Chesapeake Beach MD Homes For Sale

Welcome to 8320 Harrison Boulevard! This spacious 4-bedroom, 2-full-bath, 1-half-bath home offers comfortable living and plenty of opportunity to make it your own. Freshly painted throughout, the home features an inviting open-concept living area and kitchen, creating an ideal space for everyday living and entertaining. The spacious primary bedroom includes a private en-suite bath, while three additional bedrooms provide flexibility for guests, a home office, or other needs. The lower level offers additional unfinished space with excellent potential for future expansion, storage, recreation, or a personalized living area. Located in a desirable Chesapeake Beach neighborhood with a variety of community amenities, this home combines functional living space with room to grow. Don't miss the opportunity to make this property your next home!

8320 Harrison Blvd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 7033493900

$650,000

4 Beds ⋅ 3 Baths

Vacation everyday with a short two blocks to the Chesapeake Bay from this gorgeous two level home! Main level features open floor plan with spacious family room open to dining room and kitchen. Granite counters with seating for a crowd at the breakfast bar plus ss appliances, pendant lights, and tall cabinets make the kitchen a dream! Upstairs you will find four spacious bedrooms. including owners suite with private bath, three additional bedrooms including huge fourth bedroom over garage and hall bath. Loads of extras including hardwood and ceramic floors, separate laundry room, covered front porch, two car garage plus off street driveway parking, level and fenced back yard, rear deck and a storage shed! Easy commute to Washington DC Annapolis, and Joint Base Andrews. Close to shopping, beaches, boardwalk, restaurants, water park, marinas and all that Chesapeake Beach has to offer!

3910 28th St, Chesapeake Beach

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$475,000

2 Beds ⋅ 2 Baths

Welcome to waterfront living at Horizons on the Bay! This 2-bedroom, 2-bath condo offers the opportunity to enjoy beautiful Chesapeake Bay views from a well-appointed condo building in the heart of Chesapeake Beach. The open setting and waterfront surroundings create a relaxing atmosphere, while the community’s amenities make everyday living feel like a getaway. Residents enjoy a rooftop pool with sweeping Bay views, fitness center, private pier, library, community gathering spaces, and a picnic area with grills and firepit. The gated community is conveniently located near the Chesapeake Beach boardwalk, beaches, restaurants, shops, parks, and local entertainment. Enjoy easy access to waterfront recreation while remaining within reach of Annapolis, Washington, D.C., and surrounding areas. Whether you're looking for a full-time residence, weekend retreat, or low-maintenance waterfront lifestyle, Horizons on the Bay offers a unique opportunity to enjoy life on the Bay.

8501 Bayside Rd Unit #609, Chesapeake Beach

Listing courtesy of Redfin Corp. Contact: 3016586186

$735,000

4 Beds ⋅ 4 Baths

**VA ASSUMABLE LOAN AT (2.75%) — Ask for Details!** Welcome to 8308 Legacy Circle—a place to spread out, settle in, and embrace the easygoing Chesapeake Beach lifestyle. Tucked within the Heritage Woods community, this inviting 4-bedroom, 3.5-bath home offers the space, comfort, and flexibility to make everyday life feel a little more special. Picture slow mornings in a sun-filled kitchen, coffee in hand, as the day begins. Luxury vinyl plank flooring creates a stylish, easy-care setting for busy households, while the kitchen is thoughtfully equipped with a refrigerator, range/oven, microwave, dishwasher, disposal, and vent fan—everything you need for weeknight dinners, holiday baking, or a casual gathering with friends. With approximately 3,315 finished square feet across the main and upper levels, there is room for everyone to have their own space while still coming together at the end of the day. Four spacious bedrooms upstairs create comfortable retreats, and the conveniently located upper-level laundry helps keep daily routines simple. The finished lower level, complete with a full bath and walk-up access, adds even more possibilities. Create the movie-night hangout, a guest suite, home gym, playroom, hobby space, or the peaceful work-from-home office you have been dreaming about. Out back, the newly added deck invites you to linger outdoors—fire up the grill, enjoy a summer evening meal, sip something warm on a crisp fall afternoon, or simply watch pets and loved ones enjoy the fenced yard. Vinyl picket fencing gives the backyard a welcoming, defined feel, with room to garden, play, and make memories. A finished-drywall two-car garage, additional paved parking, public water & sewer, add the practical conveniences that make life easier. Beyond your front door, Chesapeake Beach offers an exceptional coastal lifestyle. Spend weekends exploring Bay-front parks and trails, meeting friends for waterfront dining, relaxing at the beach, visiting marinas and local shops, or taking in the community events that make this area feel so connected. From a boardwalk stroll to a day on the water to dinner overlooking the Chesapeake Bay, this is a community made for enjoying life close to the coast. Conveniently located for commuting to Pax River, Joint Base Andrews, Washington, D.C., Annapolis, and surrounding areas, 8308 Legacy Circle gives you the rare opportunity to enjoy Bay living without giving up accessibility. Schedule your private tour today and discover why 8308 Legacy Circle feels so easy to call home.

8308 Legacy Cir, Chesapeake Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

$399,900

3 Beds ⋅ 2 Baths

Welcome home to this charming 3-bedroom, 2-full-bath home nestled in the sought-after Breezy Point community of Chesapeake Beach, Maryland! Just a couple of blocks from year-round access to the Chesapeake Bay, this home offers the perfect blend of coastal living, privacy, and comfort. Step inside to find fresh paint and an adorable, updated kitchen ready for everyday living and entertaining. The lower level offers additional flexible living space—perfect for a family room, playroom, home office, or recreation area. Outside, enjoy a fenced in front yard and a large deck that wraps around the rear of the home, creating a wonderful space for grilling, entertaining, or simply relaxing after a day by the Bay. Tucked away near the end of a quiet street, the property offers a peaceful setting while still keeping you close to everything Chesapeake Beach has to offer. Recent improvements, including a NEW ROOF and NEW SIDING, add even more value and peace of mind. Enjoy the coastal lifestyle with nearby Chesapeake Bay access, community events, beaches, dining, and all the charm of Southern Maryland living. This adorable Chesapeake Beach home is AVAILABLE FOR SHOWINGS!—schedule your showing and come see everything it has to offer!

3309 Recker Rd, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$350,000

3 Beds ⋅ 1 Baths

Welcome to this charming, move-in-ready home in the coastal community of Breezy Point! Offering approximately 1,200 square feet, this inviting 3-bedroom, 1-bath home features an updated kitchen with a newer refrigerator and stove, beautiful hardwood floors, and a spacious living room with vaulted ceilings. The light-filled sunroom provides flexible space for relaxing, entertaining or working from home. Step outside onto the expansive wraparound deck, where you can enjoy the peaceful surroundings and seasonal views of the Chesapeake Bay. A lovely English-style backyard garden, mature fig tree offering fresh figs each August, colorful plantings and stone landscaping in the front yard add to the home’s storybook charm. Notable improvements include HardiePlank siding, a roof installed in September 2021, Andersen windows across the back of the home installed in June 2023, HVAC replaced in May 2025 and a new septic holding tank installed in April 2026. Community amenities include a private beach for residents and their guests, free access to the county park featuring approximately half a mile of Chesapeake Bay beachfront, a playground and fishing pier, plus a public marina. Enjoy the relaxed coastal lifestyle year-round or make this special property your weekend retreat!

4884 Ridge Rd, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 4439757555

$475,000

Simply Magnificent Chesapeake Bay View Lot! Pictures can not do it justice! Great community of Holiday Beach located in Chesapeake Beach brings memories of small beach towns where everyone knew their neighbors and went boating and fishing together. This lot is not only a one of a kind, it has had so much development work done, it is now ready for you to start building your own custom home . The structure for the permit shows a dwelling that is 36 foot by 41 feet (foot print of existing foundation) in size or 1476 sq ft. the permits have been pulled for demolition of the walls, permit for the septic has been approved, permit for the well has been approved and grading permits are done. The lot consists of lot 19 and 20 as well as the existing gravel driveway to the left of the structure. All 3 parcels are in the selling price along with all the permits to get started. Homes in the community range from small cottages in need of complete renovation to home over a million dollars on the waters edge as this one would be. You are not going to find something so near perfect like this any time soon. All within an easy commute to Washington DC or a great weekend get a way place with out Bay Bridge Traffic. Owner has just lowered the price and the package is ready for you!

5209 Larchmont Dr, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$890,000

3 Beds ⋅ 5 Baths

4013 Windward Key Ct, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$369,700

5 Beds ⋅ 2 Baths

More info, pictures, and a floor plan will be available soon!

7609 Bayside Rd, Chesapeake Beach

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$539,900

4 Beds ⋅ 3 Baths

Nestled in the charming Bayview Hills community, this delightful split-level home offers a perfect blend of comfort and style. With 2,368 square feet of thoughtfully designed living space, this home features four spacious bedrooms and three full bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and breakfast areas. The kitchen features stainless steel appliances, a large breakfast bar and plenty of cabinet space for everyday living and entertaining. The fully finished basement provides additional living space featuring a spacious recreation room with a cozy fireplace and brick hearth, a bedroom, full bathroom, additional storage, and convenient garage access. Outside, enjoy the deck and custom stamped concrete patio, providing the perfect setting for outdoor entertaining or simply relaxing at the end of the day. Beautiful landscaping adds to the home’s curb appeal, while the attached two-car garage and concrete driveway provide plenty of convenient parking. Additional updates include a newer roof replaced in 2022, the water heater in July and brand-new garage door openers, adding even more value and peace of mind. Located in a great Northern Calvert County location within award-winning school districts, Bayview Hills offers community amenities including tot lots and jogging paths. Enjoy the perfect combination of a convenient location, neighborhood amenities, and a welcoming community. Truly a wonderful place to call home!

8138 Bayview Hills Dr, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$579,900

4 Beds ⋅ 3 Baths

Welcome to 2630 Richfield Lane in Chesapeake Beach! This beautiful 4-bedroom, 2 full bath, 1 half bath home offers a fresh, updated feel with plenty of space to make your own. The main level features luxury vinyl plank flooring throughout main level, fresh paint, and a bright, functional layout perfect for everyday living and entertaining. The kitchen offers a spacious island, great cabinet space, brand new SS appliances, and an easy flow into the main living areas. Deck off of kitchen to enjoy peaceful mornings sipping coffee. Major updates include a new roof and new siding, giving added peace of mind for the next owner. Upstairs, you’ll find four spacious bedrooms, including a comfortable primary suite with its own private bath w/ dual sinks. The unfinished basement offers tons of potential and is already partially divided into usable areas, making it perfect for future finished living space, a home gym, storage, office, playroom, or hobby area. Located in desirable Chesapeake Beach, this home is ready for its next chapter and offers the perfect opportunity to move in now and customize over time.

2630 Richfield Ln, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 3016099000

$375,000

3 Beds ⋅ 1 Baths

Welcome to Chesapeake Beach - Easy one-level living, a huge detached garage, and the laid-back coastal lifestyle welcomes you! This three-bedroom home offers an easy, functional layout with everything you need on one floor. The spacious living room features large windows that bring in plenty of natural light, while the kitchen offers generous cabinet space and newer stainless steel appliances. Major improvements include a new roof in 2021, new HVAC in 2022 and a newer hot water heater. Outside is where this property really stands out. The massive detached garage is a rare find for the twin beaches and offers you incredible space for vehicles, a workshop, hobbies, storage, or all the beach toys! A large driveway provides plenty of additional parking, and the fenced-in yard gives you room for pets, entertaining, gardening, or relaxing outside. Living in Chesapeake Beach means enjoying everything that makes Northern Calvert County so desirable. Spend weekends along the Chesapeake Bay, walk the nearby North Beach boardwalk, enjoy local restaurants and shops, visit the beach, or take advantage of the area's parks and waterfront activities. Best of all, you can enjoy the slower-paced beach-town lifestyle while still being within commuting distance of Joint Base Andrews and Washington, D.C. If you have been searching for one-level living with an oversized garage and a location that gives you the best of both coastal living and commuter convenience, this is one you do not want to miss!

3905 17th St, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$369,000

3 Beds ⋅ 1 Baths

Adorable 3 bd 1 ba in Holiday Beach. Short walk to a private community beach. The Living room has vaulted ceilings and dining area. Deck off Living area to a large back yard. Stackable washer / dryer in laundry area in bathroom. 30 minute drive to DC and approximately 40 minutes to PAX.

4215 Calvert Dr, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$535,000

5 Beds ⋅ 4 Baths

New and improved price! Welcome home to this beautifully updated 5-bedroom, 3.5-bath residence, where thoughtful updates, spacious living areas, and everyday comfort come together in a sought-after neighborhood. Located within a highly rated school district, this home offers the space and functionality today’s buyers are looking for—with plenty of room to grow. Inside, light-filled living spaces create a warm and inviting atmosphere, while generously sized bedrooms provide comfort and flexibility for family, guests, or a home office. The updated kitchen features sleek finishes, stainless steel appliances, and ample space for both everyday meals and entertaining. Beautifully renovated bathrooms add a fresh, modern feel throughout the home. Out front, the inviting front porch creates the perfect spot to enjoy your morning coffee, unwind at the end of the day, or welcome guests. Step into the expansive backyard and you’ll find a blank canvas ready for your vision. With no existing deck, you have the opportunity to create the outdoor space that best fits your lifestyle—whether that means a large entertaining deck, a patio, a fire pit, a garden, or your own private backyard retreat. Additional highlights include a cozy fireplace, energy-efficient windows, and a spacious two-car garage providing plenty of storage and convenience. Move-in ready and thoughtfully updated, this home blends modern style with timeless comfort while leaving room to make it uniquely yours. Come see everything this home has to offer and imagine the possibilities!

3693 Brookeside Dr, Chesapeake Beach

Listing courtesy of Real Broker, LLC - Dunkirk. Contact: 8554500442

$424,900

3 Beds ⋅ 2 Baths

Welcome to 6417 Brookeside Court! This 3-bedroom, 1.5-bath home offers plenty of space, recent updates, and an opportunity to make it your own. SPECIAL OPPORTUNITY—The seller will provide and pay for a brand-new roof with an acceptable offer, and YOU, the buyer, may select the shingle color from the contractor’s available options! Personalize the home’s exterior before you even move in while enjoying the added value and peace of mind of a new roof. Motivated Seller - bring your offer! Inside, you’ll find fresh paint and new carpeting, creating a clean, move-in-ready feel. The home offers approximately 1,040 square feet on the main level plus an additional 800 square feet of finished basement space, providing flexibility for a family room, home office, recreation area, or guest space. Located in Chesapeake Beach, you'll enjoy convenient access to local restaurants, shopping, parks, beaches, and everything the Twin Beaches area has to offer. This home is a great opportunity to add your own finishing touches and make it yours.

6417 Brookeside Ct, Chesapeake Beach

Listing courtesy of EXP Realty, LLC. Contact: 8888607369

$364,000

4 Beds ⋅ 3 Baths

Chesapeake Bay Views and Two Homes in One for under 375k!! . UNIQUE CHESAPEAKE BEACH LIVING * One home with 3 bedrooms and 2 bathrooms. The other is over-top of the attached garage apartment with one bedroom and one bathroom. Both Updated/Renovated in 2023! 2 - All New Kitchens and 3 Bathrooms include NEW: Paint, Flooring Lighting, Appliances! 2 Sets of Washer/Dryers * LARGE - fenced Yard in the rear! Rental Income Potential in Both units or the garage apartment. Live in both or Rent Both or Live in one and rent the other. Over $21,000/year rental income potential in the apartment alone. 1 Car Oversized Garage has TONS of storage! Great HOME(s) and Investment Opportunity! Home is Outside of Chesapeake Beach Town limits.

4215 Chesapeake Ave, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$390,000

4 Beds ⋅ 4 Baths

Welcome to 8445 Clear Spring Drive, where updated living, a flexible floor plan, and a peaceful wooded setting come together in the heart of sought-after Richfield Station! Offering three finished levels, 4 bedrooms, and 3.5 baths, this spacious townhome gives you plenty of room to spread out while keeping everyday life comfortable and convenient. The main level feels bright and inviting with an easy flow designed for both everyday living and entertaining. At the heart of the home is the gourmet kitchen, featuring rich black cabinetry, newer appliances, ample counter space, and plenty of storage in the pantry. Whether you're making dinner on a busy weeknight or gathering with friends and family, there's room to cook, entertain, and actually enjoy the space. The adjoining living and dining areas make it easy to stay connected, while views of the woods behind the home create a peaceful backdrop that's hard to beat. Upstairs, the deluxe primary suite gives you a private place to unwind at the end of the day, complete with a spacious walk-in closet and private ensuite featuring a soaking tub and separate shower. Two additional bedrooms and another full bathroom complete the upper level, providing plenty of flexibility for family, guests, or a home office. The finished lower level adds an entirely different dimension to the home. With a fourth bedroom, full bathroom, and generous additional living space, it's perfect for movie nights, a game room, overnight guests, extended family, a gym, or whatever fits your lifestyle. Plenty of storage throughout the home means there's a place for everything without sacrificing your living spaces. Outside, enjoy a setting that feels surprisingly private for community living. With the home backing to mature woods, you'll love having a peaceful place to relax and recharge while still enjoying everything Richfield Station has to offer. And the location makes everyday life even better! Richfield Station offers walking and biking trails, playgrounds, tennis and basketball courts, and beautifully maintained community spaces. You're just minutes from the Chesapeake Bay, beaches, boardwalks, marinas, restaurants, shopping, and everything Chesapeake Beach and North Beach have to offer, with convenient commuter access toward Joint Base Andrews, Washington D.C., Annapolis, and beyond.

8445 Clear Spring Dr, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$895,000

4 Beds ⋅ 4 Baths

OPEN HOUSE! SATURDAY SEPTEMBER 12, 2026, TIME 1-3 Welcome Home to 3912 17th Street, Chesapeake Beach!! THIS HOME IS SO SPACIOUS!!So Charming! Nestled in the heart of Chesapeake Beach, this extraordinary custom residence offers over 5,000 square feet of beautifully designed living space where timeless craftsmanship, luxurious finishes, and modern efficiency come together to create a truly exceptional home. From the moment you arrive, you’ll appreciate the extensive updates throughout. Freshly painted from top to bottom, this stunning home also features two brand-new air conditioning units, abundant new luxury flooring, updated designer lighting, a brand-new commercial-grade gas range, brand-new double wall ovens, a brand-new refrigerator, a new custom kitchen island, and countless additional improvements that make this home feel better than new. COME Add a pool to the backyard!!! Designed with both comfort and efficiency in mind, the home features a three-zone heating system for year-round comfort and energy savings. The heart of the home is an impressive gourmet kitchen created for both everyday living and entertaining. Beautiful marble and granite countertops complement the custom cabinetry, oversized island, walk-in pantry, wine refrigerator, commercial-grade gas range, premium exhaust hood, double wall ovens, and designer finishes. The kitchen opens seamlessly into the spacious family room while the formal dining room provides an elegant space for holidays and special occasions. Step outside to the recently rebuilt 16’ x 42’ deck, overlooking the beautifully fenced backyard and lush green lawn—perfect for outdoor dining, entertaining, or simply relaxing. Upstairs, the luxurious owner’s suite feels like a private five-star retreat. Enjoy your own private balcony for peaceful mornings, evening stargazing, and seasonal glimpses of the Chesapeake Bay. The spa-inspired bath features a jetted soaking tub, while the oversized custom walk-in closet with built-in organization offers exceptional storage. Brand-new flooring extends throughout the entire second and third levels, creating a fresh, cohesive look. Additional upstairs features include spacious secondary bedrooms connected by a Jack-and-Jill bathroom, abundant natural light throughout, and a conveniently located second-floor laundry room. The third-floor bonus level offers an expansive 28’ x 22’ recreation room, ideal as a media room, playroom, guest quarters, home office, or private retreat. The walkout lower level offers soaring ceilings, direct access to the backyard, and a bathroom rough-in already in place, providing endless possibilities for a future home theater, fitness room, guest suite, or additional living space. Outside your door, experience everything Chesapeake Beach has to offer. Enjoy the nearby boardwalk, marina access for boating enthusiasts, waterfront parks, boutique shopping, fitness amenities, rooftop pool access, and an incredible selection of waterfront restaurants. Rich in history and coastal charm, Chesapeake Beach offers an unmatched lifestyle while remaining approximately 45 minutes from Washington, D.C., Annapolis, Joint Base Andrews, and NAS Patuxent River. Every detail of this remarkable home has been thoughtfully updated and meticulously maintained, offering the perfect combination of elegance, comfort, and modern convenience. 3912 17th Street is more than a home—it’s a lifestyle. Schedule your private tour today and experience luxury Chesapeake Beach living at its finest.

3912 17th St, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$624,700

4 Beds ⋅ 5 Baths

Welcome home to this spacious colonial in the sought-after, water-privileged community of Willows Colony. Featuring 4 bedrooms, 4.5 bathrooms, and hardwood floors throughout, this home offers plenty of room and a flexible unfinished basement with a workshop. Outside, you can relax on the front porch or enjoy the private, wooded backyard with a deck, patio, fish pond, shed, and 2-car garage. Best of all, the neighborhood gives you exclusive access to a private beach on the Chesapeake Bay for swimming, fishing, kayaking, and so much more!

4325 Willows Rd, Chesapeake Beach

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$395,000

4 Beds ⋅ 3 Baths

Welcome to this bright and airy end-unit townhome in the Richfield Station community of Chesapeake Beach. Sun-filled living spaces include a beautiful kitchen with an island and stainless-steel appliances that opens to the dining area and a spacious living room. The home backs onto serene, mature trees, filling the interior with abundant natural light through multiple windows and doors that lead to the deck. Located on a quiet, non-through street with minimal traffic, this residence offers peaceful everyday living. Condo association fees offer true low-maintenance convenience, covering trash service, lawn maintenance, and exterior maintenance. The roof was replaced in 2026. Richfield Station residents enjoy direct access to the Chesapeake Beach Railway Trail system and the Fishing Creek Boardwalk. You are just minutes from the Chesapeake Bay, its scenic boardwalk, beaches, restaurants, and the full "Bay Life" lifestyle. Calvert County provides convenient access to the region's major metropolitan areas, including Washington, D.C., Annapolis, Northern Virginia, and Ronald Reagan Washington National Airport.

8418 Clear Spring Dr Unit #1, Chesapeake Beach

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

$359,900

3 Beds ⋅ 3 Baths

Nestled in the charming Richfield Station Village, this delightful Colonial townhouse offers a perfect blend of comfort and style. Built in 2007, the home features a warm and inviting interior, highlighted by beautiful flooring and recessed lighting that create a cozy ambiance throughout. The spacious living area seamlessly flows into a dining area, ideal for gatherings and entertaining. The well-appointed kitchen boasts an island, perfect for casual meals or meal prep, and comes equipped with essential appliances including a built-in microwave, electric oven/range, and refrigerator. A pantry provides additional storage, ensuring your kitchen remains organized and functional. Upstairs, you'll find three generously sized bedrooms, providing ample space for relaxation and personalization. Outside, the property is enhanced by well-maintained sidewalks, inviting you to enjoy leisurely strolls in the neighborhood. An attached garage with a garage door opener offers secure parking and extra storage space. This home is not just a place to live; it's a sanctuary where memories are made. With its thoughtful design and modern conveniences, it's ready to welcome you home. Don't miss the opportunity to make this charming townhouse your own!

2221 Ivy Ln Unit #G-9, Chesapeake Beach

Listing courtesy of ExecuHome Realty. Contact:

$549,900

3 Beds ⋅ 2 Baths

Welcome to coastal living at its finest! This beautifully updated 3bed/2ba home blends modern luxury with everyday comfort. The large kitchen features upgraded quartz countertops, stainless steel appliances, and island, flowing seamlessly into the spacious living room with lots of natural light and luxury vinyl plank flooring throughout. Unwind in the spa-inspired bathrooms or relax on the private screened porch after a day at the beach. Situated on a large double corner lot, this home offers a fully fenced yard with plenty of room for outdoor living, entertaining, pets, or play. Ideally located just minutes from the boardwalk, restaurants, shopping, and entertainment, this home offers the perfect combination of luxury, convenience, and coastal charm. Whether you're searching for a full-time residence, vacation getaway, or an investment opportunity, this is one you won't want to miss!!

3800 28th St, Chesapeake Beach

Listing courtesy of Curtis Real Estate Company. Contact:

$439,000

3 Beds ⋅ 2 Baths

Welcome to your turn-key coastal sanctuary! This 3-bedroom, 2-bathroom home in the heart of Chesapeake Beach has been completely transformed from top to bottom. Enjoy complete peace of mind with a brand-new roof, fresh siding, brand-new deck, new flooring, and fresh paint throughout. The kitchen features modern finishes and feeds seamlessly into bright, spacious living areas, while both bathrooms are fully updated with stylish, modern touches. Outside, you'll find a spacious detached garage offering extra storage space for tools, gear, or a workshop. Situated just minutes from Chesapeake Beach amenities—including the bay, boardwalk, water park, charter fishing, and local dining. Perfect as a primary residence, coastal getaway, or turn-key investment. Move right in!

6114 4th St, Chesapeake Beach

Listing courtesy of Taylor Properties. Contact:

$739,900

3 Beds ⋅ 3 Baths

Rich solid bamboo flooring flows throughout the main living areas, while replacement windows maximize the breathtaking Bay views. The remodeled gourmet kitchen features quartz countertops, stainless steel appliances, and opens to a full-width waterfront deck—perfect for morning coffee, outdoor dining, or simply watching the boats pass by. The spacious family room also opens onto a private waterfront deck, creating seamless indoor and outdoor living. Upstairs, the primary suite becomes your personal waterfront retreat with its own private deck overlooking the Chesapeake Bay, beautifully updated bath, and the convenience of a dedicated washer and dryer. Two additional bedrooms enjoy water views as well, allowing family and guests to wake up to the beauty of the Bay every day. The walk-out lower level offers even more flexibility with a second washer and dryer, access to a stamped concrete waterfront patio, and a covered sitting area just steps from the shoreline—an ideal place to unwind after a day on the water. Residents enjoy exclusive access to a private community pier complete with a boat lift and fishing opportunities. Every Independence Day, neighbors gather to watch the spectacular fireworks display reflected across the Chesapeake Bay, creating a tradition you'll look forward to year after year. Located less than an hour from Washington, D.C., this home offers an exceptional primary residence, weekend escape, or second home without the hassle of Bay Bridge traffic. Enjoy the charm of Chesapeake Beach with its waterfront boardwalk, community beach, farmers markets, local breweries, boutique shopping, restaurants, outdoor concerts, marinas, and year-round events—all just minutes from your door. If you've been searching for true Chesapeake Bay waterfront living with modern updates, unforgettable views, and an unbeatable coastal lifestyle, this is the one.

8337 Bay Crest Ct, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$650,000

4 Beds ⋅ 4 Baths

Welcome to 8475 Saint Andrews Drive! This lovely home offers tons of space, and is the largest home in the neighborhood! The main level offers a living room, formal dining room, kitchen with granite countertops and stainless steel appliances, a breakfast room, a huge family room, and an expansive back deck. The 2nd level offers a palatial primary suite, including a full primary bathroom with a stall shower and separate soaking tub, a walk-in closet, and a private office. There are also three more bedrooms on the 2nd level along with another full bathroom. The basement features a rec room, plenty of storage space, a laundry/utility room, and an office/theater room with a separate outside entrance! The side yard area is fenced and there is also a storage shed in the back yard. The home is located in the awesome Highlands neighborhood, with recreation fields and a playground, and you're only a few minutes from everything that Chesapeake Beach and North Beach have to offer! This house is currently tenant-occupied, the tenants plan to move out by August 31st. Owner plans to repaint and clean property before going on the market.

8475 Saint Andrews Dr, Chesapeake Beach

Listing courtesy of Cerrito Realty, LLC. Contact: (301) 780-5880

$650,000

5 Beds ⋅ 4 Baths

Looking for true privacy with NO HOA, then look no further to this quaint Colonial nested in 5.09 acres of wooded area in Chesapeake Beach. The sprawling acreage has so much to offer - sit in your screened in porch, on your back deck, or build a fire pit & experience the nature. Inside you will find a well designed floor plan with room where you need it-5 bedrooms, 3.5 baths and over 3800 finished square ft. You will be welcomed with a separate living room/office & dining room at the front of the house. The kitchen is has lots of prep space & opens to the family room allowing you to cook & converse at the same time! The family room also has a cute bay window & a cozy pellet stove for those cold nights. The screened in porch off the kitchen is & a great space to gather & relax & gives the home character. Upstairs you will find a sunlit primary suite with walk in closet, a hall bath & 3 more SPACIOUS bedrooms. The walk out basement is fully finished, with 5th bedroom & full bath, HUGE recreation space with wood stove- an entertainers dream. The home has a newer ROOF with gutter guard system, newer windows, brand new carpeting on upper level. The kitchen, baths & the main level flooring are in need up updating & are awaiting for your personal touches. Second set of washer/dryer in garage, laundry sink, 2 sheds, and a fish cutting station. Zoned for AWARD WINNING SCHOOLS, northern Calvert county for easy commuting to DC, Annapolis, Andrews Air Force Base & more. Also enjoy the proximity to the twin beaches, offering boardwalk, swimming, farmers market and many great restaurants. Seller is also including a 1 year HOME WARRANTY through American Home Shield. You will not want to miss this WELL PRICED gem! Set up your showing today.

3555 Christiana Ct, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$469,900

3 Beds ⋅ 3 Baths

Open House Rescheduled for September 12th, starting at 1pm. Priced to SELL!! Charming home located in Summer City! You will discover a unique home that would be perfect for the family, with a mother in law/au pair suite downstairs. Definitely an air BNB vibe, that is ready to go, and the location is perfect! Close to the water, beaches, resorts and restaurants in Chesapeake Beach, and no HOA. This home is nestled on a beautiful lot that backs to the trees, and landscaped with mature Rose of Sharons and large shade trees. An easy commute to DC, Annapolis or Baltimore is about 35 minutes. This stunning split foyer residence, boasts a generous 1,978 sq. ft. of thoughtfully designed living space, perfect for an exclusive lifestyle, or entertaining the night away under the stars! The extra living spaces can easily be made into an office, or additional bedroom. Step inside to find a harmonious blend of comfort and functionality of a relaxed beachy lifestyle. The first level features a second kitchen and a traditional floor plan that flows seamlessly into a family room off the kitchen, ideal for entertaining. Perfect for an aging parent is the mother in law suite. The home includes 2 dishwashers, 2 electric oven/range, 2 refrigerator/freezer, 1 washer and 1 dryer, and one combo unit upstairs and have seperate electrical meters for each floor. The luxurious vinyl plank flooring and new plush carpeting downstairs creates a warm and inviting atmosphere throughout the home. Outside, the property is a private oasis, nestled on a 0.23-acre lot that backs to serene trees, offering a secluded retreat. The new improvements of expanding the deck to the whole length of the house, adding a 9 foot 3 panel sliding door to gain access via bedroom #2. The new balcony off the 1st Bedroom, with the another new 9ft 3 panel sliding door provides the perfect setting for al fresco dining or simply soaking in the breathtaking bay views while enjoying your morning coffee with a sunrise! Paved driveway parking and secure storage options, every detail has been considered for your comfort and convenience. Located within a bayblock setting, this home offers year-round access to the stunning Chesapeake Bay, inviting you to indulge in water-oriented activities at your leisure. Experience the ultimate in beach living, where every moment is a celebration of nature and sophistication. Don't miss your chance to call this exceptional property home! If you are looking for that perfect home that is versatile, with no HOA the opportunities are endless.

3932 Summer City Blvd, Chesapeake Beach

Listing courtesy of TCB Realtor, LLC.. Contact: 4438758847

$575,000

4 Beds ⋅ 3 Baths

NEW PRICE, MOVE-IN READY, easy drive to Andrews AFB, Washington DC , the Beltway. Looking for the perfect blend of privacy and accessibility? This low maintenance Colonial-style home, nestled on a generous 2.49-acre lot offers just that! No HOA!! A private paved driveway and surrounding hardwood trees provide privacy and a quick drive to Route 4 provides the convenience. Built in 2016, this 4 BR/ 2.5 BA residence features 2,464 square feet of living space plus an unfinished basement for storage and future improvements. The kitchen has been upgraded to include app-controlled LG Thin-Q appliances and granite counters, connected to a spacious family room with modern electric fireplace. It is a great entertaining flow! The lot is very private, and from the newer rear deck you will enjoy the hardwood trees and changing seasonal colors, also many varieties of birds. The parking area is plentiful, with a front-entry attached two car garage and a detached carport that is equipped with two 240v EV-ready NEMA 14-50 outlets. This home is more than just a property; it's a sanctuary where you can create memories that last forever. Chesapeake Beach town center with stores and restaurants is close by, and Prince Frederick is a 10 minute drive for more shopping and services. The lot has a Forest Retention Area (FRA) and a natural path for hikes and discovery! See boundary line survey notes for details.

3955 Breezy Point Rd, Chesapeake Beach

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 4103940990

$1,298,000

6 Beds ⋅ 5 Baths

Welcome Home to an Extraordinary Private Estate in Owens Soper Estates Hidden beyond a long, winding private driveway that gracefully meanders through 57 breathtaking acres of pristine woodland, this exceptional custom Colonial is the definition of luxury, privacy, and timeless elegance. Nestled within the prestigious Owens Soper Estates of Northern Calvert County, this is far more than a home—it is a once-in-a-lifetime opportunity to own an irreplaceable estate where every day feels like a private retreat surrounded by natural beauty, refined craftsmanship, and an unmistakable sense of grandeur. From the moment you enter the driveway, the outside world begins to disappear. Towering hardwoods, peaceful streams, abundant wildlife, and the soothing sounds of nature create an unforgettable arrival, leading you home to a place where serenity and sophistication exist in perfect harmony. Properties offering this level of privacy, luxury, and recreation are exceptionally rare and nearly impossible to replicate. Built in 2022, this stunning residence offers over 6,000 square feet of beautifully designed living space that blends refined craftsmanship with modern comfort. Every room has been thoughtfully designed to maximize elegance, functionality, and the breathtaking views surrounding the home. The expansive floor plan features four spacious bedrooms with the flexibility to easily accommodate up to six bedrooms, making it ideal for multigenerational living, guests, or personalized spaces. The home also offers 4.5 luxurious bathrooms, including a spa-inspired owner’s suite featuring a spectacular custom tiled dual shower, relaxing Jacuzzi soaking tub, and elegant finishes that create the perfect private retreat. At the heart of the home is a magnificent chef’s kitchen complete with premium finishes, an oversized center island, abundant cabinetry, and an impressive walk-in pantry. Whether hosting elegant gatherings or enjoying quiet evenings at home, this space was designed to bring people together. Two beautiful wood-burning fireplaces add warmth, charm, and timeless character throughout the living areas. The fully finished lower level expands the home’s versatility with an impressive recreation room, oversized home gym, additional flex rooms, guest accommodations, and abundant storage. Designed for today’s lifestyle, high-speed internet and two dedicated home offices allow you to work remotely while enjoying complete privacy and breathtaking natural surroundings. Outside, approximately 2.5 acres surrounding the home have already been cleared, providing the perfect canvas for a future resort-style pool, outdoor kitchen, guest house, gardens, or luxury entertaining space while preserving the beauty and privacy of the surrounding forest. Beyond the homesite, your own private outdoor paradise awaits. Miles of established trails, wide enough for ATVs, utility vehicles, horseback riding, or peaceful hikes, wind through mature hardwood forests alongside picturesque streams. Private bridge crossings provide easy access throughout the property, making every acre an adventure waiting to be explored. Rich with deer, turkey, and abundant native wildlife, this property is a dream for hunters, outdoor enthusiasts, photographers, hikers, and nature lovers alike. Mature walnut, pawpaw, and valuable hardwood trees further enhance the property’s beauty while offering future stewardship opportunities. With no HOA, you’ll enjoy the freedom to create the lifestyle you’ve always envisioned. Whether your dream includes a family compound, luxury outdoor amenities, a private homestead, or simply preserving your own secluded sanctuary, the possibilities are endless. Despite its incredible privacy, you’re only minutes from top-rated Calvert County schools, shopping, restaurants, hospitals, parks, marinas, and the charming waterfront communities of Chesapeake Beach and North Beach, offering waterfront dining, fishing boutique shops.

4485 Bristol Dr, Chesapeake Beach

Listing courtesy of CENTURY 21 New Millennium. Contact: 4439689595

$650,000

5 Beds ⋅ 4 Baths

Welcome to 2643 Richfield Lane! If you've been looking for a home with plenty of space, thoughtful updates, and room for everyone, this is one you won't want to miss. This beautifully maintained 5-bedroom Colonial offers the perfect blend of comfort, functionality, and classic style. From the moment you arrive, you'll appreciate the welcoming front porch—a great spot to enjoy your morning coffee or unwind in the evening. Inside, you'll find bright, inviting living spaces with updates throughout, making this home truly move-in ready. The kitchen is the heart of the home and opens to a sunny four-season sunroom that's perfect for casual meals, relaxing with a book, or simply enjoying the view of the backyard. Just outside, the spacious deck provides the ideal setting for cookouts, entertaining friends, or spending time with family. The fully finished basement adds even more living space and includes a fifth bedroom, making it perfect for guests, a home office, a recreation room, gym, or whatever fits your lifestyle. Whether you need space for a growing family, work from home, or simply enjoy having room to spread out, this home offers the flexibility you've been searching for. Located in the desirable Richfield Station community, you'll enjoy the convenience of being just minutes from Chesapeake Beach, North Beach, marinas, restaurants, shopping, parks, and commuter routes while still coming home to a quiet, established neighborhood. This is more than just a house—it's a place to make memories. Schedule your private showing today and come see everything 2643 Richfield Lane has to offer.

2643 Richfield Ln, Chesapeake Beach

Listing courtesy of Taylor Properties. Contact:

$459,900

3 Beds ⋅ 2 Baths

**LESS THAN 2 MILES TO THE CHESAPEAKE BAY!** Live the Salt Life Year-Round in Chesapeake Beach! Situated on **1.28 private acres** and backing to woods, this home offers space, privacy and a fantastic location in **The Highlands**. Recent updates include **NEW LVP flooring – June 2026 * Stainless Steel Kitchen Appliances & Hot Water Heater – 2025 * Shed & Lower-Level Flooring – 2024 * Heat Pump – 2022 * Metal Roof – 2014.** Enjoy new flooring throughout the main level plus a **FULLY FINISHED LOWER LEVEL** offering plenty of additional living and entertaining space. The Highlands offers walking trails, playgrounds and sports courts with an HOA of only **$85/year**. Just minutes to the Twin Beaches and all the Chesapeake Bay lifestyle has to offer—beaches, marinas, fishing piers, boardwalks, restaurants, Farmers Market and more! Convenient to **D.C., Annapolis, Baltimore & Joint Base Andrews.** Great schools, great neighborhood, and your chance to enjoy Chesapeake Beach living!

2811 Glasgow Way, Chesapeake Beach

Listing courtesy of RE/MAX United Real Estate. Contact:

$360,000

3 Beds ⋅ 2 Baths

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 large and great for entertaining. 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.

4820 Sherwood Ave, Chesapeake Beach

Listing courtesy of O'Brien Realty ERA Powered. Contact: 3018632400

$685,000

5 Beds ⋅ 4 Baths

BUYER failed to perform so we are BACK on the MARKET! Now is your opportunity! Welcome to 3671 Middle Ground Court, where comfort, space, and the Chesapeake lifestyle come together in one exceptional home. This beautifully maintained traditional Colonial offers five bedrooms, three and a half bathrooms, and a thoughtfully designed floor plan that's perfect for everyday living and entertaining alike. Step inside to discover refreshed hardwood floors (2026), new carpet in the front living room (2026), and spacious living areas filled with natural light. The fully finished lower level expands your living space with brand-new flooring (2018), a full bathroom, and a versatile bonus room that's already wired for a theater system—ideal as a media room, home gym, or fifth bedroom. Outside, the fully fenced backyard provides a private retreat where children and pets can safely run and play, while the oversized attached two-car garage offers ample room for vehicles, storage, and hobbies. Recent updates provide peace of mind, including a new dishwasher (2024), privacy fence (2022), custom primary closet system (2021), and sump pump (2018), making this home truly move-in ready. Located just steps from Bayfront Park and Brownie's Beach, you'll love being able to walk to the waterfront, enjoy beach days, fossil hunting, stunning Chesapeake Bay sunsets, and all the charm that Chesapeake Beach has to offer. Don't miss this opportunity to settle into your new home just in time to enjoy everything summer on the Bay has to offer!

3671 Middle Ground Ct, Chesapeake Beach

Listing courtesy of Real Broker, LLC - Severna Park. Contact: 8445517325

$1,200,000

5 Beds ⋅ 4 Baths

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.

4011 27th St, Chesapeake Beach

Listing courtesy of Keller Williams Realty. Contact: (703) 679-1700

$515,000

3 Beds ⋅ 3 Baths

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.

4010 Beach Dr, Chesapeake Beach

Listing courtesy of Paul Wesley Real Estate. Contact: 7032822709

$190,000

3 Beds ⋅ 2 Baths

This property is being sold as-is and is perfect for investors, flippers, or buyers looking for a renovation opportunity. With solid bones and endless potential, this home is a blank canvas ready for your vision. Whether you’re looking to fix and flip, hold as a rental, or bring new life to a great location—this is the one. Cash, hard money, or renovation loan preferred. Don’t miss this chance to invest in a property with serious upside!

6231 8th St, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 7033788810

$799,000

2 Beds ⋅ 1 Baths

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!

3713 & 3711 Bayview Dr, Chesapeake Beach

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$759,900

3 Beds ⋅ 5 Baths

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!

8048 Windward Key Dr, Chesapeake Beach

Listing courtesy of Compass. Contact: (410) 429-7425

$749,900

4 Beds ⋅ 5 Baths

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.

8076 Windward Key Dr, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$774,900

4 Beds ⋅ 5 Baths

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.

8054 Windward Key Drive, Chesapeake Beach

Listing courtesy of RE/MAX Realty Group. Contact:

$179,000

Build you coastal escape! Large Corner lot is perfectly situated in new 4 lot community ready for your custom dream home. Imagine weekends spent exploring the boardwalk, beaches, crabbing, charter boat fishing or just enjoying the many local restaurants. Bring your builder and start experiencing the Chesapeake Bay lifestyle you've always imagined.

Lot 22R Block 8, 18th St, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$99,000

Your chance to build your dream home above it all. Perched on a hill in the coveted Chesapeake Beach area, this nearly 1/2 acre lot offers an unparalleled lifestyle. You're just minutes to the Boardwalks, beach, resort style dining, charter fishing, and more! Don't miss this rare opportunity. Come see the potential for yourself.

Lot 22R Block 7, 18th St, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$199,000

Your Private Sanctuary Awaits! Escape to this exclusive, wooded retreat. Imagine building your dream home nestled among mature trees, just moments from the best of the Chesapeake Bay. Whether it's a morning stroll on the boardwalk, a day of crabbing and fishing or an evening of dining and entertainment, everything is at your fingertips. This is more than a lot; it's your gateway to endless coastal fun. Previous Percs but will need new. Buyer to confirm all with county.

Lot 30 A, Block 6, 18th Street, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291

$699,999

4 Beds ⋅ 3 Baths

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.

8314 Bayside Rd, Chesapeake Beach

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895

$165,000

PRICE IMPROVEMENT on this amazing lot in Chesapeake Beach. Rare opportunity to build your custom home on a prime lot with Chesapeake Bay views. Located at 8314 Bayside Road, this property offers year-round water views, coastal charm, and the convenience of public water, sewer hookups, and electric availability. Relax on your new front porch soaking in the bay breeze and peaceful surroundings. Enjoy easy access to the North Beach boardwalk, marinas, Brownie’s Beach, and local restaurants. Create your ideal waterfront lifestyle while remaining conveniently located near Annapolis, Washington, D.C., Andrews AFB, Baltimore, and Northern Virginia. Build your vision in Chesapeake Beach!

8314 Bayside Rd, Chesapeake Beach

Listing courtesy of JPAR Real Estate Professionals. Contact: 3016844895

$390,000

6 Beds ⋅ 2 Baths

This is the chance to own 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 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.

6337 Dory Ct, Chesapeake Beach

Listing courtesy of Hyatt & Company Real Estate LLC. Contact: 4107056296

$55,000

This Does have a old well on it. It will need to be perc for septic. Nice flat lot to build on close to the beach in Randle Cliff area. Close to shopping/beach/ waterpark.

4200 Chesapeake Ave, Chesapeake Beach

Listing courtesy of Samson Properties. Contact: 4439757555

$136,900

Beach and pier access on the Chesapeake Bay. Wooded 1.75± acre homesite with a partial water view. Located in an established waterfront community offering natural privacy and coastal ambiance.

4685 Camp Roosevelt Dr, Chesapeake Beach

Listing courtesy of Home Towne Real Estate. Contact: 8882252736

$90,000

Incredible value in Northern Calvert County! Priced aggressively at $90,000, this perced and private 3 acre lot offers a rare chance to secure a buildable homesite well below market value. To achieve a fully buildable status, the buyer will need to complete the final subdivision process (estimated at $25k and roughly 12 months to process) and handle the TDR allocation (estimated at $30k). With an all-in land investment of approximately $145,000, the equity potential here is unmatched for the northern end of the county. Perfect for a savvy buyer or builder looking to lock in a great price now while finalizing their custom home plans over the next year.

3164 Dalrymple Rd, Chesapeake Beach

Listing courtesy of RE/MAX One. Contact: 4105356291