About This Home

This 6-bedroom, 5-bathroom single family at 12903 WINDY Drive in Ocean City, MD is listed for $9,500,000 ($1,100 per sqft). Built in 1985, the home offers 8,638 sqft of living space on a 37.00 acres lot.

Key Features

  • Built in 1985
  • 37.00 acre lot
  • 2 stories
  • 3 parking spaces
  • Private pool
  • Fireplace

Property Details

2 stories
4 full, 1 half
3 spaces
1985

Amenities

PoolFireplaceWaterfrontA/C
Listing 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.

Monthly Cost Estimate

$50,808/mo

20% down · 6.5% · 30 years

Principal$6,871
Interest$41,167
Insurance$2,771

Estimates only. Actual payments may vary.

Location

12903 WINDY Drive

Ocean City, MD 21842

CAPTAINS HILL

Features & Amenities

Interior Features

Built-InsCrown MoldingsDining AreaFloor Plan - OpenFormal/Separate Dining RoomKitchen - Eat-InKitchen - IslandPrimary Bedroom - Bay FrontWalk-in Closet(s)Wood FloorsAdditional Stairway

Property Details

Construction

Frame Rock Stick Built

Parking

Garage - Attached

Heating

Heat Pump (Heating)

Cooling

Central Air

Appliances

CooktopDishwasherIcemakerMicrowaveOven - DoubleRefrigeratorWasherWaterHeaterDryer - Electric

Questions & Answers

This 6-bedroom, 5-bathroom single family at 12903 WINDY Drive is listed at $9,500,000 ($1,100/sqft). The estimated monthly payment is $50,808 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance.

Key features include: Built in 1985, 37.00 acre lot, 2 stories, 3 parking spaces, Private pool, Fireplace. Interior Features: Built-Ins, Crown Moldings, Dining Area.

This property is listed by Jay Phillips and can be reached at 4107268631.

JP

Jay Phillips

Agent at Holiday Real Estate

(410) 726-8631

Listed by Holiday Real Estate · View on Broker Site

MLS# MDWO2039854· Source: listhub· 1 day on market

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.

12903 WINDY Drive, Ocean City, MD 21842

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