If I pay my property taxes twice within the same calendar year (say Jan 2021 (for 2020) and Dec 2021 (for 2021)), can I deduct them both when I do my taxes for 2021 next year?
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Yes, you can deduct the property taxes you actually pay in the tax year. It does not matter what year these taxes are for.
Presuming, of course, that you don’t deduct them also in 2020. You deduct the taxes when actually paid, regardless of what year they were for.
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