As Joshua pointed out earlier, your long term capital gains would be capped at a flat 15%, regardless of your income tax bracket. So, if your capital gains are $288,000 as you said, your taxes would be 0.15*288,000 = $43,200. That's a pretty big tax hit, but like someone else said, you hit the jackpot a few times with this investment. Take your gains, pay your taxes, and be really happy about it, if you do decide to sell all of it. Having to pay taxes is not reason alone not to sell a stock at a gain.