luxury waterfront houses for sale Shelter Island, United States

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

This income-producing property sits prominently on the pristine swimmable waters of Gardiner's Bay, nestled by the wild acreage of Blue Bay Camp, abutting the natural dune beauty of Maidstone Park with front-row seats to East Hampton's most breathtaking sunsets. The Bay Beach is literally at your doorstep. The primary structure on the beach is a legal two-family house on three levels, with 5 bedrooms, 3 baths, two kitchens, and living spaces open to the waterside. Additionally, there is a separate legal dwelling with 2 bedrooms, 1.5 bathrooms, and a full basement and garage with access from Gallatin Lane. There are 102 feet of sandy beach frontage, a heated pool, and a separate two-car garage with additional storage. Swim, fish, paddle, and sail from your own front yard and within the private compound. The possibilities of your enjoyment, potential income, and/or stellar renovation into a thoroughly modern home are limited only by your imagination. Call for an appointment. Showings are easy.

Waterfront Living on the North Fork- Wake up to breathtaking views of the Peconic Bay, where sunlight dances across the water, birds soar above the neighboring nature preserve, and a tranquil deep-water inlet stretches beyond your deck. This charming beach cottage offers a rare opportunity to experience the very best of North Fork waterfront living. Featuring 3 bedrooms and 2 baths, the home offers a comfortable, open-concept layout connecting the waterside living room, dining room, kitchen, and entertainment areas—perfect for relaxed summer mornings, afternoon gatherings, and memorable evenings with family and friends. Step outside onto the spacious wraparound deck and take in 120 feet of pristine waterfront. Spend your days swimming, kayaking, sunbathing, or simply enjoying the ever-changing beauty of the bay. The property is extremely private and peaceful, yet just steps from the private sandy association beach. A rare and special waterfront retreat, this quintessential cottage captures the effortless beauty of North Fork living—a place where every day feels like summer.

An extraordinary offering on the Peconic Bay, this refined Cedar Beach waterfront estate presents over 200 feet of direct, sun drenched, south facing shoreline and beach with a protected, private dock deep enough for a mid twenty ft boat, a truly rare combination of attributes to find on the North Fork. Thoughtfully designed to embrace its breathtaking setting, the house is set on a double lot whose southern exposure also produces the luxuries of southerly breezes and a true, useable and enjoyable beach not encumbered by prolific rocks or muck. The home itself is defined by soaring cathedral ceilings, sun-drenched interiors, and elegant entertaining spaces that seamlessly transition to expansive waterside terraces overlooking endless bay views and spectacular sunsets. Private ensuite accommodations and beautifully curated living spaces evoke a sense of understated coastal sophistication. Complementing the property, a separate waterfront parcel directly across the street features a newly refurbished private dock with direct bay access, offering an exceptional opportunity for boating, fishing, quick trips to Shelter Island, Sag Harbor, the Hamptons and other beautiful East End destinations. A exceptional and rare North Fork lifestyle centered around the beach, sun and water.

Fully renovated and exceptionally private, this sophisticated waterfront contemporary is a true North Fork retreat, pairing stylish interiors with a serene setting and an effortless outdoor lifestyle. Hardwood floors and walls of glass define the open-concept, where a beautifully appointed kitchen flows into the living and dining spaces and an inviting sunroom, all oriented toward the water. Two main-level primary suites and three modern baths offer exceptional comfort and flexibility. Outside, the setting takes center stage. Expansive mahogany decking wraps around a heated saltwater pool overlooking the water, creating a private resort-like escape. A semi-enclosed gazebo, generous lounge areas, and open-air dining space make entertaining effortless, while the spacious lawn beyond is perfect for a fire pit, lawn games, and summer afternoons. A private dock accommodates a 20-foot boat with easy access to Peconic Bay, while the HOA’s private bay beach offers another coveted way to enjoy the waterfront. Elevated above the shoreline, the property enjoys beautiful water views and abundant wildlife from nearly every vantage point. Polished yet relaxed, private yet perfectly connected to the water, this is North Fork living designed to be enjoyed all season long.

Nestled between the Atlantic Ocean and Georgica Pond lies a storied property synonymous with Hamptons history. The 8.22-acre two parcel compound has changed hands just three times despite being one of the first properties developed in the Georgica Dunes, with each owner treating the estate as a sacred trust - honoring its remarkable legacy while elevating its elegance. The offering comes with the last vacant buildable oceanfront parcel in the Village. Among the landscaped grounds, you'll discover over 500 feet of ocean frontage, unobstructed views, the last working boathouse on the pond, a tennis court, a nearly 9000-square-foot main residence, and room for thoughtful additions. With award- winning design, bespoke craftsmanship, and a provenance that reads like a chapter of American cultural history, this is an unmatched residence ready to greet its next generation of proud stewards. Completed in 1894 by Laura Brevoort Sedgwick James, the residence is thought to be one of the oldest on the Georgica Dunes. In 1935, Juan Trippe, founder of Pan American World Airways, acquired the home and expanded the compound. In 1981, the property was sold to fashion designer Calvin Klein and his wife, Kelly Rector Klein, who launched a meticulous transformation of the home under renowned French architect Thierry Despont. The residence is a classic Shingle Style abode featuring gambrel roofs and over 5,000 square feet of decks, patios, and gardens for seamless indoor-outdoor living. Inside, the showplace expertly pairs glamorous contemporary design with original elements for a timeless aesthetic spanning more than a century of elegant living. Soaring beamed and coffered ceilings rise above original wide-plank pine, new oak, imported French stone, custom millwork and eight fireplaces. A gracious foyer with a two-story metal fireplace makes a dramatic first impression, while the formal dining room sets the stage for lavish entertaining. Linger in the charming tearoom, or gather in a living room topped by a glass catwalk or enjoy all-season enjoyment of the surrounding landscape in the attached screened-in porch. Entertaining is effortless with a main kitchen, prep kitchen and staff kitchen equipped with La Cornue, Viking and Sub-Zero appliances. A chic bar/lounge keeps refreshments within easy reach. Across the deck, the iconic tower is a retreat within a retreat featuring a curved staircase, a dome, a family room with its own wet bar, and a private bedroom suite above. The home's upper level includes a palatial owner's suite featuring a fireplace, two bathrooms with walk-in closets, and access to a large deck. Three secondary suites enjoy water vistas, while a study and wraparound decks complete the top floor. The thoughtfully appointed lower level - complete with a sixth bedroom suite, staff quarters, mudroom, laundry and sauna - ensures the estate runs effortlessly. Extensively updated for modern living, the residence boasts new hurricane-rated windows and doors, geothermal systems, a generator, fully integrated security and smart home automation. Thanks to its unrivaled location, the sanctuary commands virtually unimpeded, 360- degree views from dawn to dusk. Enjoy sunrise strolls on the beach, take a sunset paddle on the pond, and perfect your backhand on the clay tennis court featuring a viewing terrace. Garden paths amble past irrigated landscaping, native plantings and fountains, while the outdoor shower rinses sandy toes and paws. An automated entry, locked garden gates, a four-car garage, and ample parking complete the property. Alongside the tennis court, you'll find the ideal setting for a two-bedroom guest cottage and pool/spa addition. On the adjacent 1.63-acre parcel, architectural plans envision a three-story residence with a garage. Designs for both have been developed and will be permitted as part of the sale - a rare opportunity to continue the growth and improvement of one of the Hamptons most storied compounds.

Rarely does a property like this become available in Sagaponack. Set on half acre on a quiet lane with only a few neighboring residences, this exceptional three-bedroom, three-bathroom contemporary beach house allows its extraordinary setting to take center stage. With direct access to one of the East End's most beautiful stretches of beach, it is designed to embrace its remarkable setting, with stunning ocean vistas from almost every room. The open plan first floor is flooded with light, with sliding doors on two sides open to a wrap around deck perfect for indoor outdoor oceanfront entertaining. Upstairs there are three bedrooms, also with magnificent views, and a covered deck. If you have dreamed of a carefree, low maintenance, barefoot living, listening to the sound of the surf and watching the iridescent Sagaponack light over the sea, look no further!

With approximately 200 feet of direct ocean frontage on one of Sagaponack's most private and prestigious lanes shared by only three other homes, this is a generational opportunity rarely seen on the East End. Two separate parcels (both with deeded beach access), protected by a non-conforming pre-existing rock revetment, offer extraordinary potential in a setting that is as private as it is breathtaking. The main residence is a commanding, nearly 9,000 sq. ft., modern beach house-built with substance and intention. Floor to ceiling walls of glass open the home to the serene ocean landscape, offering uninterrupted views of the Atlantic Ocean and dramatic sunsets over a neighboring pond. Terraces spill out toward a pool, spa, and wildflower meadow that runs all the way to the dunes, where a pre-existing (and grandfathered) pavilion and private stairs deliver you directly to one of the widest stretches of beach in the Hamptons. A pre-existing, non-conforming lower level is fully built out with staff quarters, wine cellar, gym, game room and more. The home's scale, quality construction, and excellent condition make it an ideal canvas for reimagination-whether reconfiguring the interior or elevating the existing design to match its surroundings. Directly across the private gravel drive, the second parcel offers a blank slate with deeded ocean access and its own executive golf course. It's perfectly suited for a guest house, expanded estate grounds, or added amenities like tennis and pickleball. This is not just a property - it's a true compound - in one of the most coveted oceanfront enclaves in the world.

With approximately 200 feet of direct ocean frontage on one of Sagaponack's most private and prestigious lanes shared by only three other homes, this is a generational opportunity rarely seen on the East End. Two separate parcels (both with deeded beach access), protected by a non-conforming pre-existing rock revetment, offer extraordinary potential in a setting that is as private as it is breathtaking. The main residence is a commanding, nearly 9,000 sq. ft., modern beach house-built with substance and intention. Floor to ceiling walls of glass open the home to the serene ocean landscape, offering uninterrupted views of the Atlantic Ocean and dramatic sunsets over a neighboring pond. Terraces spill out toward a pool, spa, and wildflower meadow that runs all the way to the dunes, where a pre-existing (and grandfathered) pavilion and private stairs deliver you directly to one of the widest stretches of beach in the Hamptons. A pre-existing, non-conforming lower level is fully built out with staff quarters, wine cellar, gym, game room and more. The home's scale, quality construction, and excellent condition make it an ideal canvas for reimagination-whether reconfiguring the interior or elevating the existing design to match its surroundings. Directly across the private gravel drive, the second parcel offers a blank slate with deeded ocean access and its own executive golf course. It's perfectly suited for a guest house, expanded estate grounds, or added amenities like tennis and pickleball. This is not just a property - it's a true compound - in one of the most coveted oceanfront enclaves in the world.

With approximately 200 feet of direct ocean frontage on one of Sagaponack's most private and prestigious lanes shared by only three other homes, this is a generational opportunity rarely seen on the East End. The existing modern beach house is a commanding, nearly 9,000 sq. ft. home built with substance and intention. Walls of glass open the home to the serene ocean landscape, offering first floor views of the Atlantic Ocean and dramatic sunsets over a neighboring pond. Terraces spill out at ground level toward a pool, spa, and wildflower meadow that runs all the way to the dunes, where a pre-existing (and grandfathered) pavilion and private stairs deliver you directly to one of the widest stretches of beach in the Hamptons. The home's scale, quality construction, and excellent condition make it an ideal canvas for reimagination- whether simple enjoying as is, updating the luxurious interior or elevating the existing design to current standards and styles to match its surroundings. Alternate, the home could be completely rebuilt within a generous building envelope. Directly across the private gravel drive, a second parcel offers a blank slate with deeded ocean access and its own executive golf course. It's perfectly suited for a guest house, expanded estate grounds, or added amenities like tennis and pickleball. This property offers luxury and opportunity that few oceanfront homes can match anywhere in the Hamptons.

Set on .94+/- acres, this rare south of the highway opportunity is on a private Sagaponack cul-de-sac with deeded ocean access and water views of the Ocean, Sagaponack Pond, and sweeping Farm Fields. Spanning three levels with a rooftop deck offering three scenic outlooks, this existing residence can be renovated or replaced, offering tremendous upside in one of the Hamptons' most desirable locations. The existing residence offers approximately 5,000+/- square feet of living space with 5 bedrooms and 6.5 bathrooms, with elevator access, thoughtfully designed for both comfortable living and seamless entertaining. Generous gathering spaces include both indoor and outdoor living areas. The primary suite is a standout feature, offering 2 full bathrooms and dual walk in closets, benefiting from western exposure over Sagaponack Pond. The suite enjoys breathtaking sunsets throughout the year. A private pathway leads directly from the property to the beach, creating a unique access to the ocean, rarely found today. Surrounded by premier estates and endless potential, this is an extraordinary opportunity to create a custom Hamptons retreat in a truly special setting. Combining privacy, natural beauty, protected views, and direct beach access, this is a sought after opportunity in one of Sagaponack's most desirable settings.

Water Front Living at its best! With over 116' of waterfront, launch a paddle board or kayak and explore the pristine waters of North Sea Harbor and the Peconic Bay. This is a rare opportunity in the coveted Southampton Cove enclave next to a town reserve. This newly renovated 3-bedroom, 2-bath home sits on a generous waterfront parcel on Fish Cove, offering serene views, direct access to the water and endless sunsets. The property features private water front frontage on Fish Cove with dock plans currently in progress, creating exceptional potential for boaters, paddle boarders, and anyone who dreams of stepping outside and onto the water. Inside, the home offers bright, comfortable living spaces with an easy flow and room to expand or reimagine. Whether you're seeking a year-round residence, a summer escape, or an expansion opportunity in a premier location, this property delivers tremendous value-especially with the recent price reduction. Plans are also available to add an additional 500 sq' plus onto the current home and possible pool or hot tub. This is a rare chance to secure a waterfront address in Southampton with future dock access and endless potential. A bonus room on the first floor has a separate kitchenette and laundry. Within minutes to both the bay beaches and Southampton Village amenities and the ocean. Enjoy kayaking in the peaceful waters of the Cove, or bring your canoe and picnic at the nearby bay beach. Centrally located just minutes from Southampton Village shops, dining, and world-class beaches.

Some homes are simply owned. This one has been loved. For decades, the same family has cared for 302 Shore Road - tending to it, gathering in it, and watching the tides of Napeague Bay mark the seasons. Now, this private beachfront retreat is ready for its next chapter. Here, mornings begin with the hush of the bay and the comfort of knowing the sand outside your door is truly yours. Featuring three bedrooms, two full baths, a renovated kitchen, a three-season porch, 80 feet of bulkhead, and scenic views of Gardiners Island. The home is designed for relaxed afternoons on the generous deck, where laughter carries softly through the breeze. Evenings settle into a quiet only a private shoreline can offer. This isn't just a home; it's a legacy waiting for its next steward. Please note: The property is privately owned and not a land lease, thus the buyer does not need to be an existing resident of East Hampton to purchase.

Tucked away along Terry Path, a rustic country lane within, an offshoot of the Camp Mineola Beach Association, this exceptional waterfront property is nestled in a quiet seaside enclave along the Great Peconic Bay. Opportunities to purchase within this historic neighborhood are exceptionally rare, making this a truly special offering. Set on approximately 1.4 acres with more than 110 feet of unobstructed frontage on the Great Peconic Bay, the classic Cape Cod-style residence offers timeless charm and tremendous potential. The spacious interior is centered around a striking stacked red brick wood-burning fireplace, while outside, a private sugar sand beach and full bulkhead provide an ideal setting for enjoying the waterfront. A substantial original boathouse, complemented by a newer three-car garage and expansive bonus space above, offers endless possibilities for storage, recreation, or future customization. The level, cleared grounds enjoy abundant sunlight throughout the day and provide ample space for expansion from the house, an in-ground pool as part of a remarkable waterfront compound. Combining a coveted Bayfront setting, generous acreage, and the enduring character of one of the North Fork's most treasured beach communities, this is a rare opportunity to create an exceptional coastal retreat.

Embrace North Fork living in this beautifully maintained Mattituck home, where water views, beautifully appointed interiors, exceptional outdoor spaces, and a coveted location come together. Offering 3 bedrooms and 3 full baths, the home is thoughtfully designed for both everyday living and effortless entertaining. Abundant natural light, relaxed finishes, and a gas fireplace create a warm and inviting atmosphere. The open-concept kitchen, dining, and living areas flow seamlessly together, while the well-appointed kitchen features stainless steel appliances and generous counter space. Upstairs, the spacious primary suite overlooks Mattituck Inlet and includes a spa-like private bath and expansive walk-in closet. Two additional bedrooms and a full bath provide comfortable space for family and guests. A finished lower level with a dedicated tv room offers additional flexibility for movie nights, recreation, or quiet retreat. Outside, beautifully landscaped grounds create a private setting for enjoying the outdoors. The spacious patio and built-in BBQ area are made for entertaining, while Sonos speakers extend throughout the home and backyard. Ideally located near sought-after Love Lane, North Fork wineries, farm-to-table restaurants, local beaches, and farm stands, this turnkey home offers an exceptional opportunity to experience the North Fork lifestyle year-round.

Welcome to your coastal sanctuary. There's a certain kind of morning that only happens here - sunlight spilling across the water, the breeze carrying in off LIS, and the promise of a day spent outdoors. Set on 1.64 sun-drenched acres w/breathtaking views to the Sound, this 4-bdrm retreat invites you home from the moment you arrive. An open, light-filled floor plan & hardwood floors welcome you, anchored by a kitchen built for gathering: an oversized quartz island, induction stove, and a prep sink for effortless entertaining, and a wine fridge for evening toasts. Warm up by one of two propane log fireplaces in the living room and sitting room, or retreat to the primary suite with its walk-in closet & spa-like bath. Radiant-heated baths, plush upstairs carpet, and central air keep every season comfortable, while a new roof, HVAC system, and new Thermopane windows, (2020), mean this home is move-in ready. Outside is where it comes alive: coffee at sunrise in the three-season sunroom, gatherings on the sprawling Trex deck, evenings in the hot tub, and swims in the deck-framed pool with water views from every angle. Steps from a sandy beach and moments from the Four Mile River Boat Launch, your days can start with sunrise walks and end with sunset sails. With I-95 nearby NYC and Boston.