Alan Jackson – $28 Million, Franklin

You may know of Alan Jackson as a well-known country singer, but you may know him better as the country singer who always wears a cowboy hat. Since his rise to stardom, Jackson has sold over 75 million albums worldwide, and it only means one thing—big bucks!

Unlike other celebrities, Jackson did not just buy a million-dollar residence. He built the house of his dreams. After acquiring 135 acres of land from Franklin, Tennessee, in the ’90s, Jackson constructed an opulent mansion that was 18,600 square feet big. Along with every facility one can dream of, his daughters grew up there. However, the family sold it at $28 million in 2010.