On the premier estate lane with sweeping views over Peconic Bay, is a world-class home that transcends time and sets itself apart on all levels. This landmark residence rises from the head of a bluff with lush "green lawns" rolling from the wraparound porch to the shores of the Shelter Island Sound. Its flag pole is the mast from the vessel Sir Thomas Lipton raced in the 1930s for the America's Cup and an impressive maple tree by the entrance is a reminder of the long history this special home has lived. Built in 1880, this Queen Anne-style house is sited on 4.8+/- sound front acres with 400+ feet of water frontage, and an 80 foot L-shaped dock with a romantic boat house perfect for relaxing. The three-story 7000+ sq. ft. main house offers 7 bedrooms and 7 baths, living room with fireplace, multiple sitting rooms for both formal and informal gatherings, dining room with exquisite hand drawn etchings and chef's eat-in kitchen which gives to the round dining cabana. The windmill guest house has an entertainment level and guest suite with kitchen and living/dining area. The park-like grounds feature a waterside heated gunite pool with gazebo, spa, basketball court and har-tru tennis. With the most breathtaking sunsets and sumptuous water views, this gated property offers total privacy evoking quintessential Shelter Island beauty.