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If I realize a sizable capital gain on the sale of an investment during the year, when do I need to make the estimated tax payment?

Estimated Taxes
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Stephen Cohen
In the same manner that taxes are withheld from wages as they are earned during the year, estimated tax payments should be made as the corresponding taxable income is received. In this case, the prudent approach would be to include estimated taxes on the capital gain income as part of the quarterly estimate due following realization of the gain.
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