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Do I have to pay a capital gains tax if I rebuy different stocks?
Probably.  It sounds like you're looking for a 1031-exchange for stocks and bonds.  From the wikipedia page for 1031-exchanges: To qualify for Section 1031 of the Internal Revenue Code, the properties exchanged must be held for productive use in a trade or business or for investment. Stocks, bonds, and other properties are listed as expressly excluded by Section 1031 of the Internal Revenue Code, though securitized properties are not excluded.  1031-exchanges usually are applicable in real estate.