Holiday Harbor Homes for Sale

Welcome to Holiday Harbor, a hidden gem nestled in the heart of Bishopville, Maryland. This charming subdivision offers a unique blend of tranquility and community spirit, making it the perfect place for families, retirees, and anyone looking to escape the hustle and bustle of city life. With its picturesque surroundings and proximity to the stunning shores of the Atlantic Ocean, Holiday Harbor is an ideal location for those who appreciate nature, leisure, and a tight-knit neighborhood atmosphere.

The homes for sale in Holiday Harbor boast a variety of architectural styles, catering to diverse tastes and preferences. From cozy single-family homes to spacious waterfront properties, there’s something for everyone in this delightful community. Many of these residences feature modern amenities, open floor plans, and beautifully landscaped yards, providing both comfort and style. Imagine waking up to serene views and enjoying evenings on your deck, all while being just a short drive from the vibrant attractions of Ocean City.

Beyond the beautiful homes, residents of Holiday Harbor enjoy a range of recreational activities. Whether you’re an avid boater, fisherman, or simply love spending time outdoors, the nearby waterways and parks offer endless opportunities for adventure. The community also hosts seasonal events and gatherings, fostering a warm and welcoming environment for all.

If you’re searching for a place that combines the beauty of nature with the comforts of home, look no further than Holiday Harbor. Explore the available homes for sale today and discover the lifestyle you’ve always dreamed of in this idyllic Maryland community!

Newest Holiday Harbor Homes for Sale

$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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