David Letterman  – $10 Million, North Salem

David Letterman is undoubtedly one of the most famous talk show hosts and recognizable faces from TV. His career began in 1970 and he was best known for his own long-running program Late Night with David Letterman that debuted in 1982 and ended in 2015. It had a total of 6,080 episodes, all hosted by David, which made him the longest-serving host of late night shows in American history. David owns this mansion in North Salem, New York. The property reportedly didn’t come as a whole, but David bought both parts separately, first in 1994 and second in 2007, for $5M each.