Alan Jackson – $28M, Franklin

Alan Jackson was able to live a comfortable lifestyle for many years thanks to the success she garnered in the country music scene. He is a huge family man and just like many fathers, he wanted to give his things the best in life. Their family used to live in a massive house in Franklin, Tennessee.

The four-bedroom estate had a swimming pool, tennis court, theater, and game room. He eventually sold the cool mansion for $28 million since his children have grown up already. In 2018, Jackson was awarded the Cliffie Stone ICON Award at the Academy of Country Music Awards.