Former New York, Westchester, and Boston Railroad Administration Building, 1928.

This Italian Renaissance Style building was once the headquarters of the New York, Westchester, and Boston Railway. The company intended to operate lines from New York City to Boston, though Boston proved too far and the company was dissolved after only reaching as far north as Westchester. The building was designed in 1912 by an all-star trio of Railroad Station designers: Allen H. Stem, Charles Reed, and Alfred T. Fellheimer. Stem and Reed were concurrently designing Grand Central Terminal, which would open a year later. The city of New York repurposed the station as a stop for the 2 and 5 lines in 1937.

The headquarters was designated a New York City Landmark in 1976 and listed on the National Register of Historic Places in 1980, making it the only free-standing New York subway station on the list. The ground floor's loggia is the entrance to the subway station, while the upper flowers houses employees of the New York Transit Authority.

The station underwent a major renovation from 2010 to 2013, which included a restoration of the terminal's clock that is crowned by winged-helmet Mercury, the mascot of the New York, Westchester, and Boston Railway.