The Metropolitan Life Insurance Company Tower (also Met Life Tower) at One Madison Avenue, New York City was the world's tallest building from 1909 to 1913, when it was surpassed by the Woolworth Building. As the address suggests, it is located at the southern end of Madison Avenue, directly across the street from Madison Square Park. The building is a National Historic Landmark and was first added to the National Register of Historic Places on February 6, 1978. Later, the entire complex of buildings was added to the National Register on January 19, 1996.

Madison Square Park Tower, previously 45 East 22nd Street, is, as of July 2017, a topped-out skyscraper located between Broadway and Park Avenue South in the Flatiron District neighborhood of Manhattan New York City. The building was designed by Kohn Pedersen Fox. When completed it will be the tallest building between Midtown and the Manhattan Financial District. It was the second skyscraper to be built on that block, the first being One Madison.

One Madison, formerly "One Madison Park", is a luxury residential condominium tower located on 23rd Street between Broadway and Park Avenue South, at the foot of Madison Avenue, across from Madison Square Park in the Flatiron District of Manhattan, New York City. The building's private entrance, and address, will be at 23 East 22nd Street when construction of the lobby building is complete in Spring 2013.

To the right of One Madison can be seen the Eternal Light Flagstaff in Madison Square Park, dedicated on Armistice Day 1923 and restored in 2002, which commemorates the return of American soldiers and sailors from World War I.