89 Wainscott Main Street

Eighty nine Wainscott Main Street is one and eight tenths acres of cleared ground on the west side of the road, south of the highway. It is one of five building lots carved out of the Osborn Farm, the subdivision the hamlet's founding family filed over their own fields, and it is the last of the run still open. The three parcels east of it are already built.

The Osborns have farmed this ground since John Osborn kept a homestead in Wainscott by 1668. The lot's own record in the town's mapping still carries the subdivision under the family's name.

The house drawn for the site is by Robert A.M. Stern Architects: seven bedrooms, nine full baths and two half baths, with a detached garage, a pool house and a pool, breaking ground in 2027.

Every image on this page is a rendering. There is nothing standing on the site to photograph yet.

Stern's office has spent four decades arguing that new houses on the East End should be continuous with the old ones rather than a rebuke to them, and this design follows that line closely. The drawings show shingled walls, a steep pitched roof, brick chimneys at both ends, shutters, and a small columned entry porch, all of it drawn from the vernacular architecture of East Hampton.

The massing is deliberately broken up. Rather than one block, the house reads as a main body with lower wings running off it, so it registers closer to a farmhouse that grew over time than to a single new build of its size. That restraint is not only taste. East Hampton rewrote its house-size formula in July 2025, capping gross floor area at seven percent of the lot plus fifteen hundred square feet; on this parcel that yields 6,988 square feet, and the design works to that ceiling.

Behind the house the plan opens up. A pool runs out from the terrace toward the fields, with a pool house of its own, columned and open on one side, a brick fireplace set into its back wall. A grove of pears is drawn over gravel to one side, with long timber benches beneath it.

The farm view off the north side is not a matter of luck or of what the neighbours decide to do. The parcel sharing that boundary runs twenty four acres and is carried in the town's own records as an agricultural reserve, the land the Osborn Farm subdivision set aside in exchange for the building lots. It cannot be built on.

Wainscott Pond lies to the south, and Beach Lane, with the ocean at the end of it, is under a mile down the road.

Wainscott Main Street runs south off Montauk Highway through farmland the town has spent heavily to keep open. In December 2024 East Hampton closed on roughly thirty acres of the Osborn farm along Wainscott Pond for fifty six million dollars, the largest preservation purchase in its history, and in March 2025 it designated the John Osborn Homestead at number 66, with its 1904 Louisa Edwards Osborn house and a seventeenth century barn, a town landmark.

The chapel down the street is an Osborn story too. It was built in 1891 as the Bridgehampton school, and in April 1908 Jacob Hopping's horses hauled the building across the potato fields and set it down on Main Street land Elisha, Oliver and Ruth Hedges Osborn gave the hamlet. The Wainscott Sewing Society has owned it since 1953.

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