Change Real Estate Presents:

12903 Windy Drive
Ocean City MD 21842

For Sale: $9,500,000.00 Active

List Date: 2026-07-31

Ocean City
6 bedrooms
5 bathrooms
8,638 build ft2
37.00 land acres

About This Property

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.

Listing Agent: Jay Phillips. Holiday Real Estate 410-726-8631 jphil10425@aol.com

Property Features

Location Information
County:
Subdivision: CAPTAINS HILL
click to open map in a new window
Interior Features
Appliances: Cooktop, Dishwasher, Icemaker, Microwave, Oven - Double, Refrigerator, Washer, WaterHeater, Dryer - Electric
Interior: Built-Ins, Crown Moldings, Dining Area, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Island, Primary Bedroom - Bay Front, Walk-in Closet(s), Wood Floors, Additional Stairway
Laundry:
Furnished: No
Flooring: Wood
Water: Private
Cooling: Central A/C
Heating: Heat Pump(s)
Fireplaces: 2
Windows:
Utilities:
Sewer: Public Sewer
Exterior Features
Year Built: 1985
Subdivision Name: Captains Hill
Garage Spaces: 3.0
Schools
Elementary School: None
Junior High School: None
High School: None

IDXListing Courtesy of Jay Phillips. Holiday Real Estate 410-726-8631 jphil10425@aol.com

Property Photos [Click to enlarge]

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