Holiday Harbor Homes with Coastal Style

Welcome to Holiday Harbor, a picturesque subdivision nestled in the serene surroundings of Bishopville, Maryland, within the charming Worcester County. This coastal gem is a haven for those seeking a tranquil lifestyle infused with the beauty of nature and the allure of the sea.

Holiday Harbor is renowned for its stunning homes that embody the essence of coastal living. Each residence is thoughtfully designed to reflect a relaxed, beach-inspired aesthetic, featuring open floor plans, large windows that invite in natural light, and outdoor spaces perfect for soaking up the sun or enjoying the gentle ocean breeze. Whether you’re sipping your morning coffee on a spacious deck or hosting friends for a sunset barbecue, these homes are crafted for both comfort and style.

The community is ideally situated just a stone's throw away from the pristine beaches of the Atlantic Ocean, making it a perfect retreat for water enthusiasts. Residents can indulge in a variety of outdoor activities, from boating and fishing to kayaking and beachcombing. The nearby Assateague Island National Seashore offers breathtaking views and opportunities for wildlife observation, ensuring that adventure is always at your fingertips.

In addition to its natural beauty, Holiday Harbor fosters a warm, welcoming community spirit. Neighbors become friends, and local events bring everyone together, creating a vibrant atmosphere that makes you feel right at home.

If you’re looking for a slice of paradise where coastal charm meets modern living, Holiday Harbor is your ideal destination. Discover your dream home in this enchanting subdivision and embrace the coastal lifestyle you've always desired!

Newest Holiday Harbor Homes with Coastal Style

$525,000

3 Beds ⋅ 2 Baths

Welcome to this well-appointed 3-bedroom, 2-bathroom home in Bishopville, MD, built in 2021 and offering modern finishes, an inviting open floor plan, and a peaceful canal-front setting. Relax on the covered front porch before stepping inside to a spacious living room featuring vaulted ceilings and a cozy propane fireplace. The kitchen is designed for both everyday living and entertaining with upgraded countertops, an island with seating, stainless steel appliances, and a bright breakfast area. The private primary suite features elegant tray ceilings, an oversized dual-sink vanity, a soaking tub, and a walk-in tile shower. Two additional bedrooms share a full bathroom, providing comfortable accommodations for family or guests. Step outside to the back patio and enjoy the canal views, creating the perfect backdrop for relaxing or entertaining outdoors. Built in 2021, this home offers the benefits of modern construction while being conveniently located just a short drive from the beaches, shopping, dining, and attractions of Maryland and Delaware's coast. Don't miss the opportunity to make this beautiful property your own!

11207 Charlie Dr, Bishopville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: 3028460200

$724,900

4 Beds ⋅ 3 Baths

Welcome to your waterfront 1.35 acre retreat in Holiday Harbor—where coastal charm meets everyday comfort. This beautifully maintained 4 bedroom, 2.5-bath home offers the perfect blend of relaxed living and functional space. From the moment you step inside, you’ll appreciate the light-filled interiors, open flow, and thoughtful layout designed for both entertaining and quiet evenings at home. The spacious main living area invites you to unwind while enjoying serene water views. The well-appointed kitchen offers ample cabinetry and counter space, making meal prep effortless whether you're hosting guests or enjoying a quiet dinner in. The adjoining dining area provides the perfect setting for gathering with family and friends. Upstairs, the primary suite serves as a private retreat, complete with an en-suite bath and generous closet space. Two additional bedrooms provide comfort and flexibility for family or guests. A versatile den adds even more value—ideal as a home office, playroom, or easily converted into a 5th bedroom to suit your needs. Step outside and experience the true highlight of this property: direct boat access to the Saint Martins Neck River. Whether you enjoy early morning fishing trips, sunset cruises, kayaking, or simply soaking in the peaceful waterfront setting, this home makes it all possible right from your backyard. With its prime waterfront location, flexible living space, and easy access to the river, this Holiday Harbor gem offers the lifestyle you’ve been dreaming of. Don’t miss your opportunity to make it yours. Sellers are offering a $5000 flooring allowance with acceptable contract.

11244 W Marie Dr, Bishopville

Listing courtesy of Coldwell Banker/Bud Church Rea. Contact: (410) 524-7888

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