Mike Singletary – California, $3.295 Million
Mike Singletary might have stopped playing in the NFL, but he is still active in the scene as the head coach of the Memphis Express. Apart from that, he also has investments in real estate for financial security. Smart!

Mike Singletary – California, $3.295 Million
Terry Bradshaw, Pittsburgh Steelers – Hawaii $2.7 Million
Terry Bradshaw earned a much-deserved spot in the NFL Hall of Fame! He also bought his ranch in Hawaii, added luxury amenities, and then sold it for $2.7 million. Good job, Terry.

Terry Bradshaw Pittsburgh Steelers – Hawaii 2.7 Million