David Letterman – $5 Million, North Salem
After 33 years on national television, hosting the Late Night With David Letterman on NBC, Letterman is amongst the richest and most influential TV personalities of the past 3 decades, with a net worth of over $400 million. He bought this terrific North Salem mansion in the ’90s for $5 million, and what a deal it was! Designed in colonial style, Letterman’s crib sits on 102 acres of land and includes 8 bedrooms and 7 bathrooms. Famous neighbors include Martha Stewart, Glenn Close, and Susan Sarandon. Before moving to North Salem, David Letterman lived for 19 years in a converted barn in Connecticut.