If you have acquired multiple primary homes over the years (bought 1 and then moved/bought another primary residence) and decide to sell both homes - would the capital gain tax exemption for up to 500K (married couple) apply to both properties or just one ?

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The home which is not the primary residence needs to be converted to a primary residence by moving into it and then waiting another 2 years.

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You also have to have lived in the house 2 of the last 5 years as your primary residence.

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The rules in IRC 121 are plain text and should help with any of your further questions.

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well you can only do this once every two years so you can’t apply it to both at the same time if that’s what you are asking

Yes. You can only apply for exemption once every two years. Under current rules

You can only have one primary residence at a time. And there is criteria to define which property that would be.

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