Technically, I think there is a MA renter's law that states that he must return your security deposit when an old lease is expired. IE if you have to sign a new lease then he is required to give you the deposit back the DAY the old lease is expired. Also, if he does not return it to you in a timely fashion (usually a week) He is required to give you the interest you would be gaining if it were in a bank account. He is also required to tell you where the deposit is being held (if in the bank) and give you documentation of any interest earned by your money annually. You have a right under Ma law to have any interest earned by your security deposit as he is merely holding your money in case of damages and it is technically not owner of the money. You should definitely bring these up to him and not give him the new deposit until he gives you back the old one. If he refuses you should bring up MA law on interest incurred anually as well as the "timely fashion" interest and show him what your bank account gives for interest and that you will charge him that much on the lump sum.
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