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 3,206 +/- sq. ft. of living space on 2 levels, 5 bedrooms, 4.5 baths, an attached 2-car garage, 3 fireplaces, a waterside heated HYDRAZZO gunite pool and room for expansion. 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 with HYDRAZZO finish combines a silky smooth texture with the proven durability of exposed aggregates. The bluestone patio is 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 250 feet of 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.