Alan Jackson – $28 Million, Tennessee

The country singer Alan Jackson definitely used his music earnings wisely when he acquired this 135-acre property located in the exclusive rural community of Franklin, Tennessee. It was then when he decided to build something of a fantasy home—literally. Turns out, the home was inspired by Tara in Gone With The Wind.

He built an 18,622-square-foot house that took almost two years to construct and was completed in 1997. Jackson’s dream house features an interestingly designed dining room, four-bedroom suites, an exercise room, and even a nanny’s quarters. In 2015, Alan released his most recent album titled Angels and Alcohol.