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Cast-iron architecture flourished in New York in the late 19th century, as a way to produce decorative elements such as columns and arches and create impressive buildings inexpensively. Greene Street, between Canal and Grand streets, and between Broome and Spring streets, has 50 of these beauties, rows of columned façades creating a striking streetscape.

This group of six townhouses in a bend in the street was developed by grocer Samuel Cocks, who thought that having residents nearby would help his business at No. 18. But while such private courts are prized today, they were not considered respectable in the 1850s, and the disreputable types who moved in earned it the nickname “Mixed Ale Alley.” O. Henry used the block as the setting for The Last Leaf .

Once part of the country estates of the wealthy, like Alexander Hamilton whose 1802 home, Hamilton Grange, is here, this location on a hill above Harlem became desirable in the 1880s when an elevated rail line was built. Fine residences went up between 1886 and 1906, and in the 1920s and 30s they attracted Harlem’s elite, when the area was dubbed Sugar Hill. Chief Justice Thurgood Marshall and musicians Count Basie, Duke Ellington, and Cab Calloway were among those who lived here.

The 1885 schooner Pioneer offers 90-minute family sails and two-hour cruises in the afternoon and evening.

A cast-iron masterpiece, this structure was built in 1857 to house a fashionable china and glassware emporium. The design of colonnaded arches flanked by taller Corinthian columns was adapted from the façade of the Sansovino Library in Venice. This motif is repeated 92 times across the front of the building. A 1995 restoration removed grime and restored the elegant original pale color. This building boasted the first Otis safety elevator, an innovation that made the skyscraper possible.

Built in 1881 by the developer John C. Henderson for “persons of moderate means,” these winning Queen Anne houses made of brick and stone are embellished with towers, bays, gables, dormers, and slate roofs. They were an investment and remained in Henderson’s family until the 20th century. Today they are unique in the city and rank among the most desirable places to live. Each block front was composed as a unit, with small towers at the end. Twenty-four of the original 32 units remain.

The center of a rowdy theater district known as the Tenderloin in the 1870s and 80s, until it was reformed. The Manhattan Opera House was razed in 1901 to make way for Macy’s, and other stores soon followed. The clock on the island where Broadway meets 6th Avenue is all that is left of the building occupied by the New York Herald until 1921.