I'm in the exact same situation where a house in an area we have been long interested in came down to a price range we could comfortably afford, and we agreed to an Oct. 1st possession date which was less than two months after acceptance of our offer. I felt it was pointless to list our old house while we were packing and tearing things down and after moving out it was easy to bring in painters and freshen the place up for sale. We can afford to carry both mortgages as long as we are both working so that's really the only scary part but of course I would like to sell the old property as soon as possible so we priced it to sell. Ideally we would have sold our place in the summer as we have a nice backyard and the premature snow kind of masks it, also it's kind of annoying as I have to shovel two places daily.
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