# 12903 WINDY Drive, Ocean City, MD 21842

> **TL;DR:** 6bd/5ba single family, $9,500,000 ($1100/sqft), built 1985, 8,638 sqft.
> Pool, Fireplace, Waterfront, A/C. Est. $50,808/mo. Listed 92 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $9,500,000 |
| Price/sqft | $1100 |
| Bedrooms | 6 |
| Bathrooms | 4 full, 1 half |
| Square Feet | 8,638 |
| Year Built | 1985 |
| Lot Size | 1,611,720 sqft (37.00 acres) |
| Stories | 2 |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 92 |

## Why This Home Stands Out

- **Pool** - Pool listed; type not specified
- **Waterfront** - Waterfront location listed

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $48,037 |
| Estimated Insurance | $2,771 |
| **Total** | **$50,808** |

## Key Amenities

- Pool
- Fireplace
- Waterfront
- A/C

## Property Highlights

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

## Description

### Agent 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.

## Location

- **Address:** 12903 WINDY Drive, Ocean City, MD 21842
- **County:** WORCESTER
- **Neighborhood:** CAPTAINS HILL
- **Coordinates:** 38.35008441, -75.10349649
- **Google Maps:** https://www.google.com/maps?q=38.35008441,-75.10349649

## Listing Agent

- **Name:** Jay Phillips · **License:** 523297
- **Brokerage:** Holiday Real Estate, Inc
- **Broker Phone:** (410) 524-7700
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/12903-Windy-Dr_Ocean-City_MD_21842_M94112-59568?f=listhub&s=TRENDPA&m=MDWO2039854&c=propsimple)

## Photos

![12903 WINDY Drive - Photo 1](http://lh.rdcpix.com/d3ace52424c60240b922c574c4f5f1c9l-f2123201630r.jpg)

![12903 WINDY Drive - Photo 2](http://lh.rdcpix.com/d3ace52424c60240b922c574c4f5f1c9l-f3920357995r.jpg)

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---

**MLS#:** MDWO2039854 | **Updated:** 2026-10-20
**Source:** listhub

*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.*

[View on PropertySimple](https://www.propertysimple.ai/listing/12903-windy-drive-ocean-city-md-21842-3d9c65aef3f14cfcad3a4874aec3344a)

---

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  "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.",
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