Shelter Island, NY 11964

For the first time in over a century, this extraordinary collection of generationally owned properties is being offered together as a singular and rare opportunity. Nestled along the serene and picturesque Menantic Creek, these three distinct parcels span a combined 4.9 acres, presenting an unrivaled waterfront retreat. At the heart of this offering is 15A Menantic Road, a legally designated two-family residence with a breathtaking 3,944 square feet of meticulously renovated living space. This refined home features five bedrooms, 4 full, two 1/2 baths, and a 483-square-foot garage, all thoughtfully designed to maximize the stunning creek views. Taxes: $12,206.00 Adjacent to this residence is 15 Menantic Road, a pristine and vacant 1.3-acre parcel, offering endless potential to further enhance this exceptional estate. Taxes: $4,325.00 Completing the trio is 13 Menantic Road, a charming 1930s bungalow with two bedrooms and one bath set on 1.47 acres and a brand new two story 4 bedroom, 2.5 bath home with attached two car garage in the final stages of completion. Taxes: $8,521.00 What truly sets this estate apart is its extraordinary arboretum-like setting, adorned with a curated collection of rare and mature specimen trees, including Copper Beech, Southern Magnolia, White Birch, Monkey Puzzle, Dawn Redwoods, Linden, Osage Orange, Red Japanese Maple, and Dogwood. The natural beauty of this land is simply unparalleled. For the boating enthusiast, this offering includes a 100-foot stationary dock, complete with a 6-foot-wide walkway with a bench, as well as a 12-foot plastic ramp leading to a 30x6 floating dock with three anchor pilings. Two moorings on the creek are also available, pending reapplication. This is a once-in-a-lifetime opportunity to own a waterfront compound with limitless potential—a legal multi-family residence, a historic bungalow, a new construction home and an untouched parcel—all in one of the most coveted locations. A truly rare find for the discerning buyer seeking exclusivity, natural beauty, and unparalleled waterfront living.