4. Google Headquarters: 111 8th Avenue $1.8 Billion

In 2010, Google purchased 111 8th Avenue for $1.8 billion. The large building, which encompasses an entire city block between 15th and 16th Street, and 8th and 9th Avenue, was originally constructed in 1932 as the Port Authority Commerce Building/Union Inland Terminal. Later, it served as the headquarters for the Port Authority until the agency relocated to the original World Trade Center in 1970.

Initially, goods were moved by truck from this building to railroad and shipping lines, with the upper floors constructed as manufacturing space. As a warehouse, it did not have to subscribe to the zoning laws of the time period and avoided having to be “set back,” like other buildings. As a result, there is more square footage in 111 8th Avenue than there is in the Empire State Building. Today, there are numerous tenants inside the building besides Google, which has been unable to end the leases of some companies that were already in the building. As a result, Google still rents office space in other buildings in the city, including above Chelsea Market.