Luxury Properties for sale in Shelter Island, New York

A Cinematic Waterfront Estate on Shelter Island At the meeting point of sky and sea, this extraordinary modern waterfront retreat redefines island living. Designed to embrace...

Presented by Nick Brown | Sotheby's International Realty - East Hampton Brokerage

Designed by Norman Jaffe in 1971 and expanded by him in 1981, the Osofsky House is a rare waterfront estate that has been meticulously renovated while fully honoring Jaffe's...

Presented by Nick Brown | Sotheby's International Realty - East Hampton Brokerage

In the Midst of Nature: A Modern Masterpiece Discover unparalleled privacy and serenity within the heart of the 2,350-acre Mashomack Nature Preserve, a rare and cherished enclave....

Presented by Tina Marika Kaasik | Daniel Gale Sotheby's International Realty

A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the...

Presented by JoAnn Wind | Daniel Gale Sotheby's International Realty

Nestled on over an acre along Shelter Island's coveted Dickerson Creek, this Scandinavian-style waterfront cottage offers a serene escape with 100 ft. of gorgeous shoreline....

Presented by Tina Marika Kaasik | Daniel Gale Sotheby's International Realty

Set on a beautifully level 1.47 acre lot adjacent to a serene town-owned park, this delightful cottage-style home offers a unique opportunity just moments from Montclair Colony,...

Presented by Debra Von Brook-Binder | Daniel Gale Sotheby's International Realty

25 West Neck Road, Shelter Island, ny 11964

Presented by Paula Quesnel-Jerman | Daniel Gale Sotheby's International Realty

Nestled on a serene .58-acre parcel just minutes from Wades Beach and Fresh Pond, this well-maintained ranch-style home offers the perfect blend of classic Shelter Island charm...

Presented by Debra Von Brook-Binder | Daniel Gale Sotheby's International Realty