture this: You step onto the deck as the sun stretches across the yard, a quiet breeze rustling the trees at the edge of your property. Below, your backyard unfolds in layers, open and green, bordered by woods with a creek winding through. This is your everyday. Room to breathe, space to spread out, and a home that just feels right from the moment you arrive. This charming two-story brick rancher sits on over an half an acre of land in the heart of Cape St. Claire. The upper level features beautifully kept hardwood floors, three bedrooms, and a full bath. Downstairs, the walkout basement offers even more opportunity, complete with a full bath, laundry, and space ideal for a future in-law suite, guest quarters, or home office. The home is move-in ready, but there’s room to add your own touch and build more value along the way. And here’s something rare for Cape: Public Water and Public Sewer. Add in a long, generous driveway with space for multiple vehicles, boats, or trailers, and you’re ready for life on the go—or the quiet weekend at home. Living here means more than owning a home, it’s being part of a vibrant community with multiple beaches, a marina, ball fields, and access to everything from the Cape St. Claire shopping center to downtown Annapolis and commuter routes. You’re close to everything, but once you’re here, it truly feels like home.
#MDAA2117300

ANNAPOLIS

972 WOODLAND CIRCLE

3 Beds

2 Baths

1,944 Sq.Ft.

$515,000

MLS#: MDAA2117300

New Phase at Element at Mill Creek! Building B, The Banyan, is already half-sold, featuring lounge areas, party room, 2-story clubroom, upper & lower terraces, and more! Start your exciting new chapter in this amenity-rich 55+ community located minutes to downtown Annapolis, shopping, waterfront dining and Bay Bridge. Spacious home with large private balcony boasts desirable southern exposure and showcases stylish design upgrades throughout. Includes true chefs kitchen, huge owners closet, reserved parking. Low condo fee. Tour this stunning home and the building's incredible amenities today!
#MDAA2115854

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 308

1 Beds

2 Baths

1,076 Sq.Ft.

$511,400

MLS#: MDAA2115854

1 ... 14 15 16 17 18 ... 26
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 $$

properties found. properties found. Page of .

Message successfully sent.

What would you like to know?

- property

Submit a message

Message successfully sent.

Your message

Reason for contacting?

Sign Out

Virtual Assistant

Would you like to receive some additional information on this specific property or similar properties?

Yes, I would like more information.

Thank You for Your Reply, One of Our Agents will contact you as soon as possible

No, maybe later.

Thank you, you can always contact me via email, phone number or through the contact form.

Realhub AI

Update Your Temporary Password