luxury houses for sale Shelter Island, United States

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.

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.

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 1.5 acres with approximately 245 feet of waterfront and a separate .12-acre waterfront parcel with private 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 refreshed or reimagined. Inside the home, beautifully proportioned rooms unfold toward the water. Expansive windows, French doors and multiple wood burning fireplaces give the house warmth and character, while gracious living and dining rooms, an inviting kitchen with butler's pantry, intimate den and generous bedroom accommodations make the home equally suited to relaxed living and elegant entertaining. The primary suite is a private retreat with its own sitting room or office, fireplace and ensuite bath. Upper-level guest rooms capture elevated harbor views, allowing the water to remain a constant presence throughout the house. The opportunity extends well beyond the waterfront estate itself. The residence, waterfront grounds, garage, pool and private dock are now offered at $15,995,000, together with a right of first refusal to purchase 3.2+ additional buildable acres. For those who envision a larger compound, the additional acreage may be acquired with the estate for a total offering of $17,995,000, creating the rare possibility for a substantial guest residence, tennis, or expanded gardens and recreation. Few waterfront properties offer the opportunity to acquire an estate of this character today while also preserving the ability to substantially expand its scale for the future. This is more than waterfront real estate, it is an opportunity to live with the grandeur and graciousness of the Gilded Age, with the comforts of modern life. Proudly presenting 6 Harbor Lane, what is a century in the making, impossible to recreate, and a once-in-a-lifetime opportunity to become its next steward.

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

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature. Spanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise to sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level. The upper level reveals the home's most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor-outdoor lifestyle experience. The living room, dining area, and gourmet chef's kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range. Designed for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six person barrel sauna and cold plunge. Beautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature.nnSpanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise-to-sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level.nnThe upper level reveals the homes most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor outdoor lifestyle experience. The living room, dining area, and gourmet chefs kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range.nnDesigned for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six-person barrel sauna and cold plunge.nnBeautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

Perched along the pristine shoreline of Sag Harbor Bay, this newly constructed waterfront estate offers one of the most extraordinary settings in the Hamptons. Situated on 1.7 private acres surrounded by a protected tidal estuary, the property delivers uninterrupted panoramic water views, exceptional privacy, and a seamless connection to nature.nnSpanning over 6,000+/- square feet across three finished levels with elevator access throughout, the residence features six beautifully appointed bedroom suites designed to maximize light, space, and the breathtaking surroundings. The main level primary suite is a true retreat, complete with floor to ceiling glass walls and a private covered terrace showcasing spectacular sunrise-to-sunset vistas with no neighboring homes in sight. Three additional guest suites are also located on this level.nnThe upper level reveals the homes most dramatic living spaces, where soaring open concept interiors are framed by expansive walls of glass and oversized sliding doors that create a seamless indoor outdoor lifestyle experience. The living room, dining area, and gourmet chefs kitchen all overlook the stunning bayfront scenery. Thoughtfully curated finishes include exquisite Italian stonework selected to complement the natural landscape, anchored by a statement Officine Gullo range.nnDesigned for both relaxation and entertaining, the outdoor living spaces feature expansive terraces, an elevated pool, sun drenched lounging areas, and covered waterfront dining. The garden level offers two additional family suites, a media and recreation lounge, and a waterfront fitness studio complete with a six-person barrel sauna and cold plunge.nnBeautifully landscaped grounds lead to a private walkway and bayfront beach, where a secluded picnic area creates the perfect setting for peaceful waterfront afternoons. Rarely does a property combine architectural sophistication, resort level amenities, and such an unparalleled natural setting in one offering. A truly exceptional Hamptons waterfront estate.

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 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. The screened-in porch, equipped with storm shutters, offers breathtaking views of the harbor, creating an ideal space for relaxation and entertainment. Outdoor amenities are equally impressive, including a private dock, a water-side gym, and a pool with an automatic cover. The magical landscaping enhances the property's allure, while the garden and irrigation system with a cistern ensure year-round beauty. The block paver driveway leads to a two-car garage, providing ample parking and storage. For those seeking leisure and community engagement, the estate offers access to community tennis courts and a beach club. The village lifestyle is serene, with no need for a car to access local restaurants, shops, coffee bars, and the post office, all within walking distance. Additional features include a bar, sauna, and an office room lined with bookcases offering stunning water views. The entry foyer sets the tone for the home's elegance, while the extensive use of luxury finishes throughout ensures a sophisticated living experience. This property is a testament to refined living, combining privacy, luxury, and convenience in one of New York's most coveted locations. Don't miss the opportunity to own this exceptional estate, where every detail has been thoughtfully curated to provide an unmatched living experience.

New to the market, On The Bluff in North Haven, a beautiful waterfront home offering privacy, sweeping views from every vantage point, plus beauty and tranquility. Situated on 2 +/- acres, the 5,500+/- sq. ft. light-filled home offers 5 bedrooms, bathrooms, and ample entertaining spaces indoor and outdoor. The gunite waterside pool, finished lower level, 2-car garage and private beach access make this truly a very desirable home and property. First time offering exclusively at $6.9M.

Surrounded by the natural beauty and tranquility of West Banks, a private waterfront community in North Haven , 16 Barclay dr is a well appointed modern traditional residence. This gated enclave is a true boaters paradise featuring a deep water dock , a private beach and the most glorious westerly sunsets in all the Hampton's. Sited on 1.72+/- acres and surrounded by a 20 acre reserve, this property offers elegant style and sophistication. The desirable floor plan offers 4200 square feet of beautiful living spaces, and an additional 2050 square foot lower level with high ceilings just waiting to be finished. Upon arrival, the coastal light cascades through the double height ceiling living room with over sized windows overlooking this lush property. The first level offers a wonderful flow with a large eat in kitchen, granite counters and center island, offsetting all the amenities for entertaining one would appreciate. A formal dining room , office or family room anchor the living area's. A first level private and spacious primary suite with walk-in large closets, and a luxurious bath with jacuzzi tub is a great addition. The second level's open landing divides two wings, offering an en-suite second primary bedroom and bath with a spacious walk in closet and additional unfinished area's that can be reimagined as a sitting room or extra living space. There are 2 additional bedrooms on the opposite wing with a shared Jack and Jill bath completing the second level. Numerous unfinished area's across this level just waiting to be expanded and customized. Mature plantings and beautiful landscaping create a park like setting surrounding the sparkling salt water gunite pool and lovely patio's for lounging and entertaining . A two car over sized attached garage also is a wonderful addition. This two-story traditional residence provides a serene and beautiful Hampton's retreat in a uniquely private and rare setting. The expansive acreage gives room for this residence to be substantially increased in sq footage with additional living area's if desired. A live in community caretaker is part of this wonderful offering, and conveniently available for concierge needs. Additionally, community tennis and a designated mooring for the boating enthusiast enhances this coastal experience. The natural beauty and tranquility of North Haven, also offers 'Love Lady Park' a new addition to this area, with walking trails and gathering area's for all season enjoyment. This exceptional North Haven, Sag Harbor property and lifestyle, is just 10 minutes to the Historic Sag Harbor Whaling Village with coastal waterfront dining and marina's. The iconic Bay Street Theater features high profile entertainment and the Historic Whaling museum, are just a few local favorites. This sought-after private community and the residence at 16 Barclay Drive present an opportunity to own a substantial Hamptons residence in a World Class location! Listing ID 934515

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.