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12903 Windy DriveOcean City, MD 21842Price: $9,500,000

  • Price: $9,500,000
  • Est. Mortgage of $/month
  • 24 Days on Market
$
$
%
$/month over payments
Federal 30-year interest rate: 6.65% last updated on Aug 20, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.
  • $9,500,000List Price
  • 6Bedrooms
  • 5Bathrooms
  • 8,638Square Feet
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.
Listed by Jay Phillips of Holiday Real Estate

Driving Directions

Railey Vacations
Railey Vacations
Office: 301-387-2124
5 Vacation Way
McHenry, MD 21541

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More Info

Location Information

  • Date Listed07/31/2026
  • ZoningA
  • MLS Area MajorWest Ocean City
  • UsmAreaOcean City - West Ocean City

Location

  • Address12903 Windy Drive
  • Area Total10,568
  • SubdivisionCaptains Hill
  • TownOcean City
  • StateMD
  • Zip21842
  • CountyWorcester

Exterior

  • RoofShake, Wood
  • FoundationBlock, Other

Utilities

  • Water SourcePrivate
  • SewerPublic Sewer
  • Central Air YNYes
  • Cooling FuelElectric
  • Water HeaterElectric
  • Heating FuelElectric
  • Electric120/240V
  • Heat SystemHeat Pump(s)

Amenities

  • PoolYes - Personal
  • Accessibility AmenitiesOther
  • PricePerSqFt1100
  • Other AmenitiesBasement, Fireplace, Pool, Waterfront, Water View

Other

  • View Count4

Basic Information

  • MLS NumberMDWO2039854
  • Ownership InterestFee Simple
  • List Price$9,500,000
  • Square Feet8,638
  • Acreage37
  • Year Built1985
  • MLS Property TypeResidential
  • StatusACT

Property

  • New Construction YNN
  • Building Sites18

Interior

  • FlooringWood
  • Appliances Included
    • Cooktop
    • Dishwasher
    • Dryer - Electric
    • Icemaker
    • Microwave
    • Oven - Double
    • Refrigerator
    • Washer
    • Water Heater
  • Heating YNYes
  • CoolingCentral A/C
  • Basement YNYes

Property Information

  • Lot Size Square Feet1,611,720
  • Above Grade Finished Area8638
  • Below Grade Area Total1,930
  • Below Grade Unfinished Area1930

Water Body

  • Water View YNYes
  • Waterfront FeaturesNavigable Water
  • WaterfrontYes
  • Water Body TypeBay
  • Water AccessYes
  • Tidal Water YNYes

Tax Information

  • Total Taxes Payment FrequencyAnnually
  • Tax Year2026
  • Taxes$17,155

Parking

  • Parking TypesAttached Garage
  • Total Garage And Parking Spaces3

Building

  • ViewBay
  • Water Oriented YNYes
  • Interior FeaturesBuilt-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
  • Association Fee IncludesNone
  • Security FeaturesElectric Alarm
  • High School DistrictWorcester County Public Schools
  • LocationTypeBayfront
  • Broker NameHoliday Real Estate
  • Building Number12903
  • DirectionsRt 50 East Left onto Golf Course Rd. Left onto Windy Dr..Property has sign
  • Num Attached Garage Spaces3
  • Main Level Total Baths2
  • Main Level Bedrooms1
  • Main Level Half Baths1
  • Main Level Full Baths1
  • Upper Levels Total Full Baths3
  • Upper Levels Total Bedrooms5
  • Upper Levels Total Baths3
  • Upper Level1 Bedrooms5
  • Upper Level1 Full Baths3
  • Upper Level1 Total Baths3
  • Story ListMain, Upper 1
  • Structure Design TypeDetached
  • Construction MaterialsFrame, Rock, Stick Built, Other
  • Property StyleOther
  • Bedrooms6
  • BasementInterior Access, Rear Entrance
  • Full Bath4
  • Bathroom5
  • Half Baths1
  • Levels2
  • Fireplace FeaturesStone
  • Fireplace YNYes
  • Fireplace2
  • Garage TypeGarage Door Opener, Inside Access, Oversized
  • Garage Spaces3
  • GarageYes

Copyright 2026 BRIGHT, All Rights Reserved.  Information Deemed Reliable But Not Guaranteed. 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 Railey Vacations 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.Data last updated August 23, 2026. 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.

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