6.3 out of 10

Woodside Highlands

37.3855621134622 -122.240475867556
Great for
  • Clean & Green
  • Neighborly Spirit
  • Peace & Quiet
  • Safe & Sound
  • Parks & Recreation
Not great for
  • Pest Free
  • Public Transport
  • Childcare
  • Eating Out
  • Parking
Who lives here?
  • Professionals
  • Country Lovers
  • Families with kids
  • Retirees
  • LGBT+


4/5 rating details
  • Neighborly Spirit 5/5
  • Safe & Sound 5/5
  • Clean & Green 4/5
  • Pest Free 1/5
  • Peace & Quiet 4/5
  • Eating Out 2/5
  • Nightlife 2/5
  • Parks & Recreation 5/5
  • Shopping Options 2/5
  • Gym & Fitness 2/5
  • Internet Access 3/5
  • Lack of Traffic 4/5
  • Parking 2/5
  • Cost of Living 1/5
  • Resale or Rental Value 5/5
  • Public Transport 1/5
  • Medical Facilities 3/5
  • Schools 5/5
  • Childcare 2/5

"Nice, Quiet Little Nook"

Woodside Highlands—not to be confused with either Woodside Hills or Woodside Heights which are actually in neighboring Woodside, is actually a tiny Portola Valley neighborhood. It is basically made up of a half dozen or so woody lanes nestled up in the hills in northwest Portola Valley.

Homes here are, of course, expensive. Portola Valley is the number 6 most expensive location in California (in terms of home prices, I believe). Currently there is only one home for sale here currently. It is a 3000 ft. 3 bedroom home with pretty nice view and a wooden deck. It is going for $2.5 million.

This is a very leafy area with narrow roads (some unpaved) winding up to very nice homes. You definitely do feel that you are away from it all. And this is about as un-walkable as it gets, narrow winding roads with no sidewalks basically force you to get into your car for just about everything—even if you just need to go into to town for the paper or cup of Jo.

You are actually not that far from Palo Alto and other centers; which is good because there isn’t much in Portola Valley itself.

Overall, a nice neighborhood, but I’m not sure it is worth the ridiculously high home prices.
  • Nice Homes
  • Quiet and Secluded
  • Good Schools
  • Over Priced
  • Unwalkable
  • Far from Everything
Recommended for
  • Professionals
  • Families with kids
  • Retirees
  • LGBT+
  • Country Lovers
3/5 rating details
  • Neighborly Spirit 4/5
  • Safe & Sound 4/5
  • Clean & Green 5/5
  • Peace & Quiet 5/5
  • Nightlife 1/5
  • Parks & Recreation 3/5
  • Shopping Options 1/5
  • Gym & Fitness 1/5
  • Cost of Living 4/5

"Secluded ranch-lands and nothing else"

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.
Recommended for
  • Professionals
  • Country Lovers

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