Woodside Heights

Unlike a lot of Woodside, most of the homes here come right up near the streets they are on so that you can get a good look at them. Many of the homes here have U-shaped driveways in front and tennis courts in the back.
Home styles vary, ranging from large, luxuriously kept Ranch Style homes to Mediterranean villas to imposing manors. On the far eastern end of the neighborhood you will find the Buck Estate. It is a basically an English style mansion of the kind where you could film Pride and Prejudice without too much strain of credibility.
It happens to currently be on sale for just shy of $11 million. Homes here tend not to rise to this level for the most part, however, with a fair number of homes for around $2.5 million. These prices tend to be for large 50’s style Ranch homes which, anywhere else, would probably not break $1 million. As they say in real estate, however, location is everything.
On the far eastern end by the Buck Estate, you also find Woodside High, Woodside’s main high school. Woodside is an above average school with an API of 7. This is good but not as good as many other nearby Peninsula high schools whose APIs are 9s and 10s.
I am not sure why Woodside should be slightly below its neighboring high schools. Parents seem fairly involved and administrators and teachers are praised for their involvement with and commitment to students. It may simply be one of those stats that is true for a year or two and then will disappear again. (And, of course, above average is not failure.)
Overall, this is one of the highly coveted neighborhoods in all of the Peninsula. I would certainly not have minded having the wherewithal to move here.

Although extremely small, Woodside Heights is for the very wealthy with its luxury style homes and abundantly leafy properties. In fact, it is home to a community that’s somewhere between the upper middle and upper-class. The district is also exclusively residential and offers a bushy residential aesthetic that most surrounding communities tend to evoke. It’s biggest luxury is its close to downtown and about a 10 minute drive to the prestigious Stanford University.

Woodside Heights shouldn’t necessarily qualify as its own neighborhood, but only because it encompasses just about two residential streets. For the perspective resident, the community has everything from wealthy, secluded dream homes to some long country roads, with no sidewalks. Homes are rather hard to define, considering most are obscured from street view. But of the ones you can see, they are rather large (some two-story colonials here and there) and sparse. In essence, you’ll have to dig deep into your pockets to afford these places. Also, they are usually situated on enormous ranch-like properties, sometimes fenced in and sometimes perfectly manicured. They tend to lay ground to long, deep driveways with luxury cars parked out front (almost like a car commercial). To get to this area, you’ll have to travel through an abundance of woodsy, uninhabited real-estate and climb some very steep hills...so don’t get too attached just yet.

For those with teenagers, Woodside High School (along with Menlo Country Club) lies adjacent to the community’s quarters. The institution is part of the Sequoia Union High School District and has scored a perfect 10 on California’s similar school rankings in both 2009 and 2010. Elsewhere, Bear Gulch Reservoir is just down the hill from the neighborhood and acts as a nice secluded escape. For those commuting, you’ll be situated right next to Highway 280, which tends to make life a lot easier for long distance travel.