Tottenville is the southern tip of Staten Island, the southernmost neighborhood in both New York City and New York State. Water runs along three sides. The Arthur Kill runs along the west and north, and the New York Bight is to the south.
Captain Christopher Billopp named the settlement Bentley Manor, after one of his ships. It became Tottenville in 1869, renamed for the locally prominent Totten family. A ferry to Perth Amboy, New Jersey ran from the colonial period until 1963, though the Outerbridge Crossing took over most of that traffic when it opened in 1928.
The neighborhood has a Victorian architecture heritage unusual for the South Shore, where other neighborhoods developed later. Seven of its buildings have won a Preservation League of Staten Island Award, including the house at , with its gingerbread trim and wraparound porch. The rest of the neighborhood is quieter, with detached wood frame houses, porches and yards.
Those streets end at Conference House Park. The stone Conference House, built before 1680 by Captain Billopp, stands near Ward's Point. It hosted the Staten Island Peace Conference on September 11, 1776. Lord Howe failed there to negotiate an end to the war with delegates from the Continental Congress. Three more historic houses stand in the park, including the , built between 1845 and 1853.
Main Street meets Arthur Kill Road at , the Staten Island Railway's southern terminus since 1860 and the southernmost railway station in New York State.
Horror filmmaker Andy Milligan lived in Tottenville in the 1970s and ran a hotel at , now the site of an Italian restaurant.
