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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
320
# of Listings
3
Avg # of Bedrooms
$467
Avg. $ / Sq.Ft.
$1,067,310
Med. List Price

Browse Annapolis Real Estate Listings

320 Properties Found. Page 11 of 22.

Waterfront Townhouse in Chesapeake Harbour. 
Your search ends here if you want a mint-condition, fully renovated waterfront townhouse in Chesapeake Harbour combines modern luxury with resort-style living. Renovated in 2022 and offering a 2-car garage, this pristine home showcases marina views and designer finishes throughout.
Inside, you’ll find engineered hardwood flooring, a custom staircase, solid wood doors, detailed mouldings, and updated baths and closets. The gourmet kitchen features quartz countertops, new cabinetry, tile backsplash, recessed lighting, pantry, stainless steel sink with disposal, and premium appliances—including a KitchenAid side-by-side refrigerator, GE 5-burner gas stove, dishwasher, and a brand-new 2025 washer/dryer.
The primary suite offers a custom bath and walk-in closet, while the second bedroom with pocket doors doubles perfectly as a guest space or home office. Mechanical updates include a new gas hot water heater (2022) and furnace/AC (2018). An oversized garage with a spacious front storage area adds convenience.
Enjoy  views of the Chesapeake Harbour Marina and community amenities: two swimming pools, tennis/pickleball courts, fitness center, private beach, marina, and the newly opened waterfront restaurant with outdoor dining and weekend live music.
All just minutes from Downtown Annapolis, Eastport, the Naval Academy, shopping, dining, and with easy access to Washington DC, Baltimore, and BWI Airport. Whether for a year-round residence or a weekend retreat, this home offers the best of Chesapeake Bay living.
Enjoy views of the Chesapeake Harbour Marina and take advantage of community amenities including two pools, pickleball/tennis courts, fitness center, private beach, marina, and the newly opened waterfront restaurant offering outdoor dining and live music on weekends.
Ideally located just minutes to Downtown Historic Annapolis, Eastport, the US Naval Academy, shopping, and dining—with easy access to Washington DC, Baltimore, and BWI Airport—this townhouse is perfect for a year-round residence or weekend retreat.
#MDAA2124540

ANNAPOLIS

2022 SAMS WAY 12A

2 Beds

2 Baths

1,923 Sq.Ft.

$675,000

MLS#: MDAA2124540

Beautiful 2 bedroom 2 bath condo in Park Place. This unit faces the fountain and courtyard. Stainless appliances, beautiful hardwood floors. Top tier amenities in The Residence at Park Place makes this the ideal location for in town living. A 24-hour staffed from desk in lobby. Secured lobby with controlled access. Outdoor pool with lifeguard during the season. Hot tub, Party Room, club room, library, Gym, Dog Park, garden courtyard with grills. An active social committee organizes events and gatherings. Secure underground parking garage with 2 deeded parking spaces. Enjoy the historic charm of Annapolis combined with modern luxury! Walk to restaurants and shopping.
 There is a one time Move- in Fee.
#MDAA2125914

ANNAPOLIS

5 PARK PLACE 602

2 Beds

2 Baths

1,213 Sq.Ft.

$675,000

MLS#: MDAA2125914

Welcome to this beautifully updated 3-bedroom, 2.5-bath Colonial nestled in the highly sought-after Arundel on the Bay community in Annapolis. This sun-drenched home features a bright and open floor plan with contemporary doors and trim, new replacement windows, and gleaming hardwood floors throughout the main level.  The gourmet kitchen is a chef’s delight, showcasing 42" white shaker cabinets, absolute black countertops, brand-new stainless-steel appliances, and direct access to a screened-in porch—perfect for relaxing or entertaining. Upstairs, you'll find three spacious bedrooms and two updated full baths. The primary suite offers a beautifully appointed custom shower designed for comfort and style. Located in a waterfront community, Arundel on the Bay provides an array of amenities including a private pier, boat slips, beach access, boat ramps, playground, and scenic walking trails. Enjoy a serene yet convenient lifestyle just minutes from downtown Annapolis, shopping, and top-rated restaurants, with easy commutes to Washington, D.C., and Baltimore.
#MDAA2127094

ANNAPOLIS

3410 NEWPORT AVENUE

3 Beds

2 Baths

1,654 Sq.Ft.

$665,000

MLS#: MDAA2127094

Welcome to the luxury condominium community known as the Residence at Park Place in Annapolis.  This two bedroom, two bathroom condo has been lovingly cared for during the owner's tenure.  This airy, light and bright second floor condo offers expansive views of the scenic front courtyard and fountain,  The open floor plan integrates the living and dining areas creating a spacious environment.  The remodeled gourmet kitchen/dining area boasts of granite countertops, stainless steel appliances, a gas range, plenty of cabinetry for storage and a built-in glass door closet in the dining area. Primary bedroom offers a built-in desk, built-in Murphy bed, a walk-in closet and ensuite bath with a double vanity and tub/shower.  The second spacious and bright bedroom also offers an ensuite bath with walk-in shower, closet area and shelving behind professional curtains and built-in bookcases.  Park Place offers an array of amenities including 24 hour concierge service, secure lobby, outdoor pool, hot tub, fitness center, party room w/full kitchen and pool table, a library, a garden area, backyard court, outdoor grill & dining area, etc.  This condo also comes with two parking places.  Park Place is located within walking distance to nearby restaurants or hopping on the free downtown circulator bus to visit the restaurants and specialty stores or just sit by the city dock and enjoy the views.
#MDAA2124954

ANNAPOLIS

5 PARK PLACE 224

2 Beds

2 Baths

1,188 Sq.Ft.

$647,000

MLS#: MDAA2124954

Looking for a two-car garage home in popular, active Heritage Harbour with true MAIN level living? You will love this END-UNIT villa on a CORNER lot and forget you're in an attached home the moment you step inside. On the main level,  easily access your upgraded kitchen with granite and stainless, and your family room with vaulted ceilings, skylights, and gas fireplace. You're just down the hall from your huge owner's suite, second bed and bath, laundry, and second living room.  As a bonus, the upstairs loft and another owner's suite is perfect for storage, future live-in help, or privacy for guests!  Seller has upgraded almost everything during their ownership. Highlights include all flooring (including brand new carpet), a large walk-in shower in the renovated owner's bath, plantation shutters, AC and water heater, plus more.  Ballast Way has tons of guest parking, unlike other streets. Heritage Harbour is Annapolis' premier 55+ community with clubs and events galore - golf course, swimming, social clubs, outings, fitness center, indoor/outdoor pool, and more!
#MDAA2127278

ANNAPOLIS

772 BALLAST WAY

3 Beds

3 Baths

2,704 Sq.Ft.

$630,000

MLS#: MDAA2127278

Buyer's home contingency fell through. Now is your chance to call this HOME! Welcome to this totally updated condo in the desirable Chesapeake Harbor section of Annapolis. Whether you're looking for a worry-free vacation spot or a serene place to call home, this 3-bedroom, 3 full bath sanctuary with a gourmet kitchen and totally updated baths has you covered with over 1,700 square feet of style and comfort. This Bayfront community allows you to vacation at home year round. Take a stroll around the marina or decide if you want to lounge at one of the 2 pools, play tennis or pickle ball, or take your kayak out and watch the sunrise over the Bay Bridge, the choices are endless. Enjoy visiting The Beacon where you can grab a drink at the outdoor bar, Proud Mary's or go inside for brunch or dinner as you watch the boats bob in the marina. Looking for more options? Historic downtown Annapolis's fantastic restaurants and shopping are just a stone's throw away making every day feel like a vacation. Enjoy the tranquility of a pet-friendly environment and embrace the best of both a coastal retreat and vibrant city life!
#MDAA2120052

ANNAPOLIS

2108 CHESAPEAKE HARBOUR DRIVE E 201

3 Beds

3 Baths

1,700 Sq.Ft.

$630,000

MLS#: MDAA2120052

This colonial-style residence, situated in the desirable Murray Hill subdivision, offers a blend of classic architecture and modern amenities. Built in 1900, this detached home features a traditional floor plan with 2,280 square feet of finished living space, ideal for both entertaining and everyday living. Interior highlights include three spacious bedrooms and a well-appointed full bathroom featuring a tub shower. The kitchen, designed with a country aesthetic, is equipped with stainless steel appliances and a breakfast area, perfect for casual dining. Hardwood floors and carpeted areas enhance the warmth of the living spaces, while ceiling fans and centralized air conditioning provide comfort. The exterior boasts a corner lot with sidewalks, enhancing the neighborhood's walkability. A welcoming porch invites relaxation, while the attached two-car garage offers convenience and additional storage. Located in an urban setting, this property provides easy access to local amenities and services. The proximity to Acton Cove allows for water-oriented activities, enhancing the lifestyle appeal of this home. This residence combines historical charm with modern functionality, making it an excellent choice for those seeking an opportunity in a vibrant community.
#MDAA2128268

ANNAPOLIS

34 LAFAYETTE AVENUE

3 Beds

1 Baths

3,000 Sq.Ft.

$629,900

MLS#: MDAA2128268

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.

$629,900

MLS#: MDAA2124730

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

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