His probation officer should be able to help him get it transferred. It may have to be approved by the court.
My standard disclaimer: I am not offering legal advice, assume I do not know the law in your state and that I am just making suggestions for starting points for when you do speak with an attorney. Do NOT rely on anything I write and contact a lawyer in your area immediately after reading my posting.
When he gets out, he is going to tell them where he lives. Probaion will set it up so he can do his probation there. It is a simple matter and all he needs to do is talk to the probation officer.
If he is in a Work Release program, he should have a probation officer assigned to him already. As such, he just needs to let his PO know where he will be living so the PO can verify the residence.
In the rare instance that he cannot just start his probation in Lee County, he should be able to get travel permits to allow him to travel to Lee County until the probation is fully transferred.
Richard E. Hornsby