Date
Details
Price
Change
Source
7/31/2026
Listed
$9,500,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$9,500,000
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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.
Full Property Details
Full Property Details for 12903 Windy Dr
General
- Price: $9,500,000
- Taxes: $17,155 (2026)
- Status: Active
- Type: Single Family
- Source: BrightMLSMidAtlantic
- MLS ID: MDWO2039854
- Updated: 8/3/2026
- Added to Site: 28 day(s) ago
Interior
- Interior Features: 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
- Fireplace: Yes
- Number of Fireplaces: 2
- Fireplace(s): Stone
- Appliances: Cooktop, Dishwasher, Icemaker, Microwave, Oven - Double, Refrigerator, Washer, Water Heater, Dryer - Electric
- Flooring: Wood
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 4
- Half Bathrooms: 1
- Upper Floor Baths: 3
- Upper - Full Baths: 3
- Main Floor Baths: 2
- Main - Full Baths: 1
- Main - 1/2 Baths: 1
Bedrooms
- Total Bedrooms: 6
- Bedrooms Upper: 5
- Bedrooms Main & Up: 1
Additional Information
- Pool: Yes
- Private Pool: Yes
- Security/Safety: Electric Alarm
Parking
- Garage: Yes
- Garage Spaces: 3
- Total Spaces: 3
- Parking Type: Attached Garage
- Garage Description: Garage Door Opener, Inside Access, Oversized
Location
- Area: West Ocean City (85)
- County: WORCESTER
- Subdivision: CAPTAINS HILL
- Driving Directions: Rt 50 East Left onto Golf Course Rd. Left onto Windy Dr..Property has sign
- Location Details: Bayfront
School Information
- School District: Worcester County Public Schools
Community
- Assoc. Fees Include: None
Heating & Cooling
- Central air: Yes
- Cooling Type: Central A/C
- Cooling Fuel: Electric
- Heating Type: Heat Pump(s)
- Heating Fuel: Electric
- Water Heater: Electric
Utilities
- Sewer: Public Sewer
- Water: Private
Structural Information
- Architectural Style: Other
- Structure Type: Detached
- Construction: Frame, Rock, Stick Built, Other
- Basement: Yes
- Basement Entrance: Yes
- Basement Desc.: Interior Access, Rear Entrance
- Foundation: Block, Other
- Roof: Shake, Wood
- Stories Description: Main, Upper 1
- Square Feet: 10,568
- Sq. Ft. Source: Estimated
- Living Area: 8,638 Sq. Ft.
- Finished Above Grnd: 8,638 Sq. Ft.
- Year Built: 1985
- Year Built Source: Estimated
Lot Features
- Property View: Bay
- Lot Size (Acres): 37
- Lot Size (Sq. Ft.): 1,611,720
- Lot Size Source: Estimated
- Building Sites: 18
- Zoning: A
Water Features
- Water Front: Yes
- Water View: Yes
- Navigable Water: Yes
- Water Access: Yes
- Water Front Type: Bay
Financial Considerations
- Price Per Sq. Ft.: $1,099.79
- Tax Amount: $17,155
- Tax Year: 2026
Disclosures and Reports
- Ownership: Fee Simple
Listed by Holiday Real Estate, Jay Phillips and Holiday Real Estate, Denise A Milko
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agents
— 12903 Windy Dr —
Jay Phillips
Holiday Real Estate
Denise A Milko
Holiday Real Estate
Listing Office Email: jmilko@holidayoc.com
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 12903 Windy Dr
School District:Worcester County Public Schools
| Name | Grades | Distance |
|---|---|---|
Ocean City Elementary School 12828 Center Drive, Ocean City, MD 21842 | PK-4 | 0.3 mi |
Stephen Decatur Middle School, Berlin, MD 9815 Seahawk Road, Berlin, MD 21811 | 7-8 | 4.8 mi |
Stephen Decatur High School 9913 Seahawk Road, Berlin, MD 21811 | 9-12 | 4.8 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 12903 Windy Dr
Estimate the Cost
Estimate the Cost for 12903 Windy Dr
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12903 Windy Drive, Ocean City, MD 21842 (MLS# MDWO2039854) is a Single Family property with 6 bedrooms, 4 full bathrooms and 1 partial bathroom. 12903 Windy Drive is currently listed for $9,500,000 and was received on July 31, 2026. Want to learn more about 12903 Windy Drive? Do you have questions about finding other Single Family real estate for sale in Ocean City? You can browse all Ocean City real estate or contact a Coldwell Banker agent to request more information.