Now managed by Historic Richmond Town, Voorlezer's House was built before 1696. The name stems from the house's role as a schoolhouse as Voorlezer is a Dutch word that translates to "one who reads to others." It is the oldest known schoolhouse in America and has been fully restored.

Though some doubt its claim that it was established 1854, McSorley's Old Ale House is the oldest “Irish tavern” in New York City. The only significant change since then happened in 1970 when McSorley’s was forced by the courts to admit women. After that, the motto was amended from “Good Ale, Raw Onions, and No Ladies” to “good Ale and Raw Onions.” McSorley’s, in every other way, has not changed

Designed in 1883-1884 by the German-born architect William Schickel, the Ottendorfer Library is the oldest branch library in Manhattan and one of the earliest buildings in the city constructed specifically as a public library. The Ottendorf Library was the personal philanthropic project of Oswald Ottendorfer and preexisted the NYPL system

Sandy Ground is the oldest continuously inhabited free black settlement in the United States. Its records indicate that the first African American resident, John Jackson, purchased land here in 1828.

The Cherry Lane Theater has the distinction of being New York City’s oldest, continuously running Off-Broadway theatre. The building itself was originally constructed in 1836 to house a brewery for one Alexander McLachlan and later served as a tobacco warehouse and box factory. In 1924, the Provincetown Players, which included the poet Edna St. Vincent Millay, founded the Cherry Lane Theatre here, which opened on May 24 of that year. Since then, Cherry Lane has served as an off-broadway theater for close to a century.

The Lorillard Snuff Mill, the foundation for the family's wealth and the property that would become the New York Botanical Garden, is the oldest existing tobacco manufacturing building in the U.S. While the family moved the production to New Jersey in the 1870s, the Mill would remain and it was purchased along with the estate in the 1880s by the city.

This 1881-station house is the oldest original police precinct in the city. (Though the Central Park Precinct is in an older building, that structure was built as a stable and wasn't taken over by the police until the 20th century.) This four-story Italianate building was designed by the Police Department’s architect Nathaniel D. Bush, who was also a sergeant on the force! Originally called the 6th Precinct, it was known as the "Bloody Sixth" for the violence in nearby Chinatown, largely enacted by the local Tong gang. The local police dealt with rampant gambling, opium dens, and gang murders. By 1911, the station had been renamed the 5th, and a new fancy police patrol telephone booth had been added to the entranceway. On two separate occasions in the 1960s and 1970s, the NYPD expressed a wish to demolish the building for a new station house and the community fought to preserve the old building. Instead of being razed, the building was renovated and modernized.

St. James is the oldest surviving Anglican building in New York City and the oldest structure in Elmhurst. Built in 1735, the single-story wood-frame church served the Anglican community in what was then the town of Newtown. By 1848, the parish had outgrown the building and moved to a new church, though the old building remained, as did its small churchyard cemetery. After the church moved to the new structure, this building was used as a Sunday School and parish hall.

The Girls’ School is the oldest surviving structure built as a high school in New York, and it served as the prototype for later high schools constructed in the city. A combination of Victorian Gothic and French Second Empire styles, the school is faced with red brick, terra cotta, and contrasting stone.

A section of the Pieter Claesen Wyckoff House is the oldest structure in New York City. A few sources suggest the house was built in 1638 as one of the number of structures ordered constructed by Wouter Van Twiller, the Director-General of New Netherlands before he returned to Europe. The more accepted date for construction is circa 1652. Amazingly most American and Canadian Wyckoffs can trace their lineage to one of Pieter and Grietje’s eleven children.

The New York Eye and Ear Infirmary was founded in 1820, originally located at 83 Park Row. It is the oldest specialized hospital in the Western Hemisphere and the third-oldest hospital in New York City after the New York Hospital and Bellevue. In its first year, the hospital attempted the first surgery to restore sight to the blind