Shelter Island Real Estate

Welcome to Shelter Island, a hidden gem nestled in the heart of Suffolk County, New York. This enchanting island, bordered by the pristine waters of the Peconic Bay and the Atlantic Ocean, offers an idyllic escape from the hustle and bustle of city life. With a rich history dating back to the 17th century, Shelter Island is a place where charm and tranquility harmoniously coexist.

Renowned for its breathtaking natural beauty, the island boasts lush landscapes, serene beaches, and picturesque waterfronts. Whether you’re strolling along the sandy shores of Crescent Beach or exploring the scenic trails of Mashomack Preserve, outdoor enthusiasts will find endless opportunities to connect with nature. The island's unique geography, being only accessible by ferry, enhances its allure, providing a sense of seclusion that residents and visitors alike cherish.

Beyond its natural splendor, Shelter Island is home to a vibrant community that celebrates local culture and art. The island hosts various events throughout the year, from farmers' markets to art shows, fostering a strong sense of belonging among its residents. Dining options range from quaint cafes to upscale restaurants, where you can savor fresh, locally-sourced seafood while enjoying stunning views of the bay.

For those seeking a peaceful retreat or a permanent residence, Shelter Island offers a variety of real estate options, from charming cottages to luxurious waterfront estates. With its unique blend of natural beauty, rich history, and welcoming community, Shelter Island is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the magic of Shelter Island, where every day feels like a vacation!

Newest Listings in Shelter Island

$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

$1,850,000

4 Beds ⋅ 5 Baths ⋅ 1023936 MLS

Private Retreat with Separate Studio & Pool Potential Tucked away on Shelter Island's coveted southern peninsula, 5 Osprey Lane offers a rare combination of privacy, flexibility, and natural beauty within the sought-after Shorewood Farm enclave. Set on approximately 0.78 acres of beautifully landscaped grounds with room to add a pool, the property is designed for relaxed island living and effortless entertaining. Surrounded by the waters of Peconic Bay, Shorewood Farm is known for its exceptional waterfront setting and outdoor lifestyle. Residents enjoy access to a private association beach, community tennis courts, nearby boat launches at Wade's Beach, and convenient proximity to the South Ferry. Just moments away, the protected 2,350-acre Mashomack Preserve offers miles of scenic trails, tidal creeks, and old-growth forest, preserving the area's natural beauty for generations to come. The approximately 1,750-square-foot main residence features three bedrooms, two-and-a-half baths, a flexible bonus room, and a separate laundry room. Thoughtfully updated, the home is highlighted by a renovated kitchen and an inviting primary suite, blending modern comfort with timeless Shelter Island charm. Complementing the main house is a separate one-bedroom triplex studio offering approximately 1,390 square feet of additional living space. With multiple levels of wraparound decking overlooking the surrounding landscape, the studio provides exceptional versatility and privacy, making it ideal as a guest house, home office, artist's studio, or wellness retreat. Mature plantings and thoughtfully designed outdoor living spaces create a seamless connection between the homes and their natural surroundings. A wraparound bluestone patio anchors the outdoor setting, while the generous grounds provide ample opportunity for future enhancements, including the addition of a pool. Offering two distinct structures, exceptional privacy, and access to one of Shelter Island's most desirable waterfront communities, 5 Osprey Lane presents a unique opportunity to create a lasting island retreat.

5 Osprey Lane, 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

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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.