Third-least-affordable U.S. city: San Diego "San Diego is a place where lots of people want to move, but the city is very constricted in terms of where it can build," Sante says. "As a result, it has extremely high home prices." Interest.com found that a median San Diego-area house costs $379,100 -- trailing only San Francisco as the nation's priciest housing. Above-average median property taxes ($3,384) and homeowners' insurance premiums ($922) only add to affordability woes. True, San Diego does have an above-average median household income ($59,477). But Sante says that's "not nearly enough to make up for the high property taxes and the way-way-way-above-median home prices." The bottom line: The typical San Diego family makes 26% too little to get a mortgage on a median-priced local home.