luxury houses for sale Shelter Island, United States

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. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .44-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

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 large hall bath. Step inside and start enjoying the best of Shelter Island living.

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.

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.

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 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 inviting gathering space. Privately situated off the great room, the expansive primary suite offers a large walk-in closet and a spa-inspired bathroom. Completing the property is a detached 2-car garage with a finished upper level, providing the perfect space for recreation, a home office, artist’s studio, or additional guest accommodations. A rare opportunity to enjoy waterfront living with private docks, beach access, tennis, and some of Shelter Island’s most captivating water views.

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 generous guest rooms and two laundry rooms configured for ultimate convenience. Below, the fully finished lower level serves as a private wellness and entertainment pavilion, featuring a home gym, media room, and a temperature-controlled wine cellar, balanced by an abundant bulk-provisioning storage room and an attached garage for your water toys. Situated just steps from the pristine sands of Menhaden Lane Beach and moments from the island’s premier marinas, boutiques, and acclaimed dining, this estate offers a turnkey, worry-free island lifestyle where every modern luxury is already perfectly in place.

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 take a quick drive to the South Ferry or launch a boat trip straight off your own private dock.

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 overlooked, with an emphasis throughout on quality, craftsmanship, and the finest materials and fixtures. Outdoor living is at the heart of the property. A generous deck, fully equipped outdoor kitchen, waterside lounge, and gunite pool create an exceptional setting for entertaining or simply enjoying the beauty of the Bay. The property also benefits from a grandfathered irrigation system, helping maintain lush green lawns and established gardens throughout the summer-an especially valuable amenity for a waterfront property of this scale. A beautifully renovated two-bedroom, three-bath guest house provides exceptional accommodations for family and guests, while maintaining privacy from the main residence and enjoying its own stunning water views. A full, newly refinished basement in the main house adds further living and recreational space. What makes 66 Gardiners Bay Drive particularly compelling is the remarkable breadth of what is offered in one property: privacy, expansive lawns and gardens, a private beach, sweeping open-water views, a waterside pool, sophisticated outdoor entertaining spaces, a renowned architectural pedigree, a beautifully renovated guest house, and a comprehensive renovation already completed. Rarely at this price point can one find so much on the water. The combination of setting, amenities, privacy, architectural significance, and turnkey condition makes 66 Gardiners Bay Drive a truly unique and compelling Shelter Island offering.

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 rare and compelling offering on Shelter Island where historic character and modern sophistication exist in perfect harmony. 7 Stearns Point Road presents a unique opportunity to live expansively-either as a private family compound or as an owner-occupied five-bedroom Bed & Breakfast. The residence is set on 0.70 acres in the heart of Shelter Island Heights, just moments from Crescent Beach and Sunset Beach. Spanning approximately 5,838 square feet, with an additional 2,588-square-foot full-height basement, the home seamlessly blends timeless architectural details with contemporary comfort. Arranged across two distinct structures connected by a covered breezeway, the property's nine bedrooms and nine bathrooms are thoughtfully distributed between the original Annex-offering seven bedrooms-and a recently completed extension featuring two additional ensuite bedrooms. The new wing is further distinguished by a dramatic double-height living area and a dedicated wellness room, equally suited for private residential use or boutique hospitality. Generous entertaining spaces include two living rooms and a well-equipped kitchen designed to accommodate both intimate gatherings and larger-scale hosting. Outdoors, the grounds evoke a private resort atmosphere, featuring a heated 40' x 18' gunite pool, mature landscaping, and multiple areas for relaxation and entertaining. Two separate driveways provide added convenience and privacy for owners and guests alike. With zoning and approvals allowing for an owner-occupied five-bedroom Bed & Breakfast, along with the benefit of an existing liquor license for guest use, the property offers a rare level of versatility. Whether envisioned as a legacy family retreat, a refined island escape, or a boutique hospitality venture, the possibilities are both flexible and compelling.

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 beautifully landscaped grounds. Enjoy warm summer days by the heated gunite pool, relax around the firepit area, and take in the peaceful surroundings of this southwest-facing property. Across the street, access to West Neck Creek makes kayaking and paddleboarding effortless, offering a true water-lover’s escape. A rare opportunity that captures the essence of coastal living on Shelter Island—where comfort, style, and exceptional indoor-outdoor spaces come together in a truly special setting

This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

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. A private sanctuary comprising a four-bedroom main residence, a dedicated large art studio, and an independent two-bedroom casita, the property is thoughtfully arranged to maximize natural light, privacy, and sweeping water views. The architecture recalls relaxed modernism of iconic beach houses, an approach rooted in simplicity, creativity, and a fluid relationship with the landscape. Clean lines, a sleek pool and an intuitive indoor-outdoor flow create spaces that feel both intentional and effortlessly livable, ideal for a design-minded coastal lifestyle. The separate studio enhances the compound's creative sensibility, offering a quiet, light-filled environment for work or reflection, while the two-bedroom casita provides comfortable, private accommodations for guests or extended stays. Together, the structures form a cohesive yet flexible retreat, equally suited to intimate living and hosting. Comprised of 3,400 sq. feet living space across 3 levels in the main house plus additional storage, an expansive art studio of 1,400 sq. ft and 2-bedroom Casita living 1,140 sq feet with multiple decks and outdoor entertaining spaces this incredible compound is moments from Wades Beach. The property offers a rare combination of architectural character and proximity to one of Shelter Island's most celebrated shorelines. Longtime Shelter Island residents David Rankin OAM and Lily Brett OAM, both internationally recognized for their contributions to the visual arts and literature, have stewarded the home with a deep appreciation for creativity and place. (OAM denotes the Order of Australia Medal, a national honor recognizing distinguished contribution.) A compelling offering for those drawn to thoughtful design, privacy, and coastal modernism, 126 South Midway Road is a singular Shelter Island retreat.

Set along the quiet shoreline of Pipers Cove Bay in Shelter Island Heights, this west-facing waterfront retreat is tucked at the end of a private drive and has been thoughtfully reimagined by Heiberg Cummings, whose signature approach to layered design transforms the home into something both sophisticated and deeply connected to its surroundings. Every room on both levels is oriented toward the water, creating a constant dialogue between the interiors and the landscape beyond. Natural textures, a restrained palette, and carefully considered details allow the landscape to remain the focal point. The house unfolds around the view with a central wood-burning fireplace anchoring the open living room, kitchen and dining space. Glass doors open onto a series of waterfront decks, blurring the line between indoors and out and offering a front-row seat to the island's spectacular western sunsets. The primary suite occupies the main level, complete with an en-suite bath and private waterfront terrace. Downstairs, two bedrooms and a full bath are complemented by a generous waterfront den and library, creating an inviting second living space with uninterrupted views across the cove. On the opposite side of the den, a shaded terrace offers another quiet place to read, relax, or escape the afternoon sun. Outside, the property reveals itself one destination at a time. Multiple outdoor living spaces, perfect for hosting summer dinners on the terrace overlooking the water, or sunset cocktails in the private beach garden with two fire pits and a lantern lit dining area. Fully equipped beach bar , integrated outdoor sound system disappears into the landscape. Mooring rights for a vessel up to 40 feet make it easy to explore the surrounding waters before returning home for sunset. Private, thoughtfully designed, and deeply connected to the water, this is a home that captures the quieter side of the East End, where mornings begin on the beach, afternoons are spent on the water, and each day ends with the sun setting over Pipers Cove Bay. Residents also enjoy access to the Shelter Island Heights community tennis courts, while the Ferry, Marie Eiffel Market, Leon 1909, and the Heights' shops and waterfront are all just a short distance away, placing some of the island's favorite destinations within close proximity.