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If you pay them in 2024 it goes on your 2024 return, not 2025. That way you can double up every other year. but you can only deduct up to 10,000 for state taxes & property tax each year if you itemize. Then all your itemized deductions have to be more than the Standard Deduction to give you any benefit.
For 2024 the standard deduction amounts are:
Single 14,600 + 1,950 for 65 and over or blind (16,550)
HOH 21,900 + 1,950 for 65 and over or blind (23,850)
Joint 29,200 + 1,550 for each 65 and over or blind (30,750/32,300)
Married filing Separate 14,600 + 1,550 for 65 and over or blind (16,150)
Probably not. To be deductible, the taxes must actually be assessed on the property as a matter of law. Just because you expect the taxes to be a certain amount, does not mean they have been assessed. You need to look at the property tax assessment schedule in your state or county. For example, in New York State, school taxes are assessed on September 1 of the tax year. If you prepaid your 2024 school tax in July 2024, it would not be deductible because it had not been assessed yet (even though the bill was paid in the same tax year, it's not deductible if it is paid before it is assessed.)
So you need to look at the tax calendar for your area.
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