Detached house (needs work) $359k https://www.redfin.com/CA/Gilroy/7270-Alexander-St-95020/hom...
Condo in Morgan Hill @ $446k: https://www.redfin.com/CA/Morgan-Hill/112-La-Crosse-Dr-95037...
Detached 3/2 SFH @ $500k https://www.redfin.com/CA/Gilroy/374-Walnut-Ln-95020/home/10...
Nice townhouse @ $495k: https://www.redfin.com/CA/GILROY/7664-GENNARO-WAY-9502/home/...
$250k gets you a two-story house with an actual YARD there.
Pittsburgh's tech scene is great now, too: Carnegie Mellon (CMU), Google Pittsburgh, Uber (self-driving car lab), Oculus Research, Duolingo, and a plethora of other startups. There's even seed investors here now! Even Paul Graham, a Pittsburgh native, is getting involved again.
I mention this to someone here, and 9 times out of 10 the reaction is along the lines of "Pittsburgh?! Why would you EVER want to live there?" Oftentimes, the person who cannot conceive the possibility of living a happy life outside of Silicon Valley's bubble either has an inherited house that ballooned in value, or they're still renting at age 35.
I'm a huge fan of getting out of Silicon Valley. Cashing in on BigCo salary for a few years and then buying a house in TX/PA/wherever in cash is a totally valid game plan. I think it's hilarious that our industry essentially invented modern telecommuting yet uses it so rarely.
As an aside, $250k may get you a nice house in PA, but the salaries are correspondingly lower. If you can't get paid substantially more in the Bay Area there's really no good reason to be/stay/move here since everything's so expensive.
It's not even that though, $1M now gets you what's called a "fixer-upper" in SF -- a euphemism which actually means a house with broken gas lines that you literally risk your life occupying.
It's also impossible to save money here for a future house in a cheaper city when the median rent is $4000/month.
You mentioned Gilroy, the price situation (800k, 4M, 1M, 1M, 600k are the first 5 results) doesn't even look much better than in SF proper:
http://www.zillow.com/gilroy-ca/
Moreover, they don't really have condos in Gilroy.