I have a Roth account that is 5 years old. There is only a small amount in the account and was thinking of rolling over some of my IRA (rollover) into the Roth.The Original Roth had significant losses ($30,000). I am 55 Years old, would I be able to withdraw all funds from my Roth without taxes, in a year or two because the 'Account' was opened 5 Years ago or is the 5 year waiting period based on each deposit into the account.

The money in the Roth RIGHT NOW can be withdrawn with NO tax liability at all, because the Roth has LOST money.

If you roll money over into the Roth, the five-year clock restarts for the rolled over funds.