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RE/MAX One

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MLS MDWO2039854

12903 Windy Drive

Ocean City, Maryland 21842

$9,500,000Price
8,638Sq ft
5Bath
6Bed

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.

Property details
Style
Detached
Year built
1985
Lot size (acres)
37
County
Worcester
School district
WORCESTER COUNTY PUBLIC SCHOOLS
Interior
Total sq ft
10,568
Above grade sq ft
8,638
Below grade sq ft
1,930
Heating
Heat Pump(s)
Heating fuel
Electric
Cooling
Central A/C
Basement
Interior Access, Rear Entrance
Fireplace
Yes
Exterior & construction
Architectural style
Other
Construction
Frame, Rock, Stick Built, Other
Foundation
Block, Other
Parking
Attached Garage
Parking spaces
3
New construction
No
Utilities
Water
Private
Sewer
Public Sewer
Waterfront
Yes
Water view
Yes
Financial
Annual taxes
$17,155
Ownership
Fee Simple
Condo / co-op association
No
Listing courtesy of Holiday Real Estate (410) 524-7700
© 2026 Bright MLS. All rights reserved. Information Deemed Reliable, but Not Guaranteed. Listing information is from various brokers who participate in IDX and not all listings may be visible on the site. The property information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Listing courtesy of Holiday Real Estate. Data last updated on Saturday, October 31st, 2026 09:54:01 AM.
Data services provided by IDX Broker
The Indian River Inlet Bridge at sunset, Delaware Seashore State Park
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