26 Rocky Point Rd, Shelter Island, NY 11964

Perched at the top of a gentle driveway on 2.3+/- quiet gated acres in Shelter Island's estate section, this recently renovated 1954 cottage rests on a rise with visual advantages, surrounded by a landscape that has been nurtured with care and intention. The property is the result of years of dedicated stewardship by its current owners, who have propagated seeds collected from notable gardens across the country, cultivating an environment where native species and subtle beauty thrive. Designed for both the layperson and serious gardener: the raised vegetable and cutting gardens can be cultivated and the planted shrubs and trees can be trimmed and nurtured as desired. Winding paths lead through a setting where turkey hens nest undisturbed and turtles can often be seen on unhurried strolls. Indigenous orchids, documented by the Long Island Botanical Society, bloom quietly among oak, linden, beech, conifers and flowering perennial shrubs. An enclosed, raised vegetable garden is just beyond a shaded meditation area and is designed for seasonal harvests. The atmosphere is one of calm, a setting for contemplation and connection to the natural world - and just a short distance from sandy beaches and resort amenities. The single-story cottage is welcoming, with sunlit living and dining areas with natural pine overlooking the gardens and outdoor entertainment decks. A wood-burning Godin poêle anchors the common space, while the kitchen, updated in 2025, features granite countertops, custom cabinetry, and access to a deck that is well-suited to outdoor meals or quiet reflection. On one end of the home is a private bedroom with a half bath, and on the other, two additional bedrooms with a full bath, recently renovated. A full basement with garage access provides ample storage, functional space and future finishing possibilities. 2024-2025 renovations include: roof, siding, windows, kitchen, central air and bathroom. Located just a stone's throw from the Pridwin Hotel, the Perlman Music Program, and the Crescent Beach, this home offers not just a place to live, but a place to observe, to preserve, and to appreciate the land and its quiet stories.