289 properties for sale in Shelter Island

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 entertaining and a welcoming wraparound porch ideal for relaxing summer evenings. Inside, the home boasts a spacious living room with a wood-burning fireplace, a gracious parlor, formal dining room, and a first-floor bedroom with a full bath. Upstairs are two additional bedrooms and another full bath. A full basement provides ample storage and utility space. Just a stone’s throw from downtown shopping, restaurants, and all that the Heights has to offer, this is a rare find in one of Shelter Island’s most sought-after neighborhoods

Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offers thoughtfully designed spaces, beautiful hardwood flooring throughout, and an impressive collection of amenities for year-round living or the perfect island escape. The well-appointed kitchen features a refrigerator, dishwasher, built-in microwave, garbage compactor, kitchen-sink water filtration, and plenty of space for everyday cooking and entertaining. The adjoining living room is warm and welcoming with a gas fireplace, while an impressive 12-foot sliding glass door opens onto the expansive deck, creating a wonderful flow between indoor and outdoor living. The deck features a complete grilling station with its own sink and refrigerator, perfect for entertaining family and friends. The showpiece of the home is the extraordinary 17' x 24' primary suite. High ceilings and skylights create a bright, airy atmosphere,

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail, featuring an open floor plan with elegant white oak and porcelain tile flooring, stone countertops, and premium Thermador appliances throughout. Expansive living spaces are designed to embrace the surrounding views, while the second level covered deck offers the perfect setting for unwinding against a picturesque bay backdrop. Additional amenities include a heated gunite pool, radiant heat, wet bar, fireplace, pantry, and other thoughtful features that enhance everyday living. Ideally situated in Shelter Island, the property provides a peaceful retreat with convenient access to local amenities, beaches

Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private. 76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to beautiful Silver Beach. The home has a distinctive character, combining comfortable interiors, hardwood floors and an abundance of natural light with wonderful water and landscape views from both levels. The kitchen and baths are fully functional and well maintained, while the home’s more traditional finishes offer an opportunity for a new owner to update and personalize the style over time. The waterfront setting is the true centerpiece. An expansive lawn framed by mature trees leads to the canal and an approximately 20-foot grandfathered dock with water and electric, creating direct access for boati

Opportunity awaits with this property being sold strictly as-is. The home is currently uninhabitable and will require a full restoration or renovation down to the frame. Interior access is not available. Seller makes no representations regarding the condition or functionality of heat, water, plumbing, electrical, or other systems. Ideal for investors, builders, or buyers looking for a complete rehab project or potential rebuild. Bring your vision and unlock this property’s full potential. Construction-to-permanent financing options may be available for qualified buyers

Beautifully and meticulously maintained, this traditional 3-bedroom, 2.5-bath turnkey home is tucked away on a very quiet street, surrounded by lovely landscaping and offering a wonderful sense of privacy. Inside, a beautifully renovated kitchen with high-end appliances flows into an inviting open floor plan, creating a warm and welcoming setting for everyday living and entertaining. The inviting primary suite opens onto a screened-in porch and wraparound deck, offering a lovely connection to the outdoors. A fireplace adds warmth and charm, while outside, a completely fenced-in yard features a beautiful new Gunite pool and a cozy fire pit with surrounding seating, perfect for gathering with family and friends. Ideally located near Wade’s Beach, Fresh Pond, and the South Ferry, the gateway to the Hamptons, this special property offers the best of Shelter Island living, with comfort, privacy, and convenience all in one

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank