75 + 77 Wainscott Main Street

Wainscott begins with the Osborns. Thomas Osborn reached East Hampton in 1648, and his son John, credited as a founder of the hamlet, kept a homestead in Wainscott by 1668. The family farmed this stretch for generations, and in 1986 the land was mapped and filed with the Town of East Hampton as The Osborn Farm, map no. 8046. Two of its lots, 75 and 77 Wainscott Main Street, are now offered together by Outline Real Estate Group, the design-focused investment firm founded by Harrison Rowen and Robert Levine.

The chapel the lots sit behind is an Osborn story too. Built in 1891 as the Bridgehampton school, the building was pulled across the potato fields by horses in April 1908 and set down on Main Street land that Elisha, Oliver, and Ruth Hedges Osborn gave the hamlet.

The offering is two single-and-separate parcels: lot 75 carries 1.8 acres (1.63 net of the common drive), lot 77 carries 1.55 acres (1.44 net), and both come with agricultural easements that keep the adjoining fields as fields. A proposed site plan shows what the land will take, a residence with a first floor of roughly 4,000 square feet, a guest house, a pool, and full landscape details.

Outline's development page lists two Wainscott Main Street projects in progress, one with Robert A.M. Stern Architects and one with Adam Jordan Architects.

Wainscott Main runs south of Montauk Highway through some of the most protected farmland on the East End. The town agreed to pay $56 million for the 30-acre Osborn farm along Wainscott Pond, one of the largest preservation deals in its history, and in 2025 designated the John Osborn Homestead at 66 Wainscott Main Street, with its 1904 Louisa Edwards Osborn House, a town landmark. The views from these lots are held open by law: potato fields to the north, Wainscott Pond and the ocean to the south, and Beach Lane's ocean beach less than a mile down the road.

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