luxury houses with pool for sale Shelter Island, United States

Nestled in the charming neighborhood of East Hampton, 6 Terry Road exudes timeless elegance and modern comfort. This beautiful property boasts a well-manicured garden and a welcoming facade that instantly captures your attention. As you step inside, the spacious living areas are bathed in natural light, creating a warm and inviting ambiance. The chef's kitchen features top-of-the-line appliances and sleek countertops, perfect for culinary enthusiasts. Upstairs, you'll find the serene bedrooms offering a peaceful retreat. The backyard oasis is an entertainer's dream, with a sparkling pool, a cozy patio, and lush landscaping providing an ideal setting for gatherings with family and friends. With its prime location and exquisite features, 6 Terry Road is a haven of luxury and relaxation.

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.

Welcome to *Dancing Oaks*, an extraordinary French Mediterranean estate tucked behind gates on approximately 4 acres in the exclusive Grace Estate of East Hampton. This elegant residence offers a rare blend of timeless European-inspired architecture and modern amenities, all set within one of the most protected and ecologically significant enclaves on Long Island. A winding, formal driveway sets a refined tone on approach, leading to a stately double-door entrance. Step inside to a dramatic two-story foyer with a sweeping staircase and a direct sightline to expansive slate terraces, adorned with balustrade railings. The main level showcases grand entertaining spaces including a formal living room that opens to the terrace, a sophisticated dining room, a media/family room, and a screened garden porch ideal for three-season enjoyment. The first-floor primary suite is a private retreat, complete with a sitting room featuring a gas fireplace, a generous walk-in closet, and direct access to a private terrace. The spa-inspired bathroom includes a jacuzzi tub, a glass-enclosed double shower with six heads and multiple spray features, offering a true at-home spa experience. The chef's kitchen is built for both function and style-equipped with granite countertops, a large center island, wine cooler, dual sinks, hot water dispenser, two dishwashers, top-of-the-line appliances, and an adjacent pantry with additional refrigerator, laundry, and storage. Upstairs, you'll find four ensuite bedrooms with beautifully appointed marble baths and a spacious family room with fireplace overlooking the grand foyer. A separate guest wing includes a three-bedroom suite, ideal for visitors or extended stays. The fully finished lower level offers lifestyle versatility, with space for a screening room, gym, wine cellar, expansive storage, and a family sitting area. Outdoors, the amenities are equally impressive: a Har-Tru tennis court, a heated gunite pool with integrated spa designed to resemble a natural pond (complete with spouting crane fountain and dual stone waterfall), and two guest cottages with kitchenettes, laundry, and outdoor showers-perfect for summer entertaining or private guest quarters. The landscape is a living masterpiece with towering rhododendrons, forsythias, lilacs, hydrangeas, crepe myrtles, and more-all curated to ensure continuous blooms from spring through fall. Over three acres are dedicated to native plants, sustaining local birdlife and wildlife and reinforcing the estate's eco-conscious footprint. **The Grace Estate** is a 623-acre sanctuary of protected forest, beach, and wetlands. Its preservation is one of East Hampton's greatest conservation success stories, ensuring permanent tranquility and privacy for its residents. As part of this premier enclave, owners enjoy access to a resident-only trail leading to a quiet bay beach with picture-perfect sunsets. With 8 bedrooms and 9 bathrooms in the main home, plus 2 additional poolside cottages, *Dancing Oaks* offers the perfect balance of luxury, comfort, and natural beauty in one of the Hamptons' most coveted settings. Discover refined living with deep roots in conservation and serenity-just moments from the best of East Hampton.

Located in the premier Landfall community just 500 ft +/- from private resident-only beach access, this beautifully updated East Hampton contemporary offers a private retreat designed for effortless Hamptons living. Set on .92 +/- acres at the end of a long private drive, the 4-bedroom residence blends modern design with serene natural surroundings. Sun-filled interiors feature soaring ceilings, an open-concept living and dining area anchored by a wood-burning fireplace, and walls of glass sliders that seamlessly connect to expansive outdoor entertaining spaces. The gourmet kitchen is both refined and functional, complete with a substantial center island, Sub-Zero, Viking, and Bosch stainless steel appliances, and an ideal flow for gatherings large or small. The primary suite serves as its own peaceful escape with direct deck and pool access, while the finished lower level offers additional flexible living space including a media area, workspace, guest accommodations, and full bath. A second attached garage presents excellent potential for a gym, studio, or recreation space. Outdoors, the property is tailored for summer living with a 20' x 40' heated pool, expansive decking for lounging and dining, fire pit area, outdoor shower, zen walking garden, sprawling lawn framed by mature trees and natural landscaping, and a removable child safety fence for the pool. Additional highlights include an EV charger and a strong history of short-term summer rentals, offering excellent lifestyle and investment appeal. Just moments away, enjoy endless stretches of shoreline, calm bay waters, and unforgettable sunset skies.

Recently transformed with a stylish new renovation, this turn-key contemporary retreat is set on 1.6± exceptionally private acres backing directly onto a breathtaking 56-acre town reserve. Surrounded by protected natural beauty and located near one of the area's most pristine bay beach communities, the property offers an increasingly rare combination of modern luxury, tranquility, and seamless access to the Hamptons lifestyle. Hidden behind lush landscaping and enveloped by reserve land, the setting feels remarkably secluded and serene. Just moments from Sammy's Beach and Cedar Point, the home is ideally positioned to enjoy kayaking, paddle boarding, sunset walks, and easy access to both Sag Harbor and East Hampton Village. Inside, more than 4,000± square feet of beautifully reimagined interiors are designed for effortless indoor-outdoor living. Natural light pours through oversized windows and skylights, illuminating soaring ceilings, refined finishes, and an airy open layout. At the center of the home is a stunning chef's kitchen anchored by a dramatic 9-foot waterfall island, premium stainless steel appliances, and seamless flow into the dining and living areas. Multiple sliders open to expansive mahogany decking, creating an effortless connection to the outdoors, while a towering fieldstone wood-burning fireplace adds warmth and character to the main living space. The thoughtful floor plan on one story with finished lower level includes the primary suite occupying its own private wing behind a sliding barn door and featuring a spa-like bath with heated floors, freestanding soaking tub, oversized shower, and a spacious dressing room. The finished lower level enhances the home's turn-key appeal with a large guest suite, spa bath, sauna, dedicated laundry room, pantry with additional refrigerator, and separate entrance-perfect for extended stays or flexible entertaining. Outside, the property unfolds like a private resort in total privacy. A 20x40 pool is surrounded by mahogany decking, complete with hot tub, multiple lounge areas, and outdoor dining spaces. Elegant, modern, and completely move-in ready, 56 North Woods Lane is a rare offering in one of East Hampton's most desirable bay beach enclaves-where stylish design, total privacy, and protected natural surroundings come together effortlessly.

Newly built modern estate on approximately 3.65 acres overlooking Fresh Pond and Sag Harbor Bay. Located in coveted North Haven, less than one mile from Sag Harbor Village, this 8,960± SF residence offers privacy, scale, and proximity to beaches, marinas, and dining. The home features 8 bedrooms and 8.5 bathrooms, with expansive glass walls, a double-height foyer, and open-concept living areas designed to maximize natural light and water views. The chef's kitchen includes Sub-Zero and Wolf appliances, marble countertops, an oversized island, and a full butler's pantry. Indoor-outdoor living is emphasized with multiple covered porches, terraces, and retractable glass doors. The main level includes a junior primary suite with spa-like bath and sitting room, along with additional living, dining, and service spaces. The upper level offers a water-view primary suite with dual walk-in closets and a luxury bath, plus five ensuite guest bedrooms and a secondary lounge with wet bar and terrace access. Outdoor amenities include a 20' x 50' heated gunite infinity-edge saltwater pool with spa, limestone patios, mahogany terraces, and a 320± SF pool house with kitchenette and firepit. The property also allows space for a future pickleball or padel court. A refined North Haven offering combining modern design, privacy, and convenient access to Sag Harbor Village.

Newly built cedar-shake estate on approximately 2.37 acres overlooking Fresh Pond and Sag Harbor Bay. in coveted North Haven. Offering 8,030± SF of living space, this traditional-style residence blends classic Hamptons architecture with modern scale, just minutes from Sag Harbor Village, marinas, beaches, and dining. The home features 7 bedrooms, 7 full and 2 half bathrooms, with wide-plank white oak floors, tray ceilings, and a wood-burning fireplace anchoring the main living spaces. Walls of sliding glass doors create seamless indoor-outdoor flow and enhance natural light throughout. An eat-in chef's kitchen with premium appliances serves as the heart of the home, complemented by a first-floor office/den. Multiple living and dining areas provide flexibility for everyday living and entertaining. Upstairs includes a beverage center, spacious bedroom suites, and two rear balconies with pond and bay outlooks. The layout is designed for comfort, scale, and easy living. Outdoor amenities include a 20' x 50' heated pool with bluestone patio, covered dining and lounge areas, and a fireplace-centered outdoor living room for year-round enjoyment. A rare highlight is the opportunity to add a 2,500± SF guest house, offering exceptional flexibility for future expansion. A refined North Haven offering with water views, privacy, and timeless design close to Sag Harbor Village.

Orient – Set high above the Long Island Sound in the storied enclave known as The Hill, this rare offering captures the essence of classic Orient living. Authentic, timeless, and grand in scale, the home showcases architectural details including five fireplaces, elegant 16-over-1 windows, and a front entry framed by original sidelights. The 1.3-acre grounds unfold across rolling terrain with mature landscaping, stonework, and meandering garden paths. A sparkling swimming pool sits tucked into the landscape, creating a private retreat. Inside, generous rooms and a waterside screened porch invite gatherings large and small, all set against the backdrop of unforgettable sunsets. The home offers space, character, and endless potential. Cherished by the same family for 65 years, it now awaits its next steward. Properties of this caliber and in this location are exceedingly rare. It doesn’t get more quintessentially North Fork than this. A truly special Orient opportunity.

Welcome to 150 Hillcrest Dr N, located in Hillcrest Estates. This offering is a to be built opportunity and the images are of another Orient property that this builder wrapped up in 2023. At this point, a very similar style home can be built on this lot or the builder can be hired to do a custom build and tailor the property to a buyer's specifications. The property is elevated, slopes gently SW and will offer sweeping farm/water-views over Orient and out to Narrow River and Long Beach Bay. More information on previous Orient projects can be provided by request or bring your plans and allow your vision for your forever home to come to life!

The pinnacle of Luxury Living In the historic heart of Sag Harbor — a village shaped by its storied whaling past and now celebrated for its cultural sophistication — Residence A stands as a singular architectural statement along one of the most coveted stretches of waterfront. Commanding approximately 250 feet of prime frontage on the harbor, this exceptional estate is far more than a home; it is a four-level masterwork of glass, stone, and light, created for a global buyer seeking complete privacy, effortless luxury, and direct nautical access.This extraordinary property is the result of a visionary collaboration between J. Bialsky of Bialsky Premiere Design & Development and the internationally acclaimed Hollander Design Landscape Architects. Together, they have crafted a residence that exists in perfect harmony with the Peconic Bay — a seamless dialogue between architecture, landscape, and water. Every line is intentional, every perspective framed, and every material selected to endure the coastal environment while maintaining an elevated, timeless aesthetic.Spanning an impressive 16,974 square feet across four levels, the estate is conceived as a vertical sanctuary where grand-scale entertaining and intimate retreat coexist effortlessly. Interiors encompass approximately 12,551 square feet of meticulously designed living space, defined by a palette of organic textures, refined finishes, and state-of-the-art systems. The residence offers eight expansive bedroom suites and ten beautifully appointed baths, thoughtfully arranged to accommodate family, guests, and live-in staff with complete comfort and privacy.Outdoor living unfolds across multiple levels of tiered terraces and lounge decks, creating a dynamic al fresco experience that keeps the water constantly within view. At the pinnacle, a private rooftop sanctuary serves as a crowning architectural achievement — featuring a pool and spa seemingly suspended above the harbor, offering uninterrupted 360-degree vistas and breathtaking sunset views across Sag Harbor’s golden coastline.For the yachting enthusiast, the property delivers a level of functionality rarely found in village waterfront estates. A private, deep-water marina includes two 60-foot boat slips, placing you at the center of the Hamptons’ maritime lifestyle with immediate access to the open Atlantic and the protected waters of Shelter Island Sound.Beyond its beauty, the residence operates with the precision of a modern high-security retreat. A rare private garage provides secure parking in the heart of the village, while fully integrated smart-home technology manages climate, lighting, and security seamlessly from anywhere in the world.Turn-key in every sense, Residence A represents a rare convergence of location, design prestige and waterfront capability — an exceptional offering for the most discerning buyer seeking a legacy property in one of the Hamptons’ most iconic destinations.

Freshly updated and effortlessly stylish, this Sag Harbor retreat includes coveted private beach access. Sunlight pours through the home, creating a bright, airy atmosphere that feels as inviting in the off-season as it does at the height of summer. The interior offers five well-proportioned bedrooms and 3.5 beautifully finished marble baths, along with a seamless open-concept layout. A modern kitchen flows into the dining and living spaces, ideal for both relaxed everyday living and entertaining. Outdoors, a heated gunite pool with spa anchors the backyard, offering a perfect setting for warm-weather enjoyment. Upstairs, the primary suite features a generous private balcony overlooking the grounds, providing a quiet escape. Just minutes from both Sag Harbor Village and East Hampton, this property strikes the perfect balance between convenience and tranquility.

Custom renovated 1920's Long Island Potato Barn with pool, set on .83 acres in Orient. Large foyer with 2 closets. Expansive open concept living/dining/kitchen with wood burning fireplace and sliding doors leading to the brick patio and garden. Master ensuite bedroom with full bath with tub & stall shower, 2 additional bedrooms, full bath, and laundry room. Spacious full basement with high ceilings that was formerly used as a workshop. Exceptional privacy with mature landscaping, heated in-ground pool, brick patio for entertaining, 2 accessory outbuildings. Association Sound Beach rights. Proximity to Orient State Park, Orient Village amenities and marinas. 24 hr. notice for showings.

Rare 1.07-Acre Coastal Compound on The StrandnSet along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Set along one of East Marion's most coveted waterfront stretches, 875 & 785 The Strand present a rare opportunity to own a combined 1.07-acre coastal compound in an exceptionally private and tightly held location. Spanning two adjoining parcels, this offering delivers scale, flexibility, and long-term potential rarely found on the North Fork. Perched just above the shoreline and directly across from the Long Island Sound, the property captures the quiet luxury that defines East Marion-unspoiled, understated, and deeply connected to the water. 785 The Strand features a light-filled, two-story residence with four bedrooms and three baths, designed for seamless indoor-outdoor living. Expansive windows frame the surrounding landscape, while clean architectural lines and warm finishes create a relaxed yet refined atmosphere. An oversized pool, multiple deck areas, and two fireplaces anchor the home as both a private retreat and an exceptional entertaining space. The adjoining 875 The Strand adds an additional .51 acres, opening the door to a range of possibilities-expanded outdoor living, guest accommodations, or the creation of a true multi-generational estate. The compound, which abuts protected communally-owned Pebble Beach non-buildable parcels on the east and south sides, is buffered by mature landscaping, offering a level of privacy and separation that is increasingly rare this close to the water. Beach access is just moments from your door. Also ideally located near marinas, farm stands, wineries, golf courses and a short drive to Greenport Village. This is a rare opportunity to secure a significant landholding in one of the North Fork's most desirable waterfront corridors, offering the scale to enjoy today, and the flexibility to shape for years to come.

Conveniently located 5 BR, 5 Bath sun filled traditional home in Sag Harbor Village perched on a hill is a quick stroll, bike ride or even quicker two minute drive to downtown Sag Harbor and bay beaches. Centrally located, 18 Cuffee Drive is a ten minute drive to East Hampton and Bridgehampton by car. The private backyard oasis features a heated gunite pool and hot tub, patio and deck areas. This 4300 square foot home on .5 acre boosts two floors with an additional large finished lower level. Gracious double height entry leads to spacious, open kitchen with oversized center island and great room with vaulted ceilings, beautiful skylights, flat screen TV and French doors. In addition, there is a first floor guest bedroom, bath, sitting area, and laundry room. On the second level, a primary bedroom overlooks the pool and gardens with ensuite bathroom, 2 guest bedrooms and 2 baths (one ensuite) provide ample quarters for entertaining guests. The finished lower level is 1100 sq. ft. with oversized windows, natural light, oversized sectional sofa, flat screen TV/cable, workout room with cardio equipment (elliptical machine, treadmill, recumbent bike), foosball and ping pong table, electronic keyboard, 5th guest bedroom and bath, and playroom. Additionally, the house provides ample parking, whole house filtered water system, and a multi-zoned heating and air conditioning system. Recently renovated and updated.

Tucked at the end of a long private driveway in East Hampton's Northwest Woods, this well-kept saltbox home offers three bedrooms, two baths, and nearly one acre of well-kept landscaped grounds. A wall of glass floods the open living, dining, and kitchen area with natural light while framing sweeping views of the expansive deck and the 18' x 36' heated pool, ideal for lounging or entertaining. Additional features include central air, updated appliances, a charming pool house, and mature specimen plantings, all set within a peaceful, secluded environment.

Phil Kouffman, one of The Hamptons' most revered builders is poised to break ground on these two striking homes, both well situated equidistance to Sag Harbor or East Hampton village. There is room for Pickle Ball on both properties. (#15 could have Tennis if a buyer prefers.) These homes are not just destined to be wonderful small estates, but at pre-construction pricing they are currently great values

Phil Kouffman, one of The Hamptons' most revered builders is poised to break ground on these two striking homes, both well situated equidistance to Sag Harbor or East Hampton village. There is room for Pickle Ball on both properties. (#15 could have Tennis if a buyer prefers.) These homes are not just destined to be wonderful small estates, but at pre-construction pricing they are currently great values

Welcome to 34 Bull Path, a private and luxurious estate only minutes from Sag Harbor & East Hampton villages, bay beaches, and acres upon acres of preserved land. This beautifully maintained 4-BR, 4-BA designer contemporary on an exceptionally large (3.39 acre) lot features abundant sunshine and peace. The house's layout is gracious and flexible, with two main-floor bedrooms on each side of the house, including a extra-large primary with wood-burning fireplace, triple closets, sliding doors to the pool deck and a grand spa-like bathroom. The grand foyer and central gathering area are ideal for hosting dinners and parties, and the kitchen offers high-end appliances and a dining peninsula. Upstairs is a substantial loft with a media room, full bathroom, an office area and storage. Out back, with verdant landscape in every direction (and an 8' deer fence), there isn't a house in sight. The 20' x 40' pool is surrounded by extensive outdoor decking and entertaining space, along with an outdoor shower and cabana bathroom access, and the detached two-car garage with loft offers extensive storage. Find serenity and nature at this beautiful oasis close to both East Hampton and Sag Harbor.