Captains Hill Real Estate

Welcome to Captains Hill, a picturesque subdivision nestled in the heart of Ocean City, Maryland. This charming community offers a perfect blend of coastal living and suburban tranquility, making it an ideal choice for families, retirees, and anyone looking to embrace the beach lifestyle.

Captains Hill is renowned for its beautifully designed homes, each exuding a unique character that complements the serene surroundings. With a variety of architectural styles, from classic beach cottages to modern coastal estates, there’s something to suit every taste and preference. The meticulously landscaped yards and tree-lined streets create an inviting atmosphere that residents are proud to call home.

One of the standout features of Captains Hill is its proximity to the stunning beaches of Ocean City. Just a short drive or bike ride away, residents can enjoy sun-soaked days on the sandy shores, indulge in water sports, or take leisurely strolls along the iconic boardwalk. The area is also home to a vibrant dining scene, featuring everything from casual seafood shacks to upscale restaurants, ensuring that there’s something to satisfy every palate.

Families will appreciate the nearby parks and recreational facilities, providing ample opportunities for outdoor activities, picnics, and community events. The local schools are highly regarded, making Captains Hill a great place to raise children in a nurturing environment.

Whether you’re seeking a vacation getaway or a permanent residence, Captains Hill in Ocean City, MD, offers a delightful lifestyle enriched by the beauty of nature and the charm of coastal living. Discover your dream home in this idyllic community today!

Newest Listings in Captains Hill

$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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