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The question is which method saves you more money. Here's what it boils down to: If your standard deduction is less than your itemized deductions, you probably should itemize. If your standard deduction is more than your itemized deductions, it might be worth it to take the standard deduction and save some time.
Itemizing means deducting each and every deductible expense you incurred during the tax year. For this to be worthwhile, your inevitable deductions must be greater than the standard deduction to which you are entitled. For the vast majority of taxpayers, itemizing will not be worth it for the 2018 and 2019 tax years.
You can claim the standard deduction or itemize deductions to lower your taxable income. The standard deduction lowers your income by one fixed amount. On the other hand, itemized deductions are made up of a list of eligible expenses. You can claim whichever lowers your tax bill the most.
If the amount on Line 40 of last year's Form 1040 ends with a number other than 0, you itemized. If this amount ends with 0, it's likely you took the Standard Deduction. If this amount ends with 00 or 50, you probably took the Standard Deduction.
The standard deduction amounts will increase to $12,200 for individuals, $18,350 for heads of household, and $24,400 for married couples filing jointly and surviving spouses. For 2019, the additional standard deduction amount for the aged or the blind is $1,300.
You should itemize deductions if your allowable itemized deductions are greater than your standard deduction or if you must itemize deductions because you can't use the standard deduction. You may be able to reduce your tax by itemizing deductions on Schedule A (Form 1040 or 1040-SR), Itemized Deductions (PDF).
Who Should Itemize Deductions. To decide whether itemizing is worth it, you will need to do some math. Add up all the expenses you wish to itemize. If the value of expenses that you can deduct is more than the standard deduction ($12,200 for 2019) then you should consider itemizing.
Yes. You can deduct your real estate taxes on your federal income tax return. But limits apply, and you have to itemize to take the deduction. The Tax Cuts and Jobs Act limits the amount of property taxes you can deduct.

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