Set along the tranquil shores of Menantic Creek, this extraordinary 2.9-acre waterfront offering presents a truly rare opportunity to own a multi-generational compound comprised of two separate parcels, thoughtfully assembled into one remarkable estate. Surrounded by natural beauty and commanding picturesque creek views, the property offers unmatched waterfront living, with over 100ft of water frontage collectively, in one of Shelter Island's most coveted locations. For boating enthusiasts, Menantic Creek provides convenient access to both the North and South Forks, with Montauk just a short cruise away. The estate is exceptionally equipped for life on the water, featuring a 100-foot stationary dock, floating dock, anchor pilings, and the opportunity for two moorings, creating a seamless connection to the surrounding waterways. 15A Menantic Road showcases 3,944 square feet of renovated living space spanning across two floors. Designed to embrace its waterfront setting, the residence offers five bedrooms, multiple living and entertaining areas, a garage, and stunning views from many of its principal rooms. Adjacent to the main residence, #15 Menantic Road is a pristine 1.3-acre vacant waterfront parcel that presents endless possibilities for future expansion, further enhancing the estate's compound potential. Mature specimen trees and beautifully established grounds create a park-like setting throughout the property, offering a sense of serenity and seclusion rarely found along the waterfront. Combining significant acreage, boating infrastructure, and future potential, this is a once-in-a-lifetime opportunity to establish a legacy compound on Shelter Island.