7.2 out of 10

Woodside Hills

37.4463324657207 -122.248124922927
Great for
  • Peace & Quiet
  • Clean & Green
  • Safe & Sound
  • Neighborly Spirit
  • Parks & Recreation
Not great for
  • Gym & Fitness
  • Public Transport
  • Childcare
  • Eating Out
  • Medical Facilities
Who lives here?
  • Professionals
  • Families with kids
  • Retirees
  • Trendy & Stylish
  • Singles


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

"A Mansion and Million Dollar Homes"

Woodside Hills, located just to the south of Canada College (the local two year college) and just to the north of Woodside High, is about what it sounds like, a hilly neighborhood with large, overpriced homes in a very affluent community.

The most expensive home currently on sale in this neighborhood is Le Soleil (the “sun”), which is an actual mansion (in a French Chateau style). It is currently listed for just shy of $13 million. It was built in 1929 and looks like the sort of place where they could have set scenes from The Great Gatsby. It has 7 bedrooms and 7 baths, a front driveway fountain, a pool, symmetrically shaped topiary gardens and a tennis court.

It will be going on sale on June 14 of this year, with bids starting at $8 million. (The home was originally listed at $21 million.)
So we will have to keep an eye on how that turns out.)

The vast majority of homes in this area however are not in the mansion category. The median home in this area runs $2.5 million, which is hardly chump change, but is nowhere in the same galaxy as Le Soleil. These other homes also get a special bump because of being in affluent Woodside. For one of these mid-level homes you get perhaps 4000 ft., pool and koi pond and 4 bedrooms. Pretty nice, I suppose and worth it if you work in Silicon Valley and would like to shorten your commute.
  • Attractive Homes
  • Very Leafy
  • Strong Schools
  • Very, Very Expensive
  • A Bit Out of the Way
  • Kind of Snooty
Recommended for
  • Professionals
  • Families with kids
  • LGBT+
  • Country Lovers
  • Trendy & Stylish
4/5 rating details
  • Neighborly Spirit 4/5
  • Safe & Sound 4/5
  • Clean & Green 4/5
  • Peace & Quiet 5/5
  • Nightlife 1/5
  • Parks & Recreation 4/5
  • Shopping Options 2/5
  • Cost of Living 4/5

""Woodside Hills" is a perfect name for it"

Woodside Hills is a wealthy, well-connected neighborhood located in the shallow foothills of the Santa Cruz Mountains. It is for the truly rich, mostly upper middle to upper-class residents who love the great outdoors and the open ranch lands that it comes with. Geographically speaking, the neighborhood is fitted between Woodside Road and Highway 280, the latter of which gives residents a quick and convenient commuting option up and down the San Francisco peninsula. Moreover, the neighborhood is close enough to the busy goings-on of Stanford University, but still far enough to keep its peaceful residential bubble intact.

Woodside Hills is not really known for much within the city because it shares the same woodsy terrain and residential aesthetic that Woodside is so unwaveringly known for. But for those who don’t know, the district is made up of long, country roads, beautiful dream homes and secluded and sometimes gated properties. And although it offers a divergent style of homes, most are extremely pricey, costing upwards of a couple million (and that’s on the low end). If you travel through the area, you’ll notice some nice, luxury cars parked in driveways, enormous (countryside) properties, a couple half circle driveways and a few picture-perfect front yards. You also might come across the small Woodside Plaza Shopping Center, the neighborhood’s commercial pit-stop for household essentials.

For young families, Woodside Hills is adjacent to Woodside High School, the communities primary educational institution. Elsewhere, Canada College lies at the western fringe of the neighborhood, while John F. Kennedy Middle School skirts the northern end. With all of these schools nearby, the district tends to cater to the local school spirit and all the activities it brings with it. Also, if you like to enjoy the outdoors, the Menlo Country Club offers a beautiful 18-hole golf course, a couple tennis courts, a swimming pool and a lodge fit for all things dining.
Recommended for
  • Professionals
  • Families with kids
  • Retirees
  • Students
  • Trendy & Stylish

Unranked Streets in Woodside Hills

Woodside Dr

"Country club area"
37.4451584758458 -122.244300260958

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