COASTAL LUXURY MEETS EVERYDAY VACATION LIVING in Windward Key on the Chesapeake Bay. Experience the ultimate waterfront lifestyle in this four-level townhome nestled in the sought-after Windward Key community in the heart of Chesapeake Beach. Whether you are searching for a full-time residence or the perfect weekend retreat, this exceptional home offers resort-style living with water views and upscale amenities throughout. Designed for both comfort and entertaining, the home features 4 bedrooms, 4 full baths, and 1 half bath across four spacious levels filled with natural light. The main living level showcases a well-appointed kitchen, dining area, and expansive great room with a cozy gas fireplace — all enhanced by water views and an open, airy feel. The upper level hosts the primary suite along with two additional bedrooms, while vaulted ceilings create an inviting sense of space and elegance. The top level offers exceptional flexibility with its own full bath, wet bar, and private deck, ideal for a home office, guest suite, lounge, or entertainment space overlooking the Bay. The entry level provides additional finished living space with a full bath, perfect for guests, recreation, fitness, or flex living. Direct access to the attached one-car garage adds convenience and functionality. Outdoor living is elevated with multiple decks on every level, creating seamless indoor-outdoor enjoyment and endless opportunities to relax and take in the coastal setting. Residents of Windward Key enjoy exclusive amenities including a waterfront pool overlooking the Chesapeake Bay and a private beach. Located within walking distance to restaurants, shops, parks, boardwalks, marinas, nature trails, and local entertainment, this is Chesapeake coastal living at its finest.
MAJOR PRICE IMPROVEMENT. Experience an elevated waterfront lifestyle in the coveted Windward Key community, ideally positioned along the shores of the Chesapeake Bay in the heart of Chesapeake Beach. This exceptional four-level townhome blends refined design with water views, offering 3 bedrooms, 4 full baths, and 1 half bath across thoughtfully designed living spaces. Sunlight pours through expansive windows, illuminating rich cherry hardwood floors that flow throughout the main and upper levels. The main living level is designed for both elegant entertaining and everyday comfort, featuring a spacious great room with a gas fireplace, an inviting dining area, and a well-appointed gourmet kitchen with stainless steel appliances, pantry, and wine refrigerator. Step onto the private deck to take in tranquil bay and fishing creek views—perfect for morning coffee or evening gatherings. The lower level offers a versatile recreation space with a full bath and dedicated laundry room, ideal for guests or extended living, with seamless access from the attached garage. From here, step outside to your deck and connect directly to the waterfront walkway, embracing the true essence of coastal living. Upstairs, the primary suite serves as a luxurious retreat, complete with a custom closet system, additional storage, and a spa-inspired bath featuring a jetted soaking tub and separate shower. A private deck off the suite captures breathtaking water views, creating a serene escape. This level also includes an additional bedroom and full bath. The top level provides exceptional flexibility, offering a private suite with full bath and walk-in closet—perfect as a fourth bedroom, executive office, or fitness studio—opening to yet another deck with sweeping, unobstructed views of the bay. An attached garage, additional storage, and private driveway ensure convenience, while Windward Key residents enjoy exclusive amenities including a pool and private beach. Just moments from and walking distance to local dining, shopping, marinas, water sports, and the Chesapeake Beach Water Park, this home also offers easy access to Washington DC, Annapolis, Joint Base Andrews, and Northern Virginia. Live where you play—and indulge in the luxury of waterfront living every day.
Nestled on a spacious and private 1.28-acre cul-de-sac lot in the highly sought-after Highlands community, this beautifully maintained home offers the perfect blend of comfort, privacy, and convenience. Backing to woods and featuring a large, private backyard, it's a peaceful setting while remaining close to everything the area has to offer. Recent updates include: New Luxury Vinyl Plank (LVP) Flooring – June 2026; New Hot Water Heater – 2025; New Stainless Steel Kitchen Appliances – 2025; New Shed – 2024; New Heat Pump – 2022; Metal Roof – 2014 * Inside, you'll find new flooring throughout the main level and a finished lower-level offering additional living and entertaining space. LL flooring New in 2024. Residents of The Highlands enjoy neighborhood walking trails, playgrounds, sports courts, and access to highly rated schools. Located less than two miles from the Twin Beaches, you'll love LIVING the coastal CHESAPEAKE BAY lifestyle this area provides, including public beaches, marinas, fishing piers, 3 boardwalks, a variety of local restaurants and pubs, the Rod 'N' Reel Resort, Casino & Spa, and the area's beautiful new public library * Easy Commute to Washington, D.C., Annapolis, Baltimore, and Joint Base Andrews. Experience the Salt Life year-round on over 1.25 private acres—where space, privacy, and coastal living come together.
Opportunity to obtain a spacious home in a community with beach access. The Breezy Point Community has access to the beach through voluntary dues, not mandatory ones. The beautiful beach is within walking distance and also offers a large picnic area. The home is being sold as is by the estate. The special features include new carpet on the main level and a new roof between 2021 and 2022. Solar panels have been installed and will be paid in full at closing. The family is working on cleaning out the home, which is why we haven't displayed pictures of all the rooms. There are 2 bedrooms on the main level, and a 3rd bedroom was converted into a laundry/storage room. There is also a w/d hookup in the basement if you want to convert that room back to a bedroom. The lower level is partially finished and in need of renovation. There is a wood stove in the lower-level family room that heats the house during a cold spell. There are 2 spacious garages, currently full of belongings. The screened-in porch is great for entertaining and very large. There is a covered area for parking 2 cars or grilling, and plenty of concrete driveway spaces for parking. The front yard is fenced in to keep the children and pets safe. The home is being sold as is by the estate.
** PRICED UNDER VALUE - OWNER READY TO GO ** - Location location location - Lovely Chesapeake Beach split foyer with enclosed sunroom. Upper-level updated in 2021 with hardwood flooring, ceramic tile and huge kitchen. Seller owned solar panels are added plus for managing lower utility costs. Seller still clearing our rooms. Being sold AS-IS for simple transaction. Inspections for informational purposes only. Basement set up for future rental income or in-law area with large rec room, kitchenette, 2 bedrooms, second washer/dryer and separate entrance doors. Ready to go with your cosmetic touch-up. Large yard with shed. Enjoy the close proximity to the Chesapeake Bay. Walk to beach attractions and ENJOY beach life. Upstairs rooms virtually cleared and yard enhanced for your visual experience. Schedule your showing TODAY.
Everything you want in a true Chesapeake Bay waterfront property is right here. Nestled on a rare, oversized double corner lot in Chesapeake Beach, this one-of-a-kind historic waterfront estate offers unmatched charm, versatility, and income-producing potential. With a location that simply cannot be duplicated, this property delivers the ultimate coastal lifestyle just 35 minutes from Washington, D.C. Offering approximately 3,100 square feet, the main residence features five spacious bedrooms and four full bathrooms, along with a newly installed HVAC system for modern comfort while preserving its timeless character. Enjoy exceptional waterfront living with a commercial-style private pier featuring approximately 5 feet of water depth, deeper than most in the area, making it ideal for boating, fishing, and waterfront entertaining. Best of all, no flood insurance is required for this location. The property also includes a one-car garage and a livable studio with a full bathroom and kitchenette, ideal for a guest suite, private office, artist retreat, or bed-and-breakfast use. The entire third floor functions as a private apartment with its own separate exterior entrance. This fully self-contained suite includes a bedroom, living room, kitchenette, built-in washer and dryer, and a private balcony with breathtaking waterfront views, perfect for rental income, extended family, or independent guest accommodations. Ideally located within walking distance to the Chesapeake Beach Resort & Spa, as well as the boardwalk, marina, and a variety of waterfront attractions, this home offers easy access to nearby restaurants, shops, local entertainment, the water park, concerts, gaming, and seasonal events. Enjoy the best of coastal living with Bay breezes all summer long, historic charm throughout, and spectacular waterfront views from multiple rooms, including two bedrooms on the upper level. Rich with original heart of pine flooring, architectural character, and modern updates, this home stands apart from anything else on the Bay. Set on a block-long parcel that is nearly impossible to find, it offers space, privacy, and long-term value. Whether you are seeking a primary residence, vacation retreat, or income-producing investment, this truly rare Chesapeake Bay waterfront property delivers it all.
Tucked into the sought-after Holiday Beach community in Chesapeake Beach, this classic colonial offers the perfect blend of comfort, charm, and the relaxed southern Maryland lifestyle so many buyers are searching for. Enjoy community water access along with easy proximity to all the dining, shopping, marinas, and recreation that make the Chesapeake Bay lifestyle so special. Inside, hardwood floors, plush carpeting, and a beautifully appointed kitchen create warm and inviting living spaces designed for both everyday living and entertaining. Formal living and dining rooms flank the dramatic two-story foyer, while the eat in kitchen is the perfect place to unwind and take in peaceful wooded views that surround the home from every room. Upstairs, the spacious primary suite features a walk-in closet and private full bath, complemented by two generously sized secondary bedrooms and an additional hall bath. The unfinished walk-out lower level provides endless possibilities for future expansion, recreation space, or storage — ready for your personal vision and finishing touches. Located just minutes from local favorites, waterfront dining, beaches, boating, and the highly anticipated reopening of the Chesapeake Beach Water Park in 2027, this home offers a lifestyle that feels worlds away from the city while remaining convenient to everything you need.
Wake up to breathtaking sunrises and sweeping waterfront views in this charming coastal retreat with access to the Chesapeake Bay and a sandy beach area. Perfect as a vacation getaway or year-round residence, this property offers the ideal blend of relaxation and waterfront living. An additional building lot is included, 3711 Bayview Dr. providing endless possibilities — keep it separate for added value or combine the parcels to create your dream waterfront estate with room for a much larger home. Enjoy boating, beach days, and peaceful coastal living in a truly special setting. A very unique and rare opportunity!
Motivated Sellers with Incredible 2.75% FHA Assumable Interest Rate Available! Escape to your own private woodland sanctuary at the end of a peaceful, quiet cul-de-sac. This enchanting home is truly an artist’s dream, bathed in dappled sunshine and offering a level of tranquility that is hard to find. The interior serves as a creative canvas, currently featuring vibrant custom murals that can remain to inspire the next owner or be returned to a neutral palette—the choice is yours. Beyond its charming exterior, the home offers significantly more space than appears, boasting a versatile layout with two distinct living areas: a shared living space on the upper level and a spacious secondary living room downstairs. The heart of the home is the beautifully updated kitchen, complete with modern stainless steel appliances and stylish finishes. Durable LVP flooring flows throughout the main living areas, while plush carpeting adds comfort to the bedrooms. This expansive floor plan includes six true bedrooms with two separate living spaces. The upper level features three bedrooms, including a primary suite that serves as a private getaway with its own turf-covered walk-out deck overlooking the trees. For added convenience, the laundry is also located on the upper bedroom level. The lower level provides excellent separation of space with three additional spacious rooms that can be used for sleeping or are perfect for a home office, playroom, or studio. There is a wet bar rough-in in the lower family room to make this a great hangout spot, or create another Kitchen for a basement apartment with private rear entrance. Major updates provide peace of mind, including two updated bathrooms and a brand-new well pump installed in 2024. Outside, the backyard is primed and ready for a custom patio, offering the perfect spot to host gatherings or simply enjoy the surrounding nature. Combining modern updates, significant financial value, and a serene atmosphere, this home is a rare find for those seeking both function and inspiration.
TO BE BUILT HOME in the sought-after Chesapeake Beach community. This exceptional NEW CONSTRUCTION opportunity co-marketed with Schaefer Homes allows you to build your dream home on a prime lot with views of the Chesapeake Bay. The featured Eastport model blends Colonial and Coastal architectural elements with an open-concept layout. The main level offers a spacious family room flowing seamlessly into the kitchen with a large center island — perfect for everyday living and entertaining. Upstairs, the primary suite includes a private en suite bath, complemented by three additional bedrooms, a full hall bath, and a conveniently located laundry room. An attached garage and driveway offer ample parking. Pictures and renditions are examples only. Price will vary depending on model and selected options. Available upgrades include a larger front porch, screened porch, patio, or deck for enhanced outdoor living. A finished basement may also be an option. Additional home models are available. Ideally located with convenient access to the North Beach boardwalk, marinas, and Brownie’s Beach. Enjoy walkability to local restaurants and an easy commute to Annapolis, Washington, D.C., Joint Base Andrews, Baltimore, and Northern Virginia. TO BE BUILT home. Price shown includes base house price, lot and estimated lot finishing cost only. Lot and home are sold under separate contracts. Pricing is subject to change. Site development costs may vary.
This 5-bedroom, 3-bathroom home is ready for new owners! Located on a quiet cul-de-sac with a huge fenced-in backyard and a spacious deck off the kitchen. Convenient Chesapeake Beach location, close to the Chesapeake Bay, and all the amenities that Chesapeake Beach has to offer! Bayfront Park, shopping, restaurants, the water park, ballparks, playgrounds, community center, marina, boardwalks, and nature trails! Easy commute to Joint Base Andrews, Pax River, Annapolis, and DC.
Chesapeake Beach is located in Maryland. Chesapeake Beach, Maryland has a population of 6,303. Chesapeake Beach is more family-centric than the surrounding county with 44.43% of the households containing married families with children. The county average for households married with children is 34.94%.
The median household income in Chesapeake Beach, Maryland is $120,194. The median household income for the surrounding county is $120,295 compared to the national median of $69,021. The median age of people living in Chesapeake Beach is 42.5 years.
The average high temperature in July is 86.9 degrees, with an average low temperature in January of 24.7 degrees. The average rainfall is approximately 44.2 inches per year, with 15.8 inches of snow per year.
