Shelter Island Heights Real Estate

Welcome to Shelter Island Heights, a hidden gem nestled in the heart of Suffolk County, New York. This enchanting village, part of the picturesque Shelter Island, offers a unique blend of natural beauty and small-town charm that captivates both residents and visitors alike.

Surrounded by the serene waters of the Peconic Bay and the Long Island Sound, Shelter Island Heights is renowned for its stunning waterfront views and lush landscapes. The area is characterized by its quaint streets lined with historic homes, many of which date back to the late 19th century, showcasing the architectural elegance of a bygone era. Here, you can enjoy leisurely strolls under the shade of majestic trees or take a bike ride along the scenic paths that wind through this idyllic community.

The village boasts a vibrant local culture, with an array of charming boutiques, art galleries, and delightful eateries that serve up fresh, locally-sourced cuisine. Residents take pride in their tight-knit community, where neighbors become friends and gatherings are frequent. For those who appreciate the outdoors, Shelter Island Heights is a paradise, offering ample opportunities for sailing, fishing, and hiking in the nearby nature preserves.

With its tranquil atmosphere and rich history, Shelter Island Heights is not just a place to live; it’s a lifestyle. Whether you’re looking for a seasonal retreat or a permanent residence, this enchanting village invites you to experience the perfect blend of relaxation and adventure in one of New York’s most captivating locales. Discover your dream home in Shelter Island Heights today!

Newest Listings in Shelter Island Heights

$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

$499,000

1 Beds ⋅ 1 Baths ⋅ 976321 MLS

Discover effortless living in this beautifully renovated one-bedroom, one bath co-op on Shelter Island. The apartment is set within a serene and private eight-acre community. Thoughtfully updated, the residence features a modern kitchen and bath, with Bosch appliances, including an in-unit washer and dryer for ultimate convenience. The home opens to a private deck-perfectly suited for outdoor dining or relaxing evenings-creating a seamless extension of the living space. As an added benefit, the apartment is offered fully furnished and thoughtfully equipped with all essential kitchenware, making it truly move in ready or ideal as a turnkey getaway. Residents enjoy access to an exceptional suite of amenities including a heated pool, gym, and tennis courts, offering a resort-like lifestyle in a tranquil setting. Ideally located, this property places you moments from both the North Fork and the Hamptons. A short ferry ride brings you to the historic waterfront village of Greenport, known for its charming harbor, boutique shopping, and acclaimed dining scene. Equally close is Sag Harbor, a storied destination celebrated for its maritime heritage, vibrant Main Street, and exceptional restaurants. Surrounded by water and natural beauty, this is an ideal retreat for those seeking a refined yet relaxed East End lifestyle-with effortless access to beaches, boating, vineyards, and some of the region’s most beloved historic towns. 1% Flip tax paid by buyer.

13 Winthrop Road Unit #24, Shelter Island Heights

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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.