2. Bellevue Homeless Shelter (462 First Ave, Kips Bay)

Since it is located near many of NYU’s medical buildings, this building from 1931 might be mistaken for a university facility. It was actually once the Bellevue Psychiatric Hospital, part of the oldest public hospital in the United States: the Bellevue Hospital Center. Though not technically an asylum, many of the city’s criminally insane were unceremoniously dumped here. Often, they were readmitted, signifying the severity of their cases. Perhaps because of this, the hospital building slowly transformed into a men’s homeless shelter, completing the metamorphosis in 1998. In recent years, there have been plans to redevelop the building into a hotel and conference center, but they went unrealized.

Some of the courtyard’s windows are painted as well.