DAVID LETTERMAN – UNDISCLOSED AMOUNT, SAYPO, MONTANA

Now that he’s got a bit more time in his hands, it’s not surprising for the former Late Show host to spend his days in this quiet ranch in Montana. That is 2700 acres for the family to cultivate and enjoy, and with an abundance of space to work with, the family can comfortably place a few more houses on the property should they need it in the future. Aptly named Deep Creek Ranch, the property features a 3,276-square-foot home with 3 bedrooms and bathrooms, as well as a detached garage.

Solitude does come with some cons and in 2003, a kidnapper was thwarted before he could enact his plan of taking David’s son and the boy’s nanny from the ranch. With such a big land, ample home security is a necessity and an expense that shouldn’t be overlooked. The property has been reported to receive a few upgrades in security in the past few years.