To be honest with you Tamie, the time to stretch yourself financially if you want to, is before you have kids. Once you have children, they drain you financially in a different way, and then you'll be in a bind, since it will be difficult to stretch then, since you'll already be stretched more. If you really think you're going to need a bigger home in a few years, I can think of no better time to buy. Mortgage rates are at historical lows, allowing you to purchase a more expensive home. If rates continue to stay low, or go lower, if you bought a new house, you could just refinance to take advantage of lower rates. If rates go up, then you'll find yourself, yes, you'll be able to spend more, but you'll be able to afford possibly less, due to increased rates. You could always begin looking casually, and if that perfect home presents itself, then you'll be in the mindset to jump on it. Also, buying a home you intend on staying in for a while before kids also has advantages on being able to do the work before your kids begin to interupt!!! It is very difficult to get any work done anymore with a 5 yo and a 2yo around. We basically have to hire anyone, including painters now, since we can't do it ourselves without be constantly interupted. We've been in this house 4 years now, and the downstairs is finally completed. In terms of what makes financial sense, there really is no right answer. Selling your home, making a profit and sinking it into a larger house is a sound move. You just have to make sure that the larger payment and taxes are going to be within your constraints, and no one, can tell you that. I'd look at your current financial situation and see how much "extra" you have per month. If you can part with most of that and place it towards a larger house, then do it. Just remember, with a bigger house payment, usually comes bigger utility bills!!!! We're actually debating whether we should move, since we think our current house is a little small 4000sq ft, and need more space. We know what we can afford, but we want to move to the best school district in the area (please keep in mind when looking!!) and we don't get much more space, for the additional money. We've put a lot of $$$ into this place, landscaping, new patio and walkways, finished basement, interior carpentry, etc and really don't want to start all that again. So, we're staying put until that perfect place comes available, and then we'll reevaluate. I wish you luck!!