Bancroft Ave, Monte Sereno

Here's the funny thing about Los Gatos: I don't think it ever wanted to be a town full of million dollar homes. The funky downtown vibe seems more catered to students and modern hippie artists than to posh fashionistas of New York City and Beverly Hills. But then again, young computers geeks didn't study computer science in college so that they could make six figures walking out the door. Sometimes, these things just happen.

That being said, Bancroft Avenue seems like it should be a normal suburban neighborhood in a nice suburban town, but the Silicon Valley boom and foothills proximity have launched Los Gatos into being some of the wealthiest zip codes in the country. And Bancroft Avenue has all of the key ingredients: it is close enough to downtown walk or bike, close enough to one of the key commuter streets to get anywhere in an instant, but without the hustle and bustle or noise of either. And the houses are all tucked back behind trees, a rarity in the Bay Area.

So while some of the long-time residents here may not have planned to be millionaires, it is unlikely that one can purchase a home nowadays without being one. And if you can afford it, it comes with all of the pleasantries that one would expect, and none of the posturing.