12903 Windy Dr, Ocean City, MD 21842
Local realty services provided by:CENTURY 21 Ryon Real Estate
12903 Windy Dr,Ocean City, MD 21842
$9,500,000
- 6 Beds
- 5 Baths
- 8,638 sq. ft.
- Single family
- Active
Listed by: jay phillips, denise a milko
Office: holiday real estate
MLS#:MDWO2039854
Source:BRIGHTMLS
Price summary
- Price:$9,500,000
- Price per sq. ft.:$1,099.79
About this home
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....
Contact an agent
Home facts
- Year built:1985
- Subdivision & Development:CAPTAINS HILL
- Listing ID #:MDWO2039854
- Added:91 day(s) ago
- Updated:October 28, 2026 at 01:54 PM
Rooms and interior
- Bedrooms:6
- Total bathrooms:5
- Full bathrooms:4
- Half bathrooms:1
- Flooring:Wood
- Dining Description:Dining Area, Formal/Separate Dining Room
- Kitchen Description:Built-Ins, Cooktop, Crown Moldings, Dishwasher, Icemaker, Kitchen - Eat-In, Kitchen - Island, Microwave, Oven - Double, Refrigerator, Water Heater
- Bedroom Description:Primary Bedroom - Bay Front, Walk In Closet(s)
- Basement:Yes
- Basement Description:Interior Access, Rear Entrance
- Living area:8,638 sq. ft.
Heating and cooling
- Cooling:Central A/C
- Heating:Electric, Heat Pump(s)
Structure and exterior
- Roof:Shake, Wood
- Year built:1985
- Building area:8,638 sq. ft.
- Lot area:37 Acres
- Lot Features:Bayfront
- Construction Materials:Frame, Rock, Stick Built
- Foundation Description:Block
- Levels:2 Stories
Utilities
- Water:Private
- Sewer:Public Sewer
Finances and disclosures
- Price:$9,500,000
- Price per sq. ft.:$1,099.79
- Tax amount:$17,155 (2026)
Features and amenities
- Laundry features:Dryer - Electric, Washer
- Amenities:120/240V, Built-Ins, Crown Moldings, Electric Alarm, Primary Bedroom - Bay Front
Parking
- Parking description:Attached Garage, Garage Door Opener, Inside Access, Oversized
- Garage:Yes
- Garage spaces:3
New listings near 12903 Windy Dr
- Coming Soon
$209,000Coming Soon1 beds 1 baths416 sq. ft.13 40th St #3, OCEAN CITY, MD 21842
MLS# MDWO2042070Listed by: KELLER WILLIAMS REALTY DELMARVA - Coming Soon
$569,000Coming Soon2 beds 2 baths1,004 sq. ft.8500 Coastal Hwy #702, OCEAN CITY, MD 21842
MLS# MDWO2041982Listed by: DUGRE' REAL ESTATE COMPANY - New
$380,000Active2 beds 1 baths909 sq. ft.731 Mooring Rd #205, OCEAN CITY, MD 21842
MLS# MDWO2042130Listed by: COLDWELL BANKER REALTY - New
$58,000Active2 beds 2 baths12108 Coastal Hwy #407, OCEAN CITY, MD 21842
MLS# MDWO2042294Listed by: COLDWELL BANKER REALTY - Open Fri, 11am to 1pm
$289,900Active2 beds 2 baths1,200 sq. ft.12626 Sunset Ave #17, OCEAN CITY, MD 21842
MLS# MDWO2042082Listed by: KELLER WILLIAMS REALTY DELMARVA - New
$3,200,000Active4 beds 4 baths6,500 sq. ft.11930 Ocean Gtwy, OCEAN CITY, MD 21842
MLS# MDWO2042054Listed by: STEEN REALTY INC
$869,000Active5 beds 5 baths2,378 sq. ft.43 Sunset Island Dr #43ar, OCEAN CITY, MD 21842
MLS# MDWO2041276Listed by: SHEPPARD REALTY INC- New
$384,000Active2 beds 2 baths800 sq. ft.12005 Assawoman Dr #3s, OCEAN CITY, MD 21842
MLS# MDWO2042210Listed by: BERKSHIRE HATHAWAY HOMESERVICES PENFED REALTY - New
$1,750Active2 beds 2 baths988 sq. ft.2209-#202 Philadelphia Ave Ave #206 & 303, OCEAN CITY, MD 21842
MLS# MDWO2042222Listed by: ATLANTIC SHORES SOTHEBY'S INTERNATIONAL REALTY - Open Sun, 10:30am to 12:30pmNew
$535,000Active3 beds 4 baths2,175 sq. ft.9823 Golf Course Rd #7, OCEAN CITY, MD 21842
MLS# MDWO2042254Listed by: COLDWELL BANKER REALTY