We kid, we kid (kind of). The Flintstone House is perhaps the greatest outlier relative to local housing styles of any home in the country. It is perched on a hill just off the 280 freeway in full view of northbound commutes along this illustrious city’s western edge. The reason it is such an outlier is probably the reason people love Hillsborough the most -- massive, stunning, private homes on large lots with the only commercial spots in town being the schools, government buildings and a golf course. If you want to live an extremely secluded life in as fancy a home as possible then look at Hillsborough. We think the Flintstone House gives the city a sense of humor it could use a dose of but most locals do not agree. 


The Flintstone House

The Best Thing About Hillsborough?

Hillsborough has no commercial district - no downtown to feed or entertain the locals. The city does not allow any commercial building of this sort and so you have a city largely devoid of communal energy. The amazing schools of course bring people together but if the family wants to go out for a burger or a pizza after school or a game then you’ve got to head east to Burlingame or south to San Mateo. Plenty of locals appreciate that isolation but it can feel a bit lonely. 


My Kingdom for a Pizza

The Worst Thing About Hillsborough? 

This is as pure a bedroom community as you can find. It’s really only massive homes amidst the tree-lined streets. Which means that the lifestyle for families is largely school-centric or spending time in neighboring cities when you want to do something other than hunker-down in your home. The city does host some community events, most famously the Concours D’Elegance, a vintage car celebration. There is also the Family Fun Run and the Annual Tennis Classic, both put on by the Hillsborough Schools Foundation. 

There is an outdoor culture that permeates the city. In part that is due to the healthy/fitness passionate populace and partly due to outdoor spaces within city limits and the fact the western side of the city borders some of the most beautiful land and hills in the country. Within Hillsborough are three parks: [**Centennial, Vista and Crossroads**](https://www.hillsborough.net/210/Parks). All three are beautiful open spaces for play and Vista the most family-friendly due to a 2006 makeover that installed climbing rocks, a huge playfield and playground and picnic spots for families and larger group events. To the west are [**Crystal Springs Park**](https://www.smcgov.org/parks/crystal-springs-regional-trail), Golf Course and Reservoir. These are amazing areas for hiking, play and just taking in the beautiful landscapes. 

The lifestyle of locals is primarily driven by their families and the schools. While the homes and privacy are a big draw, many locals cite the quality of the public and private schools as the magnet for driving their move to Hillsborough. 


Lifestyle of Hillsborough

Hillsborough is one of the highest rated elementary school districts in the state with an A+ rating on [**niche.com**](https://www.niche.com/k12/d/hiilsborough-city-school-district-ca/). There are three elementary and one middle schools in the public school system and then high school is part of the San Mateo Union High School District, another A+ rated district on [niche.com](https://www.niche.com/k12/d/san-mateo-union-high-school-district-ca/).   There are interesting private school options here as well. [**Nueva**](https://www.nuevaschool.org/)   is a gifted student private school for PREK-12 that draws students from throughout the bay area. [**St. Matthews Episcopal Day School**](https://www.episcopaldaysanmateo.org/)(PREK-8) and [Crystal Springs Uplands School](https://www.crystal.org/)(6-12) are other excellent options. 


Schools in Hillsborough

Hillsborough is a private enclave for wealthy families. If you want to escape the commercial energies of busier cities and put your kids in amazing schools then it’s worth a look. 


Why You Should Move Here Now? 

The Brewer Subdivision comes closest to giving locals a mix of the private enclave vibe of Hillsborough with commercial access via its proximity to El Camino Real/Downtown San Mateo. Running along the southern edge of the city it remains a completely serene experience but at least you have a shorter drive to restaurants and shopping. 
Prices for single-family homes here range start at $3.6m+ and run up to $15m+.
​​​​​​​
Local schools include San Mateo High School, Crystal Springs Uplands School, Crocker Middle School, and South Hillsborough Elementary School.


Families

Brewer Subdivision/Upland

Carolands runs along the west side of the city which means you're rich in proximity to the great outdoors and poor in terms of proximity to commercial options. You get live right along the beautiful Crystal Springs Park and Golf Course and you're right along the 280 freeway if you're commuting up or down the peninsula. There aren't many homes for sale in this neighborhood but when they do the prices range from $3m to $$12m+. Lots along the west side tend to run bigger so if room to run and play for the kiddos/doggos is a priority this could be your neighborhood. 

Kids are zoned for top-rated West Hillsborough Elementary School, North Hillsborough Elementary School, Crocker Middle School, and Burlingame High School.

Carolands

Hillsborough Heights is a bit of a misnomer. The neighborhood is part of the area formerly known as "Lower Hillsborough" and it is actually quite flat (which the kids appreciate for bike riding). It's an older neighborhood than many and as such most homes are pre-war(WWII)and are built in that era's stunning architectural styles - Mediterranean, Tudor, French and Beaux Arts. These flat, leafy residential blocks are reminiscent of neighboring cities like San Mateo Park and give off a less isolated vibe than some of its hillier more private areas. 

Though its name might suggest otherwise, residents of Hillsborough Heights enjoy homes set on lovely level streets. The housing inventory here includes older, distinguished homes with styles including Mediterranean and Tudor. Homes here sell on average for ~$6.7m with a price per square foot of around $1.4k. 

​​​​Schools for this neighborhood include San Mateo High School, Crocker Middle School, and South Hillsborough Elementary School -- all A+ rated. 


Hillsborough Heights

Hillsborough Hills sits in the westernmost district in upper Hillsborough. It has large estates with deeply wooded lots and many with bay views. 

If you're looking for classic (albeit quite large) California ranch homes amidst absolutely breathtaking oaks and California Redwoods you should look at the Hills neighborhood. Many of those classic ranches have been torn down and behind those trees you can also find massive modern estates if that's your preference. The neighborhood is sparsely populated so privacy is one of the main selling points and why it averages $6.5m+ per home sale. 
​​​​​​​
Families in this neighborhood are zoned for West Hillsborough Elementary, North Hillsborough Elementary, Crocker Middle School, and Burlingame High School - all A+ options. 

Hillsborough Hills

Hillsborough Oaks is on the eastern edge of Hillsborough, bordering the city of Burlingame. It remains bucolic and quiet with large homes on beautiful flatter lots and blocks. You do however get the benefit of being within walking distance of downtown Burlingame. That gives the neighborhood a big edge over others for families that prefer closer proximity to some social opportunities and more of a neighborhood/community vibe. None other than Bing Crosby picked this neighborhood when he purchased a home on Jackling Drive in the 1960s. His widow Kathryn Crosby, continues to live there today. 

Average home prices in the neighborhood run north of $6.5m and its average price per sq ft is ~$1.7k so getting on these stunning streets don't come cheap. 
​​​​​​​
Families in the neighborhood are zoned for North Hillsborough Elementary School, Crocker Middle School, and Burlingame High School -- all A+ rated. 


Hillsborough Oaks

Hillsborough

**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, California

Yabba Dabba Do

Looklyloo Score: 85

We're on it!