Before it was rebuilt as a luxury high-rise, the Octagon was the New York City Lunatic Asylum from 1841 until 1894. Although some find the structure's history less than terrifying, others warn that the halls could be a little spooky at night.

The Octagon on Roosevelt Island carries a heavy historical "ghostly" reputation due to its origins as the New York City Lunatic Asylum, which opened in 1841. The facility was notorious for its abysmal conditions and the mistreatment of patients, famously exposed by journalist Nellie Bly in her 1887 book Ten Days in a Mad-House. After the asylum closed in 1894, the building became a hospital and was later abandoned for decades, falling into a state of ruin that fueled local legends of spirits and "tortured souls" roaming the rotunda. While it was restored and converted into luxury apartments in 2006, the building's dark past remains a staple of NYC ghost tours. Residents occasionally report "unexplained" barks from pets or cold spots in the hallways, but the management focuses strictly on the building's LEED-certified sustainability and architectural beauty. Whether it is truly "haunted" remains a matter of belief, but the Octagon's history of suffering makes it one of the most culturally "eerie" landmarks in New York City's residential landscape.