I agree with Cameron. Stieg, this really is about you and your tolerance level. Do I think the market will ever go back up, of course, in time (a long time from now). More than likely, the market, at least here in AZ, will decline a bit more. If you sold now, took whatever capital off the table and invested it in something else, would that net you more money? When we bought our new house, I had the same ? two years ago, and I decided to sell my starter house. My mother was a Realtor and did property management for 25 yrs, so I know the potential for headaches renting out properties. Long story short, the identical house next to mine just sold (2 years later) as a short sale for $65K LESS than what we sold ours for. In hindsight, we are so glad we sold. That is the thing about a decision like this, look at all the angles, all your options and in the end only you know what kind of tolerance level you have, my financial consultant agreed for whatever it is worth, that putting that money in something else other than housing right now, will get you a better return right now...who knows what the market will continue to do. I do not know if there is a "right answer" to this question, you simply need to find the "right answer" for you.