luxury real estate for sale Shelter Island, United States

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes from the South Fork. An amply equipped open kitchen pours out into the windowed dining area, with a fully screened in, covered porch just adjacent. The formal living room, complete with fireplace is spacious yet inviting. The en suite first floor primary is bright and beautiful. Upstairs are three more bedrooms and two baths, plus an open landing area, perfect for a study, at the top of the stairs. Add the two car garage and this home is a perfect fit for the Shelter Island lifestyle.

A masterful blend of timeless character and elevated modern luxury, this designer-renovated Shelter Island residence delivers a curated living experience across more than an acre of lush, private grounds. Every space has been thoughtfully reimagined with bespoke finishes, high-end materials, and a refined aesthetic that feels both effortless and elegant.nStep inside to sun-filled interiors with clean lines, wide-plank flooring, and a seamless flow ideal for year-round living and entertaining. The designer kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, and a sophisticated palette that complements the homes heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment.nFive beautifully appointed bedrooms and three spa-inspired bathrooms provide comfort and privacy for guests or full-time residents. Each room reflects a balance of luxury and warmth, from serene color schemes to thoughtfully selected fixtures and finishes. A luxurious primary suite includes a spa-style bathroom and walk-in closet, creating a private retreat within the home.nOutdoors, resort-style living comes to life. A heated gunite pool, expansive bluestone patio, and multiple lounging and dining areas create a truly elevated summer retreat. Manicured gardens, mature landscaping, and a serene pond offer tranquil views and exceptional privacy, while the acre+ setting provides ample space for recreation, entertaining, or simply enjoying the natural beauty of Shelter Island. The property also includes an outdoor kitchen, fire pit, and multiple shaded seating areas, perfect for alfresco dining and gatherings.nAdditional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The propertys layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas.nLocated moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island livingquiet, refined, and effortlessly connected to the best of the East End. Move-in ready and finished to a designer standard, this is a rare opportunity to own one of Shelter Islands most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.

A masterful blend of timeless character and elevated modern luxury, this designer-renovated Shelter Island residence delivers a curated living experience across more than an acre of lush, private grounds. Every space has been thoughtfully reimagined with bespoke finishes, high-end materials, and a refined aesthetic that feels both effortless and elegant. Step inside to sun-filled interiors with clean lines, wide-plank flooring, and a seamless flow ideal for year-round living and entertaining. The designer kitchen serves as the heart of the home, featuring premium appliances, custom cabinetry, and a sophisticated palette that complements the home's heritage. The adjacent dining and living spaces offer an inviting atmosphere, with natural light and tasteful detailing enhancing every moment. Five beautifully appointed bedrooms and three spa-inspired bathrooms provide comfort and privacy for guests or full-time residents. Each room reflects a balance of luxury and warmth, from serene color schemes to thoughtfully selected fixtures and finishes. A luxurious primary suite includes a spa-style bathroom and walk-in closet, creating a private retreat within the home. Outdoors, resort-style living comes to life. A heated gunite pool, expansive bluestone patio, and multiple lounging and dining areas create a truly elevated summer retreat. Manicured gardens, mature landscaping, and a serene pond offer tranquil views and exceptional privacy, while the acre+ setting provides ample space for recreation, entertaining, or simply enjoying the natural beauty of Shelter Island. The property also includes an outdoor kitchen, fire pit, and multiple shaded seating areas, perfect for alfresco dining and gatherings. Additional amenities include a state-of-the-art HVAC system, smart home features, and ample storage throughout. The property's layout and orientation maximize natural light, cross-ventilation, and the surrounding scenic vistas. Located moments from beaches, Mashomack Preserve, South Ferry, marinas, and local restaurants, this home captures the essence of Shelter Island living-quiet, refined, and effortlessly connected to the best of the East End. Move-in ready and finished to a designer standard, this is a rare opportunity to own one of Shelter Island's most sophisticated and lifestyle-driven offerings, where every detail has been curated for comfort, elegance, and timeless appeal.

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.

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.

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.

A thoughtfully designed retreat offering peace, privacy, and understated luxury. Tucked away on a private drive in the island's center, you're close enough to bike to all of the island’s beaches or restaurants. The approach sets the tone: a winding drive reveals the house gradually. The home emerges across an expansive lawn, its clean black lines and Anderson windows throughout creating a striking silhouette against the natural canopy. That hammock strung between two trees? Exactly where you'll spend Sunday mornings with coffee and a good read. Inside, the design philosophy is clear: let the outside take the stage. White walls, black accents, and a massive window wall make the front yard feel like your living room's best feature. The newly installed Ortal 110 TS fireplace anchors the open space, a sculptural centerpiece that warms the kitchen, dining, and living areas. Ascoli smart lighting throughout means you can set the color temperature to exactly your liking and automate it to match the rhythms of your day. The kitchen features Robern cabinets, a Thermador gas range, a double oven, and a refrigerator, plus a generous island for preparing all that local fish and farmstand produce. Upstairs, three bedrooms include a primary with an ensuite walk-in shower, a second bedroom with queen-sized built-in bunk beds and clever storage nooks, and a third with expansive windows overlooking the rolling front lawn. A second full bathroom with a tub serves the floor. Downstairs, heated floors make winter mornings civilized. The spacious bathroom features Robern cabinets and heated towel rack, while walk-in closets are generous enough that you and your partner won't need to negotiate territory treaties. Every detail considered, nothing overdone. The fully fenced backyard is its own retreat. Your dog thinks it's paradise. Your green thumb agrees. The newly built backyard office/art studio/yoga sanctuary, properly insulated with new windows and doors, offers a legitimate reason to work from home that doesn't involve your kitchen table. Whether it becomes your creative sanctuary, your focus zone, or just where you hide from houseguests, it's ready. The house comes with complete pool plans designed by Glenn Lawton at Spatial Arts. Modern amenities where they matter: EV charger, bike and board storage, without sacrificing the serenity that brought you to Shelter Island in the first place. Even the entrance makes a statement with its sculptural fountain and thoughtfully designed wood and bluestone steps.

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

Situated in the desirable Sherwood Farms neighborhood, just moments from the private beach and tennis court, this charming shingled home has been fully refreshed and is move in ready. Built in 2005 by renowned Shelter Island builder, George Phriender, it is convenient to the South Ferry as well as south shore restaurants and marinas. Enjoy the peace and quiet of Shelter Island only a few minutes from the South Fork. An amply equipped open kitchen pours out into the windowed dining area, with a fully screened in, covered porch just adjacent. The formal living room, complete with fireplace is spacious yet inviting. The en suite first floor primary is bright and beautiful. Upstairs are three more bedrooms and two baths, plus an open landing area, perfect for a study, at the top of the stairs. Add the two car garage and this home is a perfect fit for the Shelter Island lifestyle.

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.

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.

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.

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.

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.

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.

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.

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

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 often mistaken for a separate lot offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow.nnA chance to own a piece of Shelter Island's story.

Some properties are simply irreplaceable. This is one of them. 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 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. 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. Mature landscaping on all sides for privacy. The expansive side lawn - often mistaken for a separate lot - offers room for an accessory structure. Architectural Renderings available upon request illustrating pool placement and the full potential of this property, making this one of the rare waterfront opportunities with meaningful room to grow. A chance to own a piece of Shelter Island's story.

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.

Wonderful remodeled home located in secluded Silver Beach on West Neck Bay. With water on 2 sides of this lovely estate, enjoy the water views from all rooms. 5 Bedrooms, 6 baths, finished lower level and open rooms, this is a wonderful home to enjoy for the summer or year round. The large open kitchen with high-end appliances opens to a massive dining room overlooking the rolling yard down to the water. The primary bedroom on the second floor features a full bath and two very large walk in closets and French doors out the a balcony. Just off the primary bedroom is one of two laundry areas and 2 guest suites all en-suite. On the main level is an en-suite guest bedroom, library with fireplace, open kitchen and dining room, another full bath for the pool area and a living room with an additional laundry just off the service entrance. This lovely home features a veranda with a pool, detached garage, partially finished lower level and an expansive yard and deep water dock. A wonderful home with exquisite views and room for everyone.