Freeman is tied at 12-under-par with Rick Price (65) and 16-year PGA Tour member Jay Delsing (66).
Joe Daley (65), Charles Raulerson (67) and Matt Peterson (68) are all just two shots back at 10-under.
The 39-year-old Freeman, a member of the tour in 1994, recorded one eagle and eight birdies at the Hardscrabble Country Club in Fort Smith, Ark.
Two players have shot 59 in Buy.Com tournament history. Notah Begay III shot 59 in the second round of the 1998 Dominion Open; Doug Dunakey did the same in the second round of the '98 Miami Valley Open.
Full-field scores from the Buy.Com Fort Smith Classic