Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
Beautifully and meticulously maintained, this traditional 3-bedroom, 2.5-bath turnkey home is tucked away on a very quiet street, surrounded by lovely landscaping and offering a wonderful sense of privacy. Inside, a beautifully renovated kitchen with high-end appliances flows into an inviting open floor plan, creating a warm and welcoming setting for everyday living and entertaining. The inviting primary suite opens onto a screened-in porch and wraparound deck, offering a lovely connection to the outdoors. A fireplace adds warmth and charm, while outside, a completely fenced-in yard features a beautiful new Gunite pool and a cozy fire pit with surrounding seating, perfect for gathering with family and friends. Ideally located near Wade’s Beach, Fresh Pond, and the South Ferry, the gateway to the Hamptons, this special property offers the best of Shelter Island living, with comfort, privacy, and convenience all in one.
Courtesy: Douglas Elliman Real Estate
631-288-6244
Welcome to 5 Pheasant Lane, a fully renovated modern farmhouse tucked at the end of a quiet cul-de-sac in Remsenburg. Completely transformed in 2025, this home pairs clean, contemporary design with the easy, laid-back feel of a true Hamptons retreat, offering six bedrooms, four full and one half baths, and approximately 4,300 square feet on 0.91 level, partly wooded acres. Wide-plank engineered oak floors run through the open, sun-filled main level, where a wood-burning fireplace and formal dining room set the stage for long dinners with family and friends. The kitchen is made for cooks and hosts alike, with a custom rift oak island, quartz counters, custom cabinetry, GE Monogram appliances including a gas range and two dishwashers, and a butler's pantry to keep the prep out of sight. A den finished with custom built-ins and a sliding barn door works perfectly as an office, media room or playroom. A first-floor bedroom with full bath is ideal for guests, and the upstairs bedrooms offer generous space and privacy. A dedicated laundry room, central air and a full basement for storage complete the interior. Out back, your own private resort awaits: a heated in-ground saltwater pool surrounded by bluestone patios, a fenced yard and irrigated grounds, with room to dine, lounge and entertain all summer long. Just minutes to Westhampton Beach's shops, restaurants and ocean beaches, and the Speonk LIRR station, in the Remsenburg-Speonk school district. Also available as an unfurnished summer or winter rental. Some rooms are virtually staged.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
Discover a one-of-a-kind Shelter Island retreat where historic farmhouse charm meets inspired modern living. Set amid 1.8 acres of mature trees, tall privets, sun-drenched edged lawns, and open green space, this circa-1900 property offers a rare combination of character, privacy, and flexibility. The original 2-story residence showcases beautiful period details, including traditional moldings, hand-hewn beams, wood floors, and distinctive vintage glass windows. Inside, 3 bedrooms and 2 baths are complemented by comfortable living and dining rooms, a thoughtfully updated chef’s kitchen with a casual dining area, and a screened porch perfect for long summer evenings. A remarkable addition completed in 2005 is the approximately 1,300-square-foot artist’s atelier, featuring radiant-heated floors and an upper-level primary suite that opens onto a spacious rooftop deck. A detached guest cottage adds another dimension to the property, offering independent accommodations with a large bedroom, full bath, kitchen, living room, and its own garden and lawn. A charming outbuilding provides yet another opportunity, whether envisioned as a reading nook or hobby space. With its blend of historic architecture, dedicated studio space, separate guest quarters, and generous grounds, the property invites a variety of possibilities, including the potential for a swimming pool. Equally suited to relaxed summer gatherings or comfortable year-round living, this is a distinctive island sanctuary with room to create something truly your own.
Courtesy: RE/MAX Signature Real Estate
631-941-4111
Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Home is being renovated and there is till time for you to pick your colors. This 4 Bedroom 3.5 Bathroom home offers perfect blend of style & tranquility, just moments from beaches, marinas and all that island has to offer. Designer Kitchen with Quartz countertops. custom soft close cabinetry with center island & high end appliances. Located on first floor Primary Bedroom with en-suite, cathedral ceiling and french doors to balcony. 3 additional Bedrooms each with an en-suite. Sunken Den, Sitting Room & office. 5" White Oak hardwood flooring throughout first and second level. Recessed lighting, Level 5 finished walls. Central air, Gas propane heat. Hardie Board siding. Upgraded 200 amp electric. 1 Car garage. Inground gunite pool ( optional ) .50 acre. Experience the best of island living in this beautiful renovated coastal retreat
Courtesy: Douglas Elliman Real Estate
631-354-8100
Welcome to 2 Bayview Ave, a stunning modern home nestled in the serene, walkable streets of Shelter Island Heights, NY. This corner lot property boasts an expansive acre of bucolic land, offering a tranquil escape. The exterior of the home features large front and back porches with ample overhangs for three season comfort. Mahogany decking, porcelain tiles, integrated speakers and overhead fans enhance the enjoyment of picturesque surroundings. The raised backyard is a very private sanctuary of its own with a 16 x 40 gunite pool, a cozy cabana and lush greenery, creating an oasis for relaxation or entertaining. Step inside to a spacious open floor plan accentuated by 10-foot ceilings and a stunning 15ft x 20ft custom window wall that bathes the home in natural southern light. Wide-plank light oak flooring and a cohesive palette of contrasting trim elements evoke a Nordic design language throughout. The custom kitchen is a chef's dream, complete with an oversized quartz island, copious storage, a Thermador appliance suite, and a convenient walk-in pantry. The home is designed for comfortable everyday living and effortless entertaining. Down a windowed hall and separated from the entertaining areas of the home, the primary suite on the main level is a haven of comfort, featuring a large walk-in closet and a luxurious bathroom with double sinks on a floating vanity, a private toilet room and multi-fixture wet room. The main level also houses a convenient laundry room, a powder room, extra closets and a versatile bonus space with its own rear-patio entrance and an attached full bathroom. Upstairs, a cozy, windowed loft space overlooks the main living area. A bright hall joins three additional en-suite bedrooms, including a junior primary suite. Each bath boasts fine fixtures and marble work. The finished lower level provides valuable additional space for recreation, a home gym, media room or overflowing living with a full bathroom and walk-out level access to a private covered patio offers endless potential for customization. The property also includes a 3-car garage – a true rarity in Shelter Island Heights – elegantly situated below the sightlines of the home’s main living areas, thus preserving views of the beautifully landscaped surroundings. A secondary driveway that serves the garage features custom board-formed retaining walls, exquisite plantings and warm landscape lighting that add to the property's striking visual impression. 2 Bayview Ave. is more than just a home; it's a lifestyle. It's a place where modern luxury meets the tranquility of nature.
Courtesy: World Prop Intl Sea to Sky
631-961-4626
Shelter Island Waterfront with Dock. A rare opportunity to own waterfront in Silver Beach, one of Shelter Island’s most beautiful and sought-after enclaves. Set directly on the tranquil Silver Beach lagoon, this four-bedroom, 2.5-bath home offers approximately 2,289 square feet on a private .76-acre property with approximately 102 feet of waterfront frontage—all just a five-minute walk to beautiful Silver Beach. The home has a distinctive character, combining comfortable interiors, hardwood floors and an abundance of natural light with wonderful water and landscape views from both levels. The kitchen and baths are fully functional and well maintained, while the home’s more traditional finishes offer an opportunity for a new owner to update and personalize the style over time. The waterfront setting is the true centerpiece. An expansive lawn framed by mature trees leads to the canal and an approximately 20-foot grandfathered dock with water and electric, creating direct access for boating, kayaking, paddleboarding, clamming and enjoying life on the water. 3 spacious decks provide an inviting setting for outdoor dining and entertaining, and an outdoor shower is perfect after a day at the beach. Additional features include a detached garage, newer roof and windows, generous outdoor space and a peaceful location tucked away on a tranquil block of beautiful homes. Enjoy morning coffee overlooking the canal, launch a kayak from your own backyard, walk to Silver Beach, or gather on the deck at the end of the day, so many memories to be made. 7 Wheeler Road offers the increasingly rare combination of true waterfront, privacy, water access and the relaxed lifestyle that makes Shelter Island so special—with the opportunity to make the home distinctly your own.
Courtesy: RustyCap O Inc
516-222-7888
Welcome to your private Shelter Island retreat, where comfort, character, privacy, and exceptional outdoor living come together. This inviting 2-bedroom, 2-bath home offers thoughtfully designed spaces, beautiful hardwood flooring throughout, and an impressive collection of amenities for year-round living or the perfect island escape. The well-appointed kitchen features a refrigerator, dishwasher, built-in microwave, garbage compactor, kitchen-sink water filtration, and plenty of space for everyday cooking and entertaining. The adjoining living room is warm and welcoming with a gas fireplace, while an impressive 12-foot sliding glass door opens onto the expansive deck, creating a wonderful flow between indoor and outdoor living. The deck features a complete grilling station with its own sink and refrigerator, perfect for entertaining family and friends. The showpiece of the home is the extraordinary 17' x 24' primary suite. High ceilings and skylights create a bright, airy atmosphere, while authentic refurbished barn wood flooring adds warmth, character, and a distinctive touch. Sliding glass doors open directly onto the private primary bedroom deck overlooking the beautiful backyard, creating a peaceful retreat of its own. The spacious primary en-suite bath continues the feeling of comfort and luxury with radiant-heated flooring, a spacious open-concept shower with custom glass detailing, double-sink vanity, and dedicated vanity area. The home's extensive amenities include central air conditioning, a whole-house generator, whole-house water-filtration system, washer and dryer, boiler and water heater, two dehumidifiers, and a brand-new septic system. A full basement with a private walkout to a full patio provides additional space and convenient access to the spectacular grounds. Step outside and discover a backyard designed for relaxation, recreation, privacy, and entertaining. Enjoy the heated semi-inground pool with both propane and electric heating systems, surrounded by extensive wraparound decking. The fully fenced property also features a beautiful wood pergola with patio, full bocce court, putting green, fully enclosed vegetable garden, beautiful woodshed, and a large fishpond surrounded by lush greenery. A full line of arborvitae creates a wonderful sense of privacy, transforming the grounds into a peaceful island oasis. A wraparound front driveway adds convenience and completes this special property. Whether you're seeking a year-round residence, summer getaway, or private Shelter Island retreat, this home offers so much more than a place to live—it's an opportunity to embrace the relaxed indoor-outdoor lifestyle that makes Shelter Island so special. Come experience the privacy, comfort, character, and exceptional outdoor living this unique property has to offer, plus you can definitely add more Bedrooms and Bathrooms. This is A Must-See Property!!
Courtesy: Century 21 Excelsior Realty
631-734-0390
Own a distinctive piece of Shelter Island Heights history in this beautifully restored circa-1875 residence, thoughtfully updated for today’s lifestyle while retaining the character and architectural details that make a historic home so special. Set on approximately 0.40 acres, the property offers second-level water views, inviting private gardens, and a classic wraparound porch ideal for enjoying the island setting. The home features three bedrooms, 2.5 baths, a chef’s kitchen, formal dining room, living room, parlor, office, full basement, and detached one-car garage—providing flexible space for everyday living, entertaining, work, or guests. Landscaped outdoor areas create a peaceful backdrop for dining, gardening, recreation, or quiet relaxation. Conveniently located near Bridge Street, local shops, restaurants, Shelter Island Yacht Club, and other Heights destinations, the home also includes access to Heights Association parks and the Beach Club, with nearby clay tennis courts. A rare opportunity to enjoy historic character, modern comfort, water views, and the sought-after Shelter Island Heights lifestyle.
Courtesy: Corcoran
631-765-1300
There are new homes, and then there is this - a turnkey Bartilucci Construction design-build masterpiece, styled by Heiberg Cummings tucked just outside the heart of Shelter Island Heights. No detail left to chance and no corner cut. What sets this location apart is the rare balance it strikes - total privacy paired with true convenience. The Heights business district, morning coffee, boutique shopping and art galleries are all just a short stroll away, and the North Ferry is a mere 3 minute drive from your door. Inside, soaring cathedral ceilings that draw the eye straight through to the heated gunite pool beyond. The kitchen is a showpiece - custom white oak cabinetry, dramatic Taj Mahal countertops, a butler's pantry with its own sink and refrigerator. The primary suite is a true retreat, with spa inspired finishes in the same white oak and Carrara marble found throughout, anchored by a showstopping Carrara marble vessel sink. Outside, the 20x40 heated gunite pool with bluestone coping sets the stage for long summer days across 1.36 private acres with views toward Chase Creek. This is a home built without compromise, the kind of opportunity that simply doesn't come along often. Easy to view, and not to be missed.
Courtesy: Douglas Elliman Real Estate
631-354-8100
A rare turnkey Shelter Island retreat with two distinct homes tucked away on nearly an acre in the heart of Shelter Island, 64A North Midway Road presents a truly unique opportunity to own two homes on one private property. Surrounded by mature trees, expansive lawns, and a picturesque pond next door, this exceptional estate blends privacy, flexibility, and timeless charm. This rare property offers remarkable versatility to fit your lifestyle. The welcoming ranch-style main home offers a comfortable living space with 3 bedrooms and two full bathrooms. A spacious kitchen with abundant cabinetry flows seamlessly into the dining area, creating an inviting setting for everyday living and entertaining. The living room, anchored by a wood-burning fireplace, provides a warm and cozy gathering place throughout the seasons. Step outside to the expansive rear deck, complete with a hot tub overlooking a large, private backyard with room for a pool, an ideal setting for entertaining, relaxing, or enjoying peaceful evenings. A welcoming front porch, an attached one-car garage, and a carport. Privately positioned toward the rear of the property, the stunning barn-style home feels like a secluded retreat. Overlooking a tranquil pond, this approx. The residence is filled with warmth, character, and natural light. The dramatic main room features soaring vaulted ceilings with exposed beams, a gas fireplace, and an impressive wall of windows that captures beautiful views while flooding the home with sunshine. French doors that open onto an expansive 500 square foot mahogany deck with built-in storage, creating the perfect place to enjoy morning coffee, outdoor dining, or simply unwind. The barn home also features two spacious bedrooms, two full bathrooms, a large loft, and a well-appointed kitchen. The oversized lower-level garage offers exceptional storage for vehicles, recreational equipment, bicycles, tools, and more, while additional facilities and energy-efficient solar panels further enhance the home’s appeal. The beautifully landscaped .95 acre property provides an uncommon sense of privacy while remaining just minutes from the Shelter Island beaches, marinas, restaurants, shops, farm stands, and nature preserve. 64A North Midway Road offers possibilities that are rarely available on Shelter Island.
Courtesy: Douglas Elliman Real Estate
631-354-8100
Brand new in one of Shelter Island's premier enclaves along Gardiners Bay, this custom 5,535 +/- SF, south-facing residence developed by Juno Homes presents a refined blend of luxury, location, and design. Defined by soaring proportions, sleek attention to detail and bathed in natural light, the home features 5 ensuite bedrooms, 6 full baths and one half bathroom across two levels. Upon entry, a dramatic gallery corridor blurs the boundary between indoors and out, where floor-to-ceiling glass frames curated views of the surrounding landscape. Warm white oak flooring and an abundance of natural light create a quiet sense of sophistication, transforming a simple passage into an architectural experience. Anchored by dramatic wood-clad cathedral ceilings and expansive walls of glass, the main level's open-concept living spaces unfold with effortless flow. A sculptural chef's kitchen takes center stage, featuring a dramatic oversized island, custom cabinetry, and seamlessly integrated appliances. Just beyond, a thoughtfully designed entertaining bar creates a refined transition into the expansive living room, where a striking wood burning fireplace serves as the architectural focal point and oversized glass doors open directly to the poolside patio, creating a seamless flow between gathering, dining, and indoor-outdoor entertaining. Privately positioned off the main living spaces, the first-floor primary suite includes a spacious ensuite featuring a freestanding soaking tub, oversized glass-enclosed shower, custom oak dual vanity, and premium fixtures throughout, and premium fixtures throughout, where natural materials and clean lines create a calm, understated aesthetic. A separate wing features three additional ensuite bedrooms, a spacious great room and bath, with every room opening directly to the outdoors. Its thoughtful placement creates a sense of separation while complementing the home's open-concept design. The lower level offers a media room, wine cellar, guest ensuite bedroom and laundry. Set on .94± acres, outdoor amenities include a 32'x16'' heated gunite pool and integrated spa, a barrel sauna, cold plunge, outdoor shower, outdoor dining, an attached two-car garage, and professionally designed landscaping that enhances the property's sense of retreat. Just moments from Gardiner's Bay Country Club, Shelter Island's village, and renowned dining, 6 Great Circle presents a rare opportunity to own a custom-built new construction residence where thoughtful design, exceptional craftsmanship, and modern luxury come together.
Courtesy: Douglas Elliman Real Estate
631-725-0200
Shelter Island Heights Icon Gracefully positioned in the heart of Shelter Island Heights, this timeless residence has been thoughtfully renovated and restored to honor its original character while seamlessly incorporating today's modern comforts. Rich in architectural charm and classic detail, the home offers an elegant blend of historic beauty and refined living. A gracious, oversized covered porch welcomes you upon arrival, providing the perfect setting to relax and enjoy the property's elevated position and picturesque water views. Inside, a warm and inviting foyer opens to beautifully proportioned living spaces, where natural light, period details, and a sense of understated sophistication create an atmosphere of effortless elegance. Toward the rear of the home, a formal dining room and well-appointed kitchen serve as the heart of the residence. Expansive windows and French doors bathe the interiors in natural light while creating a seamless connection to the surrounding landscape and outdoor living spaces. The second level is highlighted by a spacious primary suite featuring a generously sized bath, accompanied by two well-appointed guest bedrooms designed for comfort and privacy. The third floor offers a versatile retreat, ideal as a media room, den, home office, or additional gathering space for family and guests. Outside, the beautifully landscaped grounds provide a private sanctuary framed by mature trees and established plantings, creating a tranquil setting for relaxation and entertaining alike. Ideally situated just moments from the coveted Shelter Island Heights Beach Club, tennis courts, golf, marinas, shops, and beloved local restaurants, this exceptional offering presents a rare opportunity to own a meticulously restored home in one of Shelter Island's most desirable and historic neighborhoods.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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.
Courtesy: Compass Greater NY LLC
631-251-8644
A rare opportunity to own a legacy compound on Shelter Island, this offering brings together three income-producing historic cottages and a separate buildable lot, all just moments from the water. Positioned at 2 Prospect Avenue and 38 Rock Point Road, the properties are offered as one cohesive investment, blending immediate revenue with exceptional future potential. Each of the three cottages features two bedrooms and one bath, with strong summer rental histories and an undeniable sense of place rooted in the island’s coastal charm. Rich in character and provenance, each residence tells its own story. The Hill Cottage, dating to the 1890s, is a one-of-a-kind former boathouse thoughtfully relocated from a grand Nostrand Avenue estate, with original architectural details preserved throughout. The Red Cottage, originally built in the 1920s as a fisherman’s retreat, has been expanded to include enclosed patios at both the front and rear. The Main House, constructed in the 1940s, has been carefully renovated to enhance modern comfort while maintaining the craftsmanship and warmth of its era. Completing the offering, the adjacent lot at Rock Point Road presents a rare blank canvas, ready for a primary residence and pool, surrounded by three established rental cottages. Whether envisioned as a private multi-generational retreat, a boutique rental compound, or a long-term development investment, this is a truly exceptional opportunity to own a piece of Shelter Island’s history with both immediate income and enduring upside in one of Long Island’s most sought-after enclaves.
Courtesy: Serhant East End LLC
631-500-8800
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 shingled 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 is often mistaken for a separate lot and 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.
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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.
Courtesy: Douglas Elliman Real Estate
631-725-0200
An architecturally significant modern retreat set on two private acres within coveted Shelter Island Heights owners association. Floor-to-ceiling glass dissolves the boundary between indoors and out, framing the surrounding natural environment from nearly every room. Conceived by developer Angelo Varischetti in collaboration with the award-winning team at WE+ Architecture & Design, the home is a study in light, landscape, and contemporary form. Newly constructed and spanning approximately 4,000 square feet, the residence offers four bedrooms and five-and-a-half bathrooms, thoughtfully designed for both privacy and connection. The open-concept living spaces are anchored by soaring window walls and refined materiality, creating a seamless flow between living, dining, and kitchen areas. The chef's kitchen is both functional and sculptural, featuring premium appliances, custom millwork, and an oversized island designed for gathering. Throughout the home, curated finishes including stone surfaces, bespoke cabinetry, and carefully considered architectural details reinforce the home's modern design language. Each bedroom suite is privately positioned with its own ensuite bath and direct access to the surrounding landscape, offering a retreat-like experience for both owners and guests. The lower level provides flexibility for a wellness area, gym, or media space. Outdoor living is equally compelling. A 50x14 heated knife-edge pool is set within lush, natural surroundings, complemented by expansive decking, an outdoor shower, full bath, and multiple areas for dining and entertaining. The setting is intentionally private, with mature greenery and open sky enhancing the sense of escape. Located within the Shelter Island Heights community, the property offers access to private beaches, tennis, and the island's most sought-after destinations, all while maintaining a sense of seclusion that is increasingly rare. This is Shelter Island at its best. Where architecture, landscape, and lifestyle converge to create a home that feels both elevated and effortless.
Courtesy: Keller Williams Realty Greater
516-873-7100
Welcome to Shelter Island — a place where time slows down and nature takes center stage. Accessible only by ferry, this rare island community offers a level of peace, privacy, and authenticity that is nearly impossible to find in today’s world. Set on over 2 acres of beautifully engineered rolling landscape, this property has been thoughtfully designed to enhance natural beauty while addressing elevation and drainage for long-term peace of mind. Bordering the historic Sylvester Manor, the property enjoys direct proximity to preserved land, scenic walking trails, and a setting rich in history and natural beauty—ensuring both privacy and a protected backdrop that will remain timeless. Surrounded by open skies, coastal breezes, and abundant wildlife, this is a setting where mornings begin with birdsong and evenings end under starlit skies. Enjoy biking along quiet roads, swimming in nearby freshwater lakes, boating, fishing, or simply relaxing with a book as the day slips away. Unlike the increasingly crowded Hamptons, Shelter Island preserves the essence of what made the East End special—unspoiled, understated, and deeply connected to nature. With limited inventory and growing demand, opportunities like this are increasingly rare. Whether as a private retreat, legacy property, or long-term investment, this offering represents more than real estate—it’s a lifestyle “Private Shelter Island retreat minutes from the Hamptons and North ferry-only exclusivity, privacy, wellness, retreat feel, boating, escape from overdeveloped Hamptons
Courtesy: Daniel Gale Sothebys Intl Rlty
631-749-1155
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
Courtesy: Douglas Elliman Real Estate
631-288-6244
This newly constructed modern residence offers stunning south-facing water views over West Neck Bay in Shelter Island. Thoughtfully designed to maximize its prime setting, the home spans approximately 3,985 square feet and features 4 ensuite bedrooms and 5.5 bathrooms, providing exceptional comfort and privacy. The interiors showcase a high level of craftsmanship and attention to detail, featuring an open floor plan with elegant white oak and porcelain tile flooring, stone countertops, and premium Thermador appliances throughout. Expansive living spaces are designed to embrace the surrounding views, while the second level covered deck offers the perfect setting for unwinding against a picturesque bay backdrop. Additional amenities include a heated gunite pool, radiant heat, wet bar, fireplace, pantry, and other thoughtful features that enhance everyday living. Ideally situated in Shelter Island, the property provides a peaceful retreat with convenient access to local amenities, beaches, and the area's natural beauty. Whether envisioned as a year-round residence or a serene getaway, this exceptional new construction presents a rare opportunity to enjoy modern luxury in a tranquil waterfront setting. This listing may include images that have been digitally altered or virtually staged. Original, unedited images are available upon request.
Courtesy: Atlas Sales Realty
516-407-2250
Welcome to this exceptional custom-built home nestled on 1.1 secluded acres, offering the perfect blend of luxury, comfort and privacy. Hidden at the end of a long driveway, the main house boasts 3 bedrooms and 3.5 bathrooms. The 1st floor main suite features include double doors that open to a private deck, a WIC and an expansive master bathroom equipped with a spa style rain shower. To add to the resort feel, the house is equipped with radiant flooring in all rooms and levels, a two story great room with an indoor/outdoor stone fireplace and a Chef's kitchen with custom-built cabinetry and granite counters. Large sliding doors lead you onto a wrap-around, mahogany deck with views of greenery and a stunning gunite pool. Upon leaving the main house, you will find every car lover's dream. A large barn style 4-car garage with ample height for additional car lifts. The 2nd floor features a 1 BR, 1 Bath apartment, full kitchen and an open floor plan living room/dining room.
Courtesy: Coldwell Banker Reliable R E
631-287-7707
Introducing a breathtaking masterpiece nestled in the heart of Southampton’s coveted East End. This brand-new custom estate spans an impressive 7,485 square feet on a lush half-acre, drenched in natural light and designed to enchant at every turn. With 8 luxurious bedrooms and 8.5 opulent baths, every corner of this home radiates timeless sophistication. The bespoke kitchen is a culinary dream, seamlessly flowing into expansive living and entertaining spaces. A private gym and a sleek recreational area elevate everyday living. Step outside to a resort-style oasis featuring a shimmering Gunite saltwater pool and Jacuzzi—your personal sanctuary under the Hamptons sun. Just minutes from pristine beaches and the charm of village life, this residence offers an alluring blend of serenity and splendor. Prepare to fall in love with the pinnacle of East End luxury. Additional interior highlights include a refined living/dining area with elegance.
Shelter Island is located in New York. Shelter Island, New York has a population of 3,661. Shelter Island is less family-centric than the surrounding county with 13.78% of the households containing married families with children. The county average for households married with children is 32.94%.
The median household income in Shelter Island, New York is $100,094. The median household income for the surrounding county is $111,660 compared to the national median of $69,021. The median age of people living in Shelter Island is 51.3 years.
The average high temperature in July is 80.7 degrees, with an average low temperature in January of 23.1 degrees. The average rainfall is approximately 48.2 inches per year, with 26.2 inches of snow per year.
