12903 Windy Drive Captain's Hill · Ocean City
Aerial view at sunset of the shingled estate at 12903 Windy Drive, with its circular drive, the lawn and Isle of Wight Bay beyond

The Next Chapter on Captain's Hill

The Phillips Seafood family estate offers a rare combination of coastal luxury, privacy, acreage and future opportunity.

Presented by Denise Milko and Jay Phillips, Holiday Real Estate

  • 37Acres
  • 1,500 feetBay frontage
  • 6Bedrooms
  • 8,638Square feet
  • $9,500,000Offered at

The estate

Thirty-seven acres above Isle of Wight Bay.

This waterfront estate in the Captain's Hill community of West Ocean City is one of Worcester County's true legacy properties. It sits on a rise above the bay, with water and skyline views that move from sunrise to the gold of sunset.

  1. The land

    27 acres around the main house, with 1,500 feet of bay frontage, a 3-acre freshwater pond, open lawn and mature trees.

  2. The residence

    8,638 square feet with six bedrooms, two stone fireplaces, hand-laid wood floors and high ceilings.

  3. The extra parcels

    A 2.73-acre waterfront lot and 20 platted lots with their own road frontage come with the estate.

Aerial view of the estate and its lawns, with the marsh, Isle of Wight Bay and the Ocean City skyline in the distance
Across Isle of Wight Bay to the Ocean City skyline.

The family's story

A Special Message from Jessica Phillips

Our parents gave us many wonderful things, but one of the most meaningful was the chance to grow up on this remarkable property. As children, we spent entire days exploring its 37 acres, coming home only when the large dinner bell outside the kitchen rang. We built treehouses and forts in the woods with the neighborhood children and spent as much time as possible on the water—from full-contact sailing races on the lake to kneeboarding and tubing around Isle of Wight Bay.

The 3-acre freshwater pond on the estate, ringed by trees

The house was the setting for countless family gatherings: decades of Thanksgivings with both the Harrison and Phillips families gathered in the formal dining room, large crab feasts with food from Phillips Crabhouse, and one unforgettable party when a helicopter landed on the lawn and took guests for rides.

The formal dining room, with a scenic mural above wood wainscoting, two crystal chandeliers and windows facing the bay

As we grew older, visits home brought a different kind of togetherness—cold winter days camped out in the living room, building enormous fires in the stone fireplace and catching up as siblings. Our mother loved guests and encouraged us to fill the house with friends on summer weekends. Sometimes our guests were so happy spending time at the house and pool that they never even made it across the Route 50 bridge!

Close view of the fieldstone fireplace with brass andirons

Growing up here was a true privilege. As adults, we have treasured our weekends back home as an opportunity to strengthen our connections to each other and Ocean City. While we will miss our home, we're excited to see new owners discover how special a place it is.

The pool and brick deck, framed by trees, with the house behind

It is my dream that someone with kids buys the house. I mean, honestly, it was just the most idyllic place to be a kid. I would think, especially in today's climate, kids need more reasons than ever to get off the screen and go outside—but to a safe place. I'm sure the home I remember so fondly from my childhood would be a perfect place to grow up.

Open lawn running down to the marsh and Isle of Wight Bay under a blue sky

Jessica Phillips

“It was just the most idyllic place to be a kid.”Jessica Phillips

The land

27 acres of lawn, pond and marsh.

The main estate and grounds cover 27 acres, designed for both beauty and everyday use. There's a 3-acre freshwater pond, an outdoor pool with a deck around it, and a wide lawn that runs down to the marsh. A long drive leads to a covered parking entrance, a large covered porch and an attached three-car garage.

The bay side of the house: shingled gables, two stone chimneys, an arched window and a round screened porch, set on a wide lawn

The residence

A home designed for large family gatherings.

The house has the presence and scale of a coastal estate this size, with generous rooms, high ceilings and plenty of room to make it your own. You come in through a stained-glass front door. The great room has a stone fireplace and an arched window on the bay. There's a walnut-paneled library with a marble fireplace, a formal dining room wrapped in a hand-painted mural, an eat-in kitchen with an island, a screened porch, and a primary bedroom on the bay front.

Aerial view of the estate set between the marsh and a pond, with Ocean City across the bay
Between the marsh and the pond, with Ocean City across the bay
Aerial view over woods, a pond and open land toward Isle of Wight Bay and the Ocean City skyline
Woods, pond and open land, looking toward Ocean City
Aerial view of an open field along the road, with trees, a pond and the bay beyond
Open land along the road
Wide aerial view of the estate's lawns and drive beside the marsh, with woods around it
The estate grounds at the edge of the marsh
Aerial view of tidal creeks winding through marsh grass along the bay
Tidal creeks and marsh along the bay
Open field of grass ringed by woods under a blue sky
Open fields ringed by woods
Overhead aerial view of the house, pool and winding drive surrounded by open land
The house, pool and drive from above
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Future opportunity

A waterfront lot and 20 platted lots come with it.

Beyond the main estate, the offering includes a 2.73-acre waterfront lot and 20 platted lots, each with its own road frontage. A buyer could keep the land as a private family compound or a multi-generational retreat, plan a careful development, or simply hold it for the long term.

Lot details and surveys are available.

Inquire about subdividing

The details

12903 Windy DriveOcean City, MD 21842

Offered at
$9,500,000
Total land
37 acres
Main estate and grounds
27 acres
Additional parcels
2.73-acre waterfront lot; 20 platted lots
Bay frontage
1,500 feet, Isle of Wight Bay
Bedrooms
6
Baths
4 full, 1 half
Living area
8,638 sq ft, plus 1,930 sq ft basement
Built
1985, two stories
Fireplaces
2, stone
Garage
3-car attached, oversized
Pool
Private, in-ground
Pond
3-acre freshwater
Heating and cooling
Electric heat pump, central air
Roof
Cedar shake
Water and sewer
Private well water, public sewer
HOA
None
Annual taxes
$17,155
Community
Captain's Hill, West Ocean City
MLS
#MDWO2039854

Holiday Real Estate

12903 Windy Drive is Presented by

Denise Milko

Denise Milko

Vice President · Luxury Property Specialist
Diamond Award Winner

410-430-7188gotmilko@holidayoc.com
Jay Phillips

Jay Phillips

Sales Agent / Realtor

410-726-8631jay@phillipscoastalgroup.com
Holiday Real Estate, Inc.

Holiday Real Estate
410-524-7700
9719 Golf Course Road, Ocean City, MD 21842

Request a private tour

Denise or Jay will be in touch within one business day.

Are you working with an agent?

Thank you. Your request is in.

Denise or Jay will be in touch within one business day. If you'd rather not wait, call Denise at 410-430-7188 or Jay at 410-726-8631.