Iconic Waterfront Estate on Shelter Island

5 North Menantic Road, Shelter Island, NY 11964
Saunders Exclusive: $5,150,000
View Listing

Renovations, restorations, and thoughtful expansions have culminated in a stunning blend of timeless architecture, Hamptons lifestyle, and Hamptons waterfront estate living at 5 North Menantic Road, Shelter Island.

A rare offering among Shelter Island waterfront homes, this waterfront estate embodies architectural pedigree and enduring luxury. Originally built in 1860 and carefully renovated over the years, the residence 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 luxury living.

In an iconic Shelter Island setting on West Neck Bay, this timeless Federal-style home offers 3,157 +/- SF of living space over two levels with 6 bedrooms, 4.5 baths, an attached two-car garage, three fireplaces, a waterside heated gunite pool, and a deep-water dock—an exceptional amenity for buyers searching for a waterfront home with dock or boater’s property in the Hamptons area. Further expansion is possible, and there is room for tennis on the property, enhancing its appeal as a luxury waterfront compound.

The first level features a traditional floor plan with a living room, dining room, kitchen, and ensuite primary and guest bedrooms—ideal for effortless entertaining and relaxed, everyday comfort.

Enjoy all-day sun from 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 bath with waterviews. Upstairs, the open third floor awaits your imagination—an opportunity for a studio, media lounge, or additional living space for those seeking a renovated historic waterfront home with flexibility to personalize.

The restored interiors have been beautifully preserved: 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 in true Hamptons luxury real estate fashion.

The estate’s park-like grounds showcase everything that makes summers on Shelter Island so special—peace, privacy, and direct access to the water on 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—an atmosphere coveted by buyers looking for private waterfront estates and exclusive coastal retreats.

The exceptionally well-considered heated gunite pool and bluestone patio are perfectly positioned to capture western light and water views without interrupting the open vista lawn stretching down to the shore. Here, discover a boater’s paradise with a deepwater dock and western-facing waterfrontage on West Neck Bay—an increasingly rare combination for those searching Hamptons dock properties, waterfront estate with pool, or a true yacht-ready setting. 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—perfect for discerning buyers exploring Hamptons-area waterfront estates and Shelter Island luxury homes for sale.

This enviable Shelter Island location is close to renowned waterfront dining, sandy beaches, and easy access to the Hamptons by boat, or via nearby ferry to Sag Harbor Village—offering the best of Shelter Island waterfront living with a seamless connection to the Hamptons’ most iconic destinations.