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Chesapeake Beach MD Real Estate & Homes for Sale

27 Properties Found

The median home value in Chesapeake Beach, MD is $487,500. This is higher than the county median home value of $360,000. The national median home value is $308,980. The average price of homes sold in Chesapeake Beach, MD is $487,500. Approximately 81.5% of Chesapeake Beach homes are owned, compared to 13.5% rented, while 5% are vacant. Chesapeake Beach real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chesapeake Beach real estate agent to arrange a tour today!
Learn more about Chesapeake Beach Real Estate.


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Beds:
2
Baths:
1.00
Sq.Ft.:
719
Status:
NEW LISTING
MLS#:
MDCA2027710
Type:
Single Family
Subdivision:
SUMMER CITY
Lot size:
0.18 Acres
Year built:
1950
Courtesy: RE/MAX One
View additional info

Welcome to charming 6122 6th St, nestled within the Chesapeake Beach community. This home is back on the market with a new well, new roof, covered outdoor living area, separate fenced in yard, and overall refresh. This cozy home features two bedrooms, a remolded bathroom, and a spacious kitchen with lots of storage and brand-new appliances. The open floor plan allows unlimited opportunities for you to transform the space to your specific needs. This home is conveniently located near shopping, commuter routes, and has easy access to the local beaches and boardwalks.

Beds:
5
Baths:
4.00
Sq.Ft.:
2,600
Status:
NEW LISTING
MLS#:
MDCA2027692
Type:
Single Family
Subdivision:
BROOKESIDE
Lot size:
0.74 Acres
Year built:
1989
Courtesy: Real Broker, LLC - Dunkirk
View additional info

Welcome home to this beautifully updated 5-bedroom, 3.5-bath residence offering the perfect blend of space, style, and everyday comfort in a sought-after neighborhood. Situated within a highly rated school district, this home is ideal for those looking for modern upgrades, functional living spaces, and room to grow. Step inside to find spacious, light-filled living areas and generously sized bedrooms designed with both comfort and practicality in mind. The updated kitchen features sleek finishes, stainless steel appliances, and plenty of space for gathering, while the beautifully renovated bathrooms add a touch of luxury throughout the home. Outside, the expansive lot provides endless possibilities - from entertaining and gardening to relaxing evenings in your own backyard retreat. Additional highlights include a cozy fireplace, energy-efficient windows, and a spacious two-car garage for added convenience. This move-in ready home combines modern updates, timeless comfort, and an unbeatable location. Don't miss your chance to make it yours - schedule your private showing today!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,716
Status:
NEW LISTING
MLS#:
MDCA2027012
Type:
Single Family
Subdivision:
SUMMER CITY
Lot size:
0.41 Acres
Year built:
1986
Courtesy: Central Properties, LLC,
View additional info

Beautifully renovated split foyer offering fresh updates and move-in ready appeal! Major improvements completed in 2022 include the roof, windows, and deck, along with interior updates throughout. This home offers comfortable living space, a functional split-foyer layout, and outdoor space to enjoy. Conveniently located near local recreation and waterfront amenities, including the Chesapeake Bay, Chesapeake Beach Railway Museum, Chesapeake Beach Rail Trail, water park, marinas, piers, restaurants, and charter boat fishing. A great opportunity to enjoy the Chesapeake Beach lifestyle with many recent updates already in place!

Open House:

Sunday, 6/7 1:00-3:00PM

Beds:
3
Baths:
3.00
Sq.Ft.:
2,641
Status:
NEW LISTING
MLS#:
MDCA2027398
Type:
Townhouse
Subdivision:
RICHFIELD STATION VILLAGE
Year built:
2008
Courtesy: Coldwell Banker Realty
View additional info

This bright, spacious 2,600 sq. ft. townhome in Chesapeake Beach's desirable Richfield Station features 3 bedrooms, 2.5 baths, and a 1-car garage plus assigned space. Enjoy new HVAC and appliances, plus neighborhood walking trails, a playground, and basketball court - just a short distance to the Chesapeake Beach boardwalk and dining!

Beds:
3
Baths:
1.00
Sq.Ft.:
960
Status:
NEW LISTING
MLS#:
MDCA2027448
Type:
Single Family
Subdivision:
SUMMER CITY
Lot size:
0.18 Acres
Year built:
1983
Courtesy: Home Towne Real Estate
View additional info

So much to love here in the Chesapeake Beach rambler! Pull right in to your covered carport and additional off street parking. Inside you will find a traditional floor plan with a spacious family room leading to the eat in kitchen with updated appliances and granite counter tops. A separate laundry room offers potential for additional storage or pantry. Three bedrooms and updated full bath complete the inside. Newer plank floors, windows and more. Outback finds a level yard, deck and a storage shed. Close to all the beaches, entertainment, restaurants and shopping that the twin beaches area has to offer!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,504
Status:
NEW LISTING
MLS#:
MDCA2027444
Type:
Townhouse
Subdivision:
CHESAPEAKE STATION
Lot size:
0.05 Acres
Year built:
1986
Courtesy: RE/MAX One
View additional info

Welcome to 7832 C St., Chesapeake Beach, MD 20732, a rare opportunity to own an updated end-unit townhome with community Chesapeake Bay views in the highly sought-after Chesapeake Station community. This 2 bedroom, 2 full bathroom home is within walking distance to the Chesapeake Bay, restaurants, shopping, marinas, and the Rod 'N Reel Resort, offering the ideal combination of coastal lifestyle, convenience, and low-maintenance living. This beautifully maintained end-unit townhome offers additional privacy, natural light, and desirable outdoor living space. From the rear composite deck, you can enjoy peaceful views of Fishing Creek, creating the perfect setting for relaxing or entertaining. The home features numerous upgrades throughout, including an updated kitchen, upgraded bathrooms, porcelain tile flooring, quality Andersen windows, and a low-maintenance composite deck designed for beauty and easy maintenance. Inside, the home offers bright living areas, multiple levels of functional living space, and a layout designed for comfortable everyday living and entertaining. Large windows and outdoor spaces help bring the surrounding coastal setting into everyday life. The home also features a newer roof (2025), providing additional value and peace of mind. Just a short walk from the home, residents enjoy sweeping 180-degree Chesapeake Bay community views, a private sandy beach, kayak launch, and kayak storage area that make it easy to fully embrace waterfront living. Once you experience the sunsets, bay breezes, and walkable lifestyle this community offers, you may never want to leave. Walk just minutes to Roland's Grocery Store, local restaurants, boutiques, entertainment, and the waterfront districts of both Chesapeake Beach and North Beach. Commuter distances include approximately 50 miles to Annapolis; 37 miles to Washington, DC; 27 miles to Joint Base Andrews; and approximately 31 miles to Coast Guard Headquarters and DHS Headquarters. The home also offers convenient access to Route 2 and Route 4 while still delivering the relaxed feel of a waterfront retreat. Homes within Chesapeake Station rarely become available, especially with this combination of updates, privacy, water-oriented amenities, and walkable coastal convenience. If you're searching for an affordable Chesapeake Bay lifestyle home, weekend retreat, investment opportunity, or full-time residence near the water, 7832 C St. is a must-see.

Beds:
2
Baths:
1.00
Sq.Ft.:
896
Status:
NEW LISTING
MLS#:
MDCA2027370
Type:
Single Family
Subdivision:
BREEZY POINT
Lot size:
0.3 Acres
Year built:
1955
Courtesy: Samson Properties
View additional info

Chesapeake Beach Coastal Retreat Welcome to 5237 Breezy Point Rd, Chesapeake Beach, MD - your perfect escape by the water! 2 Bedrooms, 1 Bath Sleeps 5-6 comfortably Steps from the beach Fully renovated & move-in ready Breathtaking sunrises and sunsets Imagine waking up to the sound of the waves, sipping coffee while watching the sunrise over the Chesapeake Bay, and ending your evenings with stunning sunset skies just steps from your door. This charming coastal retreat offers the perfect blend of relaxation and modern comfort, making it ideal as a primary residence, weekend getaway, vacation home, or investment property. Enjoy beach walks, salty breezes, peaceful mornings, and the laid-back Chesapeake Beach lifestyle - all at an incredible value. Whether you're entertaining guests, escaping city life, or searching for your own slice of waterfront paradise, this home delivers the lifestyle everyone dreams about. You've got to come to this Affordable Coastal Living Home With Private Beach Access - Without the Million-Dollar Price Tag. Still being within commuting distance to DC/MD/VA areas At $380K, this listing hits a sweet spot for: first-time buyers, downsizers, weekend/vacation-home buyers military buyers using VA buyers priced out of Annapolis waterfront living, remote workers wanting lifestyle over square footage Come take a look and Say Yes to this Address! (The furnishings are negotiable)

Beds:
3
Baths:
2.00
Sq.Ft.:
2,597
Status:
Active
MLS#:
MDCA2027288
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.28 Acres
Year built:
1992
Courtesy: Samson Properties
View additional info

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!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,666
Status:
Active
MLS#:
MDCA2027198
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.2 Acres
Year built:
1973
A broker reciprocity listing Courtesy: Keller Williams Flagship
View additional info

Prime One-Level Living in the Heart of Chesapeake Beach - Walk to Everything! Discover effortless beach town living in this charming 3-bedroom, 2-full-bathroom rambler perfectly positioned in desirable Chesapeake Beach. Enjoy true one-level convenience with no stairs to navigate and an open concept kitchen. This home sits on a corner lot just steps from the vibrant heart of the Twin Beaches. With easy access to the scenic boardwalk, beaches, boutique shops, and an array of top-rated restaurants and cafes. You're literally moments away from dining at one of the area's finest spots, Baia Coastal Italian Kitchen & Wine Bar, renowned for its fresh seafood, house-made pasta, and stunning waterfront views. Inside, the open-concept layout seamlessly connects the spacious living room, dining area, and large kitchen - perfect for gatherings and everyday flow. Beautiful hardwood floors grace the common areas, adding warmth and timeless appeal. The kitchen is complete with Corian countertops, plenty of workspace, and brand-new stainless steel appliances. The entire home has been freshly painted throughout for a bright, move-in-ready feel. All three bedrooms are generously sized - a rare find in the Twin Beaches area - offering ample space for family, guests, or a home office. The level, easy-to-maintain yard is framed by a front deck and back deck, creating wonderful outdoor spaces (decks could use a little TLC to make them shine even brighter). Additional highlights include off-street parking for convenience, new HVAC (2024), new Water Heater (2024) and water views from the property, with exciting potential for enhanced bay vistas if a second story is ever added in the future. Live the Chesapeake Beach lifestyle - beach days, boardwalk strolls, fresh seafood dinners, and sunset views - all right at your doorstep. Don't miss this rare opportunity for single-level coastal charm in an unbeatable location!

Beds:
2
Baths:
1.00
Sq.Ft.:
1,253
Status:
Active
MLS#:
MDCA2027056
Type:
Single Family
Subdivision:
WILLOWS COLONY
Lot size:
0.19 Acres
Year built:
1952
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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!

Open House:

Sunday, 6/7 1:00-3:00PM

Beds:
3
Baths:
4.00
Sq.Ft.:
2,112
Status:
Active
MLS#:
MDCA2026834
Type:
Townhouse
Subdivision:
BAYVIEW HILLS
Lot size:
0.03 Acres
Year built:
2001
Courtesy: Caprika Realty
View additional info

7967 Delores Ct offers the perfect blend of comfort, thoughtful updates, and the coastal lifestyle Chesapeake Beach is known for. This beautifully maintained 3-bedroom, 3.5-bath home features over 2,000 square feet of living space with fresh updates throughout, including new paint (2026), new upstairs and basement flooring, updated primary bath, and brand-new low-pile carpet with Spill Guard protection designed for easier everyday living and cleaning. The home's inviting layout offers multiple comfortable living spaces along with one of the community's few screened-in porches, creating the perfect spot to enjoy beautiful sunrise views and seasonal glimpses of the bay during the winter months. Outside, the newly added front patio provides even more space to relax and enjoy the peaceful surroundings. Major system updates offer added peace of mind, including a new HVAC system installed in 2024 and a new water heater in April 2026. Located in a desirable Chesapeake Beach community, residents enjoy access to Brownie's Beach, exclusive to town residents, along with HOA access to a free boat and RV storage lot. Outdoor enthusiasts will also appreciate the home's close proximity to Fishing Creek Trail, offering convenient access to nature, walking, and recreation right nearby. Conveniently located near local shops, dining, marinas, and waterfront attractions, this home offers a wonderful opportunity to enjoy both comfort and coastal living in Southern Maryland.

Beds:
4
Baths:
4.00
Sq.Ft.:
2,613
Status:
Active
MLS#:
MDCA2026972
Type:
Single Family
Subdivision:
PINEWOOD ACRES
Lot size:
3 Acres
Year built:
1986
Courtesy: CENTURY 21 New Millennium
View additional info

10,000$$ SELLER CREDIT!! 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.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,364
Status:
Active
MLS#:
MDCA2026890
Type:
Single Family
Subdivision:
OWEN SOPER ESTATES
Lot size:
3 Acres
Year built:
1986
A broker reciprocity listing Courtesy: Deep Roots Real Estate
View additional info

Welcome to this beautifully maintained 5-bedroom, 3.5-bath home situated on 3 private acres located on a quiet dead-end street, offering space, privacy, and convenience all in one.The home features an updated kitchen and renovated bathrooms, along with a finished basement complete with a second kitchen, bedroom, full bath, and separate entrance, creating excellent flexibility for guests, extended family, or multi-generational living. Major system updates provide peace of mind, including a NEW water heater, NEW HVAC systems (2023 & 2026), a metal roof (2015), and new vinyl siding (2021). Polybutylene (Poly B) plumbing was identified during a prior home inspection. Seller is willing to provide up to a $5,000 escrow/credit toward replacement of the polybutylene piping with an acceptable offer. Enjoy everyday functionality with a convenient mudroom and outdoor living on the spacious deck overlooking a private backyard. The property is ready for your homestead dreams, perfect for chickens, gardening, or simply enjoying wide-open space. With no HOA, a highly rated school district, proximity to area beaches, restaurants, entertainment and an ideal commuter location, this property offers the best of peaceful living with easy access to everything you need. Make your appointment today.

Beds:
3
Baths:
5.00
Sq.Ft.:
3,084
Status:
Active
MLS#:
MDCA2026816
Type:
Townhouse
Subdivision:
WINDWARD KEY
Lot size:
0.04 Acres
Year built:
2002
Courtesy: Compass
View additional info

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!

Beds:
5
Baths:
4.00
Sq.Ft.:
6,715
Status:
Active
MLS#:
MDCA2026524
Type:
Single Family
Subdivision:
NORTH CALVERT WOODS
Lot size:
2.25 Acres
Year built:
2018
Courtesy: Hyatt & Company Real Estate LLC
View additional info

***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.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,028
Status:
Active
MLS#:
MDCA2026460
Type:
Townhouse
Subdivision:
SEA GATE
Lot size:
0.03 Acres
Year built:
1999
Courtesy: Long & Foster Real Estate, Inc.
View additional info

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!

Open House:

Sunday, 6/7 1:00-3:00PM

Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
MDCA2026442
Type:
Townhouse
Subdivision:
RICHFIELD STATION VILLAGE
Year built:
2007
Courtesy: RLAH @properties
View additional info

Welcome to 2183 Ivy Lane in Chesapeake Beach, MD, where comfort, convenience, and low-maintenance living come together in one beautifully updated home, now with incredible buyer incentives! The seller is offering 3% closing cost assistance, providing exceptional value and added flexibility for buyers. This sought-after 2 over 2 condo floor plan offers the spacious feel of a townhome while providing the ease and affordability of condo living. Freshly repainted and featuring brand-new carpet throughout, this move-in ready home is filled with natural light and thoughtfully designed living spaces. The main level offers an open and functional layout with a spacious living room, dining area, and a well-appointed kitchen featuring ample cabinetry and counter space, perfect for both everyday living and entertaining guests. Upstairs, you'll find generously sized bedrooms, including a private primary suite with excellent closet space and separation from the main living areas for added comfort and privacy. One of the standout features of this home is the exceptional value offered through the condo association. Condo fees cover water and sewer usage, the front foot fee, and major exterior structural maintenance including the roof and siding, allowing for truly low-maintenance homeownership and added peace of mind. The HOA also maintains the community grounds and common areas, helping preserve the neighborhood's attractive appearance year-round. Residents enjoy a variety of community amenities including playgrounds, tennis and pickleball courts, a basketball court, and a roller hockey court, offering recreation and outdoor enjoyment just steps from home. Parking is a rare bonus with three assigned parking spaces, including a one-car rear-entry garage, a private driveway parking space directly outside the garage, and an additional designated parking space located in front of the unit. The garage also provides excellent additional storage space. For even more confidence, the current homeowners are including a home warranty valid through May 2027, helping cover major systems and appliances including the HVAC system, water heater, and kitchen appliances. Ideally located just minutes from the beaches, boardwalk, restaurants, marinas, shopping, and parks of nearby North Beach and Chesapeake Beach. Residents also enjoy access to a community walking trail leading to downtown Chesapeake Beach, complete with scenic boardwalks and beautiful Chesapeake Bay water views. Convenient commuter access to Annapolis, Washington, D.C., and surrounding areas makes this location as practical as it is charming. Whether you're a first-time buyer, downsizing, searching for a weekend getaway, or looking for an investment opportunity, this beautifully updated home offers outstanding value, desirable amenities, low-maintenance coastal living, and substantial buyer savings with 3% closing cost assistance and negotiable seller terms.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,433
Status:
Active
MLS#:
MDCA2026440
Type:
Townhouse
Subdivision:
WINDWARD KEY
Lot size:
0.04 Acres
Year built:
1989
Courtesy: RE/MAX Realty Group
View additional info

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,363
Status:
Active
MLS#:
MDCA2025332
Type:
Townhouse
Subdivision:
WINDWARD KEY
Lot size:
0.06 Acres
Year built:
2002
Courtesy: RE/MAX Realty Group
View additional info

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,916
Status:
Active
MLS#:
MDCA2025422
Type:
Single Family
Subdivision:
THE HIGHLANDS
Lot size:
0.68 Acres
Year built:
1985
Courtesy: Hutchins Properties
View additional info

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!

Open House:

Sunday, 6/7 1:00-4:00PM

Beds:
2
Baths:
1.00
Sq.Ft.:
1,068
Status:
Active
MLS#:
MDCA2025794
Type:
Single Family
Subdivision:
HOLIDAY BEACH
Lot size:
0.44 Acres
Year built:
1950
Courtesy: Flag Real Estate Inc.
View additional info

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.

Beds:
4
Baths:
5.00
Sq.Ft.:
3,063
Status:
Active
MLS#:
MDCA2025610
Type:
Townhouse
Subdivision:
WINDWARD KEY
Lot size:
0.04 Acres
Year built:
2002
Courtesy: Coldwell Banker Realty
View additional info

Nestled along the tranquil shores of Chesapeake Beach, this stunning four-bedroom, four-and-a-half-bath waterfront townhome offers 2,632 square feet of thoughtfully designed living space for those who appreciate the beauty of life on the water. Expansive decks on every level provide uninterrupted views, where you can savor gentle breezes and watch local crab boats set out at sunrise. Also, the home has 2 brand new HVAC systems, new carpet and has been freshly painted. Move right in and start enjoying your new beach life! Because of its location within the community, you can also sit on any one of your decks and catch all the summer concerts, for free, being held in the resort's bandshell directly across the creek. This is also the perfect location to catch the famous, Chesapeake Beach, 4th of July fireworks without ever leaving home. Residents enjoy exclusive access to a private community beach, beach side pool, pickleball courts, and even has a marina (marina slips are extra and are not deeded to the unit) - creating an effortless blend of leisure and coastal charm. Whether you are launching a kayak right outside your backdoor or taking a scenic hike along Chesapeake Beach's Old Raildroad trail or shark tooth hunting on the beach, there are endless possibilities. Whether you dock your own boat at the Rod &Reel or Marina West, or hire a charter, world class fishing and crabbing are just footsteps away. You can also walk to the Rod & Reel Resort and all it has to offer, as well as other in-town restaurants and shopping within Chesapeake Beach. Within walking distance of Windward Key are multiple marinas. Pull your boat up to the boardwalk, right outside your door, to load it up and enjoy life on the bay! Whether you're seeking a peaceful weekend retreat or a full-time sanctuary, only 45 minutes from Annapolis and less than an hour from Washington, DC, this exceptional home offers an inviting opportunity to experience refined waterfront living at its finest.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,857
Status:
Active
MLS#:
MDCA2025486
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.21 Acres
Year built:
1988
Courtesy: Coldwell Banker Realty
View additional info

Beach living at its best in the heart of Chesapeake Beach, with bay views right from your deck. Embrace the coastal lifestyle in this spacious home offering over 2,800 square feet, four well-appointed bedrooms, and the convenience of an elevator. The property also features a fully fenced yard, a two-car garage, and a versatile detached outbuilding that can easily serve as a gym, workshop, office, guest space, creative studio or anything else you want it to be. It currently accommodates gym equipment and a full-size hot tub. Enjoy spectacular views from the upper level and the rare ability to walk to everything both Chesapeake Beach and North Beach have to offer - restaurants, boardwalks, marinas, and local attractions. Whether you're searching for a full-time coastal residence or the quintessential weekend beach retreat, this home offers the space, flexibility, and location to make it your own. The size, structure, and possibilities are all here - bring your vision and create the beach home you've been dreaming of.

Beds:
6
Baths:
2.00
Sq.Ft.:
2,080
Status:
Active
MLS#:
MDCA2025036
Type:
Single Family
Subdivision:
DORY COURT
Lot size:
0.72 Acres
Year built:
1983
Courtesy: Hyatt & Company Real Estate LLC
View additional info

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,802
Status:
Active
MLS#:
MDCA2025262
Type:
Single Family
Subdivision:
NONE AVAILABLE
Lot size:
0.15 Acres
Year built:
2026
Courtesy: JPAR Real Estate Professionals
View additional info

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.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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