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Jane Cummings
REALTOR®, Luxury Collection Specialist
Cell: (410) 790-1404
Office: (410) 583-0400
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12903 Windy Drive , Ocean City, MD 21842

$9,500,000
  • 12903 Windy Drive , Ocean City, MD 21842 Main Photo

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New to the Market Coming Soon
BEDS6 BATHS4 full 1 partial SQUARE FEET8,638 MLS#MDWO2039854
STATUSCOMING SOON PROPERTY TYPEResidential - Single Family SUBDIVISIONCAPTAINS HILL SCHOOLWORCESTER COUNTY PUBLIC SCHOOLS

Property Description

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 Drive | MLS# MDWO2039854

This single family home located at 12903 Windy Drive , Ocean City, MD 21842 is currently listed for sale with an asking price of $9,500,000. This property was built in 1985 and has 6 bedrooms and 4 full and 1 partial baths with 8638 sq. ft. Windy Drive is located in the CAPTAINS HILL subdivision within the WORCESTER COUNTY PUBLIC SCHOOLS school district. Search CAPTAINS HILL real estate on www.janecummingsrealtor.com today.

Property Features

Property Type: Residential - Single Family
Basement: Interior Access, Rear Entrance
Basement: Yes
Cooling: Central A/C
Fireplaces: 2
Fuel Type: Electric
Garage: 3
Heating: Heat Pump(s)
Lot Size: 37.00 Acres
Roof Type: Shake, Wood
Stories: 2.0
Taxes: $17,155
Year Built: 1985

Feature Descriptions

Additional Structures: Above Grade
Appliances: Cooktop, Dishwasher, Icemaker, Microwave, Oven - Double, Refrigerator, Washer, Water Heater, Dryer - Electric
Building Name: NONE AVAILABLE
Electric: 120/240V
Exterior: Frame, Rock, Stick Built, Other
Fireplace: Stone
Flooring: Wood
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
Location: Bayfront
Lot Dimensions: 37.00 Acre(S)
Parking Notes: 3 Total Parking Spaces
Sewer: Public Sewer
Special View Info: Bay
SQFT Above Finished: 8638
SQFT Total Finished: 8638
Structure Type: Detached
Total Garage/Parking Spaces: 3
Water: Private

Local Schools

School District: WORCESTER COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Holiday Real Estate
Agency Phone: 4105247700

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Estimated Payment

$ 25,343.30 per month $21,142.88 Principal & Interest $1,429.58 Property Tax $2,770.83 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided 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. Information on this site was last updated 07/28/2026. The listing information on this page last changed on 07/28/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Tue 07/28/2026 3:02:14 PM EST) or Bright MLS (last updated Tue 07/28/2026 2:57:38 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Agent License Information: 
Licensed in Maryland
Jane Cummings 

1425 Clarkview Road, Suite 700, Baltimore, MD 21209
410-583-0400

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