This time, though, he reportedly lost almost as much money as he made.
Back in 2010, Jackson listed his Tequesta, Florida home for $1.27 million, the price he paid back 10 years ago. However, according to Gossip Extra, this month Alan sold the house for just $725,000, a loss of around $545,000. Not a huge amount for someone like Alan Jackson, but when you consider the loss is almost as much as what the house sold for, it puts it in a different light.
The new owner, of course, is excited that the singer's loss is his gain.
"The coolness factor is a 10," said buyer Lawrence Dario, a Rhode Island dentist. "Ernest Hemingway wouldn't have looked out-of-place in the living room."
Alan has another Florida property for sale, this one in Jupiter Island that is listed for $14.9 million.