For example, lets say I am single and sell my house in June 2019, I get married in December of 2019 and then file my taxes for 2019 as married filing jointly, can we get both $250K capital gains exclusions totaling $500K?
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In your example, you can use the exclusion for the home you owned before you were married, if you otherwise qualify. If your spouse sells a home he owned before he was married, they can take their separate exclusion on that home.
Then, your next opportunity to use the exclusion would be at least 2 years from the latest usage of the exclusion by either one of you.
Yes. You may both claim, up to $250,000 exclusion
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