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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
301
# of Listings
3
Avg # of Bedrooms
$477
Avg. $ / Sq.Ft.
$1,098,890
Med. List Price

Browse Annapolis Real Estate Listings

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103 Properties Found. Page 5 of 7.

This beautiful home is ideally situated in a quiet cul de sac just minutes from shopping, dining, and vibrant downtown Annapolis. First floors opens to beautiful hardwood floors with wood burning fireplace in LR, kitchen with new appliances, freshly painted, upstairs with new carpeting and large closets, Master with adjoining bath, finished basement with laundry room with washer and dryer and storage, 1 car garage, fenced yard, lovely landscaping, close to schools, new roof 2019. Lovely laid out floor plan. This is a must see!!!
#MDAA2124730

ANNAPOLIS

111 JANWALL STREET

3 Beds

2 Baths

2,106 Sq.Ft.

$649,900

MLS#: MDAA2124730

The luxury waterfront lifestyle is awaiting you on Spa Creek in Eastport. This updated unit has the exterior wall opened up for a picture window to let in natural light, a modern kitchen with stainless steel appliances, and a high end mini split system for silent and efficient heating and cool. The flow of the unit is one of the highlights with the kitchen and living room opening out to the covered and private outdoor deck. Moments are to be enjoyed here with views of the yachts meandering along Spa Creek with historic Annapolis in the backdrop. The community amenities include a waterfront pool to relax and enjoy the best views in town, outdoor grilling and dining area, exercise room, and sauna. Storage space is made easy with an assigned storage unit and also a bicycle room for additional space. This maintenance free condo is walking distance from the greatest marinas and dining options in Eastport and just a short water taxi ride from City Dock.
#MDAA2124468

ANNAPOLIS

301 BURNSIDE STREET A 202

1 Beds

1 Baths

513 Sq.Ft.

$649,000

MLS#: MDAA2124468

AMAZING WATER VIEWS! Professional Interior Photos Coming Soon! Available to show this weekend. Welcome to waterfront living at its finest! This beautifully updated 2-bedroom, 2-bathroom condo offers breathtaking water views that make you feel like you’re living right on the water. Step inside to find brand-new wood floors, fresh carpet, and new paint throughout, creating a bright and inviting space. Both bathrooms have been thoughtfully updated, and the home is truly move-in ready. Enjoy your morning coffee or evening sunsets from your private deck, just steps from the water. Perfectly located in the sought-after Chesapeake Harbour community, this condo combines comfort, style, and the ultimate Annapolis lifestyle. The community is known for its incredible amenities: two pools, tennis courts, a marina, beach access, walking paths, and the Beacon waterfront restaurant — everything designed to make life feel like a vacation. All of this just minutes from downtown Annapolis, the United States Naval Academy, shopping and grocery stores. Whether you’re searching for a relaxing second home or the perfect year-round residence, this home offers it all. Don't wait - schedule your showing today!
#MDAA2124602

ANNAPOLIS

7044 HARBOUR VILLAGE COURT 102

2 Beds

2 Baths

1,196 Sq.Ft.

$649,000

MLS#: MDAA2124602

Lovely Brick home in private Water Community of Hillsmere Estates that offers 5 Bedroom, 2.5 Baths* Main Level sun-filled Living Room and Dining Room have beautiful refinished HWD Floors * LR has a brick woodburning FP and a bank of front windows with Plantation Shutters* The spacious Sun Room offers Plantation Shutters on all windows, a tiled floor and French Doors at either end opening to the side deck and brick patio* The updated kitchen has S/S appliances, built-in microwave, Quartz counters, recessed lighting & table space* Primary BR has Powder Room, lighted ceiling fan and slider door with access to patio* Lower Level has a family room with FP & mantel, additional kitchen with toaster, microwave, S/S appliances, refrigerator, movable island, counter-top burners* Shed* Fenced in rear yard with landscaping* Two bedrooms and full bath* Laundry Room with plenty of shelving* The Community Swimming Pool (you would need to join) and Soccer field is right across the street* This Community has an Volunteer Improvement Association for a yearly fee of $25 but not required* This Community has super amenities that include the private beach with pavilions for picnicing, boat ramp, etc. A Must See*
#MDAA2123236

ANNAPOLIS

130 GREAT LAKE DRIVE

5 Beds

2 Baths

2,014 Sq.Ft.

$647,000

MLS#: MDAA2123236

Welcome to sought-after Cape St. John! This split-level home sits on a spacious and private wooded lot, offering privacy, nature, and access to water just steps from your backyard. Inside, the upper level features gleaming hardwood floors, recessed lighting and an upgraded kitchen with a large granite island and plenty of storage in rich wood cabinetry. The kitchen flows seamlessly into the dining room, which opens to a spacious deck - perfect for grilling or unwinding while overlooking the trees. Three bedrooms are on the upper level, including a primary suite with en-suite bath. The newly renovated lower level offers incredible versatility with brand new flooring, fourth bedroom, and half bath. Entertain or relax fireside in the generous family room that opens to a screened-in brick patio - a peaceful retreat year-round. A large laundry room with ample storage space completes this level. Recent upgrades include a new HVAC system, heat pump, and EV charger, ensuring comfort and efficiency. The lot backs to a walking trail that leads directly to community water access. Cape St. John residents enjoy community beach, dock, boat launch, kayak storage, and playground—everything you need for the ultimate water-oriented lifestyle just minutes from downtown Annapolis, shopping, dining, and commuter routes to DC and Baltimore! Don't miss this opportunity - schedule your showing today!
#MDAA2125214

ANNAPOLIS

144 ISLAND VIEW DRIVE

4 Beds

2 Baths

1,612 Sq.Ft.

$630,000

MLS#: MDAA2125214

Priced to sell. Compare vs. buying new. Welcome to The Element at Mill Creek, an exclusive 55+ community offering luxury, low-maintenance living just minutes from historic Annapolis. This stunning first-floor corner unit is filled with natural light from two sides, has 9-foot ceilings, and only one shared wall, creating a spacious and private living experience. Designed for comfort and convenience, this two-bedroom, two-bath home plus a large study boasts modern finishes like Timberlake cabinetry with crown molding, stone countertops, recessed lighting, and Samsung stainless steel appliances. The spa-like bathrooms feature DalTile floor-to-ceiling wall tile with shower niches, and the living spaces showcase elegant plank flooring with customizable features such as LED mirrors and barn doors. As part of The Element at Mill Creek, residents enjoy resort-style amenities, including a state-of-the-art fitness center, golf and sports simulator, walking trails, and multiple indoor and outdoor social areas. Pickleball courts and a dog park are coming in the upcoming months, adding even more to this vibrant community. Secure entry, optional garage parking, and proximity to downtown Annapolis further enhance the appeal. Included with the sale is Garage Parking Space #31, now a $25,000 value, offering added convenience and security. Don’t miss this opportunity. B4-Alt is said to be the most popular floor plan in the community and all 16 units of buildings 1C and 2B are sold out. This is also the largest of the 2-bedroom units. *Builder claims 1723 sqft though published taxed sqft is less. Buyer to confirm which may be accurate.
#MDAA2124492

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 101

2 Beds

2 Baths

1,723 Sq.Ft.

$629,000

MLS#: MDAA2124492

Dreaming of a life by the water, with Bay views? Now’s your chance to make it a reality in the coveted, amenity-rich community of Chesapeake Harbour. This serene top-floor 2-bedroom, 2-bath retreat offers sweeping views of the sparkling bay and an easy, light-filled layout designed for comfort. The sunlit living room with its cozy wood-burning fireplace flows effortlessly into the dining area and spacious eat-in kitchen, where you’ll find generous counter space and a large pantry. The updated primary suite includes a walk-in closet and full bath, while the versatile loft upstairs is perfect for a quiet home office, a movie night hideaway, or even a third bedroom. For peace of mind, the A/C has been recently updated, in April 2025 with a 5 year warranty. Step outside and take in the scenery—sip your morning coffee from the enclosed front balcony, or unwind for the evening on the rear balcony overlooking tranquil green space with a view of the Bay. When you’re ready to explore, the community has everything you need to relax and recharge: boating, fishing, swimming, or enjoying a meal by the marina at the new Beacon restaurant—all just a short stroll from your door. Come and make your appointment today to experience the Chesapeake Harbour lifestyle for yourself.
#MDAA2124556

ANNAPOLIS

2010 QUAY VILLAGE COURT 201

2 Beds

2 Baths

1,489 Sq.Ft.

$625,000

MLS#: MDAA2124556

This impeccably maintained 2-bedroom, 2.5-bath Everest floor plan offers high-end living, privacy, and a prime location. Enjoy a professionally managed building with secure entry, welcoming staff, and exceptional amenities. Boasting rich hardwood floors and 10' recessed ceilings finished with fine crown trim, the home is filled with natural light from oversized windows with plantation shutters. The open-concept living and dining areas flow into a gourmet kitchen with granite countertops, ample storage, and custom "pull-out" cabinetry. Two spacious bedroom suites, each with walk-in California Closets and spa-like baths with dual vanities, are positioned for privacy. A well-placed half bath is convenient for guests and enhances everyday functionality. Additional features include an in-unit laundry room, a separate office, and a private balcony for sunset views. Amenities include a rooftop pool, hot tub, grill area, and outdoor dining with panoramic views of Annapolis — one of the rarest offerings in the area. Two assigned garage spaces (one conveniently close to the elevator) provide unmatched convenience. Located on the quiet side of the building, you’re still moments from Whole Foods, Target, Lifetime Fitness, Rise Up Coffee, dining, shopping, and seasonal events. Easy access to Routes 50, 97, and 2 puts downtown Annapolis, the Naval Academy, marinas, and medical facilities just minutes away. Unit 301 offers the serene, convenient, and luxurious lifestyle you’ve been searching for.
#MDAA2123224

ANNAPOLIS

1915 TOWNE CENTRE BOULEVARD 301

2 Beds

2 Baths

1,684 Sq.Ft.

$625,000

MLS#: MDAA2123224

Enjoy luxury condo living in this first-floor 2-bedroom, 2-bath home. Featuring gleaming hardwood floors, spacious and bright layout, and a stylish kitchen, this residence combines comfort and convenience. Park Place offers exceptional amenities including 24/7 concierge service, a pool, fitness center, meeting and party rooms, library, and a rear outdoor patio with a kitchen and grilling area—perfect for entertaining. The unit comes with a storage space as well as parking. Additional perks include a dog park and easy access to restaurants and shopping. A fabulous in-town location you won’t want to miss!
#MDAA2123662

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$625,000

MLS#: MDAA2123662

Price adjustment!!!!! Discover your slice of paradise in the heart of Annapolis! This exceptional property combines two complete homes with productive fruit trees, creating the ultimate in flexible living. Main Home (3BR/2BA): Beautiful hardwood floors flows through the large living room and bedrooms, while the spacious kitchen with Island connects to a separate dining area - perfect fro daily living and entertaining. Three comfortable bedrooms and two full baths complete this well designed space. In-Law suite Addition (1BR/2BA - 1200 sq ft): This isn't just and addition - It's a complete second home! Features include a large living room, Full eat-in kitchen, bedroom, two full baths, and generous laundry room. The crown jewel? An incredible 8x28 Sunroom with natural gas fireplace - your year round sanctuary with garden views. Separate entrance ensures complete privacy. Step outside to your personal orchard featuring mature pear, apple, cherry, plum and chestnut trees, plus established grapevines. Imagine morning coffee in the sunroom or out the back patio surrounded by blooming fruit trees and harvesting your own fresh produce each season. Entertaining made effortless with a sprawling 650 sq ft deck - perfect for everything from intimate dinners to large gatherings. The outdoor space flows seamlessly with nature's bounty at your fingertips. Two separate driveways ensure privacy and convenience, with circular drive serving the main house (multiple car capacity) and a dedicated 4 - car driveway for the In-law suite. Storage and workspace solved with a generous 12x24 detached garage and 8x14 shed - plenty of room for vehicles, tools, hobbies and seasonal storage. Prime Annapolis location puts you in the heart of Maryland's historic capital where waterfront charm continues to fuel demand and properties remain strong. Just a mile from downtown Annapolis for all your dining and shopping needs. Walk to Truxtun park and the Pip Moyer center that houses a gym, basketball courts, and an indoor track. You can also walk to the newly renovated tennis court and Pickleball courts with lights. Around the corner is the Truxtun park pool, Public Boat ramp and fishing pier.
#MDAA2118498

ANNAPOLIS

399 HILLTOP LANE

4 Beds

4 Baths

3,808 Sq.Ft.

$620,000

MLS#: MDAA2118498

*TO BE BUILT / READY TO BE CUSTOMIZED. CONSTRUCTION STARTING SOON* Starting at a base price of $600k. Reach out to Chase Kincer today for customization options! In addition to the builder's warranty, there is a 5-year roof warranty. Listing Photos are just for representation purposes of the same spec house.
#MDAA2116188

ANNAPOLIS

14 DORSEY AVENUE A

4 Beds

2 Baths

2,762 Sq.Ft.

$600,000

MLS#: MDAA2116188

Fantastic Price!!! Amazing location, minutes to Annapolis and the Bay Bridge. Easy commute to DC. Incredible opportunity to own a beautiful parcel of land on desirable Shot Town Road area where large estates abound. Build a sprawling estate or subdivision potential giving three smaller estates.
#MDAA2113200

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$600,000

MLS#: MDAA2113200

Welcome to 8 Wainwright Drive, a rare opportunity in the highly sought-after Admiral Heights community—just minutes from the Naval Academy, downtown Annapolis, and the waterfront lifestyle that makes this area world-renowned. This charming 3-bedroom, 1.5-bath home offers you more than just a place to live—it offers a chance to secure a home in a premier neighborhood at a price that is almost unheard of in today’s market. Imagine stepping into a property that gives you instant equity and flexibility. Whether you’re looking to create your dream home, invest for long-term growth, or simply take advantage of one of the best values in Annapolis, this home delivers. The layout is functional and inviting, with generous living spaces ready to be tailored to your style. The bedrooms are well-sized, the natural light is abundant, and the outdoor space provides room to relax, garden, or entertain. Homes in Admiral Heights rarely become available at this kind of price point—most sell for significantly more. That means this isn’t just a home; it’s an opportunity. If you’ve been waiting for “the deal” that gives you a reason to act now instead of later, this is it. Compare it to anything else on the market, and you’ll see why this property is generating excitement: location, community, and the kind of value that smart buyers recognize instantly. When you live here, you’re part of a vibrant neighborhood known for its tree-lined streets, friendly atmosphere, and quick access to everything Annapolis has to offer—restaurants, shops, waterfront activities, and commuter routes. It’s no wonder homes here are so tightly held. The sellers have priced this property intentionally to sell quickly, knowing the next owner will reap the benefits. Instead of waiting for the perfect house to come along at the perfect price, this is your chance to create it—on your terms, in a neighborhood that supports long-term value. If you’ve been asking yourself whether now is the time to act, consider this your sign. The market has been competitive, inventory is low, and opportunities like this don’t last. Once this one is gone, it’s gone. Schedule your showing today and step into a home that represents not just where you live, but the lifestyle, equity, and future potential you’ve been waiting for. 8 Wainwright Drive isn’t just another listing—it’s your chance to secure a smart move in one of Annapolis’s most desirable locations.
#MDAA2124892

ANNAPOLIS

8 WAINWRIGHT DRIVE

3 Beds

1 Baths

1,899 Sq.Ft.

$599,900

MLS#: MDAA2124892

Major Price Adjustment!! Great opportunity in West Annapolis! Discover the charm of 111 Clay St, a delightful 1940s Colonial offering a fantastic chance to own near Annapolis Downtown District. This home features a huge front porch, Large windows that brings in tons of natural light, to an open floor plan. Newly updated a few short years ago, this home features modern functionality and original charms. A 3 BR's, 1.5 BA's layout w/ a huge sunken tub and separate shower, just great for relaxing. This is a prime location offering so many things to do locally. You're walking distance to arts, entertainment, local shops, and restaurants. Even Navy Football and Basketball events are within close proximity. Take a look at this rare opportunity to call this wonderful place home!
#MDAA2111920

ANNAPOLIS

111 CLAY STREET

3 Beds

1 Baths

1,872 Sq.Ft.

$599,000

MLS#: MDAA2111920

Enjoy resort style living at amenity rich Heritage Harbour...Annapolis' premier active adult community. This 3 BR/2.5 BA end of group townhome features a main level primary bedroom with en-suite bath...perfect for those seeking single level living with additional upper level bedrooms/bath for visiting family & friends. You'll marvel at the elegant millwork throughout and the dramatic 2 story living room with gas log fireplace. Adjacent is the dining area, enhanced with ceramic tile flooring and stylish wainscoted shadow boxing. The kitchen is a chef’s delight with a breakfast bar, ample counter space and stainless steel appliances including a 5-burner Samsung electric range, Whirlpool fridge with ice/water dispenser, GE microwave and dishwasher. A pantry and sliding glass door to the deck complete the space. The main level also provides a laundry room, half bath and two coat closets for added storage & garage access. Upstairs, enjoy the brightly lit balcony seating area overlooking the living room. A linen closet and 2 large closets provide additional storage. The second bedroom includes a pull down stair for easy attic access. The third bedroom offers a vaulted ceiling, walk-in closet with built-ins plus access to the dual entry full bathroom. Exterior highlights include the stately brick façade, front storm door and fenced in garden/deck area with electric awning—perfect for outdoor entertaining. The center of community activities is The Lodge which features a wide variety of recreational, cultural, social and educational activities for all residents ...an auditorium, indoor and outdoor pools, sauna, fitness center, library, boutique, arts & crafts studio, woodwork shop, billiard & game rooms plus meeting rooms. From the garden lounge, there and walking trails leading past the bocce ball & horseshoe pits on your way down to the community pier with boat slips on the South River. Golfers, tennis & pickleball enthusiasts will enjoy the clubhouse featuring a pro shop and dining facility servicing the adjacent courts and the executive 9 hole golf course with putting green. The community also includes a separate lot for RV and boat storage, plus a 28-passenger community van for shopping trips and excursions. This home & community offer comfort, convenience, and style—schedule your tour today! At least one resident must by 55+. No permanent residents under 19, however, overnight visits are allowed. Buyer responsible for one time $2,075 recreation fee at closing.
#MDAA2124538

ANNAPOLIS

901 SEXTANT WAY

3 Beds

2 Baths

2,343 Sq.Ft.

$595,000

MLS#: MDAA2124538

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