Chesapeake Beach MD Real Estate & Homes for Sale

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!

**NEW PRICE** For those seeking privacy and tranquility, this residence presents an ideal opportunity. Meticulously maintained and upgraded. Upon entering, one is immediately impressed by the inherent elegance of the property. Spanning over 2,600 square feet, this home features four bedrooms and three and a half bathrooms. The main level showcases a beautifully appointed kitchen with granite countertops and custom cabinetry, a living room seamlessly integrated with the dining area, and a convenient half bath. The expansive family room includes a wood-burning fireplace and provides access to one of the property's multiple decks. The upper level comprises three bedrooms and two full bathrooms, with the primary bathroom recently updated with exquisite tile work. Proceed to the lower level to discover a comprehensive suite of amenities, including a full kitchen, family room, dining area, bedroom, office, and full bathroom. Furthermore, the property extends beyond the interior, offering a remarkable exterior landscape. This expansive 3-acre property ensures both privacy and serenity. Envision hosting events by the pristine pool or simply relaxing on the deck. The location provides convenient access to local attractions such as the boardwalk, water park, beaches, dining establishments, and retail outlets. Given the anticipated demand, we encourage you to schedule a showing promptly. Agents are advised that the access road is a shared right-of-way among three neighboring properties.

Welcome to this beautifully maintained 5-bedroom, 3.5-bath home nestled on 3 private acres on a quiet, dead-end street. Featuring updated kitchens and bathrooms, this home offers the perfect blend of modern comfort, flexibility, and charm. The spacious layout provides room for everyone. The finished lower level includes an additional kitchen, living area, bedroom, and full bath with a separate entrance offering potential for multigenerational living, guest accommodations, or possible income-producing opportunities. (Buyer and Buyer's Agent to perform due diligence to verify all local zoning laws, permitting, and feasibility of income-producing or rental use.) Dreaming of a homestead lifestyle? The property is already equipped with a chicken coop and raised planter boxes, making it easy to start growing your own food and enjoying a more self-sufficient way of life. Located in a highly rated school district and just minutes from beaches, boardwalks, waterfront dining, shopping, and everyday conveniences, you'll enjoy the best of both worlds - peaceful acreage living with easy access to local amenities. A recent home inspection identified the presence of Polybutylene (Poly B) plumbing. In consideration of this finding, the seller is offering a $15,000 BUYER CREDIT/ESCROW to be used at the buyer's discretion. Don't miss this unique opportunity to own a versatile property with space to grow, gather, and create the lifestyle you've been looking for. Schedule your showing today!

Discover coastal living at its finest at 8048 Windward Key Dr, Chesapeake Beach! This "as-is" gem offers breathtaking views of the canal and the iconic Chesapeake Bay, placing you right in the heart of everything this charming waterfront town has to offer. Located just steps away from the renowned Rod 'N' Reel Resort, you'll enjoy the convenience of walking to local restaurants, marina boat storage, and more. Whether you're an avid boater or simply love the water, this property has you covered with on-site boat slips (not deeded). Picture yourself savoring every sunrise and sunset from your private decks or hosting friends and family as you take in the dazzling Chesapeake Beach fireworks right from the comfort of your home. It's a lifestyle of relaxation, natural beauty, and endless opportunity. With so much more to discover, this is your chance to own a slice of paradise. Don't wait - this coastal retreat won't last long!

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.

***VA Assumable @ 2.375%! Welcome to 3640 Estelle Ct - where space, function, and location come together on 2.25 private acres in Chesapeake Beach. This thoughtfully designed home offers flexibility for today's lifestyle, featuring a dedicated main-level home office and a potential main-level bedroom - ideal for guests or multi-generational living. The open-concept layout flows into a stunning two-story family room and spacious kitchen, perfect for everyday living and entertaining. Upstairs, the expansive primary suite includes dual walk-in closets and a private sitting room, creating a true retreat. Additional bedrooms are generously sized, with a well-designed upper-level layout. The finished basement expands your options with a private in-law suite setup - ideal for extended stays, guests, or flexible living arrangements, with potential for rental or income-producing use (buyer to verify local regulations). Don't miss the finished third-level loft - an incredible bonus space perfect for a playroom, gym, media room, or additional living area. Outside, enjoy the privacy and space of a 2.25-acre homesite complete with a yard sprinkler system and invisible fence. Added peace of mind comes from the whole-house generator system that powers the home with the exception of the kitchen range. Located within commuting distance to Washington, DC and Joint Base Andrews, this home offers the perfect balance of peaceful living with accessibility. An added bonus for qualified buyers: existing 2.375% VA assumable loan available for buyers with VA eligibility.

Welcome to 4013 Seagate Square, ideally situated in the heart of Chesapeake Beach - one of the most desirable waterfront communities in Calvert County. This property offers the perfect blend of coastal charm and everyday convenience, just moments away. This spacious 3-level townhome nestled in the sought-after waterfront community of Seagate. Offering over 2,000 square feet of living space, this home features 3 bedrooms, 3.5 baths, an open and functional layout, and beautiful natural light throughout. A newer HVAC system provides added peace of mind and energy efficiency for the next owner. The main living area offers an inviting flow with generous room sizes, a cozy fireplace, and an open kitchen with table space and adjoining dining area - perfect for everyday living or entertaining. The second floor features the primary suite with a private bath and ample closet space, along with an additional bedroom and full bath. The third-floor bedroom and full bath create an ideal private guest suite, home office, or flexible bonus space. One of the true highlights of life at Seagate Square is the incredible waterfront setting and ever-changing natural beauty just outside your door. Enjoy peaceful water views filled with stunning sunrises, glowing moonlit reflections across the bay, dramatic rainbows after summer storms, and passing ships in the distance. Nature lovers will appreciate the abundance of local wildlife, including herons, osprey, waterfowl, and other coastal birds frequently seen throughout the community. The Chesapeake Bay and community dock create endless opportunities for fishing, crabbing, kayaking, paddleboarding, or simply relaxing by the water and taking in the coastal breeze. Whether enjoying your morning coffee watching the boats go by or winding down with spectacular sunsets over the bay, this is the kind of waterfront lifestyle that makes Chesapeake Beach so special. Enjoy easy access to the Chesapeake Beach Railway Trail, local marinas, fishing piers, and the town's beloved boardwalk. Walk to dining at waterfront restaurants, boutique shops, or taking in live entertainment at the nearby resort and water park. Check out https://www.northbeachmd.gov For commuters, this location provides a manageable drive to Washington, D.C., Annapolis, and Joint Base Andrews, and PAX River, making it a great option for those seeking a peaceful retreat without sacrificing accessibility. Whether you're looking for a full-time residence or a weekend escape, Seagate Square offers a relaxed, walkable setting with a true small-town coastal feel. Stay tuned - this is one you won't want to miss!

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.

Beautifully customized home featuring a stunning kitchen with abundant custom cabinetry, sparkling black granite countertops, and ample seating. Brazilian cherry hardwood floors add warmth and elegance throughout the main living areas. The spacious great room offers vaulted ceilings and a cozy propane fireplace. The private owner's suite features vaulted ceilings, a walk-in closet, and convenient washer and dryer. Two additional bedrooms on the opposite side from owner's suite. Enjoy the backyard from the large sunroom just off the kitchen. The finished lower level includes stylish trim work, a full bath with ceramic tile shower, and additional storage space, plus den / bedroom for guests. Behind the garage is a large bonus room, perfect for entertainment. Two car garage with additional storage under bonus room, plus additional parking for vehicles or an RV. Built with 2x6 construction and equipped with a high-efficiency 3-zone, 21 SEER HVAC system, keeping utility bills low. Pellet Stove for extra heating in the basement. A large private backyard completes this exceptional property. Contact Listing Agent for more details!

Beach cottage in a private Chesapeake front community with bay access where you can swim, sunbathe and hunt for shark's teeth and fossils. This community is tucked along the shore of The Chesapeake Bay. The cottage has a large, open kitchen, newer stainless appliances and a fireplace with a pellet stove that adds to its charm. Plentiful driveway parking 4 cars in the main, paved driveway and an additional long driveway for overflow, campers, boats or whatever and a yard with a treed view. New HVAC system 2026. Chesapeake Beach boasts lots of activities within a reasonable commute to DC, Virginia and PAX River Naval base.

Back on the market due to shaky financing! Inspected and READY! Improved price too! Welcome to 8229 Bayside Road, where elevated bayside living meets everyday convenience in the heart of Chesapeake Beach. This beautifully maintained four-bedroom, 3.5-bath residence offers views of the Chesapeake Bay and an unbeatable walkable lifestyle along the water. Spanning four finished levels and serviced by a private elevator reaching every floor, this home was designed for comfort and accessibility. The top-level primary suite is a true retreat, complete with private elevator access, stunning bay views, private bathroom and your very own lighthouse beacon that can actually be seen from the bay! Wake up each morning to the shimmer of the water and end your evenings on your private balcony with a cool breeze and your beverage of choice. The home is in excellent condition and thoughtfully laid out to maximize both space and light. Generously sized bedrooms, multiple gathering areas, and well-appointed baths provide flexibility for everyday living and hosting guests. Garage and driveway parking are off-street. Whether you're looking for a full-time residence or a weekend escape, this home offers the perfect balance of function and relaxation. Step outside and embrace the lifestyle that makes Chesapeake Beach so special. Everything you need is within walking distance - restaurants, local shops, a grocery store, marinas, fishing spots, and water activities. Spend your afternoons strolling the boardwalk, enjoying waterfront dining at local favorites like Rod 'N' Reel Restaurant, Traders & Baia Coastal, exploring the marina, or watching the boats roll in. Jet ski rentals, beaches, live entertainment, and even more dining options are just moments from your front door. In fact, you're only a short walk to neighboring North Beach, expanding your access to even more waterfront charm, restaurants events, and recreation. Here, you truly can park your car and leave it - this is bayside living at its most convenient and vibrant. Select photos are virtually staged.

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.

5 bedrooms, 3 full bathrooms, 4 car garage, 3 attics, no HOA, parking for RV's, boats, trailers, large deck, near boardwalk and beach, near grocery store and restaurants, near casino, City water and sewer, refurbishing completed years ago, current rental.

This 3-bedroom, 1-bath home on 4th Street blends modern updates with coastal charm in a prime Chesapeake Beach location. And it comes with a bonus: the sale includes the additional lot directly across the street. The exterior features fresh paint and blue accents that enhance its curb appeal, while the fenced yard adds privacy and function. "New septic system has just been installed" Inside, hardwood floors flow through the open living area, highlighted by a fireplace that creates a natural focal point. The kitchen showcases white cabinetry, sleek hardware, stainless steel appliances, and direct access to a new deck, ideal for outdoor dining and gatherings. The full bath has been thoughtfully renovated with stylish tile, contemporary fixtures, and a skylight that fills the space with natural light. Three bedrooms provide comfortable living areas with neutral finishes and closet storage. A laundry nook with a washer and dryer enhances daily living, and a one-car driveway ensures off-street parking. The new rear deck extends the living space outdoors, overlooking a fenced yard with space for pets, gardening, or relaxation. With no HOA restrictions, the property offers flexibility for future projects or personal touches. Located minutes from the boardwalk, beaches, restaurants, and local shops, this home presents an appealing lifestyle opportunity in a sought-after setting. "Some images may reflect virtual staging or digital editing, including removal of personal property, to help showcase the home."