What is prompting you to sell the stock? Does it need to be sold all at once? I'd be inclined to look at the tax brackets and sell an amount small enough to keep you in the current or next higher tax bracket each year.Looking at the link below, it appears that if you're married, you could sell ~$50k and pay 25% tax or well over $100k and pay no more than 28%. OTOH, selling it all this year would push most of the proceeds into the 33% and higher bracket. Unless the investment is a dud, I personally don't think I'd sell it all at once.http://www.savingtoinvest.com/2010/04/2010-and-2011-tax-brac...Other thoughts, you could donate portions the stock to charity and take a deduction at the current value while not paying any tax on the proceeds.Also, if you inherited the stock recently, the basis price is the date of death from whom you inherited the stock in which case the amount of tax owed could be quite low: http://www.smartmoney.com/personal-finance/taxes/taxes-on-in...-murray
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