12903 WINDY DRIVE

Ocean City, MD 21842

$9,500,000

active
6
Beds
5
Baths
8,638
Sq Ft
1985
Built

Take control of your move.

Compare agents, lenders, and next steps for this home in one place.

12903 WINDY DRIVE - Photo 1

Listing details

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.

Location

Listed by Jay Phillips, Holiday Real EstateMLS# 805176525268Listing via Bright MLS IDXUpdated Aug 3, 2026

Single Family agents in Ocean City

Sorted by how many single-family homes they have sold in Ocean City, plus speed, list-to-sold ratio, and price-band fit. Select up to 3 to interview.

No matched agents found for this area yet.

Your path to this home

  1. 1Select agents who sell this type of home here
  2. 2Interview, negotiate, and hire your agent online
  3. 3Match with a lender who funds loans for this home and area
  4. 4Interview, negotiate, and hire your lender online
  5. 5Manage contract, inspection, appraisal, and closing in one place

Similar Homes

Listing information is provided through IDX courtesy Keller Williams Capital Properties.

© 2026 BRIGHT, All Rights Reserved

Information Deemed Reliable But Not Guaranteed.

View full MLS disclosures

The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Keller Williams Capital Properties participates, and is provided by BRIGHT through a licensing agreement.

The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.

Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller.

This home sale information is not to be construed as an appraisal and may not be used as such for any purpose.

BRIGHT MLS is the (or a) provider of this home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

Interview agents for this home