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.

The Raritan band of the Unami Indians, a branch of the Lenape or Delaware nation, were the original inhabitants of all Staten Island, including Tottenville. The largest pre-European burial ground known as Burial Ridge, is located in Conference House Park.

During the colonial period and for a significant time thereafter, Tottenville was an important way-station for travelers between New York City (of which Staten Island did not formally become a part until 1898) and Philadelphia, as it was the site of a ferry that crossed the Arthur Kill to Perth Amboy, New Jersey. This ferry became less important when the Outerbridge Crossing opened in 1928, but continued to operate until 1963.

Two distinctive landmarks, the Bethel United Methodist Church (erected in 1840 and rebuilt on the same site in 1886 after a fire had destroyed the original structure), and an abandoned factory originally built in 1900 for use as a smelting plant and later operated for recycling by Lucent Technologies (which closed the facility in 2001), stand at the northern approaches to the neighborhood. Tottenville is bounded on the west and south by the Arthur Kill and on the east by Raritan Bay (the mouth of the Raritan River lies immediately to the south of where the Arthur Kill empties into the bay, which is also sometimes reckoned as being part of the Atlantic Ocean). At the opposite end is the Conference House, built by Christopher Billop and so named because it was the site of abortive negotiations in 1776 to end the Revolutionary War (it is now the centerpiece of the city park known by the same name). The Billop family, who built the estate in 1678, continued to own it and the surrounding property at the time the 1776 meeting took place, but in 1784 their land was confiscated because the family had been Tories during the war.

Many small factories once dotted the neighborhood's western shoreline, but most of these are no longer in operation. Boat construction also once flourished along this shoreline, but this industry was rendered obsolete when the practice of using steel rather than wood to build boats became dominant in the years immediately after 1900. World War I spawned a revival of shipbuilding activity, but it proved only temporary, and Tottenville's last shipyard closed in 1930. Another activity formerly prominent in Tottenville was the harvesting of oysters from the surrounding waters, which ceased in 1916 when the New York City Health Department determined that pollution had made it unsafe. As of 2005, oyster harvesting has since been reopened.

During the 1990s, the section of Tottenville southeast of Hylan Boulevard, until then nearly uninhabited, saw massive new home construction, but the district's population density still ranks among the lowest in New York City, as does the crime rate. Business establishments were largely restricted to the Main Street corridor in the heart of the neighborhood until the early 2000s, when a second commercial core began to emerge at the north end of the community, along Page Avenue west of Amboy Road; further expansion of the latter area is due in 2005 as the former Lucent Technologies property is being developed for this purpose. Starting in October 2006, the western part of the site is being cleaned up, and is scheduled to be finished within a year. The factory, Nassau Smelting and Refining, was purchased by Western Electric in the middle 20th century and used principally to recycle copper and other metals from old wires until it was closed late in the century by Lucent. The site suffered chemical contamination. Mill Creek, which runs through the site, will also be cleaned as part of the project. TOttenville 8 and HOneywood 6 in Eltingville were the last telephone exchanges on Staten Island where Operators connected all calls. In the late 1950s, the YUkon 4 dial exchange replaced the "Number Please?" girls.

On December 31, 2003, an allegedly alcohol-fueled brawl broke out at the Tottenville firehouse, home of Engine Company 151 and Ladder Company 76 of the New York City Fire Department, resulting in one firefighter, Robert Walsh, being hospitalized in critical condition after being hit with a metal folding chair. Firefighter Michael Silvestri was arrested and charged with assault in connection with the incident, which led to six members of the unit, including its commander, Captain Terrence Sweeney, being transferred to other firehouses.

Many large, stately homes built in Tottenville in the 19th Century remain standing; however, in recent years, land developers have been buying up the property on which several of these homes have stood, with the intention of demolishing them and constructing townhouses on the property. The fate of one such home, located at 7484 Amboy Road, became the focus of an intense local controversy in March, 2005, when the community rose up in opposition to plans by builder John Grossi, who had purchased the property, to raze the home and construct five townhouse units on the site. On March 17 Grossi angrily spray-painted graffiti on the house, built circa 1870, which included a threat to populate it with low-income tenants under the federal Section 8 housing program; the resulting public outcry prompted New York City mayor Michael Bloomberg to have the home declared a landmark, thus preventing its demolition. Bloomberg announced his decision to do this during a visit to Tottenville on March 22, and the New York City Landmarks Preservation Commission made the designation official on April 12. Since then, no noticeable effort has been made to restore the home, which remains in a dilapidated condition.

In March 2008, over 20 blocks in the northern section of the neighborhood were changed over to one-way streets, more effectively managing traffic on the older, narrower blocks.

Tottenville has a strong Victorian era heritage, akin to neighborhoods on Staten Island's North Shore. This is unique to this South Shore neighborhood, compared to the other South Shore areas, all of which were developed much later. Seven buildings in Tottenville have been honored with the Preservation League of Staten Island Award: 88 Bentley Street, 24 Brighton Street, 213 Wood Avenue, 115 Bentley Street, 7647 Amboy Road, 7639 Amboy Road, and the Tottenville Branch of the New York Public Library. 88 Bentley Street has even been photographed as an example of Staten Island's carefully restored Victorian homes in "New York City - The Five Boroughs: A Photographic Tour" by Carol M. Highsmith and Ted Landphair, published 1997. In addition, the Old Church of St. Joachim and St. Anne (Staten Island, New York) was restored after a fire into a home for children.

Tottenville's population is largely white (nearly 95 per cent as of 1990), with extremes of both wealth and poverty being essentially absent, and the neighborhood has a much higher proportion of Protestants than is encountered on Staten Island as a whole, which is heavily Roman Catholic. In the mid-2000s, the community witnessed the arrival of Mexican immigrants for the first time. There is also a growing number of Coptic Orthodox Christians from Egypt, as there is currently one Coptic parish in Tottenville.

The 2000 Census showed that ZIP Code 10307, essentially coterminous with Tottenville (a fortuitous circumstance as most neighborhoods of New York City do not have officially recognized boundaries) had a population of 9,207, whose median age was 35.4, and the zip code's per-capita income was found to be $27,688. The average household size was 2.99 persons.

The 123rd Precinct of the New York City Police Department has its headquarters there, as does the Engine Co. 151/Ladder Co. 76 of the New York City Fire Department, and the neighborhood also has a branch of the New York Public Library.

Tottenville has been the southern terminus of the Staten Island Railway since the railway was extended to the neighborhood on June 2, 1860, and today the three southernmost stations along this railway are generally regarded as part of the community; besides the terminal station which bears the neighborhood's name (which is the southernmost railway station in New York state), the other two are Atlantic (named after the defunct Atlantic Terra Cotta Co. factory nearby) and Nassau (referring to Nassau Smelting and Refining, the original name of the factory later taken over by Lucent Technologies). The MTA plans to close the Atlantic and Nassau stations, replacing them with the Arthur Kill Road station with a parking lot. Tottenville is also served by two full-time (S74 and S78) and one-part time (S59) city bus routes, as well as the rush hour-only express route the X22.

Tottenville High School, a public school, was originally located in the neighborhood, but a new campus was opened approximately three miles to the north, in the neighborhood of Huguenot, in 1972 (Totten Intermediate or I.S. 34, a junior high school, now occupies the original high school building). One of the area's oldest buildings is the old building of P.S.1 (the Tottenville School), dating from 1878, and is unique for its traditional sloped roof. Today it is still in operation, now served by a second, newer building as well, built in 1929. In 2000, a new elementary school, P.S.6 (the Corporal Allan F. Kivlehan School), was opened to serve eastern Tottenville's growing population, as well as other neighboring areas. Tottenville's local Catholic school is Our Lady Help of Christians School, which is run under Our Lady Help of Christians Parish. The school dates back to 1904.

The southern part of Tottenville below Hylan Boulevard is also known as Tottenville Beach.

New York Public Library operates the Tottenville Branch at 7430 Amboy Road.

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