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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
316
# of Listings
3
Avg # of Bedrooms
$463
Avg. $ / Sq.Ft.
$1,071,137
Med. List Price

Browse Annapolis Real Estate Listings

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$250,000 - $500,000

$500,000 - $1M

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Over $5M

102 Properties Found. Page 5 of 7.

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

Welcome to 212 Duke of Gloucester- a prime development opportunity in the heart of historic Annapolis-- Steps away from Church circle, this 2300 sqft split level property built in 1946 is ready for your vision. While the zoning is C2P which allows both professional offices and residential, this property now has approval from the City of Annapolis to move forward with plans to develop into a single or two unit residential dwelling. This property is ideal for visionary investors or developers seeking to create a signature residential, commercial, or mixed-use project. The upper level, with natural light provided by the high vaulted ceilings and windows across the front facade could accommodate a luxurious board room. The space has a large kitchen, an expansive multi-purpose room and large living area. The lower level includes a spacious reception area, 3 private offices & 1/2 bath. Surrounded by historic charm, waterfront attractions, and top-tier dining and retail, this is a once-in-a-generation chance to make a lasting mark on downtown Annapolis. Sold as-is. Check local zoning for commercial use, but it is set up and zoned for two professional offices. Also listed as a multifamily property: MDAA2121808
#MDAA2120582

ANNAPOLIS

212 DUKE OF GLOUCESTER STREET

None Beds

None Baths

2,304 Sq.Ft.

$615,000

MLS#: MDAA2120582

Start the New Year in this beautifully renovated Annapolis gem — featuring the largest floor plan in the neighborhood! Fully updated in 2023, this home offers the feel of new construction with all-new ductwork and HVAC systems for enhanced comfort and efficiency. The gourmet kitchen is a chef’s dream, showcasing a spacious center island, granite countertops, soft-close 42" cabinetry, stainless steel appliances, and a sleek range hood. Sunlight fills the space through glass doors that open to a newer deck overlooking a fully fenced backyard — perfect for private outdoor living and entertaining. The main level includes two generously sized bedrooms and a full bath. Upstairs, you'll find two additional bedrooms and two full baths, including a luxurious primary suite. This retreat features a custom walk-in closet with built-ins and a versatile bonus den — ideal for a cozy lounge or home office. The spa-inspired primary bath offers a double vanity and an oversized soaking tub for ultimate relaxation. The waterproofed, partially finished basement provides flexible space for recreation, gaming, or storage. Plus, enjoy peace of mind with a brand-new sewer line installed in 2025. Experience the best of Annapolis living in this exceptional home. Schedule your private tour today!
#MDAA2128802

ANNAPOLIS

1020 HYDE PARK DRIVE

4 Beds

3 Baths

2,600 Sq.Ft.

$615,000

MLS#: MDAA2128802

Welcome to 212 Duke of Gloucester- a prime development opportunity in the heart of historic Annapolis-- Steps away from Church circle, this 2300 sqft split level property built in 1946 is ready for your vision. This property is ideal for visionary investors or developers seeking to create a signature residential, commercial, or mixed-use project. While the zoning is C2P which allows both professional offices and residential, this property now has approval from the City of Annapolis to move forward with plans to develop into a single- or two-unit residential dwelling. The upper level, with natural light provided by the high vaulted ceilings and windows across the front facade could accommodate a luxurious 1- or 2-bedroom residential unit. The space has a large kitchen, an expansive multi-purpose room and large living area. The lower level currently includes a spacious reception area; 3 private offices & 1/2 bath and can easily be converted into another 1- or 2-bedroom apartment. Surrounded by historic charm, waterfront attractions, and top-tier dining and retail, this is a once-in-a-generation chance to make a lasting mark on downtown Annapolis. Sold as-is. Also listed for Commerical Sale: MDAA2120582
#MDAA2121808

ANNAPOLIS

212 DUKE OF GLOUCESTER STREET

None Beds

None Baths

2,300 Sq.Ft.

$615,000

MLS#: MDAA2121808

*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

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.

$600,000

MLS#: MDAA2124556

Welcome to 2707 Judson Place in Riva Woods. This inviting home sits on a private, fenced corner lot in one of Annapolis’s most peaceful communities. Thoughtfully updated, it offers spacious indoor living and a modern outdoor retreat. Inside, two large open living areas feature hardwood floors and abundant natural light. The kitchen includes stainless steel appliances, pantry storage, and a cozy eat-in nook framed by big front windows. A 21x21 heated sunroom adds versatility, perfect for a gym, playroom, workshop, or studio. Upstairs, three bedrooms and two full baths provide comfort and flexibility. The primary suite offers a walk-in closet and custom built-in storage. The lower level provides another bright gathering space with direct access to the backyard. Outside, a brand-new two-level patio creates a perfect setting for entertaining or relaxing, while simplified landscaping adds beauty with minimal upkeep. Highlights include energy-efficient windows, a newer roof with upgraded gutters, two floored attics for storage, and ample driveway parking. Conveniently located near schools, shopping, dining, and Historic Annapolis, this home combines everyday ease with a tranquil setting. With a voluntary HOA, 2707 Judson Place is ready to welcome its next owners.
#MDAA2126274

ANNAPOLIS

2707 JUDSON PLACE

3 Beds

2 Baths

2,156 Sq.Ft.

$600,000

MLS#: MDAA2126274

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 possible subdivision potential of three smaller lots. If you can imagine yourself here and need additional resources to build your dream home please call for more information.
#MDAA2113200

ANNAPOLIS

SHOT TOWN ROAD

None Beds

None Baths

7.83 acres

$600,000

MLS#: MDAA2113200

REDUCED AND PRICED TO SELL! STEP INTO LUXURY AT THE YACHT CLUB CONDOMINIUMS OVERLOOKING BEAUTIFUL SPA CREEK AND THE GORGEOUS GROUNDS OF ST MARYS CATHEDRAL. This 1 Bedroom, 1 Bath Condo boasts Stainless Steel Appliances, a Wood Burning Fireplace and spectacular views from your private deck. Enjoy the ultimate Annapolis Lifestyle where you can dine dockside, paddleboard at sunrise and take a dip in the waterside pool. Step inside and call it home. The Community Amenities elevate the experience with a clubroom, fitness area with shower facilities, waterside pool, grilling area, deep water marina access, assigned parking, laundry area, secure storage area and pet-friendly! This unit is being sold furnished, don't wait, schedule your tour today! Condo bylaws require a 15 day right of refusal before settlement. Possibility of buying a boat slip directly out front at marina. This complex allows long and short term rentals.
#MDAA2121698

ANNAPOLIS

301 BURNSIDE STREET C 202

1 Beds

1 Baths

513 Sq.Ft.

$599,000

MLS#: MDAA2121698

Huge 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. It is Opened up to be one home but with little work you can close off to make this two separate living areas. Main Home (3BR/2BA): Beautiful hardwood floors flow 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. You can close off addition very easily and make it a true In-Law suite or a nice rental apartment for extra income. 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.

$595,000

MLS#: MDAA2118498

New on site 2 days ago
Discover the charm of this beautiful Colonial home nestled in the desirable Atlantis community. With 4 spacious bedrooms and 2.5 bathrooms, this residence offers a perfect blend of comfort and functionality. The heart of the home features a well-appointed open kitchen equipped with modern appliances. Step outside to a serene backyard that backs to lush trees, providing a peaceful retreat and a natural backdrop for outdoor gatherings. Enjoy the community's amenities, including common grounds, a pier/dock for water activities, and tot lots/playgrounds for leisure and recreation. Just blocks away, the Magothy River invites you to explore its waters with opportunities for canoeing, kayaking, and fishing. The Atlantis neighborhood is known for its proximity to excellent schools, parks, and essential public services along with the many community opportunities it provides such as parades, egg hunts, chili cook offs and more. With an unfinished walkout basement, the potential for additional living space is at your fingertips. Experience energy efficiency with a 2022 HVAC and 2019 water heater along with leased solar panels that keep utility costs manageable even during these times of rising costs.The attached garage and ample driveway parking add convenience to your daily routine. With all new paint throughout, this home is ready for you to move right in!
#MDAA2128368

ANNAPOLIS

1179 NEPTUNE PLACE

4 Beds

2 Baths

2,805 Sq.Ft.

$590,000

MLS#: MDAA2128368

Welcome to this beautiful end unit located in Riva Trace. Perfect family home with three bedrooms and 2.5 baths and a full finished basement. The home not only has plenty of street parking but also has an oversized one car garage with a power door opener. Go around the back and you will find a custom patio and a deck off the family room.... very private!!! The kitchen features granite counter tops and newer appliances plus a built-in microwave. Walk out of the kitchen and you will find yourself in the familywith beautiful fireplace, separate formal dining room with hardwood floors and living room with a second fireplace! Take the steps upstairs to find a large master bedroom with HUGE walk-in closet and full bath. To more bedrooms and another full bath completes the upstairs. Downstairs features a large rec room with a full wet bar, a sauna, a workshop/office. Plus a washer and dryer. Seller replaced windows (double&triple pane) and sliding door off kitchen….1st class !!! Seller is providing a ONE YEAR Cinch/HMS home warranty to the lucky buyers at settlement. Paths leads to the South River where there is a pier for Riva Trace owners only.
#MDAA2120792

ANNAPOLIS

2942 WINTERS CHASE WAY

3 Beds

2 Baths

3,075 Sq.Ft.

$585,000

MLS#: MDAA2120792

New on site today
Beautifully Updated Annapolis Home Near Navy Stadium!! Welcome to 201 Bowie Ave, a turnkey 4-bedroom, 3-full-bath home in an unbeatable location. Just a short distance to Navy Stadium, local shopping, dining, and commuter routes, this home blends convenience with comfort and style. The interior has been thoughtfully updated throughout, featuring bright, open living spaces and a modern kitchen. Offering flexible living arrangements with a full bath and bedroom on the lower level, and spacious bedrooms, beautifully finished baths, and ample storage on the main level. Step outside to a fully fenced backyard — perfect for pets, gatherings, or relaxing outdoors. Whether you’re looking for a walkable Annapolis lifestyle or an easy move-in ready home, this one checks all the boxes.
#MDAA2129020

ANNAPOLIS

201 BOWIE AVENUE

4 Beds

3 Baths

1,709 Sq.Ft.

$584,900

MLS#: MDAA2129020

Welcome to this completely reimagined home in the sought-after waterfront community of Cape St. Claire. Every inch of this 4-bedroom, 3-bath residence has been renewed with exceptional attention to detail. From the new roof, siding, deck, and walkway to the recessed lighting, fresh paint, flooring, tile work, and appliances, no surface has been left untouched. Step inside to find bright, open living spaces where modern finishes and timeless style come together effortlessly. The heart of the home is a stunning, brand-new kitchen featuring custom tile backsplash, sleek countertops, and stainless steel appliances - the perfect space for cooking, entertaining, and gathering. Each bathroom has been beautifully updated with contemporary tile and fixtures, creating a spa-like feel. Outside, a new deck and walkway enhance both curb appeal and outdoor living, offering plenty of room for relaxing or hosting guests in your private backyard setting. Nestled in Cape St. Claire, one of Annapolis’s most vibrant waterfront communities, residents enjoy exclusive access to marinas, sandy beaches, playgrounds, parks, and community boat ramps—ideal for kayaking, paddleboarding, or simply taking in the beauty of the Magothy River. Local favorites like Graul’s Market and the Cape St. Claire Shopping Center are just minutes away, while Sandy Point State Park and Quiet Waters Park offer even more opportunities to enjoy the outdoors. Families are drawn to the neighborhood for its sense of community and its location within the highly sought-after Broadneck School District, known for its strong academic reputation and top-rated schools—Cape St. Claire Elementary, Magothy Middle, and Broadneck High School. All of this, just minutes from downtown Annapolis, the U.S. Naval Academy, and major commuter routes to Baltimore and Washington, D.C. This home is a true turnkey gem - fully renovated, beautifully finished, and move-in ready in one of Anne Arundel County’s most desirable waterfront communities.
#MDAA2128794

ANNAPOLIS

1168 ST GEORGE DRIVE

4 Beds

3 Baths

2,035 Sq.Ft.

$579,900

MLS#: MDAA2128794

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