58 properties for sale in Shelter Island

Amazing 1800s house with 3 bedrooms and 2 baths. Perfectly quiet location in Shelter Island! Tennis courts directly across the street and backyard view of rolling land, minutes to the beach and a few steps to restaurants and gallery

Set on a well-proportioned acre in one of Shelter Island’s most sought-after neighborhoods, this 1850s farmhouse offers charm, generous living space, and an exceptional location. The main level features a spacious living room with a wood-burning fireplace, a dining room with a second wood-burning fireplace, and a bright sunroom. The open kitchen offers two exterior doors leading to side porches, providing an inviting connection to the outdoors and an ideal setting for entertaining. Upstairs are five generously sized bedrooms and three full bathrooms. A full basement and attic provide ample storage and utility space. Just a stone’s throw from Coecles Harbor Marina, this property presents an opportunity to enjoy the tranquility of Shelter Island

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 relaxed waterfront lifestyle. Designed for both entertaining and everyday enjoyment, the property features two private docks ideal for boating, paddleboarding, and kayaking, along with a spacious waterside deck overlooking the sparkling water. The first floor has a large waterfront room that opens directly onto the deck, complemented by 4 generously sized bedrooms and 4 full bathrooms. Upstairs, soaring cathedral ceilings frame an open-concept great room encompassing the living, dining, and kitchen areas. Walls of glass capture stunning panoramic water views, creating a light-filled and inviti

Some properties are simply irreplaceable. This is one of them.nnHeld by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved.nCustom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island Shingle beach house sits on a level acre along one of the Island's most coveted stretches of waterfront 190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour.nnDeceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. Two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Mature landscaping on all sides for privacy.nnThe expansive side lawn

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 effortless living. Set on a sprawling 0.92-acre parcel with captivating winter water views of Gardiners Bay, this masterfully designed home offers a seamless daily rhythm, beginning in the light-filled foyer where exquisite millwork meets glass doors that open to the expansive grounds. Designed for both high-end entertaining and absolute ease, the flowing main level connects a stately firelit living room to a magnificent chef's kitchen—complete with a professional cooktop, a walk-in pantry, and dual dishwashers for effortless cleanup—before transitioning outside to a resort-style pool featuring an electric safety cover and direct cabana-bath access. A sanctuary of personal wellness, the second floor boasts a marble-clad primary suite with a private water-view office overlooking the bay, alongside three generou

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, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a la

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

Shelter Island Ranch style home with 3 bedrooms and 2 bathrooms. Situated close to town and easy access to all beaches and either ferry this adorable home is currently configured as a 2 bedroom (large oversize primary bedroom with sliders to deck, guest bedroom, 2 newly renovated bathrooms, kitchen with new appliances, open living and dining area has stone surround fireplace and sliders to deck area. The lower level has finished space, laundry area, and doors to steps to access pool area. Large attic space and a separate garage with second level storage space

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 escape from the ordinary. Step onto the property and be captivated by the charm of covered porches and a heated pool, inviting you to relax and soak in the picturesque vistas. Whether you're enjoying a quiet morning coffee or hosting unforgettable gatherings, this waterfront oasis provides the perfect backdrop for every occasion. Don't miss this opportunity to own a piece of paradise in Mashomack Preserve

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom,

This is a one of a kind fully reimagined, architectural masterpiece on Shelter Island, NY, boasting a flawless 2022 full-gut contemporary renovation by a serial tastemaker with an elite portfolio spanning NYC, California, and Hawaii. Located in the coveted Shorewood area, this premier estate offers a lifestyle of pure perfection and absolute privacy. Passing through the gated driveway, you instantly realize you are about to have an elevated experience. Indoor-outdoor living reveals breathtaking views at every turn, where the vast southwestern sky offers beautiful sunsets and truly magical light. Multiple designated spots allow you to dine alfresco while taking in the landscape. The interior spaces flow onto enchanted gardens, lawns, a private sandy beach, and a spectacular waterside pool, crowned by a roof deck with jaw-dropping panoramic views-leaving one to ask, why would you ever leave? Yet, when you do, a dinner excursion to Sag Harbor is entirely effortless, whether you choose to

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 is a Once in a Lifetime Opportunity. Some properties can be reproduced, this one cannot. Built in 1914 by industrialist Samuel Hird and later lovingly stewarded by cosmetics magnate Bob Ruttenberg, this extraordinary Shelter Island Estate is a surviving expression of a more gracious era when great waterfront homes were created with scale, permanence and a sense of place rarely possible today. Set on 1.6 acres with approximately 245 feet of waterfront with a private deep water dock, the approximately 4,500-square-foot residence commands sweeping western views across Dering Harbor. Mature grounds, covered porches and a heated gunite pool with spa create the privacy and romance of a true country estate. The property provides ultimate privacy, a secluded oasis sheltered from the world outside. A three-car garage and pool cabana with changing rooms, both retaining historic details, further enhance the property, with the garage and cabana offering the opportunity to be thoughtfully refr

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 shops, this inviting property blends classic charm with modern updates. Renovated in 2019 with additional recent improvements, the home features comfortable living spaces filled with warmth and character. Outside, enjoy a beautifully landscaped yard with deck perfect for relaxing, entertaining, or summer gatherings. A wonderful opportunity to enjoy easy island living in a move-in-ready home

Welcome to 12 Clinton Avenue, a distinguished waterfront estate nestled in the heart of Shelter Island Heights, NY. This remarkable property spans 1.5 acres along the serene Dering Harbor, offering an unparalleled lifestyle marked by elegance and tranquility. With 10,000 square feet of meticulously designed living space, this gated estate presents a rare opportunity to own a piece of paradise. The residence boasts seven spacious bedrooms and six and a half luxurious bathrooms, each adorned with high-end finishes and extensive use of natural marble. The grandeur of the home is immediately apparent upon entering the soaring great room, which doubles as a library, complete with a massive fireplace that serves as the focal point. The walnut flooring throughout adds warmth and sophistication to the expansive layout. The kitchen is a chef's dream, featuring a vast prep area and top-of-the-line appliances, seamlessly connected to a formal dining room perfect for hosting intimate gatherings. T

Experience a rare combination of privacy, architecture, open water, and resort-like amenities at 66 Gardiners Bay Drive, an exceptional waterfront offering on Shelter Island. Set against sweeping views of Gardiners Bay, the property features a private beach, expansive lawns and gardens, and a spectacular gunite pool positioned directly along the water. The main residence was designed by renowned architect Andrew Geller, whose distinctive modernist vision is reflected in the home's thoughtful relationship to its extraordinary setting. The five-bedroom residence features five en-suite bathrooms, an open living and kitchen floor plan, and walls of windows that bring in abundant natural light while capturing panoramic Bay views. Both the main residence and guest house underwent a comprehensive renovation in 2022, with every aspect carefully considered. The renovation encompassed the kitchen, all bathrooms, major systems, and numerous other elements of both properties. Nothing was overlooke

Beautifully and meticulously maintained, this traditional three-bedroom, two-and-a-half-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 2024 constructed 5,800-square-foot modern waterfront residence, built by Fountainhead Construction Inc offers 250 feet of sandy beach and extraordinary panoramic water views. 180 degrees of sweeping water views from Crab Creek to North Haven Point and across Great Peconic Bay, with 250 feet of sandy beach along the shoreline. Walls of glass in the kitchen, dining area, living room, and select bedrooms frame the remarkable water views and glowing sunsets, creating a seamless connection between indoors and out. Step onto the waterfront patio or terrace to experience the setting even more fully. The sleek five-bedroom home includes six full baths and two half baths, with sophisticated finishes and amenities throughout, including 10-foot doors, a kitchen with custom Italian cabinetry and natural stone countertops, a fireplace, media room, and heated waterside pool. Set on 2.12 secluded acres, this exceptional property offers a rare opportunity for refined waterfront living

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 natural light and a sense of grandeur. The main home includes four spacious bedrooms and three full baths, offering comfortable accommodations for residents and guests. An attached two-car garage provides convenience, with a versatile bonus room above—perfect for a media room, studio, or additional lounge space. Just across the yard, a charming private cottage offers two bedrooms, a full bath, a living room, and a kitchenette—ideal for guests or a private retreat. Outdoor living is equally inviting. The kitchen opens to a generous deck designed for effortless entertaining, overlooking beautiful

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

Held by a single family for nearly a century, 90 Peconic Avenue carries the kind of history that can't be manufactured - a deep sense of place, of summers lived well, of a waterfront that has remained unchanged while the world around it evolved. Custom built by Reich Eklund in 1985 and thoughtfully maintained, this classic Shelter Island shingled beach house sits on a level acre along one of the Island's most coveted stretches of waterfront -190 feet of Silver Beach shoreline, fully bulkheaded, with a private dock and unobstructed sunset views that define the property at every hour. Deceptively generous in scale, the five-bedroom, 3.5-bath residence features an open floor plan with every room oriented toward the water. two en-suite bedrooms, one on each floor. A full waterside balcony. Two-car attached garage. Full basement with poured concrete foundation. Maturenlandscaping on all sides for privacy. The expansive side lawn is often mistaken for a separate lot and offers room for an ac

Vintage waterfront cape cod style situated on a large west facing, elevated lot. Features include four bedrooms, two and a half baths, large living room with fireplace. Two car garage. Enjoy endless sunsets from the waterside deck and enclosed dining porch. Detached workshop with boat and kayak storage completes this waterfront gem. 2022 Taxes: $10, 419

Welcome to 23 Osprey Road, Shelter Island-a beautifully renovated retreat offering privacy, tranquility, and the best of island living. Available for summer or year-round rental, this exceptional property sits on over an acre of landscaped grounds with peaceful pond views and direct adjacency to Dusty Boots Farm, where horses can often be seen grazing nearby. A charming front porch welcomes you into the foyer, complete with a convenient powder room. Beyond, you

This unique property was part of the Artimus Ward Estate, Built in Circa 1895 and renovated in 1977, this Shepherds cottage and guest cottage offer an abundance of privacy set on. 75 acres on Osprey Lane in coveted Shorewood Farm. The main house offers a kitchen, living room, den and half bath on the first floor. The second floor has a master suite with bath divided by stained glass with a oversized dressing room, 2 additional bedrooms and 1 bath. The cottage built in 2006 features a southern exposure with passive solar with winter water views of South Ferry. The cottage is 1390 square feet and has one bedroom, 2 baths, eat-in kitchenette, living room and a third floor mezzanine/office/art studio. This unique property is landscaped for complete privacy, Association tennis and beach available

Set on a quiet street in the Montclair Colony section of Shelter Island, this newly renovated four-bedroom, four-bath combines the ease of single-story living with the feel of a private retreat. The turn-key residence is surrounded by mature hedges on a flat, manicured 0.70-acre lot, providing an exceptional setting for an immediate indoor-outdoor lifestyle and seamless entertaining. Inside, the. 2,000-square-foot home is designed around a light-filled, open-concept living, dining, and kitchen layout, enhanced by hardwood and ceramic tile flooring. A gas fireplace anchors the main living space, while the custom kitchen is outfitted with a premium 36-inch Bertazzoni, Sub-Zero, and Wolf appliance suite-including a professional range and refrigerator (both new as of 2025), a dishwasher, and a wine fridge. Throughout the home, premium finishes elevate the space, including Newport Brass fixtures, Duravit sinks, Baldwin hardware, and Tom Dixon lighting. Behind the scenes, spray foam insulati

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom,

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

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

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

Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef