Shelter Island Homes with Sloped Lot features

Welcome to Shelter Island, NY, a hidden gem nestled in the heart of Suffolk County. This enchanting locale is not only known for its stunning natural beauty and serene beaches but also for its exceptional school district, which plays a pivotal role in shaping the community. The Shelter Island School District is dedicated to providing a high-quality education that fosters both academic excellence and personal growth. With small class sizes and a commitment to individualized learning, students benefit from a nurturing environment that encourages exploration and creativity. The district is proud of its dedicated faculty and diverse extracurricular programs, ensuring that every child has the opportunity to thrive.

When it comes to real estate, Shelter Island offers a unique selection of homes, including those with beautifully designed sloped lots. These properties take full advantage of the island's picturesque landscapes, providing breathtaking views and a sense of privacy that is hard to find elsewhere. Homes on sloped lots often feature expansive decks and patios that invite outdoor living, perfect for entertaining or enjoying quiet evenings under the stars. The natural contours of the land not only enhance the aesthetics but also allow for creative landscaping possibilities, making each property a true reflection of its owner's personality.

Living in Shelter Island means embracing a lifestyle that balances tranquility with community. With its excellent school district and charming homes on sloped lots, this idyllic location is perfect for families seeking a peaceful yet vibrant place to call home. Come explore what Shelter Island has to offer—you might just find your dream home amidst the rolling hills and coastal charm!

Newest Shelter Island Homes with Sloped 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

$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

$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.