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.
Dering Harbor New Construction on 2.4 Acres with Water views
Rarely available in an enviable location directly across from the water with mooring rights, this new construction home in Dering Harbor delivers the best of Hamptons living on Shelter Island, ready for immediate enjoyment and for generations to come. Built in 2026 and sited on 2.4 acres, the new construction property has 7,300 +/- SF of interior living space (including the finished lower level) in the house and another 810 SF of living space over the garage, 6 bedrooms, 7 full and 2 half baths, a heated gunite pool and spa, a 2-car garage with finished space above, and a pool pavilion with all of the bells and whistles. Water views, natural light, and bay breezes envelope the gorgeous grounds, while beautiful traditional architecture and expertly manicured landscaping create an exceptional sense of arrival. Clad in cedar-shake siding, the home features elegant columns and expansive shiplap accents. Inside, gorgeous hardwood floors extend across a bright, open main level, where a traditional layout is warmed by light on all sides and an easy flow between living spaces. A sunny family room overlooking the 45’x18′ heated saltwater pool and integrated spa offers an inviting place to relax, while an ensuite study/den provides a quiet setting for reading or for use as a seventh bedroom. Upstairs, the exceptionally well-equipped primary suite includes a deck with stunning water views, three walk-in closets, and a luxe bath with a dual vanity, soaking tub, and glass-enclosed shower. The second level has 3 additional ensuite bedrooms, including one with a private balcony, a space that can be used as a home office, along with a sun lounge patio off the landing and a conveniently located laundry room. A finished living space with a full bath above the detached 2-car garage also boasts water views. The finished walkout lower level adds an ensuite bedroom, additional laundry, storage, and a large recreation room ready for game and movie nights, with ample space for a home gym and wellness amenities. Extensive patio space on all sides of the home invites easy indoor-outdoor living. The gorgeous pool pavilion with a matching architectural style, featuring a wet bar, cabana bath, and outdoor shower. Dering Harbor is among the East End’s most quaint and charming communities, with boutique shops and dining close at hand; beyond Shelter Island, the North Fork is a quick ferry ride away, while Sag Harbor awaits to the south.
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.
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.
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.
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
Welcome to 4 Bayview Avenue, a remarkable residence nestled in the historic heart of Shelter Island Heights. This expansive property, designed with the art of entertaining in mind, offers a generous six bedrooms and five and a half bathrooms, providing an abundance of space for comfortable living. Upon entering, you’ll be welcomed by an array of inviting sitting areas spread throughout the main house, each offering a unique setting for relaxation or socializing. The fully finished lower level, complete with direct access to the pool and backyard, adds a layer of versatility to the living space. This home is equipped with a variety of desirable features such as central air, a cozy fireplace, and a dedicated office space, ensuring your every comfort and convenience is met. The private guest quarters serve as a separate haven for visitors, enhancing the overall accommodation. The outdoor space is a haven of peace and privacy, with beautifully landscaped grounds and mature trees. The newly installed expansive mahogany decks, adorning both the main house and guest house, offer the perfect backdrop for outdoor gatherings and soaking in the surrounding natural beauty. The property also invites you to partake in community amenities such as a beach club and tennis, allowing you to fully embrace the joys of coastal living. A two-car garage with radiant heat flooring adds to the property’s convenience, while the heated gunite pool and outdoor shower offer additional luxuries. With a vast area of approximately 6,098 square feet, this home is designed to cater to a variety of lifestyle needs. This exceptional property in Shelter Island Heights is waiting for you to make it your own. Don’t miss this opportunity. Contact us today to schedule a private viewing.
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 October 2026. Still time to pick your colors and more
