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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

253

# of Listings

3

Avg # of Bedrooms

$405

Avg. $ / Sq.Ft.

$830,016

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

81 Properties Found. Page 4 of 6.

#MDAA2127094

ANNAPOLIS

3410 NEWPORT AVENUE

3 Beds

2 Baths

1,654 Sq.Ft.

$650,000

MLS#: MDAA2127094

10K PRICE REDUCTION MOTIVATED SELLERS! Beautifully Renovated Eastport Marina Condo with Deeded 30’ Slip & Waterfront Pool.This 3-bed, 2-bath end-unit condo in sought-after Severn House Condominiums blends coastal charm with modern luxury. Nearly every detail has been refreshed or rebuilt—new electrical, premium hardwood flooring throughout, added in-unit laundry, and a fully renovated kitchen featuring butcher-block countertops, stainless-steel appliances, gas range with vent hood, built-in microwave, and designer recessed lighting throughout the home. Custom built-ins include a butler’s pantry and laundry cabinetry for smart, hidden storage.A full wall of sliding glass doors opens to a spacious deck offering peaceful seasonal views of Back Creek. The residence also includes a large deeded basement storage unit.Enjoy exclusive ownership of a deeded deep water 30+ foot boat slip—one of the few in Annapolis with direct vehicle access, allowing you to drive right to the dock for easy loading and unloading.Located in the heart of Eastport, Severn House offers a waterfront pool, beautifully maintained grounds, and the area’s most protected deep-water marina. Sidewalks lead to Downtown Annapolis, the U.S. Naval Academy, and the city’s famed restaurants and shops.This turnkey waterfront condo perfectly balances luxury, comfort, and location—schedule your private showing today.

ANNAPOLIS

755 FAIRVIEW AVENUE 755 D

3 Beds

2 Baths

1,295 Sq.Ft.

$639,950

MLS#: MDAA2130232

SELLER IS OFFERING $10,000 SETTLEMENT HELP! 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!!!

ANNAPOLIS

111 JANWALL STREET

3 Beds

2 Baths

1,754 Sq.Ft.

$629,900

MLS#: MDAA2124730

Step into the heart of Heritage Harbour, a community where comfort, convenience, and a welcoming lifestyle come together. Tucked in a well-kept cul-de-sac, this beautifully maintained home offers a warm and inviting arrival from the moment you enter.

Fresh interior paint brightens the entire home and provides a clean, move-in ready setting. The thoughtfully designed layout places the kitchen just off the entryway, creating a practical space for everyday cooking while keeping the main living areas open and uncluttered. This separation allows the large living room to shine as the true central gathering space, filled with natural light and perfectly suited for relaxing, entertaining, or hosting family visits.

Three spacious bedrooms offer flexibility for guests, hobbies, or a dedicated home office. The converted sunroom, complete with its own half bath, provides an excellent option for a fourth bedroom, craft space, or private retreat. The home’s well-cared-for condition is evident throughout, supported by valuable updates including a roof replacement in 2017 and a water heater installed in 2022.

Step outside to a charming patio area that is ideal for morning coffee, outdoor dining, or moments surrounded by the lush landscaping the neighborhood is known for. While the home offers convenient access for quick travel around Annapolis, the interior remains peaceful and comfortable, creating a quiet environment to unwind.

Heritage Harbour continues to be one of Annapolis’s most sought-after 55+ communities, offering unmatched amenities, a strong sense of community, and a lifestyle centered around connection and ease. Opportunities like this are rare, and this home stands ready to welcome its next owner.

Schedule your visit and experience the comfort and community that make Heritage Harbour so special.

ANNAPOLIS

950 BERMUDA LANE

4 Beds

2 Baths

1,812 Sq.Ft.

$629,000

MLS#: MDAA2131736

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!

ANNAPOLIS

2108 CHESAPEAKE HARBOUR DRIVE E 201

3 Beds

3 Baths

1,700 Sq.Ft.

$625,000

MLS#: MDAA2120052

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!

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$625,000

MLS#: MDAA2123662

OPEN SAT 12-2PM. Welcome to this beautifully maintained 3 level end unit garage townhome in the sought after community of Admirals View. This sunny and spacious 3 BR, 4 BA residence offers the perfect combination of comfort, style and convenience. Step inside to find gleaming hardwood floors on lower and main levels, complemented by neutral carpeting on the upper level. The bright, open kitchen features granite countertops, stainless steel appliances, abundant cabinetry, laundry, and a French door leading to the deck, ideal for morning coffee.

Thoughtful details are found throughout including elegant millwork, decorative windows and custom window treatments. The lower level provides additional living space and gas fireplace, perfect for a family room, home office or guest area. Situated in a quiet, secluded townhome community yet conveniently located off Admiral Cochran Drive, this home offers easy access to commuter routes, shopping, dining and all that Annapolis has to offer. A rate opportunity to own a stylish, well appointed home in a prime location. Don't miss out.

ANNAPOLIS

328 BULWARK ALLEY

3 Beds

2 Baths

2,000 Sq.Ft.

$619,900

MLS#: MDAA2131964

Existing / Assumable-VA Loan at a favorable 2.5% interest rate!
Welcome to Annapolis Townes at Neal Farm — where luxury living meets everyday convenience. This stunning 4-level 2019-built end-unit townhome, owned and impeccably maintained by the original owner, offers one of the most desirable locations in the community, backing to the serene, park-like green space for added privacy and views. Featuring 3 spacious bedrooms, 3 full baths, and 2 half baths, this home blends thoughtful upgrades with effortless style across every floor.
The entry level includes a flexible room ideal for a home office, fitness space, or den, along with a convenient half bath and access to the oversized two-car garage—complete with ceiling-mounted storage racks, keeping seasonal or bulky items neatly tucked away and out of sight.
Upstairs, the main living level is an entertainer’s dream, centered around a spectacular oversized granite island that anchors the gourmet kitchen. Custom cabinetry, gas cooking, and generous prep and storage space make it perfect for casual gatherings or culinary ambitions. The adjoining dining and living areas flow seamlessly, with a gas fireplace framed by custom built-in cabinetry and shelving on both sides for a high-end designer finish. Step outside to the spacious second-level deck, ideal for morning coffee or evening cocktails.
The bedroom level features two suites, including a luxurious primary suite with a custom-designed walk-in closet system for superior organization. Laundry is conveniently located on this level.
The top floor offers the perfect guest retreat or private escape, complete with an additional bedroom, full bath, and a large rooftop deck with ample room for lounge seating and sunset views over the community.
Additional highlights include dual-zone HVAC, multiple outdoor living spaces, and plentiful natural light from the end-unit configuration.
Just steps from Annapolis Towne Centre, shopping, dining, Whole Foods, fitness studios, and commuter routes to D.C., Baltimore, and BWI, this home delivers not just a residence—but a lifestyle.
End-unit. Park views. Designer upgrades. Prime Annapolis location. Don’t wait—this one checks every box.

ANNAPOLIS

606 JAMES WALKER PLACE

3 Beds

3 Baths

2,272 Sq.Ft.

$605,000

MLS#: MDAA2129076

*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.

ANNAPOLIS

14 DORSEY AVENUE A

4 Beds

2 Baths

2,037 Sq.Ft.

$600,000

MLS#: MDAA2116188

Welcome to 224 Darlow Drive! This is a wonderful home in the 55+ Adult Living Community of Highland Woods. It consists of 2 bedrooms, 2 full baths on one level and has an open concept floor plan. It has 9' ceilings, and an adjacent family room to the kitchen that has wood flooring, a ceiling fan and a corner natural gas fireplace for the cooler evenings. Also included are lots of windows bringing in plenty of light into the home, distinctive woodwork and crown moldings. The 2-car front entrance garage with off-street driveway parking enters into the laundry room where the washer/dryer/laundry tub are located. The hall bath has ceramic floors with a tub/shower unit as well as an entrance into bedroom #2. The spacious Primary bedroom features wood flooring, a walk-in closet, a large window wall and a private bathroom. The Primary bath has ceramic flooring, double vanity sinks, a whirlpool tub, separate 4' shower with grab bar and a private toilet room also fitted with a grab bar.
The unfinished lower level provides expansion spaces, a full bath rough-in and walk out.
Enjoy your relaxed lifestyle in Annapolis with the HOA-provided lawn maintenance and easy access to Rt. 50.

ANNAPOLIS

724 DARLOW DRIVE

2 Beds

2 Baths

1,900 Sq.Ft.

$600,000

MLS#: MDAA2131664

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.

ANNAPOLIS

34 LAFAYETTE AVENUE

3 Beds

1 Baths

2,280 Sq.Ft.

$599,900

MLS#: MDAA2128268

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

ANNAPOLIS

212 DUKE OF GLOUCESTER STREET

None Beds

None Baths

2,304 Sq.Ft.

$599,900

MLS#: MDAA2130584

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

ANNAPOLIS

212 DUKE OF GLOUCESTER STREET

None Beds

None Baths

2,300 Sq.Ft.

$599,900

MLS#: MDAA2130582

✨ Waterfront living at its finest ✨
Welcome to your marina-front pearl in the coveted Chesapeake Harbour community with a 24-hour guarded gate. This 1-bedroom, 1.5-bath terrace-level condo blends coastal charm with resort-style amenities — All centered around one of the most breathtaking views in Annapolis. The Unit has been completely rehabbed from its original owners. Complete unit flooring, paint, electrical fixtures, and some lighting were updated. Complete renovations of the Kitchen, baths, and separate Laundry Room. All new stainless steel appliances and warranties are in place. The buyer may choose kitchen cabinet hardware
From your updated kitchen or your private patio, enjoy sweeping views of the marina extending all the way to the Bay Bridge. Watch stunning sunrises and sunsets, admire the Bay Bridge illuminated at night, and take in the constant rhythm of the Chesapeake waves.

🏝 Community Highlights
Dining: On-site Beacon Waterfront Galley & Bar
Relaxation & Recreation: 2 pools with bay views, private sandy beach, scenic walking & biking trails
Activities: Fishing piers, kayak launch, tennis, pickleball, playgrounds, and picnic areas
Convenience: EV charging stations, gated security, and ample parking
For Boaters: Chesapeake Harbour Marina with 81 wet slips, water, electricity, WiFi, and a full-service yacht facility

📍 Ideally located just minutes from Historic Downtown Annapolis, with easy access to Baltimore and Washington, D.C., Chesapeake Harbour is a hidden waterfront gem.

This home offers the perfect blend of luxury coastal living and everyday convenience. Don’t miss your chance to own one of the premier marina-view properties in Chesapeake Harbour.

ANNAPOLIS

7036 HARBOUR VILLAGE COURT T1

1 Beds

1 Baths

1,000 Sq.Ft.

$594,000

MLS#: MDAA2131520

Lovely and spacious 3-bedroom townhome in the sought-after Admirals View community! This beautifully maintained home features 2 full baths and 2 half baths, a gourmet kitchen with granite countertops, stainless steel appliances, double ovens, and an extra-large pantry. Enjoy effortless indoor/outdoor living with a deck off the kitchen, perfect for grilling and entertaining.

The open main level offers gorgeous hardwood floors, a gas fireplace, and a large family room filled with natural light. The upper level includes a generous primary suite with a soaking tub, huge walk-in closets, built-ins, and a California Closet system for exceptional organization. Additional highlights include a new washer and dryer, an attached garage, and abundant storage throughout.

Ideally located minutes to downtown Annapolis and close to major highways including Rt. 97 and Rt. 50, offering an easy commute to D.C., Baltimore, and surrounding areas. Truly a fantastic opportunity to own in one of the area’s most desirable locations!

ANNAPOLIS

321 BULWARK ALLEY

3 Beds

2 Baths

2,000 Sq.Ft.

$590,000

MLS#: MDAA2132398

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