Skip to main contentSkip to navigation
1 / 82

Land with Home for Sale in Ocean City, Maryland

12903 Windy Dr, Ocean City, MD 21842

$9,500,000
37 acres
Active sale
ago
Est $49,968/mo

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.

8,638
Sq feet
6
Beds
4
Full baths
1
1/2 bath
1985
Built

Location

Street address
12903 Windy Dr
Zip code
21842
Community
Captains Hill
School district
Worcester County Public Schools
Elevation
6 feet
Coordinates
38.3501, -75.1035

Property details

Acreage
37 acres
MLS #
TREND MDWO2039854
Posted

Property taxes

Recent
$17,155

Details and features

Listing

Type
Residential

Lot

Waterfront
Navigable Water, Waterfront

Exterior

Parking Spaces
3
Parking
Garage-Attached
Pool
Private

Structure

Stories
2
Heating
Heat Pump
Cooling
Central Air
Materials
Frame, Rock, Stick Built

Interior

Rooms
Basement, Bathroom x 5, Bedroom x 6, Dining Room
Fireplaces
Yes
Appliances
Cooktop, Dishwasher, Dryer-Electric, Icemaker, Microwave, Oven-Double, Refrigerator, Washer, Water Heater
Features
Additional Stairway, 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

Listing history

DateEventPriceChangeSource
July 31, 2026New listing$9,500,000TREND
Subscribe to listing updates

Payment calculator

This 37-acre property is located at 12903 Windy Dr in Ocean City, MD 21842. The property is available for sale, priced at $9,500,000. It has a 8,638 square foot 6-bedroom, 4.5-bath house built in 1985.

Listed by Holiday Real Estate, (410) 524-7700

Checked 2 hours agoUpdated Source

Report listing issue

Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

Contact listing agent Rules
By submitting, I agree to the terms of use and to be contacted by real estate professionals. Message and data rates may apply.
Contact