Colonial Homes for Sale in Shelter Island, NY

Private Retreat with Separate Studio & Pool PotentialTucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane offers a rare combination of privacy, flexibility, and natural beauty within the sought-after Shorewood Farm enclave. Set on approximately 0.78 acres of beautifully landscaped grounds with room to add a pool, the property is designed for relaxed island living and

Justin Stolarczyk Brown Harris Stevens Hamptons

Built in 1888 and thoughtfully renovated by acclaimed architect Lee H. Skolnick in 1988, this storied Shelter Island estate represents a rare convergence of architectural pedigree, cultural history, and timeless design. Set on two exquisitely landscaped acres with gardens designed by celebrated landscape designer Jeff Mendoza, the property has long served as a retreat for notable creative

Stacey Cohen The Agency Hamptons

Nestled within Shelter Island’s highly sought-after Shorewood Farms community, this exceptional waterfront beach house offers the perfect coastal retreat. Enjoy breathtaking views across Mabel’s Creek and the South Fork, with a sandy beach just steps from your door. As a resident of Shorewood Farms, you’ll also enjoy exclusive access to a private association beach and tennis courts, enhancing the

Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty

Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with

Anthony Guidice RE/MAX Signature Real Estate

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 an airy open-concept design ideal for both everyday living and entertaining. A chef’s kitchen anchors the home, seamlessly flowing into the dining and living areas, where a dramatic vaulted ceiling fills the space with

Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty