Oriole Farms, one of the largest estates on Shelter Island, comprises nearly 20% of Dering Harbor Village, with a deep water dock. A 100-year-old beech privacy hedge looks toward the water and Gardiners Bay Country Club, and a long driveway opens to 16+/- acres with a majestic allee of ancient weeping beech trees. The inland acreage is subdivided into two parcels, 7.676 acres and 8.097 acres, which together with .25 sound front acre, comprise this offering. The estate was once a grand arboretum owned by Alice Fiske, the "mistress of the manor gardens" of Shelter Island's first plantation, Sylvester Manor, and the specimen trees she planted encompass the wide landscape. Built in 2008 and sited on 7.676 acres, the Barnes & Coy designed 5,015+/- sq. ft. home blends quality craftsmanship and state of the art systems with vintage references. The double height entry foyer leads to the living room, which has garden views and one of five fireplaces. A spacious kitchen with professional-grade amenities, bar, dining and family room suits both casual and formal lifestyles. The first-floor master wing offers a paneled library with fireplace, spa-like bath and bedroom with cathedral ceilings, sitting area and deck. Four guest suites on the second floor each have their own character, two have covered terraces. The lower level features an additional 1,750+/- sq. ft. for a total of 6,765 sq. ft. of living space, with media room, fireplace, wine cellar, gym, game room, radiant heat and geothermal systems. A covered piazza has an outdoor fireplace and integrated grill. A restored Lord & Burnham greenhouse beside the 18' x 55' gunite pool and spa includes lounge areas, wet bar, half bath, Zen garden, yoga patch and outdoor shower. One of few surviving turn of the century barns on Shelter Island adjoins a recreation area suitable for tennis. The shared 300' deep water dock has a restored cabana and panoramic views.