If you are selling investment real estate and anticipate a significant capital gain, consider a so-called 1031 like-kind exchange. With this type of arrangement, you can sell your current investment real estate, purchaser other investment real estate, and not pay capital gains tax on the money used to purchase the replacement property. These transactions are complicated, are more expensive to close, and must be handled carefully in full compliance with IRS requirements. Consult a knowledgeable tax advisor or your real estate attorney for specific details and to see if this makes sense for you.
Mitch