I have two homes that I am thinking of selling in the next two years and I have a tax question. I own a co-op apartment in NYC that has a big gain on it (got lucky with the timing). I have a house in CT that will most likely sell for a loss (stupid buy at the end of 2008, but there were life considerations). If I take a loss on the CT place, can I use that to offset a gain on the NYC place? I know that I am allowed to clear up to $250,000 on a primary residence but am trying to avoid capital gains taxes if my gain is more than that (not sure yet). Thanks for your help.