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You are correct that mortgage interest is hard to prepay well in advance. Estimated property taxes can be easily paid the full year in advance, however, if there isn't any property tax escrowing being done. If it is being escrowed, it would get a bit more complicated but even in this case I bet one could directly prepay to the local community and then warn the escrow agent to expect a $zero bottom line on the next bill. The escrow agent is there to make sure the property tax is paid to protect the mortgage company, so why would they object to a homeowner paying more in advance?

I really should have said something like "one billing cycle", not one "payment". Once your full real estate tax assessment for the year is fixed, you can pay it in a single payment and can time the payment to bunch deductions.

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