Shelter Island Homes with A-Frame Style

Welcome to Shelter Island, a hidden gem nestled in the heart of Suffolk County, New York, where the charm of coastal living meets the allure of a tight-knit community. This picturesque island is not only known for its stunning waterfront views and serene landscapes but also for its exceptional school district, which is a cornerstone of the community.

The Shelter Island School District prides itself on providing a nurturing educational environment for students from kindergarten through 12th grade. With a low student-to-teacher ratio, dedicated educators, and a strong emphasis on academic excellence, children here receive personalized attention that fosters both intellectual growth and personal development. The district also offers a variety of extracurricular activities, ensuring that students can explore their passions beyond the classroom, whether in the arts, athletics, or community service.

As you explore the real estate options on Shelter Island, you’ll find a unique selection of homes, including charming A-frame style houses that perfectly complement the island's natural beauty. These distinctive homes, characterized by their steeply angled roofs and cozy interiors, create a warm and inviting atmosphere that captures the essence of island living. Many A-frame homes boast large windows that frame breathtaking views of the surrounding landscape, allowing residents to immerse themselves in the tranquility of their surroundings.

Whether you’re drawn to the exceptional education system, the stunning architecture, or the vibrant community spirit, Shelter Island offers a lifestyle that is both enriching and fulfilling. Come discover your dream home in this idyllic setting, where every day feels like a vacation!

Newest Shelter Island Homes with A-Frame Style

$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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