9. The Apthorp, 1908

For those that wanted a more private living style and garden space, The Astors had an ingenious architectural solution. Take a palazzo-style building and carve the inside out, leaving garden space in the courtyard. The result was the uniquely designed Apthorp. Though the courtyard took up valuable square-footage, it allowed more sunlight and fresh air to reach the existing apartments.

Built between 1906 and 1908, the 12-story luxury apartment building takes up an entire block. Over the years, it has been home to many celebrities including Cyndi Lauper, Rosie O’Donnell, Robert DeNiro and Nora Ephron (who wrote about her love for the Italian-Renaissance styled building in the New Yorker). While many development projects undertaken by the Astors bear the family name, such as the Waldorf-Astoria and Astor Court, this project is named after the owner of the former Apthorp mansion, merchant and Royalist Charles Ward Apthorp. Apthorp’s mansion demolished in 1891 to make way for the extension of 91st street.