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MLS: #MDWO2039854, Listed By: Jay Phillips, Holiday Real Estate, Source:Bright MLS

12903 Windy Drive

OCEAN CITY, MD 21842
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Bed 6

Bed

Bath 5

Bath

SqFt8,638

Sqft

Acres37

Acres(Lot)

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 o utdoor 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.

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Detail Ic Property Details

Property Type : Residential

Price : $9,500,000

AD Id : 88540617

MLS Id : MDWO2039854

Beds : 6

Lot Size : 37 Acres

Living Area Size : 8,638

Year Built : 1985

Garage : 3

County : WORCESTER

Subdivision: Captains Hill

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Map

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Feature Features

  • Bedroom Information

    Total beds: 6

    Bathroom Information

    Total Baths: 5 Full Baths: 4 Half Baths: 1

    Room Information

    Has Basement: Yes Basement: Interior Entry
  • Flooring Information

    Wood
  • Roofing Information

    Shake, Wood
  • Interior Features

    Eat-in Kitchen, Kitchen Island, Walk-In Closet(s), Built-in Features, Crown Molding, Open Floorplan Roof: Shake, Wood Appliances: Double Oven, Electric Water Heater, Cooktop, Dishwasher, Ice Maker, Microwave, Refrigerator, Washer, Water Heater
  • Heating & Cooling

    Has Heating: Yes Heating: Electric, Heat Pump Has Cooling: Yes Cooling: Central Air, Electric Water front: 1

  • Building Information

    Year Built: 1985 Building Area Total: 10568 Construction Materials: Frame, Other Frontage Length: 1500 Pool Features: Private Private Pool: Yes View: Water, Bay

  • Lot Information

    Lot Size Acres: 37 Lot Size Source: Estimated Lot Size Square Feet: 1611720 Lot Description: Waterfront

    Property Information

    Subdivision: CAPTAINS HILL Source Property Type: Residential Property SubType: Single Family Residence Levels: Two Property Age: 41

  • Listing Price Information

    Listing Price: $9500000

  • Tax Information

    Parcel Number: NO TAX RECORD Tax Year: 2026 Annual Tax: $17155

  • Parking Information

    Parking Total: 3 Oversized, Garage Door Opener, Garage, Inside Entrance, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 3

  • Location Information

    Direction: Rt 50 East Left onto Golf Course Rd. Left onto Windy Dr..Property has sign WaterSource: Private
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
LOT#2 Exeter Road, Ocean City, MD, 21842 $883,000 3 3 2,030 2,030 SqFt
OCEAN HIGH CM WK40 32nd.., Ocean City, MD, 21842 $7,500 3 2 1,400 1,400 SqFt
LOT #1 Exeter Road, Ocean City, MD, 21842 $631,000 3 3 1,614 1,614 SqFt
SANDY SQUARE CM 11901 W.., Ocean City, MD, 21842 $9,500 3 2 1,041 1,041 SqFt
11602 Coastal Highway #1A, Ocean City, MD, 21842 $899,000 5 3 2,541 2,541 SqFt
12505 Wight Street #18B, Ocean City, MD, 21842 $949,900 3 2 900 900 SqFt
10900 Coastal Highway #.., Ocean City, MD, 21842 $499,900 2 2 825 825 SqFt
11500 Coastal Highway #.., Ocean City, MD, 21842 $474,999 2 2 888 888 SqFt
6 140th Street, Ocean City, MD, 21842 $1,150,000 3 1 1,018 1,018 SqFt
9105 Coastal Highway, Ocean City, MD, 21842 $960,000 4 5 2,500 2,500 SqFt

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 ByOwner 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. Information Deemed Reliable But Not Guaranteed. Copyright © 2026 Bright MLS. All rights reserved.

ByOwner last updated this listing 08/09/2026 @ 06:04

MLS: MDWO2039854 LISTED BY: Jay Phillips, Holiday Real Estate 410-524-7700 SOURCE: Bright MLS

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