$9,500,000

12903 Windy Dr, Ocean City, MD, 21842

6

Beds

Baths

8,638

Square feet

37.00

Acres

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 Details

OfficeHoliday Real Estate
Contact Info4105247700

Facts & Features

MLS® # MDWO2039854
Price $9,500,000
Bedrooms 6
Bathrooms 4.50
Full Baths 4
Half Baths 1
Square Footage 8,638
Acres 37.00
Year Built 1985
Type Residential
Sub-Type Detached
Style Other
Status Active

Community Information

Address 12903 Windy Dr
Area West Ocean City
Subdivision CAPTAINS HILL
City Ocean City
County WORCESTER-MD
State MD
Zip Code 21842
Senior Community No

Amenities

Amenities Built-Ins, Crown Moldings, Formal/Separate Dining Room, Primary Bedroom - Bay Front, Walk-in Closet(s), Wood Floors, Additional Stairway
# of Garages 3
Garages Garage Door Opener, Inside Access, Oversized
View Bay
Is Waterfront Yes
Waterfront Bay
Has Pool Yes

Interior

Interior Features Floor Plan - Open
Appliances Cooktop, Dishwasher, Icemaker, Microwave, Oven - Double, Refrigerator, Washer, Water Heater, Dryer - Electric
Heating Heat Pump(s)
Cooling Central A/C
Fireplace Yes
# of Fireplaces 2
Fireplaces Stone
Stories 2

Exterior

Exterior Frame
Roof Shake, Wood
Construction Frame, Rock, Stick Built, Other
Foundation Block, Other
Other Structures 10000001172

School Information

District WORCESTER COUNTY PUBLIC SCHOOLS

Additional Information

Date Listed July 31st, 2026
Days on Market 34
Zoning A
Foreclosure No
Short Sale No
RE / Bank Owned No

Listing Map

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