For Sale
Single family home for sale at 12903 Windy Dr, Ocean City, MD 21842 | MLS# MDWO2039854 | Listing updated on 2026-08-03
Photo 1 of Single family home for sale at 12903 Windy Dr, Ocean City, MD 21842 | MLS# MDWO2039854 | Listing updated on 2026-08-03
Photo 2 of Single family home for sale at 12903 Windy Dr, Ocean City, MD 21842 | MLS# MDWO2039854 | Listing updated on 2026-08-03
Photo 3 of Single family home for sale at 12903 Windy Dr, Ocean City, MD 21842 | MLS# MDWO2039854 | Listing updated on 2026-08-03
Photo 4 of Single family home for sale at 12903 Windy Dr, Ocean City, MD 21842 | MLS# MDWO2039854 | Listing updated on 2026-08-03
78+
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Street View

$9,500,000

Monthly Est:$47,285

  • Beds Icon6 Beds
  • Beds Icon
    5 Baths
  • Beds Icon8,638sqft

12903 Windy Dr, Ocean City, MD 21842

$47,285/moEst:

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  • Single Family Residence

  • Built in 1985

  • $-- HOA

  • 37 acres lot

  • $1,100/sq.ft

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.

  • Houzeo last checked: 12 hours ago
  • Listing updated: August 3, 2026 at 3:30 pm
  • Listing Provided by: Jay Phillips (410) 726-8631 , Denise A Milko (410) 430-7188 | Holiday Real Estate (410) 524-7700
  • Source: Bright MLS-NJ | MLS#: MDWO2039854 Bright MLS-NJ

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Worcester Md County

  • City

    Ocean City

  • Neighborhood

    --

  • Year Built

    1985

  • HOA Fees

    -

  • Finished Area

    8,638 sqft

  • Lot Size

    37 acres lot

  • Basement Area

    - sqft

  • MLS Name

    Bright MLS

  • MLS Number

    MDWO2039854

  • MLS Status

    ACTIVE-BRIGHT

  • Days on Market

    4

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Location

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 5

Interior

  • Flooring

    Wood

  • Interior Features

    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, Additional Stairway

  • Sewer

    Public Sewer

  • Appliances

    Cooktop, Dishwasher, Icemaker, Microwave, Oven Double, Refrigerator, Washer, Water Heater, Dryer Electric

  • Heating

    Heat Pump(s)

  • Cooling

    Central A/c

Construction

  • Year Built

    Year Built: 1985

  • Home type

    Single Family Residence

  • Foundation Details

    Block, Other

  • Construction Materials

    Frame, Rock, Stick Built, Other

  • Architectural Style

    Other

  • Roof

    Shake, Wood

Utilities & Energy

  • Security Features

    Electric Alarm

  • Water Source

    Private

  • Basement

    Interior Access, Rear Entrance

  • Electric

    120/240v

  • Fireplace Features

    Stone

Other Features

  • Subdivision Name

    Captains Hill

Price History

DateEventPrice

07/31/2026

Source: mls_logoBright MLS-NJ #MDWO2039854

Listed for Sale

$9,500,000

$1,100/sqft

Nearby Homes

Based on information from Bright MLS through Nov 02, 2026, 02:00PM. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. © 2026 Bright MLS, Inc. All Rights Reserved. Click here for more information

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