Under Massachusetts law G.L. c. 59, s. 53. and G.L. c 60, s. 19, property taxes may be prepaid at the discretion of each municipality. Informational guidelines can be found in the following pdf.\u00a0DOR\u2019s Division of Local Services (DLS) recommends that taxpayers consult their municipality to determine whether property tax prepayments will be accepted in calendar year 2017 for calendar year 2018. \n\nThe Internal Revenue Service (IRS) issues guidance on federal tax laws. To determine federal rules on the deductibility of prepaid property taxes for federal tax purposes, please see the IRS Advisory issued on December 27, 2017.