High Quality Content by WIKIPEDIA articles! Tottenville with an area of approx. 1.7 square miles (4.4 km2), is the southernmost neighborhood of Staten Island, New York City and New York State. Originally named Bentley Manor by one of its first settlers, Captain Christopher Billop (1638-1726), after a small ship he owned named the Bentley, the district was renamed Tottenville in 1869, apparently in honor of the locally prominent Totten family whose name can be seen on tombstones in one of the earliest churches, Bethel, on Amboy Road.