2 Taylor Lane, St James, NY 11780

Directions: Take the Long Island Expressway to Exit 56N (Route 111) to Smithtown crossing over Middle Country Road (Route 25). Route 111 becomes Route 25A. Continue straight to St. James. Deepwells is on the left, just before the Moriches Road intersection.

Named for its two 125 foot wells, this 19th century Greek-Revival style agricultural estate is listed on the National Register of Historic Places. Among the notable residents of Deepwells was William J. Gaynor, Mayor of New York City from 1910 until his death in 1913.