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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

207

# of Listings

3

Avg # of Bedrooms

$516

Avg. $ / Sq.Ft.

$1,086,221

Med. List Price

Browse Annapolis Real Estate Listings

$250,000 - $500,000

$500,000 - $1M

81 Properties Found. Page 5 of 6.

Welcome to 730 Rosedale St, Annapolis, MD 21401—a traditional detached home offering a comfortable and functional layout in a convenient location. This residence features three bedrooms, two full bathrooms, and one half bathroom, providing ample space for a variety of living arrangements.

Inside, the home features hardwood flooring on the first floor and carpet flooring throughout the remaining areas, along with built-in bookcases that add both character and practical storage. The layout is designed for everyday living and easy flow between spaces.

Situated on a dead-end street, the property offers a quieter setting with reduced through traffic. Outdoor features include a spacious back deck, ideal for relaxing or entertaining, as well as a backyard with a swing set for added enjoyment.

Located just minutes from the Navy-Marine Corps Memorial Stadium, this home provides convenient access to the local amenities, dining, and neighborhood charm that Annapolis is known for, while maintaining a peaceful residential setting.

ANNAPOLIS

730 ROSEDALE STREET

3 Beds

2 Baths

1,280 Sq.Ft.

$595,000

MLS#: MDAA2140178

New on site 4 days ago

Welcome to this beautiful 2 bedroom 2 bath coveted end unit condo in the sought-after gated Chesapeake Harbour community, This home is a rare find, offering the perfect blend of privacy, natural light, and outdoor space. Inside, the additional square footage an end unit offers creates an open floor plan bathed in sunlight, thanks to windows on three sides. The living spaces are airy and inviting, with seamless flow from the cozy living room to the dining area and updated kitchen. You'll love the thoughtful details, including hardwood floors, a fireplace for those cooler evenings, and scenic views that bring the outdoors in. This home is ideally located to enjoy watching the sunrise over Chase Pond and the Bay with your morning coffee or tea. Later in the day the oversized wrap-around deck invites you to relax, entertain, or simply soak in the tranquil surroundings and watch the sunset over the Marina. Chesapeake Harbour is a vibrant, amenity-rich community with access to 2 pools, 2 tennis and pickle ball courts, kayaking, walking trails and a marina, all just minutes from downtown Annapolis. Whether you're a boating enthusiast or simply crave the coastal lifestyle, this property checks all the boxes. Don’t miss your chance to own this one-of-a-kind retreat. Schedule your tour today and experience Chesapeake Harbour living at its finest!

ANNAPOLIS

2110 CHESAPEAKE HARBOUR DRIVE 101

2 Beds

2 Baths

1,237 Sq.Ft.

$595,000

MLS#: MDAA2138114

#MDAA2126274

ANNAPOLIS

2707 JUDSON PLACE

3 Beds

2 Baths

2,156 Sq.Ft.

$590,000

MLS#: MDAA2126274

#MDAA2137752

ANNAPOLIS

123 LEJEUNE

3 Beds

3 Baths

2,152 Sq.Ft.

$589,900

MLS#: MDAA2137752

#MDAA2134520

ANNAPOLIS

102 VANGUARD LANE

4 Beds

3 Baths

2,000 Sq.Ft.

$585,900

MLS#: MDAA2134520

#MDAA2134820

ANNAPOLIS

721 FAIRWAY DRIVE

4 Beds

3 Baths

1,820 Sq.Ft.

$585,000

MLS#: MDAA2134820

#MDAA2137286

ANNAPOLIS

1041 SKYVIEW DRIVE

4 Beds

3 Baths

1,960 Sq.Ft.

$584,900

MLS#: MDAA2137286

***Major Price Reduction***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. Welcome home!

ANNAPOLIS

5 PARK PLACE 107

2 Beds

2 Baths

1,272 Sq.Ft.

$575,000

MLS#: MDAA2138356

Location Location location!!
Modern rancher style home located near everything Annapolis has to offer! It's just minutes to Downtown Annapolis. The House is much bigger than it looks. A beautiful fenced in backyard with a composite decking awaits for outdoor entertaining. This house also features 5 bedrooms and two full bath. This home is almost 2,000 sf. finished. Entire home was fully renovated in 2025. The finished basement features a laundry room, family room, 2 spacious bedrooms, and one full bathroom. The whole top level features 3 bedrooms, one full bath, open concept style kitchen with island that opens to the dining space and large living room. New HVAC, plumbing and electrical system. Move-in ready, fully furnished!! This home really offers a wonderful opportunity to enjoy Annapolis living — just minutes from shopping, dining, and commuter routes.

ANNAPOLIS

1002 TYLER AVENUE

5 Beds

2 Baths

1,920 Sq.Ft.

$565,000

MLS#: MDAA2130284

Watch sunrises over the Chesapeake Bay from this airy condo in amenity-rich Chesapeake Harbour. Updated and larger than many other two-bedroom units, this second-floor condo includes a spacious loft - ideal as a family room, home office, or third bedroom. The vaulted living room ceiling, skylights, and sliding doors bring the outdoors in while showcasing bucolic views of the water and nearby woods. The primary suite offers its own sliding doors to the deck, a walk-in closet with extra storage, and an en-suite bath. A second bedroom includes a full wall of closets and west-facing windows that capture the afternoon light. Additional highlights include a modern kitchen with glass doors opening to a front deck, stainless steel appliances, hardwood floors, and a wood-burning fireplace. Recent seller improvements include a new HVAC system (2025) and a stacked washer and dryer (2023).

Chesapeake Harbour, a popular gated community just outside historic Annapolis, offers turn-key living and exceptional amenities including outdoor swimming pools, tennis courts, walking trails, and private beaches. The community is also home to the Beacon Waterfront Restaurant and the Chesapeake Harbour Marina, managed by Trident Marine Group. The marina offers wet slips, transient slips, lifts, and concierge services.

Come enjoy the Annapolis waterfront lifestyle, peaceful Chesapeake Bay views, and turn-key living in this resort-like setting.

ANNAPOLIS

2010 QUAY VILLAGE COURT 201

2 Beds

2 Baths

1,489 Sq.Ft.

$565,000

MLS#: MDAA2137422

Picture this for your next home in historic Annapolis: a bright, open, two-bedroom, two-bath condo in the Residences at Park Place. Conveniently located near Rt. 50 and Rt. 97, with easy access to Washington, D.C., Baltimore, and BWI Airport, this home is just a short walk from Annapolis fine restaurants, unique boutiques, live entertainment, and the iconic U.S. Naval Academy. Surrounded by the charm of cobblestone streets, waterfront views, and the lively energy of City Dock and Ego Alley, this condo offers luxury living with amenities like a private outdoor pool, an enclosed pet park, a well-equipped exercise room, a community room, secure garage parking for two vehicles, and on-site professional property management. The furnishings in the images have been virtually staged to help you picture the home’s full potential and layout possibilities. Contact your real estate professional to schedule a private tour.

ANNAPOLIS

5 PARK PLACE 314

2 Beds

2 Baths

1,056 Sq.Ft.

$564,000

MLS#: MDAA2108870

Unbeatable USNA Proximity! Perfectly Located to enjoy all of what downtown Annapolis has to offer! This delightful one-level condo at 31 College Ave places you in the premier location, literally neighbors with the Naval Academy and St. John’s. Enjoy a functional, open floor plan with a decorative fireplace, gas cooking, and a luxurious custom bath in the primary suite. Includes basement storage unit and common storage space. With Maryland Avenue’s dining and the City Dock just blocks away, this is the perfect home base for Navy fans and downtown enthusiasts alike. Enjoy the spirit of the Yard and the beauty of the City Dock every single day.

ANNAPOLIS

31 COLLEGE AVENUE

1 Beds

1 Baths

632 Sq.Ft.

$550,000

MLS#: MDAA2138136

New on site 1 day ago

Welcome to 566 Fox Paw Trail, an exceptional end-unit townhome in the highly sought-after Woods Landing community of Annapolis, offering over 2,300 square feet of beautifully maintained living space surrounded by nature.

Perfectly positioned with mature trees along the side, this home enjoys a private, tranquil setting that feels like a retreat. From the side of the property, you can access a scenic walking path that leads directly to the water, creating a unique opportunity to enjoy the Chesapeake Bay lifestyle right from your doorstep.

Outdoor living is a true highlight, featuring an expansive wrap-around deck that overlooks a fully fenced backyard—ideal for entertaining, relaxing, or simply taking in the peaceful wooded surroundings.

Inside, the home showcases a spacious and versatile split-level design with four bedrooms and 3.5 baths. The upper level features hardwood flooring, vaulted ceilings, and abundant natural light, creating an open and airy feel throughout the main living spaces. The beautifully updated kitchen is the centerpiece of the home, complete with dolomite countertops, a large island with seating, soft-close cabinetry, pull-out pantry shelving, and stylish finishes that blend both function and design.

The adjoining dining area is perfect for gatherings, featuring a wood-burning fireplace and direct access to the deck for seamless indoor-outdoor entertaining.

The main level primary suite is generously sized and thoughtfully designed with a vaulted ceiling, sitting area or office space, multiple closets including a walk-in, and a private bath with dual vanities.

The lower level offers additional flexibility with three spacious bedrooms, two full baths, a large open living area, and a separate bonus room with direct access to the backyard—ideal for guests, a home office, or multi-generational living.

Additional features include a dedicated boat trailer parking space, allowing you to fully enjoy the nearby water access and outdoor lifestyle this community is known for.

Woods Landing offers an exceptional array of amenities, including a waterfront boardwalk trail, playground, dog park, tennis and pickleball courts, and more. Conveniently located just minutes from Route 50, Sandy Point State Park, and downtown Annapolis, this home offers the perfect balance of accessibility and peaceful, nature-filled living.

ANNAPOLIS

566 FOX PAW TRL TRAIL

4 Beds

3 Baths

2,676 Sq.Ft.

$549,900

MLS#: MDAA2140268

Welcome to penthouse living at Element at Mill Creek, one of Annapolis’ most stylish and thoughtfully designed 55+ communities. This 2 bed + Den, 2 bath top-floor residence with in-home laundry offers the privacy and quiet you’ll appreciate, paired with the elevated finishes and upgrades that truly make it better than new construction. From the moment you enter, you’ll notice the difference. Since purchasing, the owner has enhanced the home with carefully selected upgrades—refined lighting, custom touches, and elevated finishes that go beyond the builder’s base offerings. The result is a move-in-ready home with personality, warmth, and polish already in place. No waiting on construction timelines, no post-settlement projects—just effortless living from day one. This penthouse unit enjoys abundant natural light and peaceful views, along with the convenience of an assigned parking space in a secure garage—providing comfort and ease year-round. Life at Element at Mill Creek is designed for connection, wellness, and enjoyment. Residents enjoy a beautifully appointed clubhouse featuring indoor and outdoor dining spaces, a state-of-the-art fitness center, gathering rooms, and even a golf simulator for year-round play. Outdoors, you’ll find pickleball courts, scenic walking trails, and a dedicated dog park—perfect for staying active and social while enjoying the thoughtfully landscaped grounds. The community’s modern coastal architecture and easy layout create a fresh, welcoming neighborhood atmosphere that feels both intimate and sophisticated. Located just minutes from downtown Annapolis, you’ll have easy access to everything that makes the area so special—waterfront dining, boutique shopping, art galleries, live music, and year-round festivals. Spend afternoons strolling along City Dock, catching a sailboat race on the Chesapeake Bay, or enjoying dinner at one of the many acclaimed local restaurants. The charm, history, and vibrant lifestyle of Annapolis are right at your doorstep. And unlike many new construction purchases—where buyers are often responsible for the majority of closing costs—this resale offers a more traditional and balanced approach, with costs typically shared between buyer and seller. Title insurance discount also available. Stylish, upgraded, and ideally located, this penthouse at Element at Mill Creek offers the perfect blend of low-maintenance luxury, active living, and the best of Annapolis just moments away.

ANNAPOLIS

78 OLD MILL BOTTOM ROAD N 409

2 Beds

2 Baths

1,210 Sq.Ft.

$530,000

MLS#: MDAA2137136

MOTIVATED SELLER!!!! This is a fabulous unit, and Welcome to Chesapeake Harbour! This beautifully updated Marina VIEW 2-bedroom, 2-bath condo offers the perfect mix of comfort, style, and easy living in one of Annapolis’s most sought-after waterfront communities is just waiting for YOU!
A MOTIVATED SELLER and located in one of the best buildings, at least that's the seller's opinion with a great view of the marina...and not looking at a ton of other units!
Inside, you’ll find a fresh and modern vibe with a little fresh paint accented with ceiling fans throughout, new bamboo flooring, and a delightfully unique wooden fireplace mantel adding a cozy, custom touch to the living space. The open layout flows effortlessly from the living room to the dining area and kitchen, making it great for entertaining or just relaxing at home.
The kitchen has been upgraded with a new countertop, sink and faucet, and new dishwasher, new refrigerator, plus stainless-steel appliances including a self-cleaning oven and built-in microwave. There are even a new washer and dryer tucked away for convenience. Both bathrooms have been refreshed with stylish upgrades, giving the whole place a clean, contemporary feel.
The primary suite is a peaceful retreat with its own en-suite bath and plenty of closet space. The second bedroom and bath are perfect for guests, a home office, or whatever suits your lifestyle.
Step out onto your private balcony to enjoy views of the marina and Chesapeake Bay—ideal for morning coffee or evening wine. And when you're ready to get out and about, the community has it all: a private beach, two pools, tennis courts, jogging paths, and 24/7 gated security. Need an EV charge for your car. It's here. Take a stroll along walking path along the marina and enjoy a meal at the on-site restaurant. There’s even water access for boating enthusiasts!
With off-street parking and services like lawn care and exterior maintenance included, this home makes it easy to enjoy the good life without the hassle.
Whether you're looking for a weekend getaway or a full-time residence, this Chesapeake Harbour gem feels like a vacation every day.

ANNAPOLIS

7002 CHANNEL VILLAGE COURT 101

2 Beds

2 Baths

1,319 Sq.Ft.

$525,000

MLS#: MDAA2123516

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Buyers resources

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Buyers resources

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SELLERS RESOURCES

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