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$2,875,000The Town of Shelter Island's assessment record dates the house at 4 Winthrop Road to 1950. That is the first useful thing to know about it, because the neighborhood it sits in was drawn seventy eight years earlier. Robert Morris Copeland, the Boston landscape architect who died in 1874 at forty three, laid out Shelter Island Heights in about 1872 for a Methodist camp meeting association out of Brooklyn: curving roads cut into the slope above Dering Harbor, small lots, an open amphitheater left at the center for the Grove. Union Chapel went up inside it in 1875 and still stands under half a mile from this front gate. On May 7 1993 the National Register listed 141 of the Heights buildings as a district.

This one is younger than all of them, and that is what lets it work the way it does. Two stories and 2,920 square feet over a full basement, six bedrooms and three full baths, a primary suite on each floor. Navy clapboard, white louvered shutters, a brick chimney through the ridge, two octagonal windows set into the front gable above the garage door. The rear roof slope carries solar panels. The deed record runs 1999, 2001, 2005 and April 2018, four conveyances in a quarter of a century.

The front of the house tells you almost nothing about the back of it. That is the last quiet thing it does before you open the gate.





























Frequently asked:
What should I know about 4 Winthrop Road?
Shelter Island Heights was laid out about 1872 by the Boston landscape architect Robert Morris Copeland (Dec 11 1830 to Mar 28 1874) for a Methodist camp meeting association out of Brooklyn: curving roads cut into the slope above Dering Harbor, small lots, and an open amphitheater at the center for the Grove. Union Chapel, 1875, the oldest public building on Shelter Island and the visual center of Copeland's plan, stands about 0.45 miles from this gate (computed from OpenStreetMap coordinates). The National Register listed 141 buildings of the Heights as a historic district on May 7 1993, reference 93000335, covering 105 acres. 4 Winthrop Road is not one of them: the assessment record dates the house to 1950, and a point-in-polygon test against the National Park Service's mapped district boundary puts this parcel outside it. Separately, the Town of Shelter Island's comprehensive plan (Cultural Resources chapter) names "Winthrop Rd to Harbor Lane" as one of only eight island Paths, defined verbatim as "Key routes connecting places, the route itself having special qualities", alongside Bridge Street, Grand Avenue, the Ram Island causeways, Serpentine Drive, Nostrand Parkway, South Midway Road and Cartwright Road.
Where is 4 Winthrop Road?
4 Winthrop Road is located in Shelter Island Heights, New York.
How many bedrooms and bathrooms does 4 Winthrop Road have?
4 Winthrop Road has 6 bedrooms and 3 bathrooms.
How big is 4 Winthrop Road?
4 Winthrop Road measures approximately 2,920 square feet.
When was 4 Winthrop Road built?
4 Winthrop Road is a single-family house built in 1950.
How much is 4 Winthrop Road?
4 Winthrop Road is asking $2,875,000.
What are the monthly carrying costs at 4 Winthrop Road?
4 Winthrop Road carries property taxes of $765 per month.
Who is the listing agent for 4 Winthrop Road?
4 Winthrop Road is listed by Michael Brennan, Douglas Elliman.
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- Beds
- 6
- Baths
- 3
- Sq Ft
- 2,920
- Taxes
- $765/mo
- Type
- Single-family house
- Built
- 1950
- Building
- Shelter Island Heights was laid out about 1872 by the Boston landscape architect Robert Morris Copeland (Dec 11 1830 to Mar 28 1874) for a Methodist camp meeting association out of Brooklyn: curving roads cut into the slope above Dering Harbor, small lots, and an open amphitheater at the center for the Grove. Union Chapel, 1875, the oldest public building on Shelter Island and the visual center of Copeland's plan, stands about 0.45 miles from this gate (computed from OpenStreetMap coordinates). The National Register listed 141 buildings of the Heights as a historic district on May 7 1993, reference 93000335, covering 105 acres. 4 Winthrop Road is not one of them: the assessment record dates the house to 1950, and a point-in-polygon test against the National Park Service's mapped district boundary puts this parcel outside it. Separately, the Town of Shelter Island's comprehensive plan (Cultural Resources chapter) names "Winthrop Rd to Harbor Lane" as one of only eight island Paths, defined verbatim as "Key routes connecting places, the route itself having special qualities", alongside Bridge Street, Grand Avenue, the Ram Island causeways, Serpentine Drive, Nostrand Parkway, South Midway Road and Cartwright Road.



