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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
264
# of Listings
3
Avg # of Bedrooms
$482
Avg. $ / Sq.Ft.
$1,293,351
Med. List Price

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107 Properties Found. Page 5 of 8.

COMMUNITY WIDE OPEN HOUSE THIS SUNDAY! Look no further! Big price reduction on this Chesapeake Harbour condo, in one of Annapolis' most sought after waterfront communities. This beautifully renovated 2 BR | 2 BA | 1200 SF condo on the second level is truly turn key offering over $100K in high end improvements crafted with top of the line materials throughout. Enjoy stunning tranquil marina views from your deck and living space, creating a peaceful coastal retreat. The sumptuous Primary Suite features access to deck, a spa inspired Bath with an impressive walk in shower and custom closet with built-ins. Recent updates include new carpet throughout and a new oversized water heater, ensuring comfort and peace of mind. Residents of Chesapeake Harbour enjoy an exceptional lifestyle with front entrance security , waterfront dining at the Beacon Waterfront Bar, marina access, waterfront pools, tennis, private beach and walking trails and just minutes to Downtown Annapolis.
#MDAA2136184

ANNAPOLIS

7022 CHANNEL VILLAGE COURT 101

2 Beds

2 Baths

1,200 Sq.Ft.

$650,000

MLS#: MDAA2136184

This 2 bedroom, 2 bath condo is move-in ready! Freshly painted, and brand new carpet in bedrooms. Park Place boasts numerous amenities that make it one of the best places to live in Annapolis. With an ideal location, you can walk everywhere in town to restaurants and shopping. When you enter the lobby, you will be greeted by the 24/7 staff at the front desk. The party room is perfect for larger gatherings and meetings with friends and neighbors. The Social Committee organizes plenty of events to join in and have fun with your neighbors if you feel like it. s. Grab a book from the library and relax on the back patio. The pool is fabulous, and there is a lifeguard on duty during the season. The dog park is perfect for your pet. Grills for your convenience are also located on the back patio! Walk to the Naval Academy Stadium minutes away and enjoy the lively Football season. Come and see why Park Place is the perfect place to call home!
#MDAA2122622

ANNAPOLIS

5 PARK PLACE 626

2 Beds

2 Baths

1,314 Sq.Ft.

$649,999

MLS#: MDAA2122622

REMARKS AND PICTURE COMING SOON.
#MDAA2137776

ANNAPOLIS

1337 SWAN DRIVE

3 Beds

2 Baths

1,826 Sq.Ft.

$649,000

MLS#: MDAA2137776

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

New on site 3 days ago
**OPEN HOUSE 5/2&5/3 11-1** Welcome to Colony Hills, one of Eastport’s most coveted neighborhoods, where charm, convenience, and community come together, and there’s NO HOA. This property offers the perfect blend of comfort and lifestyle, ideally located just minutes from everything you love about Annapolis. Step inside the upper level and you’re immediately greeted by a light filled living space, highlighted by a beautiful bay window that floods the room with natural light. The tastefully updated kitchen is a standout, featuring white cabinetry with underlighting, quartzite countertops, stainless steel appliances, and gas cooking. There’s ample space for a large dining table, perfect for everything from casual weeknight dinners to hosting friends and family. On this level, you’ll find two spacious bedrooms with generous closet space and a full bathroom. The lower level offers even more room to spread out, with a large second living area anchored by a cozy Timberwolf wood burning stove, ideal for relaxing nights in. A third bedroom and second full bathroom provide flexibility for guests, a home office, or additional living space. You’ll also appreciate the sizable storage and laundry area. Outside is where this home truly shines. The back deck overlooks peaceful woods and a small creek that feeds into Hawkins Cove, creating a serene, nature filled backdrop. The fully fenced backyard is perfect for entertaining, complete with a patio and a 10x16 shed with electric, ideal for woodworking, hobbies, or extra storage. Thoughtfully landscaped with Maryland native plants and pollinators, this yard is a true retreat. Enjoy the ease of parking in your private driveway, all within a sidewalk lined, tree filled neighborhood. *2025 Dual Fuel Electric/Gas HVAC installed* 2026 New Carpet and Freshened Paint* 2021 New Windows Installed* Newer Washer and Dryer*Living here means you’re just a short walk to Eastport favorites like Vin 909, Adam’s, and Sammy’s, or a quick bike ride to Downtown Annapolis, Quiet Waters Park, and Pip Moyer Recreation Center. Commuting is a breeze with easy access to major routes, USNA, NSA Annapolis, Ft. Meade, Baltimore, Washington DC, and BWI. This is the one you’ve been waiting for. Schedule your showing before it’s gone.
#MDAA2139192

ANNAPOLIS

1231 VAN BUREN DRIVE

3 Beds

2 Baths

1,694 Sq.Ft.

$635,000

MLS#: MDAA2139192

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.
#MDAA2126696

ANNAPOLIS

100 CARROLL DRIVE

4 Beds

2 Baths

1,935 Sq.Ft.

$634,900

MLS#: MDAA2126696

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 3320 Arundel on the Bay Road—where relaxed coastal living meets thoughtful design in the water-privileged community of Oyster Harbor. This beautifully maintained and upgraded 3-bedroom, 3.5-bath coastal-style home offers the perfect blend of indoor comfort and outdoor enjoyment. Inside, you’ll find an upgraded and inviting open plan design complemented by a cozy wood-burning fireplace, and three ensuite bedrooms, each with a private bath. The finished lower level offers full daylight and a walk-out slider to a private paver patio. A versatile studio apartment with quarts counter tops and bright white cabinetry, is ideal for guests, rental income, or a private workspace—with its own separate entry. Step outside and experience the home’s exceptional exterior features. The premium IPE wood dining deck and front stairs provide a durable and stylish space for entertaining or relaxing, enhanced by a clear-view vinyl-clad railing system. The property includes five parking spaces, multiple brick paver walkways, a private entry to the studio, a brick patio with garden beds, and two rear storage sheds, including a walk-in shed with a window. Every detail is designed for both function and coastal curb appeal. Living in Oyster Harbor means enjoying unmatched access to the Chesapeake lifestyle. This sought-after waterfront community borders Oyster Creek, Fishing Creek, and the Chesapeake Bay, offering multiple shoreline access points for boating, paddling, and soaking in the views. Residents enjoy a private sandy beach with designated swimming areas, sea nettle nets, picnic spots, BBQ areas, and a gazebo perfect for gatherings. For boating enthusiasts, the community features three marinas with 30–40 slips, boat ramps, multiple piers, and docking locations. There’s even a dedicated fishing pier, dinghy racks, and floating dock spaces for small craft like kayaks, paddleboards, and Sunfish sailboats. Whether you’re crabbing, fishing, or simply enjoying the water, this community checks every box. This is more than just a home—it’s a gateway to a vibrant coastal lifestyle in one of Annapolis’ most vibrant water-access neighborhoods. Come home to your get-away lifestyle!
#MDAA2141892

ANNAPOLIS

3320 ARUNDEL ON THE BAY ROAD

3 Beds

3 Baths

1,812 Sq.Ft.

$625,000

MLS#: MDAA2141892

New on site 3 days ago
Escape to coastal serenity at 7056 Bembe Beach Road, a beautifully maintained rancher offering the perfect blend of quiet, private living and premier access to the Annapolis waterfront. This immaculate, turn-key home is situated just a block from the water, providing a seamless transition from your front door to the shores of the Chesapeake. This residence is thoughtfully designed for comfort and longevity, featuring true Single-Level Living: The main floor hosts three spacious bedrooms, including a primary suite, two full baths, and a convenient laundry room. A versatile lower level offers a third full bath and ample space for a potential fourth bedroom, home office, or recreation area. Equipped with a Geothermal heating system and a brand-new roof featuring a 50-year transferable warranty for ultimate peace of mind. A stunning, large screened-in back porch comes complete with removable vinyl panels and a wood stove, transforming it into a cozy four-season retreat. The property is set on a sprawling landscaped yard that emphasizes privacy and peace. The large, lush yard offers plenty of room for gardening, entertaining, or simply enjoying the quiet neighborhood atmosphere. A high-quality, custom-built shed provides extra storage or a workshop space. Located in one of Annapolis's most sought-after pockets, you are surrounded by natural beauty and local favorites but you still enjoy the modern convenience of being on public water and sewer. Just a short walk to the new public Annapolis Carrs Beach and a single block from the water. Moments away from the Annapolis Maritime Museum & Park, a 12-acre waterfront "Park Campus" featuring hiking trails and public paddle-craft launches. Experience world-class boating facilities at Safe Harbor Port Annapolis and enjoy artisanal treats at the Black Market Bakers (formerly Black Market Cafe). A quick drive or bike ride connects you to local favorites like Annapolis Smokehouse & Tavern and the scenic Quiet Waters Park.
#MDAA2143380

ANNAPOLIS

7056 BEMBE BEACH ROAD

3 Beds

3 Baths

1,851 Sq.Ft.

$619,900

MLS#: MDAA2143380

Recently Refreshed and Brand-New Roof to be installed by seller prior to closing!!! Ready for showings this week!! Welcome to 40 Windwhisper Lane, Updated 4 bedroom and 2.5 bath home, including a bedroom and half bath conveniently located on the main level. Enjoy an updated kitchen and numerous renovations throughout, complemented by fresh new paint, lighting, and moldings. Other updates include the upper-level primary bathroom, New HVAC & Hot Water Heater. Outside, you’ll love the fully fenced backyard, back deck, and stone patio—perfect for entertaining, pets, or peaceful outdoor enjoyment. An unfinished lower level provides ample storage and future potential. Located just a short distance to private marinas / water access and downtown Annapolis! Enjoy easy access to waterfront dining, shops, local parks, the U.S. Naval Academy, and all the charm the historic district has to offer.
#MDAA2134390

ANNAPOLIS

40 WINDWHISPER LANE

4 Beds

2 Baths

1,855 Sq.Ft.

$615,000

MLS#: MDAA2134390

Motivated Sellers!! Price Just Improved!! Rare Opportunity in an Amazing Annapolis Neighborhood! Welcome to 79 Windwhisper. A beautiful 4 bedroom, 2500 sq foot, 3.5 bath home with an office, located in one of Annapolis’ most desirable neighborhoods. This well-maintained property offers numerous recent updates, including new carpet, hardwood flooring on main level, updated bathrooms, flooring, fresh paint interior and exterior, a new refrigerator, and a new dishwasher, making it move-in ready. The home features a fully finished basement, providing plenty of additional living or entertainment space, along with the convenience of a garage. Enjoy the Chesapeake lifestyle with a private neighborhood marina just a short walk away, perfect for kayaking and paddleboarding. Outdoor lovers will also appreciate being less than 2 miles from Quiet Waters Park, offering trails, waterfront views, and year-round recreation. Ideally located near the U.S. Naval Academy and just 3 miles from Historic Downtown Annapolis, you’ll have easy access to waterfront dining, shopping, and local events. Professional landscaping is already scheduled and fully paid for, with improvements to be completed in April, adding even more curb appeal to this wonderful property. Don’t miss this rare opportunity to own in an exceptional Annapolis location!
#MDAA2138392

ANNAPOLIS

79 WINDWHISPER LANE

4 Beds

3 Baths

2,560 Sq.Ft.

$612,999

MLS#: MDAA2138392

Fully updated 4-bedroom, 2-bath home in the heart of Eastport offering modern finishes, flexible living space, and a walkable location just minutes from downtown Annapolis, marinas, restaurants, and waterfront parks. The main level features a bright living room, dining area, and upgraded kitchen with stainless steel appliances. Three bedrooms and one full bath complete this level, along with access to the back deck and patio overlooking a spacious fenced backyard with mature trees. The finished lower level includes a separate entrance, additional bedroom and full bath, and a kitchenette/wet bar with walkout access to the backyard—providing versatile space for guests, extended living, home office, or recreation. Dual washer and dryer units upstairs and downstairs add exceptional convenience. Thoughtfully updated and move-in ready, this Eastport home combines comfort, flexibility, and location in one of Annapolis’ most desirable neighborhoods. Key Features: • 4 Bedrooms | 2 Full Bathrooms • Finished lower level with separate entrance • Kitchenette / wet bar in lower level • Dual washer & dryer units (upstairs and downstairs) • Updated kitchen with stainless steel appliances • Back deck and patio • Fenced backyard with mature trees • Walkable Eastport location • Minutes to downtown Annapolis & marinas • Move-in ready-schedule your private showing today!
#MDAA2138058

ANNAPOLIS

1223 MADISON STREET

4 Beds

2 Baths

1,488 Sq.Ft.

$609,000

MLS#: MDAA2138058

Welcome to 709 Skippers Lane, a rare and versatile Live/Work townhome in the sought‑after Village Greens community—one of the only homes in the development offering this unique zoning flexibility. With 3,016 sq. ft. of beautifully finished space, this contemporary residence blends upscale living with the opportunity to operate a boutique business, studio, or professional office right from home. Step inside to discover a thoughtfully upgraded interior featuring designer touches, abundant natural light, and an open-concept layout ideal for modern living. The gourmet kitchen, spacious dining area, and inviting living room create a warm and functional environment perfect for everyday comfort or entertaining. The home offers three spacious bedrooms, two full baths, and two half baths, including a serene primary suite with generous closet space and a well-appointed en‑suite bath. Every level has been meticulously maintained, reflecting pride of ownership throughout. A new AC unit was installed in Oct 2025. The garage is painted and that floor has high temp epoxy. The street-level commercial space—previously home to a boutique yarn and knitting shop—opens the door to endless possibilities. Whether you envision a specialty retail shop, creative studio, office, or an expanded living area, this flexible zone empowers you to live, work, and play without compromise. Perfectly positioned just minutes from historic downtown Annapolis, major commuter routes, shopping, dining, and the waterfront, this home offers the ideal blend of convenience and charm. Sellers to offer a one year home warranty for the buyer at time of settlement
#MDAA2132646

ANNAPOLIS

709 SKIPPERS LANE

3 Beds

2 Baths

3,016 Sq.Ft.

$600,000

MLS#: MDAA2132646

*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

2,037 Sq.Ft.

$600,000

MLS#: MDAA2116188

Welcome to Heritage Harbour, Annapolis’ premier 55+ community offering resort-style living and an unmatched lifestyle. Now priced better, this spacious end-unit villa boasts over 2,500 square feet of living space and is filled with natural light thanks to its desirable end-unit location. Freshly painted throughout with brand new flooring and carpet, this home is truly move-in ready and features soaring ceilings that enhance the open, airy feel. The main level is designed for easy, one-level living and includes a generous primary bedroom with en-suite bath, along with a convenient half bath for guests. The bright and spacious kitchen offers plenty of room for a table or center island, making it a perfect gathering space. The family room features a cozy fireplace and opens directly to a private, fenced-in patio—ideal for relaxing or entertaining outdoors. A welcoming front porch provides yet another great space to unwind and enjoy the neighborhood. Upstairs, you’ll find a large second bedroom with ample closet space, a full bath, and a versatile loft area that works perfectly as a home office, guest retreat, or second family room. Additional highlights include a one-car garage with extra storage and low-maintenance living at its finest. Enjoy all the incredible amenities Heritage Harbour has to offer, including a clubhouse, indoor and outdoor pools, fitness center, golf course, tennis and pickleball courts, walking trails, community events, and more—all just minutes from downtown Annapolis. This is the one you’ve been waiting for—don’t miss it!
#MDAA2139088

ANNAPOLIS

906 PERRY LANDING COURT

2 Beds

2 Baths

2,569 Sq.Ft.

$599,900

MLS#: MDAA2139088

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