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

Browse Annapolis Real Estate Listings

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388 Properties Found. Page 17 of 26.

Nestled in the sought-after Four Seasons Community, this luxurious penthouse condo offers an exceptional living experience for those aged 55 and better. Located in a premier active adult community, this top-floor residence boasts soaring ceilings and an open-concept design, accentuated by a stylish loft that overlooks the main living area. Spanning 1,516 square feet, the condo features two generously sized bedrooms and two full, modern bathrooms, providing ample space and privacy. The gourmet kitchen is a chef’s dream, equipped with stainless steel appliances, granite countertops, and a breakfast bar that seamlessly flows into the bright and airy living and dining areas with balcony access. Expansive windows flood the space with natural light and the versatile loft space, accessible by a sleek staircase, is perfect for a home office, art studio, or cozy reading nook. The primary suite is a true retreat, complete with a spacious walk-in closet and an en-suite bathroom featuring dual vanities, a jetted soaking tub, and a glass-enclosed shower. The second bedroom, ideal for guests or family, is conveniently located near the second full bathroom. Hardwood floors, designer fixtures, and custom finishes throughout elevate the elegance of this sophisticated home. Residents of this exclusive 55+ community enjoy a low-maintenance lifestyle with access to premium amenities such as a fitness center, game room, library, outdoor pool and beautiful, well-maintained grounds. Just minutes from Annapolis’ vibrant downtown, the condo offers easy access to boutique shopping, fine dining, and the city’s renowned waterfront attractions, including the U.S. Naval Academy and historic sailing harbors. With private garage parking and elevator access, this penthouse condo combines luxury, convenience, and the best of Annapolis living for an unparalleled retirement retreat.
#MDAA2105660

ANNAPOLIS

903 NOAH WINFIELD TERRACE 303

2 Beds

2 Baths

1,516 Sq.Ft.

$505,000

MLS#: MDAA2105660

Enjoy a fantastic lifestyle in this beautiful and pristine 2BR/2BA condo in the very desirable and vibrant 55+ community of Four Seasons at St Margarets! Enter the very well-kept secure building and access your second floor home by stairs or elevator ...OR use your garage door remote and enter the building through your private, over-sized garage. The dramatic open floor plan is ideal with kitchen island overlooking the huge living room with gorgeous hardwood floors and plantation shutters. The living room leads to a large, private balcony. The primary bedroom is massive with a large bay window and an over-sized walk-in closet. The attached bathroom has a walk-in shower and separate soaking tub. The second bedroom has a bay window, two double closets and is served by a hall bath. A large laundry room and multiple closets complete this side of the condo. Nothing to do but move in and enjoy the incredible amenities - stunning community center has several beautifully furnished party areas to entertain your guests and meet with neighbors. There is a kitchen, bar, billiards room, library, fitness center and inviting outdoor pool with many tables and chairs to enjoy the beautiful weather and wooded surroundings. The location is ideal - tucked away, but very close to shopping, public library, hiking and bike trail, and easy access to downtown Annapolis! Smoking Restricted Community
#MDAA2114444

ANNAPOLIS

1509 FERAL DAE LANE 204

2 Beds

2 Baths

1,442 Sq.Ft.

$500,000

MLS#: MDAA2114444

This charming 1 bed + loft, 2 bath condo in West Annapolis has all the features you’re looking for! Hardwood floors, vaulted ceilings, gas fireplace, modern kitchen with granite and stainless-steel appliances, large walk-in closets for ample storage, washer/dryer and private balcony for morning coffee. Spacious loft offers extra living space, home office or guest bedroom. Covered parking and elevator access for convenience. Steps away from shopping, dining and USNA Stadium. Close to USNA, Rt. 50, Downtown Annapolis, Jonas Green Park, and the Severn River make this an unbeatable location. Fully furnished and move in ready or perfect for vacation rental. Don’t miss out-see it today!
#MDAA2112450

ANNAPOLIS

608 MELVIN AVENUE 202

1 Beds

2 Baths

1,222 Sq.Ft.

$499,999

MLS#: MDAA2112450

Beautifully updated 4 Bedroom, 2.5 Bath End Unit in sought-after Broadneck community, conveniently located to Downtown Annapolis & Rt 50! Updated features include new HVAC (gas heat and central air – 2023), Primary bedroom with private bath with separate shower and soaking tub. Large kitchen with granite countertops, table space and slider out to wood balcony. Huge dining/living room with bay window. The lower level offers bedroom/workout/play room, laundry room and a family room with gas fireplace. New fully fenced-in backyard for entertaining and pets! Slider leads to patio.
#MDAA2116420

ANNAPOLIS

1500 CHESTER TOWN CIRCLE

4 Beds

2 Baths

2,069 Sq.Ft.

$499,900

MLS#: MDAA2116420

PRICE IMPROVEMENT on this COMPLETELY renovated home comes with a REDUCED FLOATING INTEREST RATE with List & Lock™. The seller paid program reduces the interest rate for you to qualify for the lower rate and enjoy a lower monthly payment Terms apply, call your Realtor or me for details and more information. BEAUTIFULLY renovated 1940s bungalow in a prime Annapolis location! This charming home boasts freshly refinished hardwood floors throughout the main level, creating an inviting and spacious feel. The oversized living and dining area features built-ins, while the brand-new kitchen shines with sleek white cabinetry, stainless steel appliances, and quartz countertops. The king-sized primary suite includes extra space for a cozy sitting area and a brand-new private en-suite bath. Two additional bedrooms share a second fully renovated bathroom conveniently located off the back hallway. Fresh paint, trim, and beautifully refinished floors add to the home's move-in-ready appeal. Downstairs, the versatile wide open basement has been refreshed in 2024—ideal for recreation, a game room, or extra storage. Additional upgrades include a newly insulated attic and a 2024 roof; windows and HVAC in 2012 and more. A long list of improvements is available! Step outside to find freshly landscaped front gardens ready for your personal touch this spring. The spacious fenced (2016) backyard features a stone patio (2015), perfect for cookouts, with ample room for activities like volleyball. A private driveway offers parking for 3+ cars, plus a wide gate allows for additional parking inside the fence. Ask for the complete list of many updates! This must-see home combines modern updates with timeless charm—schedule your showing today!
#MDAA2100446

ANNAPOLIS

2046 FOREST DRIVE

3 Beds

2 Baths

1,068 Sq.Ft.

$499,500

MLS#: MDAA2100446

Lovely 5 Bedroom and 2 Full Bath home plus Finished Basement in the desirable neighborhood of Stevens Park, part of Eastport. Main Floor has Two bedrooms, Full Bath, Livingroom and Kitchen with Breakfast Nook. Upper Level has Two Bedrooms and Full Bath. Basement has One Bedroom, Large Family Room with Stepped Rear Walkout, and Laundry-Utility-Storage Room. New Roof and Gutters with Leaf Covers installed in 2020. Outside, the property offers a fully fenced level backyard with a huge patio for entertaining and family life. Enjoy summer barbeques, quiet mornings, or watching the stars by the fire pit on clear nights. Home is located within walking distance to the Pip Moyer Recreation Center, Truxtun Tennis and Pickleball Courts, the Kenneth R. Dunn Municipal Pool, and more. Three-minute drive gets you to Quiet Waters Park with 4.5 miles of walking/bicycle trails, Pavilions for rent, fenced dog parks, dog beach, outdoor summer concerts, and winter ice skating. Historic Downtown Annapolis, shopping, restaurants, and entertainment are all minutes away.
#MDAA2096724

ANNAPOLIS

86 SUMMERFIELD DRIVE

5 Beds

2 Baths

1,755 Sq.Ft.

$499,000

MLS#: MDAA2096724

Modern Luxury Meets Active Living at The Element! Welcome to this newly built active-adult (one resident must be 55+ years old) community designed for resort-style living just minutes from historic Annapolis. This ultra-spacious 2-bedroom, 2-full-bath residence offers the perfect blend of elegance, comfort, and convenience. Step inside to discover a luxury owner's suite featuring an oversized walk-in closet, a spa-like bath retreat, and a private balcony overlooking the serene forest retention area—your personal oasis for relaxation. The designer kitchen showcases a custom backsplash, upgraded appliances, and enhanced lighting, seamlessly flowing into the open-concept living and dining area. Enjoy reserved parking and a variety of resort-style amenities—from pickleball courts and a dog park to a golf simulator and social lounges. Whether you're staying active on the walking trails or enjoying an al-fresco meal with neighbors, The Element provides an unparalleled lifestyle in Greater Annapolis. Live close to everything you need, with effortless access to the Annapolis area's waterfront dining, shopping, and cultural attractions.
#MDAA2104438

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 108

2 Beds

2 Baths

1,076 Sq.Ft.

$497,000

MLS#: MDAA2104438

Location! Location! Resort living between two rivers in this lovely split level home! Twenty year homeowner never stopped improving the home, including recent architectural roof, HVAC with humidity control, home water filtration system, and a jumbo 75 gallon hot water heater. Oak patterned laminate floors throughout provide a warm & classy feel. The upper floor offers three bedrooms that are enhanced by a remodeled full bath. A galley kitchen is a chef’s delight, and leads to a custom rear door that takes you down to the patio and lush garden. The fully finished lower level, considered “below grade”, has several large sunlit windows and opens to a spacious living room with French doors that open to a handsome stone deck for grilling, entertaining, or just relaxing with a book. Two additional large rooms with beds and closets share a full bath. The large rear yard has a stained wooden fence, beautiful greenery, and a generous 10’ x 20’ storage shed. Driveway for you boat or vehicles. Nearby Safe Harbor Marina in Eastport offers premium resort amenities with a family atmosphere: boating, tennis, pickleball, swimming, and a poolside Cafe and Tiki bar. Also a few blocks walk from home is the Annapolis Athletic Club, offering an array of fitness classes, personal trainers, varied strength & cardio machines, massage, and locker rooms with lounge. Luxurious steam room & sauna, and showers with towel service end the ideal workout. All of the day’s activities will enhance your appetite for deluxe dining at nearby seafood & steak restaurants. The Historic District, City Dock Market House, and United States Naval Academy are a mile walk or bike ride. Or head the other direction 1 &1/2 miles to Quiet Waters Park to enjoy the 340 acres of trails, paddle boarding/kayaking, picnic pavilions, or nationally renowned Dog Park along the South River. Annapolis has a vibrant arts community hosting exhibits at local galleries and cafes, as well as the Maryland Hall for the Creative Arts, which is home to the Annapolis Symphony Orchestra, ballet, and jazz/rock concerts. Your home is walking distance to the City treasure, Truxton Park, with an active tennis and pickleball community playing on remodeled and lighted courts. The park has a large swimming pool with adjacent children’s waterfalls and a covered pavilion. Wooded walking/jogging trail leads to Spa Creek. Boater’s use a twin boat ramp that offers easy access to scenic Spa Creek, cruising past the historic Annapolis Yacht Club into the mouth of the glorious Severn River & Chesapeake Bay. Conveniently located 23 miles from Baltimore International Airport & Amtrak, and 30 miles from the White House, world class travel, museums, and entertainment are at your doorstep! Priced below condos with high monthly fees or townhomes with HOA…hurry it won’t last!
#MDAA2100100

ANNAPOLIS

1022 TYLER AVENUE

5 Beds

2 Baths

1,854 Sq.Ft.

$494,900

MLS#: MDAA2100100

New on site 1 day ago
Enjoy the Best of Both Worlds – Waterfront Community Living with Condo Convenience! Experience the ease of a lock-and-leave condo lifestyle combined with the luxury of a deeded boat slip. This beautifully updated 2-bedroom, 2-bathroom condo offers exceptional comfort and style in a prime waterfront community. Step inside to find a gourmet kitchen featuring elegant countertops, solid wood cabinetry, an expanded window above the sink for added light, and pristine light-toned parquet flooring that has just been cleaned and polished. Additional highlights include recessed lighting, crown molding, brand-new carpet in both bedrooms, renovated bathrooms, updated electrical, and an in-unit washer and dryer. There’s also ample extra storage space. Relax or entertain on the expansive outdoor deck, where you and your guests can take in elevated views of the community along with partial water views. This unit includes a deeded 42’ boat slip with a 13’ beam (Slip B12), offering direct access to Back Creek. Severn House offers fantastic amenities, including rentable canoe, kayak, and paddle board racks, EV charging stations, a waterside park, and outdoor grilling areas. The waterfront pavilion by the community pool also features tables for outdoor dining and entertaining. Located just minutes from Eastport and Downtown Annapolis, residents can easily enjoy vibrant shops, renowned restaurants, and cultural attractions. Please note: pets are not allowed in this community. Gas and water are included in the rental, and there is additional storage available on the lower level. Don’t miss this rare opportunity to enjoy waterfront living in a stylish, move-in-ready home!
#MDAA2114832

ANNAPOLIS

769 FAIRVIEW AVENUE E 769 E

2 Beds

2 Baths

1,000 Sq.Ft.

$492,500

MLS#: MDAA2114832

Welcome to 8 Ashford Ct. Close to everything Annapolis has to offer. This 2 Bedroom 1.5 Bath contemporary townhouse is ready to go. Packed with upgrades and spacious floor plan. The neighborhood of Hunt Meadow offers lots of amenities including pool, tennis court and walking paths.
#MDAA2115574

ANNAPOLIS

8 ASHFORD COURT

2 Beds

1 Baths

1,248 Sq.Ft.

$485,000

MLS#: MDAA2115574

Lovely one BR condo with eastern view towards courtyard and pool. Luxurious downtown Annapolis living style. Just blocks to restaurants, entertainment and Annapolis City Dock, the heart of the city. Condo fee includes several amenities and most utilities. Outdoor pool, Hot tub, Two outdoor gourmet kitchens for grilling, Lending Library, Party room, Fitness center, 24 hour live concierge/security person in lobby everyday. Outdoor Garden Patch area to grow vegetables, Dog park, Billiard Table area, TV/Media lounge. Secure underground parking space included, Free shuttle service to downtown City Dock. Luxury living in an ideal city location.
#MDAA2110342

ANNAPOLIS

5 PARK PLACE 325

1 Beds

1 Baths

838 Sq.Ft.

$479,000

MLS#: MDAA2110342

Exceptional value in Annapolis. Discover the charm and comfort of the beautifully maintained rancher, offering over 2,300 sq ft of versatile living space on a generous 1/4 acre lot in a quiet, convenient neighborhood. This home features a large family room/dining room. Beneath the carpet in the living room and bedrooms, you'll find original hardwood floors just waiting to be revealed. The full, unfinished basement offers endless potential to create your dream space - a home gym, office, extra bedrooms, or media space. Attached garage with plenty of additional storage. Fenced back yard - great for pets or outdoor gatherings. Handicapped accessible making it ideal for all stages of life. A perfect blend of comfort, convenience, and potential. This well-maintained home presents an excellent opportunity for those seeking one-level living and offers great potential. Its neighborhood location is private, yet offers quick and easy access to Annapolis Town Center, restaurants, shopping and major commuter routes.
#MDAA2104494

ANNAPOLIS

114 2ND STREET

3 Beds

2 Baths

1,600 Sq.Ft.

$475,000

MLS#: MDAA2104494

Price improvement! Live in the heart of desirable Eastport, as this inviting condo offers the best of Annapolis nautical living. 316 Burnside Street #304 , is just a short stroll from the serene waters of Spa Creek! This home offers an ideal retreat for those seeking both tranquility in the city of Annapolis! Updated kitchen offers rich cherry cabinetry, gleaming granite countertops, and stainless steel appliances. The kitchen is both functional and stylish. Modern, nautical ash and cherry wood floors flow seamlessly throughout, adding warmth and style to this comfortable space. Recent upgrades includes all new HVAC 2022 of 2 units, freshly painted, and recessed lighting. There is a tankless water heater inside of the unit. The Burnside Condominiums offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. These amenities provide residents with a serene retreat to enjoy sunsets, watch events like the Blue Angels' flyovers, NAVY commissioning week, and parade of lights. Partake in kayaking, and paddle boarding with private dock space. and water taxis. Deep water boat slips available for a rental fee. Entertain your friends and watch the Annapolis fireworks from your deck without fighting the crowds. The Burnside Condominiums in Annapolis offers a unique blend of urban living and waterfront charm, featuring a rooftop pool and deck with panoramic views of Spa Creek, downtown Annapolis, and the U.S. Naval Academy. Take an easy stroll to some of the best waterside restaurants, yacht clubs, shopping, grocery store, and all the charm Annapolis has to offer! This is a secured building, with keyed entry, intercom system, and elevator access. There is laundry use on all condo levels and main floor storage unit for your condo space. Off street parking for residents on lot, and guest parking available. This a beautiful home and you will not want to miss a viewing! Move right in and enjoy Annapolis living at its best!
#MDAA2114264

ANNAPOLIS

316 BURNSIDE STREET 304

1 Beds

1 Baths

526 Sq.Ft.

$475,000

MLS#: MDAA2114264

Welcome to 3290 Arundel on the Bay Road – a disco bungalow nestled in the water oriented neighborhood of Oyster Harbor. This delightful 2-bedroom home offers the ideal blend of character and efficiency, with thoughtful updates throughout. The renovated full bath (2020) adds a modern touch, while the open living spaces invite you to relax and unwind. Have peace of mind knowing the kitchen was remodeled in 2021, the roof was replaced in 2022 and the water heater was replaced in 2023. Step outside to your own private oasis – a fully fenced, serene yard that’s perfect for weekend BBQs, morning coffee, and gathering with friends. One of my favorite spots is the screened back porch. Whether you're looking for your first home, a weekend getaway, a precious Air-BnB, or a low-maintenance lifestyle in a vibrant water-access community, this gem is ready to welcome you home. New to Oyster Harbor? We love our neighborhood, multiple places to launch a kayak or paddleboard, tot-lots and basketball quarts, a boat launch, a fishing pier, a great beach with pavilions and so much more all located within a10 minute drive or boat ride to downtown Annapolis!
#MDAA2114218

ANNAPOLIS

3290 ARUNDEL ON THE BAY ROAD

2 Beds

1 Baths

1,138 Sq.Ft.

$475,000

MLS#: MDAA2114218

Estate sale being sold AS IS. Great location and lots of natural light. End unit with brand new roof. HOA fees only $135 per month. Interior needs updating and carpet removed, but this spacious end unit has lots of potential and great views to private woods in the rear. Two assigned parking spaces. Convenient location.
#MDAA2114876

ANNAPOLIS

586 WILD FLOWER GLADE

3 Beds

2 Baths

2,163 Sq.Ft.

$459,900

MLS#: MDAA2114876

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