Hillsborough, California

Best city/neighborhood on the Peninsula and why

Los Altos Hills. Beautiful, large lots, great schools, and close proximity to Silicon Valley. Only downside is fire danger.

Honorable mentions: Woodside, Belmont, San Carlos hills (Cordes, Devonshire, or the Clubb/Melendy ridges), Pacifica, Palomar Park, Brisbane. You can tell I like hills. Belmont & San Carlos have great schools too, and good communities. Pacifica has the extra benefit of the beach.

Overrated: Hillsborough, Palo Alto, Atherton. The main draws of these are expensive houses on large lots and lots of greenery (and in the case of Palo Alto, great schools), but the views are actually worse than many other communities on the peninsula, proximity to amenities is worse, parks are worse, and community is worse.

If you had the option to live in Palo Alto, Pacific Heights or Hillsborough - where would you choose and why?

10 years ago, the last possible place I’d want to live is Hillsborough. It doesn’t have the full benefits of warm weather you get on the Peninsula, and it has none of the amenities you get in SF. And unlike Palo Alto, it’s anti-walkable or even bikeable. All you get are big houses clinging to the side of a hill which look impressive but often mean a weird yard it’s hard to even use if you can afford anything there.

But life goes on.

Now, I’m a startup world guy with kids in school. My business life is in SF, but the kids want the benefits of a suburban life. The train in Palo Alto is nice, but it doesn’t really match up to an unscripted life as well as you’d hope.

So now I sort of wish we lived in Hillsborough/Burlingame. Easy to get into SF, without all the trade-offs of living in SF with kids.

The Bay Area has evolved into SF-connected segments that are so far from each other they will drive you nuts. Try going from Jackson Square to Mountain View for a meeting. Man.

Hillsborough-Burlingame-etc. may be the best family-friendly trade-off.

If you had the option to live in Palo Alto, Pacific Heights or Hillsborough - where would you choose and why?

I grew up in Hillsborough and now live in (Lower) Pacific Heights, so I will speak to those areas.

I understand why my parents left SF to move to San Mateo where I lived until we moved to Hillsborough right before I started kindergarten. The suburbs aren’t for everyone, including not all families, but there’s more open-space for kids to run around in, bike around, etc. They’re fairly safe.

The reason we left San Mateo was for Hillsborough’s public schools. Due to the high property taxes in Hillsborough, the town public schools get more money from the taxes in lieu of some money from the state of California. In short, in my parents’ opinions, Hillsborough is known for the schools.

Now that I’m a young professional, I love the Pacific Heights area. Like Hillsborough and Palo Alto, it’s a very nice area to live: nice parks and houses, and it’s pretty safe and clean. I can walk to Japantown, Chinatown, the Marina, Golden Gate Park, and I even walk to my office near the Embarcadero (when the office was open.) I feel safe as a young woman walking at night. It’s a central location.

When/if I have a family, I’m not sure if I would stay in SF. I can’t afford a house in Pacific Heights (I rent an apartment in Lower Pac Heights) but I imagine if I stayed in the city, I’d move to the Richmond and also crack and send my kids to private schools. The way SF public schools work (from what I’ve heard from family friends) is that it can be difficult to go to your neighborhood school. A family friend whose parents used to work with my mom lived across the street from a West Portal elementary school, but was assigned a school further away, so he went to Catholic school instead.

Hillsborough Community