5. Libby Castle/Woodcliffe Castle

Across from the Billings estate once stood Libby Castle, designed in 1855 by Alexander Jackson Davis, an architect also responsible for Federal Hall and various other mansions in the New York area. The most famous residents of Libby Castle included Boss Tweed, who in turn lost the home due to foreclosure to A.T. Stewart, who was owed the value of the furnishings for the Metropolitan Hotel. After Stewart’s death, the castle became the property of his business partner William Libby, for whom the castle is named. Following Libby’s death, New York mayor Hugh J. Grant bought it, followed by Rockefeller. By 1919, the mansion had become a school for choirboys under a Father Finn, given to the  Paulists for use by Rockefeller. In 1939, Libby Castle was demolished to make way for Fort Tryon Park.