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$2,199,000
5 Beds ⋅ 4 Baths ⋅ 1029569 MLS
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.

64A N Midway Road, Shelter Island
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 1027086 MLS
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.

6 Great Circle Drive, Shelter Island
$1,495,000
4 Beds ⋅ 2 Baths ⋅ 1017824 MLS
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.

6 Oxford Avenue, Shelter Island
$575,000
1016620 MLS
This quiet community known as Long View acres is the perfect place to build your Shelter Island dream home. Located just minutes from Bootleggers Alley Beach which is known for their spectacular sunsets. This .58-acre vacant lot backs up to historic Westmoreland Farms creating a beautiful backyard views.

21 Tims Trail, Shelter Island
$3,795,000
5 Beds ⋅ 5 Baths ⋅ 1016596 MLS
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.

5 Sea Gull Road, Shelter Island
$950,000
2 Beds ⋅ 2 Baths ⋅ 1015995 MLS
Pool Possible- subject to Permits and approvals.

60 W Neck Road, Shelter Island
$3,625,000
5 Beds ⋅ 5 Baths ⋅ 1012419 MLS
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.

43 Gardiners Bay Drive, Shelter Island
$1,200,000
3 Beds ⋅ 2 Baths ⋅ 1013318 MLS
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.

16 Bowditch Road, Shelter Island
$4,800,000
5 Beds ⋅ 4 Baths ⋅ 1007669 MLS
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.

90 Peconic Avenue, Shelter Island
$2,700,000
6 Beds ⋅ 3 Baths ⋅ 1005789 MLS
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.

2 Prospect Avenue, Shelter Island
$1,850,000
4 Beds ⋅ 3 Baths ⋅ 1003398 MLS
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.

4 Irene Lane, Shelter Island
$1,350,000
3 Beds ⋅ 3 Baths ⋅ 1001893 MLS
This well-maintained, single-level ranch is ideally situated in the desirable Harborview area of Shelter Island, offering association beach access for effortless coastal living. The home features a spacious kitchen with warm wood cabinetry, granite countertops, and stainless steel appliances—perfect for both everyday living and entertaining. A large, inviting living room with a wood-burning fireplace provides a comfortable gathering space year-round. Just off the kitchen, sliding French doors open to a covered three-season room/screened porch with a vaulted ceiling, creating a seamless indoor-outdoor flow and easy access to the backyard—ideal for barbecuing and relaxing. The home includes three generously sized bedrooms and two and a half baths, all set on a .46-acre lot. Additional highlights include an outdoor shower, a partial basement with finished space for added flexibility, an attached two-car garage, and a detached 1.5-car garage offering additional storage or workspace. A wonderful opportunity to enjoy the charm and tranquility of Shelter Island living.

11 Mimosa Place, Shelter Island
$2,350,000
4 Beds ⋅ 4 Baths ⋅ 991700 MLS
Welcome to your dream getaway where modern luxury meets laid-back coastal charm. This Newly renovated 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. Completion date July 2026. Still time to pick your colors and more

5 Marc Street, Shelter Island
$5,500,000
4 Beds ⋅ 6 Baths ⋅ 990118 MLS
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.

11 Sunnyside Avenue, Shelter Island
$3,499,000
4 Beds ⋅ 4 Baths ⋅ 981046 MLS
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

9 Locust Woods Drive, Shelter Island
$2,485,000
6 Beds ⋅ 4 Baths ⋅ 978923 MLS
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

14 Freds Lane, Shelter Island
$2,950,000
5 Beds ⋅ 5 Baths ⋅ 977439 MLS
Located in the desirable Harborview area of Shelter Island, this modern farmhouse blends luxury, comfort, and coastal living. Just 0.2 miles from a private waterfront association, enjoy easy access to kayaking and the beach. Set on a beautifully landscaped half acre, the home is designed for seamless indoor-outdoor living. The open-concept interior is flooded with natural light, featuring a chef’s kitchen that flows effortlessly to the dining and living areas, highlighting views of the backyard oasis. Outside, relax in the heated pool, outdoor shower, or firepit lounge, or entertain on the spacious deck with retractable awning and covered dining area. With five generous bedrooms, including primary suites on both the first and second floors, the home accommodates guests in style. The upstairs suite features a gas fireplace and covered balcony. The fully finished lower level includes a media room with theater seating, a versatile den or gym with yard access, and a fifth bedroom with a large hall bath. Step inside and start enjoying the best of Shelter Island living.

12 Terry Dr., Shelter Island
$3,850,000
4 Beds ⋅ 6 Baths ⋅ 962070 MLS
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.

8 Hilo Drive, Shelter Island
$3,999,000
4 Beds ⋅ 7 Baths ⋅ 930022 MLS
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.

141A N Ferry Road, Shelter Island
$4,295,000
6 Beds ⋅ 8 Baths ⋅ 864101 MLS
A buyers dream rooted in nature, enhanced by design. This modern farmhouse nestled in the heart of Shelter Island, NY. completed in 2024, sits on a generous 2.16 acres of immaculate grounds, is a mere half mile from the South Ferry, placing convenience at your doorstep. Boasting six bedrooms, each with their own en-suite, and two additional half-baths, this residence effortlessly blends style and function. The open floor plan is an entertainer's dream, seamlessly connecting the living, dining, and kitchen areas. The expansive living room showcases large vaulted ceilings with a floor to ceiling doors with transoms, inviting an abundance of natural light into the space, creating a warm and welcoming atmosphere with an indoor outdoor flow. The kitchen is a culinary delight featuring high-end stainless steel appliances, modern shaker style cabinetry, a wet bar, and pantry. The design is thoughtful and efficient, making it the perfect place to prepare meals and entertain guests. The primary suite, located for optimal privacy, is a sanctuary of peace and relaxation. It features a double shower with steam, creating a spa-like experience within your own home. The second-floor hosts three additional en-suite bedrooms, one of which has its own private deck, offering a tranquil space for morning coffee or evening reflection. The lower level presents a TV room and two more en-suite bedrooms, offering flexibility for various lifestyle needs. The property also includes a heated gunite pool, a large tiled patio, and a pickle ball/sport court, promising endless outdoor entertainment. The entire home is unified by stunning white oak flooring and complemented by well-thought-out outdoor landscape lighting, emphasizing the property's architectural beauty. The community environment is as inviting as the home itself. With easy access to local amenities and the South Ferry, residents can enjoy the best of Shelter Island living but also having the convenience to the “Sag Harbor Village” and “The Hamptons”. Experience the perfect blend of modern luxury and comfort in this well-designed home. No expense was spared in creating this oasis.

100 S Ferry Road, Shelter Island

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.