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Investors & landlords
The tax consequences of selling private stock are the same as when selling shares that trade on a public exchange. Thus, your option where you discuss the FIFO method may be the most accurate way of explaining these various transactions. It does appear that you sold all of your shares, and subsequently moved some of those proceeds into the new firm. Therefore, you would need to account for all of the sales, and determine your basis for each purchase, which it appears you have already done, and then determine your holding period for capital gains tax purposes (long-term or short-term), which it appears you have already done as well.
Regarding using "various" on Schedule D, the use of such term is appropriate if it reasonably characterizes your situation.
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