$3,900 monthly (YEAR-ROUND RENTAL) Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of for overflow guests.
Welcome to 23 Osprey Road, Shelter Island-a beautifully renovated retreat offering privacy, tranquility, and the best of island living. Available for summer or year-round rental, this exceptional property sits on over an acre of landscaped grounds with peaceful pond views and direct adjacency to Dusty Boots Farm, where horses can often be seen grazing nearby. A charming front porch welcomes you into the foyer, complete with a convenient powder room. Beyond, you’ll find a chef-inspired eat-in kitchen designed for both everyday living and entertaining. The spacious living room features a wood-burning fireplace and opens to the backyard, creating a seamless indoor-outdoor experience. The main level also includes a primary suite with its own en-suite bathroom, while a screened porch provides the perfect place to relax and enjoy the surrounding natural beauty throughout the seasons. An attached two-car garage adds convenience and ample storage. Upstairs, a versatile sitting area or salon is accompanied by a laundry closet with washer and dryer. Two additional bedrooms offer generous closet space, including a second en-suite bedroom ideal for guests or extended family. The unfinished basement provides abundant storage space for seasonal belongings, recreational equipment, and more. Residents enjoy access to a private beach and tennis court just down the block, while Wades Beach, the South Ferry, and many of Shelter Island’s beloved destinations are less than five minutes away. Two Weeks: $20K; September: $8K; YR: $86K – [[Rental Registration # 2026-L-0067]]
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.
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 20×40 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.
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
SHELTER ISLAND HEIGHTS CHARMING WATERVIEW FARMHOUSE
Located in the heart of Shelter Island Heights, this circa-1885 farmhouse, once a parish house, offers a rare combination of architectural character and enduring charm. A wide L-shaped porch welcomes you, with one side screened for breezy summer evenings and the other open to views of Chase Creek. The front entry opens into a generously sized living room that spans the depth of the home, with natural light filtering in from multiple exposures. Just off this space is a glass-enclosed laundry area. Toward the rear, a formal dining room, currently used as a casual gathering area, includes a pantry and an adjacent full bath. The kitchen features two exterior doors: one opens to the side lawn, and the other leads to a bluestone patio added in 2021, where many enjoyable gatherings have taken place. Two staircases connect to the upper levels: one from the kitchen leads directly to a guest bedroom, while the main staircase rises to a windowed landing, three additional bedrooms, and a full hallway bath with a classic clawfoot tub. The third floor includes a finished bonus room offering additional flexible space for non-sleeping use. The home sits on a .15-acre lot, and a separate .04-acre parcel at 4 Meadow Place is included. Just across the quiet lane are the quiet reflections of Chase Creek, adding to the scenic character of Shelter Island Heights. Within close proximity to fine dining, marina, yacht club, tennis, beach club, and ferry. “Showingtime” app showing requests will not be responded to, call or text for an appointment
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.
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
