5 North Menantic Road, Shelter Island, NY 11964

A rare offering on Shelter Island, this waterfront estate represents a legacy of architectural pedigree and enduring luxury. Built in 1860 and renovated over the years, the home is a singular blend of history and Hamptons elegance, set on nearly 3 acres with western-facing water views, a deepwater dock, and every hallmark of refined coastal living. In an iconic Shelter Island location on West Neck Bay, this timeless model of Federal-style architecture offers 3,157 +/- sq. ft. of living space on 2 levels, 6 bedrooms, 4.5 baths, an attached 2-car garage, 3 fireplaces, a waterside heated gunite pool, and a deep-water dock. Further expansion is possible, and there is room for tennis on the property. The first level has a traditional floor plan with a living room, dining room, kitchen, ensuite primary and guest bedroom. Enjoy all-day sun from the multiple patios, including a beautiful attached gazebo porch for dining al fresco and morning coffee. Bedrooms are each well-sized and bathrooms have been updated, including a bedroom and a bath with waterviews. Upstairs, the open third floor awaits your imagination. The restored interiors have been beautifully preserved, the original high ceilings with crown molding, wide-plank pine floors, marble mantelpieces, and even bannisters and newel posts-imbuing the estate with provenance and character and ready to be improved and updated to suit your lifestyle. The estate's park-like grounds showcase everything that makes Summers on Shelter Island so special - peace, privacy, with direct access to the water in West Neck Bay. This outdoor oasis is the ultimate luxury, a highlight of every season with brilliant color changes, migrating songbirds, and extraordinary all-day light. The exceptionally well-considered heated gunite pool and bluestone patio are located perfectly to capture western light and water views without interrupting the open vista lawn stretching down to the water. Here, find a boaters' paradise with a deepwater dock and western-facing waterfrontage on Westneck Bay. From lawn games and late-night dancing under the stars to elegant dinners with guests arriving by boat, the property has long served as both a vibrant social hub and a serene private retreat. Shelter Island offers an abundance of seasonal pleasures-sailing, fishing, nature trails, and beaches so peaceful they often feel private. The island's charm extends beyond summer; the estate is particularly enchanting in the shoulder seasons, when West Neck Creek glows with shifting light and the surrounding landscape turns vibrant with spring blossoms or autumn foliage. A haven for wildlife and inspiration alike, it's a rare retreat that feels both expansive and deeply personal, year-round.