Gary L. Stevens' House

The jockey, actor, TV personality & sports anchor purchased this house in 2008 for $1.3M. In 1993, he became the youngest jockey to surpass $100 million in earnings. He has been in the winner's circle three times each at the Kentucky Derby, Preakness Stakes and Belmont Stakes. He won the Santa Anita Derby a record nine times, and he's won eight Breeders' Cup races, making him the fourth-leading money winner in Breeders' Cup history so far. His mounts have collected over $221 million with 4,888 winners.