How much jail time am I facing for stealing somewhere around $500?

There is no simple answer to your question. Much rides on your past criminal history, if any, and the facts of the case. In MA, Larceny Over $250 is a Felony and carries a maximum penalty of up to 2.5 years in jail. It is highly unlikely that you will get that sentence. It is certainly nothing to be handled on your own. Hire a good criminal defense attorney and follow their advice. If it is in or around Worcester County, you can call me at the numbers listed below. There is no fee for the telephone consultation. All information and analysis provided herein is for Massachusetts law and Massachusetts cases, ONLY. If your matter or question involves the laws of another state please disregard this post and seek advice from an attorney licensed to practice law in the applicable state.