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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

277

# of Listings

3

Avg # of Bedrooms

$506

Avg. $ / Sq.Ft.

$1,381,680

Med. List Price

Browse Annapolis Real Estate Listings

All listings

$250,000 - $500,000

277 Properties Found. Page 16 of 19.

Welcome to this lovely 2-bedroom, 1-bathroom home in the heart of Annapolis, offering classic charm and modern updates throughout. Featuring beautiful hardwood floors and a traditional layout, this home provides comfort and functionality in every room. The updated kitchen boasts a center island, granite and a spacious pantry all perfect for meal prep or casual dining. The bathroom has been tastefully renovated and includes a tub/shower combo. The newly-carpeted basement offers flexible space for a home office, gym or recreation area plus dual closets for extra storage. Utilize the savings and comfort from the high-efficiency zoned dual heating/cooling system and heat pump. Outside, enjoy the fully-fenced backyard with vinyl privacy fencing and a hardscaped patio-ideal for entertaining-and a custom 16 x 12 storage shed for tools and gear. Nature & water lovers will appreciate the home's close proximity to Quiet Waters Park, where you can enjoy walking trails, a dock and boat/kayak access to scenic Back Creek. You're also just minutes from the Severn River, the Annapolis Maritime Museum, downtown Annapolis, the Eastern Shore and major commuter routes to Washington D.C., Baltimore and beyond. Don't miss this perfect blend of location, charm and convenience-your Annapolis lifestyle awaits!

ANNAPOLIS

1005 HYDE PARK DRIVE

2 Beds

1 Baths

1,190 Sq.Ft.

$489,000

MLS#: MDAA2130832

Perched on the top floor of The Tecumseh, Maryland’s first condominium building, this two-level loft offers beautiful water views and an exceptional Eastport lifestyle. W401 overlooks Spa Creek with views of Ego Alley, the community marina, and Severn Avenue. This 1-bedroom, 1-bath residence features an open-concept main level with living and dining areas, a well-equipped kitchen, mechanical room, and storage closet. The loft-style upper level showcases exposed beams, soaring ceilings, abundant natural light, and a spacious bedroom with two closets and a full bath. Recent updates include fresh paint, new carpet and bathroom flooring (2024), refrigerator (2022), HVAC (2018), and dishwasher (2017). A rare bonus: boat slip entitlement in the private marina. Community amenities include gated parking, waterfront pool and deck, private marina, kayak and bike storage, secure entry with elevator, on-site management, and laundry on each upper floor. Located in the heart of Eastport, just steps to restaurants, shops, and downtown Annapolis by foot, bike, or water taxi. This is your opportunity to own in one of Eastport’s most sought-after waterfront communities - schedule a showing today.

(The Tecumseh Condominium has a 15-day first right of refusal.)

ANNAPOLIS

312 SEVERN AVENUE W 401

1 Beds

1 Baths

660 Sq.Ft.

$485,000

MLS#: MDAA2137140

Exceptionally beautiful 1 BR/1 Bath with stunning sunset views in like-new condition.

MANY UPGRADES: New Bosch HVAC Heat Pump costing $10K, New designer walk-in shower costing $12 K , New carpeting in Bedroom., Hardwood floors, granite counters. Many amenities : 24/7 live person at the Lobby Front Desk, very secure building, One owned/ assigned underground garage parking space with remote opener, Fitness Center, Outdoor Pool and Hot Tub, Two Outdoor Gourmet BBQ kitchens, Gardening Area, Library, Party Room , TV Lounge , Free Shuttle Service to downtown, just blocks to City Dock attractions: restaurants, entertainment venues, shopping. The most luxurious condo residence in this county.

ANNAPOLIS

5 PARK PLACE 431

1 Beds

1 Baths

839 Sq.Ft.

$479,900

MLS#: MDAA2121784

PRICE REDUCED! Tons of Upgrades Throughout! Beautifully updated by the current owners, this move-in ready home offers a fresh, modern feel with stylish finishes throughout and a rare opportunity to own in Annapolis at this price point, just minutes from Eastport, Downtown Annapolis, and Quiet Waters Park. Boasting over 2,000 square feet, the spacious floor plan features a large living area, separate dining space, expansive kitchen, and walk-out deck perfect for entertaining. Upstairs offers two generously sized bedrooms, including a spacious primary suite. The beautifully finished lower level provides flexible living space with the potential for a third bedroom, home office, or guest suite. Ideally located near waterfront dining, shopping, marinas, and scenic trails, this home combines modern updates, exceptional value, and one of Annapolis’ most convenient locations. Whether you’re looking for a primary residence, weekend retreat, or investment opportunity, this is Annapolis living at an increasingly hard-to-find price point. Don’t miss your chance to make it yours!

ANNAPOLIS

149 QUIET WATERS PLACE

2 Beds

2 Baths

1,740 Sq.Ft.

$479,000

MLS#: MDAA2147928

Beautiful 1Br/1Bath facing east w pool/courtyard view. Hardwood floor, GE Stainless Steel appliances, Granite counter. Full Size W/D inside unit. 24 Hour concierge/security in lobby. 25 amenities including most utilities included in condo fee. Outdoor Pool, Fitness center, Party Room, Library, Outdoor Dining area with BBQ grills, Hot Tub, Dog Park and much more. Blocks to downtown City Dock restaurants, entertainment and shopping. Luxury Living in the heart of Annapolis.

ANNAPOLIS

5 PARK PLACE 425

1 Beds

1 Baths

838 Sq.Ft.

$477,900

MLS#: MDAA2140556

Welcome to easy living in the sought-after Heritage Harbour active adult community! This beautifully updated ranch-style townhome offers more than just a home—it’s a lifestyle. Resort-Style Living | Premier 55+ Community in Annapolis.
Step onto the inviting front porch and into a bright, open floor plan featuring a spacious living room, dining area, and a remodeled kitchen with new cabinetry, countertops, and flooring—perfect for both everyday living and entertaining.
The large primary suite includes a walk-in closet and a private en-suite bath, while the second bedroom offers direct access to a fenced rear deck with grass area —ideal for relaxing or enjoying the outdoors. New carpeting adds comfort to both bedrooms.
Additional highlights include a one-car attached garage and low-maintenance living in a vibrant, amenity-rich community. Enjoy all that Heritage Harbour has to offer—golf, indoor/outdoor pools, tennis, clubhouse activities, and lots more—just minutes from downtown Annapolis! Close to Restaurants, Shopping and more

ANNAPOLIS

2627 COMPASS DRIVE

2 Beds

2 Baths

1,234 Sq.Ft.

$477,900

MLS#: MDAA2143144

45 Randall Street is the kind of opportunity that almost never comes available in Downtown Annapolis—a charming boutique storefront positioned directly in the heartbeat of one of Maryland’s most visited waterfront destinations. Perfectly situated between the U.S. Naval Academy and the Annapolis waterfront, this high-visibility commercial property captures constant pedestrian traffic from tourists, locals, midshipmen, and boaters alike. The building’s prominent street presence and classic downtown character create the ideal setting for a boutique retail concept, coffee bar, specialty shop, studio, or investment hold in an irreplaceable location. Surrounded by established national and local retailers, restaurants, and year-round activity, this property offers the rare chance to own a piece of Randall Street in the center of Annapolis’ thriving historic district. Seller financing may be available.

ANNAPOLIS

45 RANDALL STREET

None Beds

None Baths

240 Sq.Ft.

$475,000

MLS#: MDAA2145716

New on site 2 days ago

Tucked away in a peaceful cul-de-sac, this beautiful home offers the perfect blend of comfort, style, and convenience in one of the most desirable neighborhoods around. Step inside to find fresh, neutral paint throughout that gives the entire home a bright, modern feel. The heart of the home is the stunning updated kitchen featuring elegant Silestone counters, stainless steel appliances, and a generous island with seating—ideal for casual meals, entertaining, or morning coffee. Versatility shines with a main-level bedroom that easily transforms into a private den, home office, or guest suite. Upstairs, two additional bedrooms await, highlighted by a spacious primary suite complete with its own en-suite bathroom. Best of all, enjoy resort-style living with community amenities including a sparkling pool and clubhouse. Just minutes from downtown dining, shopping, and entertainment—this home truly has it all. Move-in ready and waiting for you!

ANNAPOLIS

932 YACHTSMAN WAY

3 Beds

2 Baths

1,586 Sq.Ft.

$469,999

MLS#: MDAA2149290

We're back with fresh paint and bright spaces! BEACON WAY in HERITAGE HARBOUR! Just wait until you see the 10' x 12' Sun Room addition! It's bright and airy, and a lovely place to retreat to. Another bonus... you get to move right in! That's right, the Seller has made thoughtful updates along the way so you can envision your furniture and decorating style - the rest is done. Features I made special note of: Front porch. Vaulted ceiling in Living Room and Dining Room. Gas stove. Generous primary suite with walk-in closet. Ductless mini-split, skylight and palladian windows in the Sun Room. Roof replaced 8 years ago. HVAC is 10 years old. Water lines replaced in 2021. And, all the incredible amenities the community of Heritage Harbour has to offer! I pulled this from HHCA's site: ...an established community in Annapolis, offering beautiful wooded lots and featuring a wide variety of recreational, cultural, social, and educational activities for its residents. Residents can participate in over 90 activities, clubs and committees. The center of community activities is the Lodge, which features a welcoming atrium, an auditorium, indoor and outdoor pools, fitness center, library, boutique, activities room, woodwork shop, game rooms, coffee corner and meeting rooms. Behind the Lodge, residents enjoy a picnic area, horseshoes, bocce ball and kayaking on our waterfront on the South River. We also offer multiple tennis and pickleball courts, a nine-hole golf course, a pro shop, a clubhouse dining room, a pier with boat slips and RV and boat storage on a lot in the community. Residents enjoy the convenience of regular bus trips to shopping centers and special bus trips to cultural destinations, as well as volunteer drivers for medical appointments. Our pet-friendly community of active residents always welcomes newcomers! Can't wait for you to see this one - it's going to make you smile!

ANNAPOLIS

907 BEACON WAY

2 Beds

2 Baths

1,234 Sq.Ft.

$465,000

MLS#: MDAA2141580

Welcome to Walnut Ridge near sought-after Cape St. Claire area! This beautifully maintained 3-bedroom end-unit town-home offers extra privacy, abundant natural light, and a spacious layout designed for comfortable everyday living. The bright main level features a welcoming living room, dining area, and an updated kitchen with ample cabinetry, generous counter space, and room for casual dining. New soft-closing modern shaker style cabinets. Sliding doors lead to a private outdoor space perfect for entertaining, grilling, or simply enjoying the peaceful surroundings.

Upstairs, you'll find a spacious primary suite along with two additional bedrooms and a full bath. The end-unit location allows for additional windows throughout the home, creating a light-filled and airy atmosphere. The lower level offers flexible living space ideal for a family room, home office, gym, playroom, or future expansion, along with plenty of storage. Bonus half bath in the basement. Walk-out level that leads to a craftsman style partially covered back patio. Some improvements include new roof, skylights, and windows in 2018. New deck boards in 2022.

Enjoy the convenience of assigned parking, low-maintenance living, and access to all that the area offers, including parks, trails, shopping, and restaurants. Located in the highly regarded Broadneck School District and just minutes from downtown Annapolis, the Bay Bridge, Sandy Point State Park, and major commuter routes to Baltimore, Washington, and Fort Meade. This move-in ready home combines location, value, and lifestyle—don't miss this opportunity to make it yours!

ANNAPOLIS

421 PEACH COURT

3 Beds

2 Baths

2,057 Sq.Ft.

$449,900

MLS#: MDAA2147834

BETTER THAN NEW***SELLER MOTIVATED***
BY APPOINTMENT ONLY.
BETTER THAN NEW - 55+ Luxury 2-bedroom/den with balcony in an elevator condo building. THE ELEMENT boasts a variety of amenities to satisfy an active adult community. Natural light floods into the modern kitchen with white cabinetry, tiled backsplash, SS appliances & quartz countertops. Enhanced lighting & recessed lights throughout. Upgraded closet design w/a huge Master closet! Beautiful, light colored LPV flooring (no carpeting). Custom bathroom design with upgraded tilework. Double vanity in the master bath. Private balcony for sipping your morning coffee. Beautifully landscaped perimeter with a walking trail/path. Elegant lobby with automated golf room & pool table. Enjoy pickleball, dog park, outdoor grills & workout equipment. Assigned outside parking(Space#4) & lower-level storage unit(#20) included. (Wallpaper is peel-and-stick). Call today to see this great property with amenities galore! Quick drive to downtown Annapolis, waterfront dining, shopping & the Bay Bridge.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 209

2 Beds

2 Baths

1,210 Sq.Ft.

$449,900

MLS#: MDAA2136282

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

ANNAPOLIS

1531 HICKORY WOOD DRIVE

3 Beds

2 Baths

916 Sq.Ft.

$439,900

MLS#: MDAA2140770

New on site 3 days ago

Set within the coveted South River condominium in Heritage Harbour, 930 Astern Way #204 offers refined, low-maintenance living in one of Annapolis’s most desirable 55+ waterfront communities. This beautifully appointed residence combines generous proportions, timeless finishes, and effortless elegance, all complemented by the rare and highly sought-after convenience of a deeded garage parking space.

A gracious marble foyer introduces light-filled interiors where expansive living and dining spaces are designed for both relaxed everyday living and sophisticated entertaining. A wet bar adds a touch of classic elegance, while sliding glass doors open to a private balcony, creating a seamless connection between indoor comfort and outdoor tranquility.

The spacious primary suite is a true retreat, featuring dual walk-in closets and a luxurious marble bath with a whirlpool soaking tub, separate shower, and double vanity. A generously sized second bedroom and full bath provide ideal accommodations for guests or a private office, while a dedicated laundry room and abundant storage enhance everyday convenience.

Residents of South River enjoy exclusive building amenities, including indoor and outdoor pools, a fitness center, and beautifully maintained common spaces. Beyond your door, Heritage Harbour offers a resort-inspired lifestyle with golf, tennis and pickleball, miles of walking trails, a marina with kayak access, clubhouse, library, restaurant, woodworking shop, and an exceptional array of social clubs and activities.

Just minutes from the historic charm of downtown Annapolis, waterfront dining, boutique shopping, and major commuter routes to Washington, D.C. and Baltimore, this exceptional residence presents a rare opportunity to enjoy luxury, convenience, and an active lifestyle in one remarkable setting.

ANNAPOLIS

930 ASTERN WAY 204

2 Beds

2 Baths

1,464 Sq.Ft.

$424,500

MLS#: MDAA2149334

.
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.........

ANNAPOLIS

126 BRIGHTWATER DRIVE, ANNAPOLIS, MD 21401

4 Beds

3 Baths

1,780 Sq.Ft.

$419,990

MLS#: MDAA2144288

#MDAA2142548

ANNAPOLIS

1019 PRESIDENT STREET

3 Beds

2 Baths

1,350 Sq.Ft.

$400,000

MLS#: MDAA2142548

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