Shelter Island Heights NY Real Estate & Homes for Sale

Steeped in history and timeless architectural charm, this rare circa-1872 Gothic Revival cottage is located within the historic district of Shelter Island Heights, listed on both the National and New York State Registers of Historic Places. Beautifully preserved and largely unchanged since its original design, the home is a remarkable example of the picturesque residential style created by America's earliest landscape architects. Originally described as a 2.5-story Gothic Revival cottage with hipped roof, segmental arch window heads and two-tier veranda, the residence retains an extraordinary collection of original details rarely found today. Highlights include 39 original working double-hung windows complete with storms and screens, four original attic cross-breeze windows designed to naturally cool the home, original solid oak interior and exterior doors, spacious 10-foot ceilings, and plaster walls throughout the main house. Three spacious front bedrooms - including the primary - open directly onto a covered second-story wraparound sleeping porch, capturing the breezes and relaxed elegance of Shelter Island summers. Cottage-style clapboard accents in the kitchen and rear bedroom add warmth and authenticity to the historic interiors. Thoughtful infrastructure improvements complement the home's historic integrity, including a new roof (2006), a newly excavated full-footprint extra-deep basement with radiant heat slab (2008), and a complete rebuild of the secondary upstairs bath (2010). The property may also qualify for the New York State Historic Homeownership Rehabilitation Credit Program, offering a potential tax credit on qualified rehabilitation expenditures. A truly special opportunity to own an architecturally significant home in one of New York's most cherished historic communities.

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.