12903 Windy Drive, OCEAN CITY, MD 21842 (MLS # MDWO2039854)
Request More Info
Schedule a Showing
Share
Print
|
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 Type(s):
Single Family
| Last Updated | 7/28/2026 | Tract | CAPTAINS HILL |
|---|---|---|---|
| Year Built | 1985 | Community | West Ocean City (85) |
| Garage Spaces | 3.0 | County | WORCESTER |
SCHOOLS
| School District | WORCESTER COUNTY PUBLIC SCHOOLS |
|---|
Additional Details
| AIR | Central Air, Electric |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Cooktop, Dishwasher, Double Oven, Electric Water Heater, Ice Maker, Microwave, Refrigerator, Washer, Water Heater |
| AREA | West Ocean City (85) |
| BASEMENT | Interior Entry, Yes |
| CONSTRUCTION | Frame, Other |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Electric, Heat Pump |
| INTERIOR | Built-in Features, Crown Molding, Eat-in Kitchen, Kitchen Island, Open Floorplan, Walk-in Closet(s) |
| LOT | 37 acre(s) |
| LOT DESCRIPTION | Waterfront |
| PARKING | Oversized, Garage Door Opener, Garage, Inside Entrance, Attached |
| POOL | Yes |
| POOL DESCRIPTION | Private |
| SEWER | Public Sewer |
| STORIES | 2 |
| STYLE | Other |
| SUBDIVISION | CAPTAINS HILL |
| TAXES | 17155 |
| VIEW | Yes |
| VIEW DESCRIPTION | Water, Bay |
| WATER | Private |
| WATERFRONT | Yes |
| WATERFRONT DESCRIPTION | Waterfront |
Location
Contact us about this Property
| / | |
| We respect your online privacy and will never spam you. By submitting this form with your telephone number you are consenting for Kevin Anselmi to contact you even if your name is on a Federal or State "Do not call List". | |
Listing provided by Holiday Real Estate
The multiple listing data appearing on this website, or contained in reports produced therefrom, comes in part from Metropolitan Regional Information Systems ("MRIS"). The information provided is for the viewer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties the viewer may be interested in purchasing. All real estate listings include detailed information about them that includes the name of the listing brokers and therefore may reference real estate listing(s) held by a brokerage other than the broker and/or agent who owns this web site.
All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 7/28/26 6:21 PM PDT.
The listing information on this web site is from various brokers who participate in IDX.
Copyright 2026 MRIS. All rights reserved.
All listing data, including, but not limited to, square footage and lot size is believed to be accurate, but the listing agent, listing broker and respective Multiple Listing Services and their affiliates do not warrant or guarantee such accuracy. Therefore, all data should be personally verified through personal inspection by and/or with the appropriate professionals. Listing data last updated 7/28/26 6:21 PM PDT.
The listing information on this web site is from various brokers who participate in IDX.
Copyright 2026 MRIS. All rights reserved.
This IDX solution is (c) Diverse Solutions 2026.
Twitter
Facebook
Email