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I have several rental properties that I am thinking about liquidating. I want to avoid capital gains tax on the profits. What is the best way to do that?

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    This is the time to employ a tax accountant. Given that your proceeds are probably significant, he can examine your income and profits and come up with a tax reduction strategy. They will be well worth the money.
    – Pete B.
    Commented Jul 10 at 10:53

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You cannot contribute assets into 401k or IRA, only cash. So if you have assets outside of tax sheltered accounts then you'll need to recognize the gains and pay the taxes.

For real estate, the most useful tax deferral tool is 1031 exchange. You can purchase new properties with the proceeds of the sale of the old properties and carry forward the gains and tax basis. There are specific rules and process, and a very strict timeline, to follow.

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