Woodside Highlands

Woodside Highlands is a relatively affluent and extremely secluded Portola Valley community. The district is almost too hidden. It only encompasses about three long, winding country roads bare grasslands (i.e. nothingness) that branch off of Portola Road. To be frank, there’s nothing too exciting about this neighborhood. Homes are rarely seen from the street and any commercial activity is left to a couple churches lining Portola Road.

Woodside Highlands is an upper middle-class community with a very woodsy aesthetic. In fact, the whole neighborhood seems to be blanketed with bushy trees and dense shrubbery. If you visit here, you’ll come across roads that look more like skinny trails that carve into the hilly landscape. And if you look close enough, you can find the few expensive, brown and gray homes that hide into the background (they’re rarely seen from the street). To which point, you might think to yourself if anyone really lives here. But for those interested, most likely you’re of the ranch hand variety or a true mountain man.

For your commercial needs, you’re in for a long car ride. The nearest shopping real-estate is on the far side of Highway 280 (a good 15-20 minute drive). There is, however, the neighborhood family restaurant in Parkside Grille situated on Portola Road. And if you keep on the street, you’ll come across a variety of churches, including Christ Episcopal Church and Valley Presbyterian Church. For outdoor recreation, there are a couple woodsy trails that run through the area. Also, Thornewood Open Space Preserve is within close proximity. Both are great options for a hike or walk your dog.