Hello there

I am going to proposition the idea of moving to Northern California to my boyfriend (we currently live in SoCal), mostly because I would like to move back to the Bay Area (I grew up there), and because when we have kids, I want to send them to Lakeside Elementary School in the Los Gatos Mountains.
I'm looking for a place to buy a house that would be convenient to Los Gatos/Campbell, would get my future child into Lakeside, but is removed from the snootyness of Downtown L.G. I used to live in Los Cumbres, and according to my mom, the commute down the hill got pretty old pretty quick.
Where would you recommend we look for a house?