I sold in early 2005 and have often wondered if I should have waited for the Summer, the peak buying season. I was not under any financial pressure to sell.
My house had a nice lot, but was a horrible layout with bad construction, no a/c, bad electrical, etc. In the 10 years I lived there, I made almost zero upgrades other than a nice storage shed I built unpermitted. My realtor and I discussed frequently that I could invest in fixing up the house to make more money. Her arguments were convincing that the return on investment would not be there; someone buying this house would have their own plan for it. The offer I received covered seller’s commissions, no contingencies and “as-is”. The fact that I would not have to worry about fixing anything was a huge incentive for me. Anyway, I accepted the offer and escrow went smoothly, other than my uncertainties about selling.
The buyer instantly added a second bathroom and landscaping, it was back on the market in 3-4 months. It never sold again; I don’t know if the flipper is living in it or renting it out.
Since then, I’ve watched the market and have wondered if I should have held it a little longer. I’ve come to the conclusion that it was the right choice, given the condition of the house, my personal situation at the time, the ease of selling, etc. I would not want to be trying to sell that house now, or even 6 months ago.