Tottenville is home to many historical buildings and places. Some of them have been recognized for their architectural and/or historical significance, and have been designated historic landmarks by the New York City Landmarks Preservation Commission including:

The Conference House , 7455 Hylan Blvd. at Satterlee St., Tottenville

The Conference House , (formerly known as the Billopp House), was built c. 1680. It is famous for the peace conference held there on September 11, 1776, which, albeit unsuccessful, attempted to end the Revolutionary War . The house, also listed as a National Historic Landmark and subsequently placed on the National Register of Historic Places, is the only pre-Revolutionary manor house still standing in New York City.

Henry Hogg Biddle House , 70 Satterlee St.

The Henry Hogg Biddle house, a Greek Revival style home, was built c. 1850. Henry Hogg, who later changed his name to Henry Hogg Biddle, was a sea captain and reportedly operated the ferry at the end of Amboy Rd. in Tottenville to Perth Amboy , NJ .

One of the house's most outstanding features is the spring eaves which extend from the roofline. The front and rear facades are identical, each containing a magnificent two-story portico. A widow’s walk and cupola were removed after a devastating fire in the 1960s. The house and its property are now part of Conference House Park , NYC Department of Parks & Recreation.

Westfield Township District School No. 5 , now P.S. 1 Annex, designated 1995

Westfield District School No. 5, located at the corner of Yetman and Academy Avenues, was erected in 1878 to meet a growing population. It is currently the oldest public school remaining in use on Staten Island. This new two-story building had extra large blackboards, high ceilings, sliding glass doors on both floors, and an impressive view from the upper windows, prompting the name for the school, "Bay View Academy."

The school expanded in 1896 to include two upper grades which became one of the three high school departments established on Staten Island. Westfield District School No. 5 became Public School No. 1, Borough of Richmond, after consolidation of Greater New York in 1898. The current PS 1 building, at 58 Summit St., was built in 1905-6.

New York Public Library, Tottenville Branch , 7430 Amboy Rd., designated 1995

In February 1899, the Philemon Club of Tottenville (later known as the Philemon Literary and Historical Society), a local women's organization, and the men's Philo Debating Society, established the Tottenville Library Association, and in April of that same year, the Tottenville Free Library was opened to the public in two rooms of a Johnson Ave. house.

Four years later, on November 26, 1904, the branch moved into its new building and present location on Amboy Road, an attractive one-story structure designed by architects Carrere and Hastings.  It was built with funding from philanthropist Andrew Carnegie, and became the first public library on Staten Island.

The Tottenville Branch Library celebrated its 100^th anniversary on November 16, 2004.

James L. and Lucinda Bedell House , 7484 Amboy Rd., designated 2005

The James L. and Lucinda Bedell House , constructed between 1869 and 1874, is the only architecturally distinguished Second Empire frame house in Tottenville that retains its historic form, historic clapboarding, and considerable historic detailing. James Bedell was part of a prominent Staten Island family that included a number of the island's leading carpenters and undertakers.

Theodore F. and Elizabeth J. De Hart House , 134 Main St., designated 2005

The Theodore F. and Elizabeth J. De Hart House , built ca. 1850, was probably built as an investment on the newly laid-out Totten Street (later Main Street) by Henry Butler. Three years later it was owned by William H. B. Totten, a produce dealer, and four years after that by Joseph W. Totten, a partner in an oyster-opening firm. Theodore F. De Hart, an oyster planter, was the owner of longest duration from 1874 to 1913. The De Hart House is one of the oldest houses on this important Tottenville street.

Rutan-Journeay House, 7647 Amboy Rd., designated 2009

Constructed ca. 1848, the Rutan-Journeay House is one of the oldest houses in the former Village of Tottenville.  The 1 ½ story, three-bay clapboard cottage retains its original Greek Revival-style front porch and doorway, and has small eyebrow windows on the upper floor. It was originally owned by James Madison Rutan, a ship carpenter, and purchased in 1850 by John S. Journeay, a blacksmith.  It remains a privately owned residence.