Stockton, who hailed from a prominent political family, was a United States Senator and naval commodore, notable for the capture of California during the Mexican–American War. Stockton's grandfather, Judge Richard Stockton, was a signer of the Declaration of Independence. The original structure consisted of a three-story main residence on roughly 4.5 acres of expansive lawns and fruit orchards. Later, a small wing extending from the rear of the residence was added to house servant's quarters and stables. The wing extension is now a separate home and is separated by a wall at the back of the house. Westland was originally entered from a stone roadway off of Bayard Lane (now Route 206). Nicely kept paths intersected the broad lawn, which was shaded by an assortment of massive pines. At the rear of the house was an orchard of pear and cherry trees and a dovecote to house pigeons and doves.