David Letterman’s Massive New York Estate

Among famous talk show host homes, David Letterman’s reigns supreme in terms of sheer size: it clocks in at over 8,000 square feet. For those wondering, this colossal and pedigreed house is found in North Salem, New York. The host of The Late Show bought the home in the early nineties for $5 million. Before moving to North Salem, Letterman made his home in Connecticut. His North Salem house comes with an astounding 102 acres.


A native of Indianapolis, Indiana, Letterman once worked as a weatherman in his hometown. Even then — surprise, surprise — Letterman made a name for himself for his live wisecracking. Today, of course, he dishes out his zingers from Manhattan’s Ed Sullivan Theater. He has hosted The Late Show since 1993.

David Letterman is married to Regina Lasko, with whom he has a nine-year-old son named Harry. Though Letterman and Lasko have been together for a long time, the couple didn’t tie the knot until March 2009; their ceremony took place in Montana. Lasko is Letterman’s second wife. They should make for a happy couple in the spacious home they’ve created. The Letterman-Lasko estate didn’t start out with 102 acres. The couple bought properties surrounding their original plot and created the massive acreage they now own. Media reports speculate that David Letterman’s salary at The Late Show is approximately $32 million each year. Letterman has recently hinted that he is not considering hosting his show indefinitely. In 2011, he told Howard Stern that he was thinking of continuing his duties for two more years.