277 Park Avenue, 1962. This Emery Roth & Sons office tower is a quintessential example of the modernist steel and glass towers that sprung up along Park Avenue in the late 50s through the 60s. This building is still owned by the Stahl Organization, the original developer of the project. The tower has 1.74 million square feet of office space spread over 50 stories. The famed architecture firm Emery Roth & Sons were known for "marketable designs that maximized the net rentable area," particularly after World War 2. This block-spanning lot had previously been occupied by a McKim Mead & White apartment building, though it was never meant to stand the test of time. In order to prepare for Midtown's development as a business district, the New York and Harlem Rail Road Company, who owned the lot at the time, had a foundation poured that could support a 75-story tower.

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.

Hotel Barclay, 1928. Opened in 1926 as a residential hotel, the Barclay was designed by the architectural firm of Cross & Cross. Right in the center of the hustle of Terminal City (the lobby had a ticket booth for rail travel) the hotel was luxurious and popular among the glamorous social circles of the city. Between 1939 and 1962 the Cornell Club was headquartered in this building. The hotel was purchased by the InterContinental Hotel Group in 1978 and has seen a number of renovations in the last 40 years. The most recent renovation of the now named InterContinental New York Barclay Hotel was completed in 2016. Between 1926 and 2010 when the hotel closed briefly for renovation, it hosted the flagship location of Caswell Massey, the oldest apothecary and perfumery in the country (established 1752).