Shelter Island Homes for Sale

Welcome to Shelter Island, NY, a hidden gem nestled in the heart of Suffolk County. This enchanting island community is not only renowned for its breathtaking landscapes and serene beaches but also boasts an exceptional school district that prioritizes academic excellence and holistic development. The Shelter Island School District is dedicated to nurturing the minds and talents of its students, providing a small, tight-knit environment where personalized attention and innovative teaching methods thrive. With a strong emphasis on community involvement and extracurricular activities, students are encouraged to explore their passions, whether in the arts, athletics, or academics.

As you consider making Shelter Island your home, you'll discover a diverse array of charming properties currently on the market. From quaint cottages with coastal views to modern family homes tucked away in lush greenery, there’s something to suit every lifestyle. Each residence reflects the island’s unique character, inviting you to embrace the tranquility and beauty that surrounds you.

Living in Shelter Island means not only enjoying the picturesque scenery and vibrant community but also providing your family with access to quality education. The local school district is committed to fostering a supportive environment where students can thrive academically and socially, preparing them for future success.

Explore the homes for sale in Shelter Island today and take the first step toward a life filled with beauty, community, and educational excellence. Your dream home awaits on this idyllic island!

Newest Shelter Island Homes for Sale

$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

$2,595,000

4 Beds ⋅ 3 Baths ⋅ 1022345 MLS

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.

11 Prospect Avenue, Shelter Island Heights

$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

$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

$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

$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

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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.