Shelter Island Homes with Views Lot features

Welcome to Shelter Island, New York – a hidden gem nestled between the North and South Forks of Long Island. This enchanting island is known for its serene landscapes, stunning waterfront views, and a welcoming community that embraces both tranquility and adventure. With a rich history dating back to the 17th century, Shelter Island offers a unique blend of charm and modern amenities, making it an ideal place to call home.

The island boasts a variety of outdoor activities, from sailing and fishing to hiking and biking along its picturesque trails. With its pristine beaches and lush parks, residents can enjoy the beauty of nature year-round. The vibrant local culture is reflected in its art galleries, boutique shops, and delightful eateries that serve fresh, locally-sourced cuisine.

When it comes to real estate, Shelter Island is renowned for its breathtaking homes with views that capture the essence of coastal living. Picture waking up each morning to panoramic vistas of the serene bay or lush greenery, with the gentle sound of waves lapping at the shore. Properties here often feature expansive decks and large windows designed to maximize the natural beauty that surrounds them.

Whether you are seeking a cozy cottage or a luxurious waterfront estate, Shelter Island offers a diverse range of homes that cater to every lifestyle. Embrace the opportunity to own a piece of this idyllic paradise, where every day feels like a vacation. Discover the charm of Shelter Island and let the breathtaking views inspire your next move!

Newest Shelter Island Homes with Views Lot features

$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

$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

$2,485,000

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

$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

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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.