My husband and I, both 53, wish to sell our vacation home in early 2006(it has appreciated greatly in 11 years and we want out before another hurricane season!) and our primary home in 2007 (it has appreciated modestly in 21 years.) We plan to buy another home as soon as possible after the vacation home sale to take advantage of still-low mortgage rates and then put proceeds from the primary home sale into paying down the new home's mortgage. (For reasons of distance, logistics, etc., we cannot actually move full time into the new home until after our daughter's 2007 wedding.) Can anyone give me insight into the tax issues we will face? This is a very important move for us, and the most money we will have had to manage. Advice? Thanks.