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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
$505
Avg. $ / Sq.Ft.
$1,381,189
Med. List Price

Browse Annapolis Real Estate Listings

277 Properties Found. Page 12 of 19.

Enjoy resort-style waterfront living with harbor and Chesapeake Bay views in the gated community of Chesapeake Harbour. This beautifully updated two-level residence offers the ideal blend of comfort, natural light, and low-maintenance coastal living. Freshly painted throughout with new carpet, the home features a thoughtfully designed floor plan with over 1,900 square feet of living space, an attached 2 car garage with additional storage, and interior access for everyday convenience.

The entry level features an eat-in kitchen with white cabinets and counters, powder room and laundry  room with a few steps up to the living room. The thoughtfully designed split-level layout creates a natural separation between the home’s functional spaces and its main entertaining areas, allowing gatherings to flow effortlessly while keeping day-to-day tasks discreetly tucked away. The dramatic living area where soaring ceilings, gas fireplace with custom built-ins, and walls of windows fill the space with natural light while framing the harbor views. Step outside to the expansive full-width waterside deck, the perfect setting for morning coffee, evening cocktails, or simply enjoying the marina activity and views stretching toward the Chesapeake Bay.

Upstairs, the spacious primary suite offers a balcony, an ensuite bath with new cabinet and drawer fronts, and a peaceful retreat  for relaxing after a long day. A loft-style flex space overlooks the living room below and can easily function as a second bedroom, home office, or additional lounge area, complemented by a full hall bath.

Life in Chesapeake Harbour feels like a year-round vacation with an unmatched collection of resort-style amenities, including two waterfront pools, a private sandy beach, exclusive fitness center for a small enclave of residents, tennis and pickleball courts, fishing piers, walking and jogging paths, picnic areas with grills, scenic Chase Pond, and the security of a 24-hour attended gatehouse. The newly opened waterfront marina restaurant adds to the vibrant atmosphere with outdoor dining and live music on weekends.

Ideally located just minutes from Downtown Annapolis, Eastport, the United States Naval Academy, waterfront dining, shopping, and historic attractions, this exceptional residence also offers easy access to Washington, DC, Baltimore, and Baltimore/Washington International Thurgood Marshall Airport. Whether you are searching for a full-time residence or a lock-and-leave waterfront retreat, this home offers the very best of the Annapolis waterfront lifestyle. Welcome Home!
#MDAA2145178

ANNAPOLIS

2002 DAKOTA PLACE 2A

2 Beds

2 Baths

1,915 Sq.Ft.

$650,000

MLS#: MDAA2145178

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!
#MDAA2140810

ANNAPOLIS

2108 CHESAPEAKE HARBOUR DRIVE 201

3 Beds

3 Baths

1,700 Sq.Ft.

$650,000

MLS#: MDAA2140810

1009 Dulaney Lane in Annapolis, Maryland, offers a rare opportunity to build a custom waterfront home in the sought-after Annapolis Roads community. The 0.47-acre wooded lot is situated at the end of a quiet cul-de-sac, providing privacy and scenic views of Lake Ogleton. With 137 feet of waterfrontage, the elevated lot allows for the potential to maximize water views throughout the property.
Residents of Annapolis Roads enjoy community amenities such as a private beach, pavilion with fire pit, boat launch, pier, and walking trails. The location offers easy access to the Chesapeake Bay and is just minutes from downtown Annapolis, Eastport, and the U.S. Naval Academy. Commuters will appreciate the proximity to Route 50 and I-97, providing direct routes to Baltimore, BWI Airport, Fort Meade/NSA, and Washington, D.C. .
The lot is connected to public sewer, simplifying the building process. Potential buyers can bring their architect to design a peaceful waterfront retreat that takes full advantage of the natural surroundings and community features .
#MDAA2144350

ANNAPOLIS

1009 DULANEY LANE

None Beds

None Baths

0.47 acres

$650,000

MLS#: MDAA2144350

New on site 3 days ago
Welcome to 617 Wayward Drive in the highly sought-after Rolling Knolls community of Annapolis. Situated on a spacious corner lot, this well-maintained home offers exceptional outdoor space with a large driveway, fully fenced backyard, and two storage sheds providing ample room for hobbies, tools, and equipment.

Inside, you’ll find 3 generously sized bedrooms and 2 full bathrooms, including a beautifully renovated primary bath and updates to the hall bath. The bedrooms feature large closets, providing comfortable everyday living and abundant storage.

The heart of the home is the brand-new kitchen, thoughtfully designed with extensive cabinetry, abundant countertop space, and a bright eat-in area perfect for casual dining and entertaining.

The lower level offers incredible flexibility and untapped potential. A built-in bar with sink creates the perfect gathering space, while two separate finished rooms can easily accommodate a home gym, office, media room, playroom, guest space, or hobby area. One room features walk-out access to the driveway, bringing in natural light and enhancing functionality. A large utility room and oversized laundry area provide even more storage and workspace.

With its generous lot, extensive updates, versatile floor plan, and desirable Annapolis location, this home offers the perfect combination of comfort, convenience, and opportunity. Enjoy the convenience of nearby Rolling Knolls Elementary School, as well as easy access to shopping, dining, parks, and major commuter routes. Welcome Home!
#MDAA2149288

ANNAPOLIS

617 WAYWARD DRIVE

3 Beds

2 Baths

1,920 Sq.Ft.

$645,000

MLS#: MDAA2149288

Welcome to 7006 Channel Village Ct #101, a beautifully maintained 2-bedroom, 2-bath condo located in the highly desirable Chesapeake Harbour community. This light-filled unit offers an open floor plan, a spacious living area with a fireplace, and a private outdoor space perfect for relaxing or entertaining. Enjoy resort-style living with amenities including multiple pools, tennis courts, private beach access, marina with boat slips, on-site restaurant, and 24-hour gated security. Conveniently located just minutes from historic downtown Annapolis, Naval Academy. shopping, dining, and major commuter routes to Washington, DC, and Baltimore. Ideal for full-time living, weekend retreat, or investment opportunity.

Pools - Outdoor
Tennis Courts
Marina/Boat Slips
Private Beach
Gated Community
24/7 Security
Jog/Walk Path (if available)
Club House / Gym 
Fishing Pier 
Common Grounds
Restaurant
Grills
#MDAA2141588

ANNAPOLIS

7006 CHANNEL VILLAGE COURT 101

2 Beds

2 Baths

1,092 Sq.Ft.

$640,000

MLS#: MDAA2141588

Welcome to easy, one-level living in Heritage Harbour, Annapolis's premier 55+ active adult community. This well-maintained, detached single-family home offers 3 bedrooms, 2 full baths, and a desirable floor plan designed for comfort and convenience.

A spacious family room addition provides extra living space for relaxing, entertaining, or gathering with family and friends. The cozy natural gas fireplace creates a warm and inviting focal point, while natural gas heat offers efficient year-round comfort. The attached two-car garage provides ample storage and everyday convenience. The huge kitchen has an island, table space, window seat, hidden laundry area and access from the garage for the utmost convenience. In addition to a very large living/dining room there are two bonus areas that offer a multitude of uses. 

The Golfers Ridge section of the community is highly desirable. Stately situated on a lovely corner lot, this home offers the perfect balance of outdoor enjoyment and low-maintenance living. Major systems have already been updated, giving the next owner peace of mind and a solid foundation to make the home their own. Bring your decorating ideas and personal touches to update the interior and create the home you've always envisioned.

Enjoy the exceptional Heritage Harbour lifestyle with access to a clubhouse, indoor and outdoor pools, fitness center, golf course, tennis and pickleball courts, walking trails, and a vibrant calendar of social activities. Conveniently located near shopping, dining, healthcare, and historic Annapolis, this is an outstanding opportunity to customize a home in one of the area's most desirable active adult communities.

Don't miss your chance to unlock the potential of this charming home and enjoy all that Heritage Harbour has to offer.
#MDAA2146498

ANNAPOLIS

852 WOODMONT ROAD

3 Beds

2 Baths

1,910 Sq.Ft.

$639,900

MLS#: MDAA2146498

Welcome to 100 Carroll Drive, a fully remodeled four-bedroom, two-bath split foyer in the desirable and sought-after waterfront community of Hillsmere Shores in Annapolis. The upper level features a completely renovated open-concept layout with a stunning kitchen showcasing new cabinetry, new appliances, countertops, and luxury vinyl flooring throughout, flowing seamlessly into the dining and living areas—perfect for everyday living and entertaining. Just off the living room, enjoy an enclosed deck that adds extra flexible space and a great place to relax or entertain. This level also includes three spacious bedrooms and an updated full bathroom. Downstairs, the home continues to impress with tiled flooring throughout, heated floors, and a large primary suite with a private full bathroom, plus walkout access to an enclosed patio featuring a heated exercise pool or hot tub. Outside, the property offers a large cleared lot with beautiful landscaping, an irrigation system, and a shed for additional storage. Hillsmere Shores is known for its exceptional community amenities including a marina, multiple boat ramps and kayak launches, a beach, playground, and access to Quiet Waters Park, with the Key School conveniently located right across the street. An electric vehicle charger is also included, adding even more value and convenience—this move-in ready home is a rare opportunity to enjoy a renovated property and an unmatched Annapolis lifestyle.
#MDAA2146848

ANNAPOLIS

100 CARROLL DRIVE

4 Beds

2 Baths

1,935 Sq.Ft.

$635,000

MLS#: MDAA2146848

Priced to attract serious buyers and offering exceptional value in Hillsmere Shores, this is an opportunity you won’t want to miss. The motivated sellers have thoughtfully transformed this 4-bedroom, 2-bath home into a move-in-ready retreat where timeless design meets modern convenience.

Completely renovated from top to bottom, the heart of the home is a stunning brand-new kitchen featuring stylish cabinetry, contemporary finishes, and all-new appliances. Both bathrooms have been fully redesigned with clean, classic aesthetics, while extensive additional updates provide confidence and peace of mind for years to come.

Every renovation was completed with intention, using quality materials and enduring design choices rather than quick cosmetic fixes. The result is a home that feels cohesive, fresh, and truly turnkey—allowing its next owners to move in and immediately enjoy everything it has to offer.

Beyond the front door, discover the unmatched lifestyle of sought-after Hillsmere Shores. Just minutes from downtown Annapolis, this water-privileged community offers a voluntary HOA through the Hillsmere Shores Improvement Association, providing optional access to outstanding amenities including a private marina with boat slips, multiple boat ramps and kayak launches, a sandy community beach with pavilions and waterfront gathering spaces, and more.

Residents also enjoy convenient access to Quiet Waters Park, shopping, dining, and everyday essentials, creating the perfect balance of natural beauty and modern convenience.

With extensive updates already completed, exceptional community amenities, and sellers ready to make a deal, this beautifully renovated home represents one of the best opportunities to enjoy the Hillsmere Shores lifestyle from day one.
#MDAA2143408

ANNAPOLIS

420 EDGEMERE DRIVE

4 Beds

2 Baths

1,725 Sq.Ft.

$635,000

MLS#: MDAA2143408

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#MDAA2137264

ANNAPOLIS

76 OLD MILL BOTTOM ROAD N 310

2 Beds

2 Baths

1,558 Sq.Ft.

$632,400

MLS#: MDAA2137264

Welcome to 130 Summer Village Drive, a beautifully maintained three-bedroom, two-and-one-half bath townhome located in the highly sought-after Riva Trace community of Annapolis. Nestled within the desirable Summer Village section, this residence offers a rare blend of comfort, charm, and low-maintenance living surrounded by mature landscaping and exceptional community amenities.

The main level features an inviting and functional layout enhanced by hardwood flooring, abundant natural light, and thoughtfully designed living spaces. A spacious living and dining area flows seamlessly into a cozy sitting space anchored by a striking two-sided fireplace, creating warmth and character throughout the home. The kitchen features granite countertops, stainless steel appliances, ample cabinetry, and an ideal setup for everyday living and entertaining. Just beyond the main living area, the rear deck provides a peaceful outdoor retreat perfect for morning coffee or unwinding among the natural surroundings.

Upstairs, the spacious primary suite serves as a private retreat complete with its own balcony, walk-in closet, and an ensuite bath. Two additional bedrooms and a full hall bath provide comfortable accommodations for family, guests, or flexible workspace needs.

The finished lower level adds valuable additional living space and features a custom bar area ideal for entertaining, movie nights, or game-day gatherings. A one-car garage and additional storage space add convenience and functionality.

Residents of Riva Trace enjoy coveted water privileges and access to a community dock, along with tennis courts, walking trails, and beautifully maintained common grounds. Ideally located just minutes from Downtown Annapolis, shopping, dining, and major commuter routes, this home offers the perfect balance of tranquility, convenience, and the Chesapeake Bay lifestyle within one of the area’s most desirable communities.
#MDAA2144804

ANNAPOLIS

130 SUMMER VILLAGE DRIVE

3 Beds

2 Baths

2,488 Sq.Ft.

$625,000

MLS#: MDAA2144804

Waterfront living at its finest. Welcome to this marina-front gem in the highly sought-after, 24-hour gated Chesapeake Harbour community. This beautifully renovated 1-bedroom, 1.5-bath terrace-level condo offers effortless coastal living paired with resort-style amenities and some of the most breathtaking views in Annapolis. Completely rehabbed from top to bottom, this home features all-new flooring, fresh paint, updated lighting, and full renovations of the kitchen, bathrooms, and separate laundry room. The kitchen shines with brand-new stainless-steel appliances (with warranties in place) and allows the buyer to select a few personal finishing touches.   Please be sure to register at the main gate- combo will be supplied after the showing is scheduled. Home Warranty is negotiable. From the updated kitchen or your private patio, enjoy sweeping marina views stretching all the way to the Bay Bridge. Take in unforgettable sunrises and sunsets, watch boats glide by, Blue Angels when in town, and admire the Bay Bridge glowing at night—all set to the soothing rhythm of the Chesapeake Bay. Chesapeake Harbour Amenities Include: On-site dining at Beacon Waterfront Galley & Bar, two bay-view swimming pools and a private sandy beach, Scenic walking and biking trails, Fishing piers, kayak launch, tennis and pickleball courts, playgrounds, and picnic areas, EV charging stations, ample parking, and 24-hour gated security. Chesapeake Harbour Marina features 81 wet slips with water, electric, 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 true waterfront hidden gem. This exceptional home offers the perfect blend of luxury, lifestyle, and convenience. Don’t miss the opportunity to own one of the premier marina-view residences. Seller will hold a private note.
#MDAA2146146

ANNAPOLIS

7036 HARBOUR VILLAGE COURT T1

1 Beds

1 Baths

1,000 Sq.Ft.

$625,000

MLS#: MDAA2146146

848 Deerwood Court offers a wonderful opportunity to enjoy life in Heritage Harbour, one of Annapolis' most sought-after active adult communities. Situated on a desirable corner lot at the end of a quiet cul-de-sac, this well-designed ranch-style home features three bedrooms, two full bathrooms, a spacious side addition, and a two-car garage.

The home has been lovingly maintained over the years and offers a comfortable floor plan with generous living spaces, abundant natural light, and excellent flow for both everyday living and entertaining. The side addition provides valuable extra living space rarely found in many homes of this size, while the corner lot setting offers attractive curb appeal and additional privacy.

This property presents an excellent opportunity for buyers to personalize a home to their own tastes and style while enjoying all that Heritage Harbour has to offer. Whether you're looking to make updates immediately or over time, the solid layout and desirable location provide a strong foundation for future improvements.

Residents of Heritage Harbour enjoy an exceptional lifestyle with access to a community lodge, indoor and outdoor pools, fitness facilities, walking trails, waterfront amenities, clubs, activities, and countless opportunities to stay active and connected.

Conveniently located near shopping, dining, downtown Annapolis, medical facilities, and major commuter routes, this home combines comfort, convenience, and community in one of the area's most desirable neighborhoods.

Don't miss the opportunity to make this Heritage Harbour home your own and enjoy the active lifestyle that has made this community such a popular destination for buyers seeking the very best of Annapolis living.
#MDAA2146412

ANNAPOLIS

848 DEERWOOD COURT

3 Beds

2 Baths

1,900 Sq.Ft.

$605,000

MLS#: MDAA2146412

Welcome to brand-new luxury living at Element at Mill Creek, a new construction community of modern condominiums designed for style, comfort, and convenience. This spacious, light-filled home offers southern exposure and a private balcony with serene views of lush forest retention—perfect for relaxing or entertaining. Inside, enjoy a chef-inspired kitchen with quartz countertops, upgraded cabinetry, stainless steel appliances, and a large center island. The open-concept living and dining areas create a warm, inviting atmosphere ideal for gatherings or quiet evenings. The primary suite features a generous walk-in closet and a spa-style bath with high-end finishes. Additional features include a full-size washer and dryer, included window treatments, ample storage, and reserved parking. As part of the new Element at Mill Creek community, you’ll enjoy low condo fees, resort-style amenities, and the ease of low-maintenance living in a brand-new home. Inquire today about available floor plans and pricing—your perfect new home is waiting!
#MDAA2136300

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 112

2 Beds

2 Baths

1,621 Sq.Ft.

$602,602

MLS#: MDAA2136300

Tucked away on a gorgeous, private lot in the highly sought-after Cape St. Claire community, this beautifully maintained home combines exceptional outdoor living with the unmatched lifestyle that makes this waterfront neighborhood one of Annapolis' most desirable places to call home. From the moment you arrive, you'll appreciate the outstanding curb appeal featuring professional landscaping, an impressive retaining wall system, mature trees, and expansive outdoor living spaces designed for relaxing. Multiple decks provide the perfect setting to enjoy the peaceful surroundings and natural beauty of the property. Inside, the updated kitchen serves as the heart of the home, offering modern finishes and functionality while flowing seamlessly into the living spaces. Additional details and professional photos will be available soon. Living in Cape St. Claire means more than just owning a home. Residents enjoy access to community beaches, parks, playgrounds, walking trails, marinas, boat ramps, fishing and crabbing areas, and a variety of community events throughout the year. Located along the Magothy River and just minutes from Annapolis, the community offers a unique blend of waterfront living, outdoor recreation, and everyday convenience. Conveniently located near shopping, dining, Broadneck schools, Route 50, the Chesapeake Bay Bridge, and all that Annapolis has to offer, this is a rare opportunity to enjoy the Cape lifestyle on a beautiful private homesite. More details coming soon.
#MDAA2147922

ANNAPOLIS

1178 GLENWOOD DL

4 Beds

2 Baths

1,828 Sq.Ft.

$600,000

MLS#: MDAA2147922

Summer is here, and the time is right for moving into that new place to call your own! 
Tucked away on a quiet cul-de-sac just minutes from downtown Annapolis, this 2,000± square foot home offers the rare combination of privacy, meaningful upgrades, and everyday convenience. The shaded backyard is a summer favorite spot for your hammock or fire pit with s'mores. 

Since 2021, major improvements have already been handled for you, including a new roof, windows and sliders, vinyl siding with upgraded gutters, HVAC system, water heater, and fully updated kitchen and bathrooms... giving buyers confidence in both condition and long-term value.

The layout offers 4 bedrooms and 2.5 baths with a flow that allows you to live comfortably day-to-day while still having that work-from-home dedicated bonus space without sacrificing an entire bedroom.

Set on a manageable, low-maintenance lot with no HOA, this is an ideal fit for those who want space and freedom without added restrictions. Extend the driveway, add a garage, put in a swing set, or a tree-house. Heck, add both! This is a great place to make it exactly what you want it to be.

With its location just minutes from downtown Annapolis dining, boutique shopping, water access, and commuter routes, the home delivers both accessibility and a tucked-away feel.

This home is waiting for you! Turn key and ready to move in. Or consider it as an investment property and enjoy the fruits of the demand from the US Naval Academy, traveling nurses, or LTR.
#MDAA2141372

ANNAPOLIS

2 SILOPANNA COURT

4 Beds

2 Baths

2,000 Sq.Ft.

$599,900

MLS#: MDAA2141372

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