Los Gatos Saratoga Rd, Monte Sereno

While technically part of highway 9, Los Gatos Saratoga Road is one of the nicer connector roads in the Bay Area, and hardly feels like a highway. The beautiful, tree-lined side streets feel like they could be part of a state park and are characteristic of the foothill towns, as are the two vibrant but charming downtown areas that the street runs through.

Given the location and the area's proximity to Silicon Valley, the Santa Cruz Mountains, and the two downtown areas, prices here are astronomical and homes on any of the streets off to the side can easily retail for over a million dollars. Traffic here does not seem too bad, but I never driven through here during rush hour.