Luxury Properties for sale in Shelter Island, New York

A Cinematic Waterfront Estate on Shelter Island, designed by acclaimed architect James Merrell. At the meeting point of sky and sea, this extraordinary contemporary waterfront...

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

Architecturally distinctive and deeply connected to its coastal setting, 126 South Midway Road is a private compound that captures the spirit of Shelter Island's artistic legacy....

Presented by Jenny Landey | Sotheby's International Realty - East Hampton Brokerage

Nestled in the highly coveted Hay Beach enclave of Shelter Island, 43 Gardiners Bay Drive is a grand, ˜ 6,100-square-foot coastal estate that redefines luxury through the lens of...

Presented by Mackenzie Needham | Daniel Gale Sotheby's International Realty

Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association,...

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

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views...

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

Nestled on a full acre in the heart of Shelter Island, this exceptional island retreat offers the perfect blend of relaxed elegance and modern comfort. The main residence features...

Presented by Debra Von Brook-Binder | 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

Discover a serene sanctuary amidst the natural beauty of Shelter Island. This stunning residence offers breathtaking water views of Miss Annie's Creek, providing an unparalleled...

Presented by Debra Von Brook-Binder | 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

This 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc., offers 250 feet of sandy beach and extraordinary panoramic water...

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

Rare opportunity to own a charming early-1900s Victorian farmhouse in the historic Heights. Set on a quiet road, this inviting home features an extra-large yard perfect for...

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

This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living....

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

Charming cottage-style home offering 3 bedrooms and 2 full baths in a highly desirable central location. Just moments from beautiful beaches, local restaurants, and boutique...

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