Captains Hill Homes for Sale

Welcome to Captains Hill, a hidden gem nestled in the heart of Ocean City, Maryland, where coastal charm meets modern living. This picturesque subdivision offers a unique blend of tranquility and convenience, making it the perfect place to call home. With its tree-lined streets and friendly neighborhood atmosphere, Captains Hill is ideal for families, retirees, and anyone seeking a serene coastal lifestyle.

The homes for sale in Captains Hill boast a variety of architectural styles, each designed to capture the essence of beachside living. From cozy single-family homes to spacious townhouses, there’s something to suit every taste and budget. Many properties feature open floor plans, updated kitchens, and outdoor spaces perfect for entertaining or simply enjoying the fresh ocean breeze. Imagine sipping your morning coffee on a sun-drenched deck or hosting weekend barbecues in your backyard oasis!

Beyond the beautiful homes, Captains Hill is conveniently located just minutes away from the stunning beaches of Ocean City, renowned for their soft sand and vibrant boardwalk. Enjoy a day of sun and surf, or explore the local shops and restaurants that line the coast. For those who appreciate nature, the nearby Assateague Island National Seashore offers breathtaking views and opportunities for hiking, birdwatching, and spotting the famous wild ponies.

With a welcoming community and an unbeatable location, Captains Hill is more than just a place to live; it’s a lifestyle. Discover your dream home today and embrace the coastal living you’ve always desired!

Newest Captains Hill Homes for Sale

$9,500,000

6 Beds ⋅ 5 Baths

This 37-acre Waterfront Estate in the desirable West Ocean City Community of Captains Hill stands among Worcester County’s true legacy properties. A rare combination of Coastal Luxury, privacy, acreage and future opportunity. Set on a expansive rise overlooking the bay, the Estate commands sweeping water and skyline views that shift elegantly from sunrise to the golden glow of sunset. A long driveway leads you to the 8000+ Sq Ft Coastal Residence, a grand yet serene retreat surrounded by park-like grounds and mature landscape that creates an atmosphere of total privacy. The main Estate and grounds encompass 27 acres that feature a diverse landscape designed for both beauty and functionality. Such highlights include a 3-acre freshwater pond that anchors the properties tranquil setting, an outdoor pool with surrounding deck ideal for families and entertaining, an expansive lawn for gatherings and pets, a large covered porch perfect for enjoying the broad water views and nature, covered parking entrance and a three-car garage. The residence itself offers the architectural presence and scale expected of a Coastal Estate of this magnitude, with generous living spaces, impressive ceiling heights and endless potential for customization or enhancement. In addition, this Estate offers additional parcels and development potential that allows for flexibility for future use. Included in the offering is a 2.73-acre Waterfront Lot and 20 plated lots with their own road frontage. This rare land portfolio provides exceptional opportunities, ideal for a private compound, multi-generational retreat, curated development or long-term investment that makes this property uniquely valuable. Opportunities of this size, location and versatility rarely ever come to market. With commanding views, coastal proximity, and expansive acreage, this Captain’s Hill Estate stands as one of the region’s premier offerings, a property with both present-day grandeur and limitless future potential. A Coastal Treasure without equal.

12903 Windy Dr, Ocean City

Listing courtesy of Holiday Real Estate. Contact: 4105247700

$795,000

3 Beds ⋅ 3 Baths

Located in one of West Ocean City's most sought-after communities, this traditional Colonial-style single-family home offers timeless charm and a prime location—just minutes from downtown Ocean City, the boardwalk, outlets, restaurants, and entertainment. Set on over 1/3 acre, this 3-bedroom, 2.5-bath home features a traditional floorplan with 2,228 square feet of living space. The main level includes a formal living room, dining room, and a cozy family room with a brick wood-burning fireplace framed by built-in shelving. The kitchen opens to the family room, creating a warm and functional space for everyday living, complete with granite countertops, recessed lighting, and crown molding throughout. Additional highlights include a newer roof, newer water heater, pull-down attic storage, a full-size laundry room, powder room, and a spacious two-car garage. Upstairs, the owner's suite offers a peaceful retreat, accompanied by two additional bedrooms and a full bath. Step outside to enjoy the spacious backyard, complete with a patio and firepit—perfect for relaxing evenings or entertaining guests. Whether you're seeking a year-round residence or a coastal getaway, this home combines classic style, generous space, and unbeatable location in the heart of West Ocean City.

12943 Windy Drive, Ocean City

Listing courtesy of Keller Williams Realty. Contact: 3023600300

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