Their 16-property portfolio is now worth some $3.5 million. "I've done much better here than in the stock market," says John. Best of all, the couple haven't paid federal capital gains taxes on a single sale.
What the Stouffers have taken advantage of is a decades-old tax law that lets you roll the gains on one investment property into another without incurring a tax bill. This strategy-called a like-kind / 1031 exchange after the IRS code establishing it-is attracting more attention today with the real estate market so strong. (The median price of second homes-including vacation and investment properties-soared 27% from 1999 to 2001, according to the National Association of Realtors, well outpacing gains on primary residences.) These exchanges are also becoming more common among pre-retirees who buy rental homes where they intend to retire one day.
Of course, to qualify for this generous tax break, you must clear several hurdles. Here's what you need to know.
- What properties qualify?







