277 Park Avenue, 1926.

This apartment building designed by McKim Mead & White was completed in 1925. The structure took up the entire block with its 12 sections and 432 apartments and included a "drive-in...giant interior court" according to the New York Times. The building was funded by the New York & Harlem Rail Road through the construction of the new Grand Central Depot, who's railyards below prompted a redevelopment of Park Avenue. One notable previous tenant was John F. Kennedy's presidential campaign.

In 1931, the Real Estate Record and Guide noted that of this part of Park Avenue, "no further long-term leases are being granted," to make way for the area's growth as a business district. The building was leased in 1923 for a maximum of 63 years, though in 1948 it was repossessed by the New York and Harlem Rail Road Company. After a much-disputed demolition in the 50s, construction began on a new 50-story office tower to take its place in 1962. Surprisingly, the foundation which the (much shorter by comparison) original apartment sat on had been cast strong enough to support a 70-story building. The rail company had anticipated a tower all along.