3. Sagamore Hill, Cove Neck, Long Island

Theodore Roosevelt lived on his estate in Sagamore Hill from 1885 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.  In 1880, Roosevelt purchased this property 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. Today, the house can be visited as one of the sites of the National Park Service, with guided tours.