A pair of massive stone pillars sits at the foot of a winding unpaved drive in the center of Shelter Island, its length typical of grand country properties. Rambling past bleating sheep, farm fields, and woodlands, the road gently levels out and rounds a bend, revealing Sylvester Manor, an early Georgian house clad in cheery bright yellow clapboard and black shutters.
Nothing remains of the original 1652 manor home that belonged to Nathaniel Sylvester, his wife, Grizzell, and their 11 children, although Grizzell’s boxwoods, the cuttings of which were brought from England, still tower over the gardens. The pretty house that stands here now dates from 1737, when Nathaniel’s grandson, Brinley Sylvester, leveled the original structure to create a gentleman’s farm with a new home—the oldest extant Georgian on the East End, according to Maura Doyle, Sylvester Manor’s historic preservation and programs coordinator. The front parlor’s original paneling has received only two coats of paint: Prussian Blue, applied in 1737, and a modest biscuit color, added in 1842. Read the rest of the article on HC&G (Hamptons Cottages & Gardens)210