ALAN JACKSON – UNDISCLOSED AMOUNT, TENNESSEE
NET WORTH: $95 MILLION

After Alan Jackson rose to fame and became one of his generation’s most popular country singers, he quickly built the house he had been dreaming of. His home in the wealthy rural Nashville suburb of Franklin, Tennessee, is said to be something like the movie. He first made investments in a 135-acre land that he eventually built a home on, inspired by Tara from the movie Gone with the Wind.

It carries a southern plantation-style and boasts 22,012 square feet of living space. With its vast size, the house took 23 months, almost two years to build, and was only completed in 1997. A “monumental stone residence” best describes the house. The bedrooms are luxurious suites. Arched doorways, elaborate woodwork, and oversized windows are finished in the formal living and dining area, giving the vast house a much more feel.