3. Theodore Roosevelt

Theodore Roosevelt was born on October 27, 1858, the only U.S President before Donald J. Trump that was born in New York City. He was born in the townhouse at 28 East 20th Street in Manhattan, where his family lived until 1872. The original home was completely demolished in 1916, but in 1919 the property was purchased to erect a replica of Roosevelt’s birthplace.

The Roosevelts rented Wave Hill House in the Bronx in 1870 and 1871, when Theodore was 12 and 13, in hopes to aid his asthma. The historians at Wave Hill believe these summers inspired Theodore’s later contributions to the conservation of natural parkland.

Sagamore Hill

In 1880, Roosevelt purchased his own estate in Sagamore Hill on Long Island at the youthful age of 22, buying 155 acres of land for $30,000. By 1886, the Queen Anne style house was up, designed by the Manhattan firm of Lamb & Rich, who also designed Pratt Institute in Brooklyn and Barnard College.  He lived here from until he died in 1919, using the house as his “Summer White House” while President of the United States for two terms from 1901 to 1909. Today, the house can be visited as one of the sites of the National Park Service, with guided tours.