Not sure what price of home you were looking at Patrick, but 100,000 seems a bit excessive in difference between the two cities. One huge factor in Brookfield's favor is the lower taxes. Waukesha & Wauwatosa had such high taxes that we basically ruled them out. When we were looking we found that a very similar cape cod home in Waukesha would be 150,000 and in Brookfield 170,000. However, due to the difference in taxes, the Brookfield home would be a lower monthly payment. Also, keep in mind that with a starter home we are talking about relative value and the ability to gain/resell more than absolute square footage value. Don't get trapped into that mindset. A small home in a desirable neighborhood where more expensive homes surround it is generally a safe bet. Always make sure to avoid buying the 'nice' house in a blah neighborhood. Having bought 2 homes in Waukesha County in the last 5 years, I think you'll be very happy with the current prices. Golden opportunity with the prices, rates, and govt tax breaks.