luxury properties for sale Shelter Island, United States

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.

Dating back to the original 1871 layout of the Shelter Island Grove and Camp Meeting Association, Spring Garden Avenue is celebrated for its organic, rolling streetscapes and preserved 19th-century architecture. 5 Spring Garden Avenue is an authentic 1880 Victorian residence that embodies the classic style of the era, from its steeply pitched rooflines to its expansive exterior woodwork. The interior layout is expansive and true to its vintage, characterized by distinctive octagonal rooms on both the first and second floors. With five bedrooms, a sprawling third-floor attic loft, and a substantial footprint of covered decks and porches, the home offers a generous canvas within a historic setting. A significant structural update was completed in 2008, replacing the older foundation with a new poured concrete basement and structural footings, alongside the installation of a new roof. Featuring full access to the Shelter Island Heights Association tennis courts and beach club, this property represents an authentic piece of island history.

This expansive North Fork property offers idyllic privacy, boundless potential, and exceptional versatility across three separate parcels. The spacious 4-bedroom, 4.5-bath main residence awaits your finishing touch - customize and craft your dream home exactly as you envision. Ample natural light, flexible open spaces, and generous proportions provide a canvas ready for refinement inside and out. A single and separate buildable 3/4 acre parcel offers a charming, 2-bedroom, 1-bath cottage offers ideal accommodations for guests, caretaker quarters, rental opportunity, investment, or expansion. This unique estate is agricultural-zoning with development rights sold land. Currently operating as a thriving privet farm, featuring 16,500 mature California Privet shrubs and an additional 8,000 seedlings - yielding opportunities for wholesale, landscaping, and horticultural expansion. Embrace the outdoors with tranquil features including a picturesque pond, a greenhouse for year-round cultivation, and extensive grounds perfect for farming, equestrian pursuits, or simply a peaceful sanctuary away from the hustle and bustle. The layout and multiple outbuildings offer versatility for hobby farming, horses, or creative pursuits. Whether you seek a working agricultural venture, a retreat, or an extraordinary setting for your next chapter, this exceedingly rare North Fork treasure presents an unparalleled opportunity in a coveted location. Could Be You!

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.

This charming Greenport cottage blends warmth, character, and easy coastal living just moments from Greenport Village. Located only a short stroll from Main Street, shops, restaurants, and the waterfront, it offers the rare combination of village-adjacent convenience while still feeling peaceful and residential. Full of natural charm, the home features a comfortable two-bedroom layout with a relaxed, inviting feel throughout. It’s the kind of space that immediately feels easy to settle into, with potential to enhance over time. Out back, a deck and separate patio create seamless indoor-outdoor living—perfect for morning coffee, summer dinners, or quiet evenings at home. The outdoor space becomes a true extension of the home and adds meaningful lifestyle value. Filled with character and opportunity, this is a special chance to enjoy the best of Greenport living—walkable to everything that makes the village so desirable, yet tucked into a quieter setting with a true North Fork charm.

A rare opportunity to own an historic house with land that runs between Union and Jefferson Streets allowing for a south-facing light, room for a large garden and swimming pool is listed for sale. Included are permitted plans plans for a substantial addition on one of the largest residential parcels within this location of Sag Harbor Village. A three-quarter (.75 acre) site with mature landscaping and perimeter evergreens all makes for a securing a rare jewel in this convenient and central location and moments from the best of what Sag Harbor has to offer for one of the best lifestyle experiences on the East End.

Down a long winding driveway, tucked away on a .67-acre flag lot - this location is the ideal setting for your oasis in the idyllic hamlet of Springs. Less than 5 miles from the vibrant village of East Hampton, this setting provides a quiet backdrop on a dead-end, waterfront street where you can launch your kayak or paddleboard into the harbor and watch the sun go down. This 3 bedroom, 2 bathroom contemporary ranch has lofted ceilings, exposed beams, a wood-burning fireplace, and plenty of light. The kitchen, dining, and living room all open into each other, so whether you're cooking for a crowd or just hanging out, it flows seamlessly. Slide open the back doors and you're on a full-length deck with built-in seating- an ideal extension of the living space for warm evenings outdoors. The welcoming front deck adds another spot to relax and unwind. The primary bedroom has vaulted ceilings, skylights, its own deck access, and a bright, airy bathroom. The two additional bedrooms are a good size and there is an additional full bathroom set down the hall. The large, .67 acre lot provides ample opportunity for expansion and a pool. All of the best waterfront restaurants are all less than a mile away, as well as country markets, The Springs Tavern, the best bay beaches and farmers markets and art shows. This one's a keeper in an unbeatable location- or a really solid investment with an excellent rental history so call for your own private tour.

Welcome to 6 Sawmill Lane, a luxurious modern traditional home just outside of East Hampton Village. This stunning 6,800 sq ft, 6-bedroom, 6.5-bathroom residence blends contemporary design with timeless elegance, featuring Maibec cedar wall shingles and Alaskan yellow cedar roof shingles. Step inside to a grand entryway with double African Mahogany doors and a natural bluestone walkway. The formal living room boasts a 20-foot ceiling, vast glass doors, and a breathtaking Carrera Consentino Dekton stone fireplace. The informal living room and loft also offer expansive views and seamless indoor-outdoor living. The gourmet kitchen is equipped with high-end Jennair Noir appliances, a spacious Cosentino Dekton island, and custom cabinetry. An adjoining wet bar with a beverage fridge and ice maker is perfect for entertaining. The smart home system, controlled via Lutron, integrates lights, temperature, and Sonos sound systems throughout the home. All six bedrooms offer luxury and privacy, with en-suite bathrooms featuring Porcelanosa Xtone tiles and Brizo fixtures. The first-floor primary suite includes a private terrace, while each of the four second-floor bedrooms has balcony access. Enjoy leisure and entertainment with a state-of-the-art media room, a climate-controlled wine cellar, and a flexible gym or office space. The outdoor kitchen, complete with a sink, grill, refrigerator, and a 55-inch TV, complements the 40x20 saltwater gunite pool and 7x7 spa. This home also features a solar-paneled roof, a 400 Amp electric panel. A spacious two-car garage with an electric charging station caters to modern transportation needs. Experience unmatched luxury and sophistication at 6 Sawmill Lane, your East Hampton sanctuary.

Tucked away on a quiet lane just moments from East Hampton Village and pristine ocean beaches, 12 Garbis Lane is a brand-new modern estate that defines Hamptons luxury living. Set on 1.15 beautifully landscaped acres, this +7,000-square-foot residence offers seven bedrooms, five full and two half baths, and an effortless blend of sophistication, comfort, and resort-style amenities. The grand entry opens to sun-drenched, open-concept living spaces with soaring ceilings, wide-plank oak floors, and floor-to-ceiling glass doors that frame the stunning outdoor setting. A sleek chef's kitchen with top-tier appliances and a custom oversized island anchors the home, seamlessly connecting to elegant dining and entertaining areas. The first-floor junior primary suite is a serene retreat with a spa-like bath, while six additional bedrooms provide generous accommodations for family and guests. Designed for wellness and recreation, the home features a state-of-the-art gym, sauna, theater, and temperature-controlled wine cellar. Outside, a 20x46 heated gunite pool and spa take center stage, complemented by a chic pool house, pickleball court, and expansive white marble patio ideal for lounging and dining al fresco. A three-car garage with an EV charger, smart home technology, and premium finishes throughout complete this exceptional offering. Combining modern architecture, thoughtful craftsmanship, and a premier village fringe location, 12 Garbis Lane delivers the ultimate East Hampton lifestyle-private, polished, and moments from everything that makes the Hamptons extraordinary.

It’s All About the Location! Perfectly situated along the Long Island Sound in the coveted hamlet of Southold. This quintessential North Fork beach cottage captures the very essence of coastal living, offering 100 feet of prime, sandy beachfront—a rare and exceptional find. While intimate in scale, the property delivers a lifestyle that’s nothing short of extraordinary. Spend your days seaside, basking in the sun amid Mediterranean-like surroundings, and your evenings savoring a cocktail as the sky transforms into a canvas of breathtaking sunsets. Set on .8 of an acre, this property presents a unique opportunity—enjoy it in its current charming form or plan and build your custom waterfront dream home. Either way, this offering embodies the timeless appeal of beach front living at its finest.

Welcome to 3 Jody's Path, a modern ranch-style home situated on nearly 2 acres in the coveted Northwest Woods of East Hampton. This completely renovated residence offers 1,852 square feet of sophisticated living space, featuring three bedrooms (potentially four) and two bathrooms. The home is designed to capture an abundance of natural light, highlighted by new seven-inch white oak hardwood floors and vaulted ceilings. The open-concept living area includes a spacious living room with a wood-burning fireplace, a dining area, and a gourmet kitchen equipped with Thermador appliances. The primary bedroom is a luxurious retreat, featuring a wood-burning fireplace, en-suite bathroom, dual closets including a walk-in, cathedral ceilings, and access to a private deck area. Additional interior amenities include a den or office that could potentially serve as a fourth bedroom, subject to permitting and septic review. The home is wired for a sound system of your choice and includes a new security system. Multiple skylights and four sets of sliding glass doors enhance the indoor-outdoor flow, leading to expansive deck areas and a beautiful free-form heated pool surrounded by a bluestone patio. The exterior of the property is equally impressive, with cypress board siding and an expansive mahogany deck, perfect for outdoor entertaining. The backyard is a private oasis, enclosed with fencing and lush landscaping. The cul-de-sac location ensures tranquility and privacy, while the spacious grounds offer room for expansion or the possibly to add a recreational space such as a pickleball court. This turnkey Hamptons home is a rare find, offering both modern luxury and the potential for further customization.

Located in one of the most exclusive waterfront enclaves in the Hampton's, this modern home sits on 1.7 bay front acres and hosts incredible bay and ocean views! Across the street to the ocean, the location and sunset views don't get any better! Includes great detailing, all amenities, and clean modern spaces, pool, and dock! The ultimate modern beach house.

Pristinely maintained and thoughtfully manicured, this quality custom-built traditional residence in East Hampton Village South of the Highway offers timeless elegance with every modern convenience. Designed and constructed by renowned builder Michael Davis, renovated in 2009, and impeccably maintained including new roof and new pool. This classic spans approximately 6,400 square feet across two levels and is tailored for your Hamptons lifestyle. Upon entering, one is immediately welcomed into the gracious living room with a stately fireplace, flowing seamlessly into an intimate formal dining room ideal for entertaining. The heart of the home is the large eat-in cook's kitchen, complete with an adjoining den and fireplace, overlooking shy 2 acres of open, landscaped lawns that are beautifully hedged for privacy. Outdoors, the setting is a private resort-like oasis. Nestled among flowering gardens, the oversized custom gunite pool invites leisure, complemented by a charming pool house with outdoor shower and an all weather tennis court-perfect for summer enjoyment. A stone patio enhances the outdoor living experience, ideal for hosting gatherings or quiet relaxation. The first-floor primary suite is a true sanctuary, featuring its own fireplace, spa-like bath with oversized stall shower and soaking tub, and French doors leading directly to the patio and gardens. The main level also includes a generous library suite with custom wood built-ins, easily serving as a seventh guest room, staff quarters, a full laundry room, powder room, and an additional full bath with exterior patio access. Upstairs, accessible by both a beautifully crafted staircase and a convenient elevator, are multiple guest suites-six bedrooms in total and seven-and-a-half baths-along with a comfortable bonus TV room for casual relaxation. Additional amenities include a two-car garage and a partially finished basement offering further potential. This exceptional home, offered for the first time, represents a rare opportunity to own a distinguished East Hampton Village estate, meticulously crafted for enduring style and comfort.

Located in one of the most beautiful and private neighborhoods of Southampton North This spacious and beautiful gabled traditional was custom built by Farrell Building Co. Impeccably maintained, the 6,300+/- sq. ft. home on an acre landscaped for privacy offers six en-suite bedrooms, eight full baths, state-of-the-art kitchen, and a location convenient to Southampton, Sag Harbor, and Bridgehampton, with ocean and bay beaches minutes away. Gracious, light-filled living areas include a living room with fireplace, coffered ceiling and French doors to an expansive rear deck, formal dining room, and eat-in kitchen with island seating, breakfast area, and glass doors to the deck. The bright, airy master suite has vaulted ceilings in the bedroom with a sitting area, a private balcony overlooking the unlimited reserve and a luxurious bath. In the finished lower level find a theater, sauna and billiards room. Outdoors relax or entertain on the sunny deck or spacious covered porch with outdoor fireplace; enjoy the heated gunite pool and spa.

A rare and highly coveted estate parcel in bucolic Sagaponack South just half a mile from the Atlantic Ocean. This perfectly proportioned 2.2 acre building site enjoys a premier setting at Town Line Road and Hedges Lane, directly across from a 15 acre conservation easement - an area of preserved scenic beauty that enhances the natural openness and enduring value of the property. Create a distinguished legacy estate on one of the largest parcels in Sagaponack South with the potential for extraordinary development, with allowances for 32,000+ SF of lot coverage and the opportunity to construct an 11,000+/- SF residence across three levels with amble room for pool, pool house, a north-south facing tennis court and expansive front, rear and side lawns. This exceptional double-wide parcel ensures privacy and flexibility making it a truly unique canvas with no clearing restrictions. Sagaponack stands among the most prestigious and sought-after zip codes in the United States, renowned for its natural beauty, exclusivity and legacy of estate properties.

Kayak and paddle board to the ocean on Sagg Pond. Enjoy this beautiful 2 acre waterfront setting in Sagaponack featuring 300 feet of frontage and Sagg Pond via the 200' private dock. This exceptionally renovated 6,100 Sq. ft. six bedroom, six and one-half bathroom home offers a traditional façade with modern interior features. Large bay windows provide expansive water views of Sagg Pond. Exquisite details throughout this luxurious two story home include extensive millwork, Brazilian cherry hardwood floors, three fireplaces, a superbly appointed paneled library, and an expansive first floor jr. master bedroom. The fully equipped chef's kitchen is complete with marble countertops and top of the line Wolf and SubZero appliances. On the second level, you'll find the luxurious master retreat which features a custom fireplace, a balcony, and an expansive modern bath with double sinks, an air-spa tub, glass enclosed shower, and marble floors. Four additional immaculate guest suites and a laundry room complete this level. Soak in the water views on a sunny mid afternoon from the comfort of your covered porch in the back of the house, or cool off in the heated gunite pool and spa while listening to the soothing sounds of the manmade koi pond and waterfall. Tranquility and natural beauty await the discerning purchaser of this waterfront masterpiece, located just a short distance to ocean beaches and Bridgehampton's Main Street.

Tucked into 2.8 wooded acres in Amagansett North, 62 Canvasback offers privacy, scale, and a home designed equally for entertaining and quiet weekends. Designed by architect Andrew Pollock and built by fourth-generation builder Ronald Webb, this newly constructed residence draws from the traditional Hamptons vernacular-cedar shingles, white trim, and long eaves-reinterpreted through more modern rooflines and proportions, resulting in a fresh transitional design. Spanning approximately 8,300 square feet of total buildable area, the home features eight bedrooms, all located above grade-an increasingly hard-to-find offering. Inside, the main level is organized around a 22-by-50-foot great room with 9-foot French doors opening to the south lawn and pool deck. Adjacent to the great room, a chef's kitchen in custom white oak is equipped with Wolf and Sub-Zero appliances and a 10-foot bifold window that opens directly to the pool deck. Outside, over 5,000 square feet of multi-level Red Balau decking extends across the rear of the property, with more than 4,000 square feet centered around the pool. The pool and spa are separately heated. A cedar-shingled pool house includes a full bathroom, changing room, outdoor shower, sauna, built-in bar, and a large covered overhang for shaded dining and lounging. The lower level extends the living space with a 22-by-50-foot recreation room, nearly 9-foot ceilings, a wet bar, dedicated media area, gym, and three above-grade bedrooms, all with direct access to the outdoors. Upstairs, the 1,500 square foot primary suite features 14-foot cathedral ceilings, two custom white oak walk-in closets with integrated LED lighting, and a separate office or nursery. A covered balcony overlooks the property from within the tree canopy. The primary bath is centered around a freestanding soaking tub, flanked by two walk-in showers, and a custom 7-foot white oak vanity with oversized 48-inch medicine cabinets. .Polished nickel finishes are carried throughout. A rare combination of craftsmanship, architectural sophistication, and lifestyle design-all set within one of the Hamptons' best-kept secrets, Amagansett North.

Discover this elegant Water Mill summer retreat, perfectly situated in the heart of the Hamptons. Surrounded by meticulously landscaped grounds, the residence offers sunlit interiors, refined yet comfortable living spaces, and a thoughtfully designed layout that seamlessly accommodates both everyday living and entertaining. Outdoors, a private pool is framed by lush greenery, creating a tranquil escape ideal for summer relaxation and gatherings. The home's effortless indoor-outdoor flow enhances the experience, whether hosting guests or enjoying quiet moments. Just minutes from pristine beaches, charming village shops, and acclaimed dining, this property offers the quintessential Hamptons lifestyle in a private, stylish setting.