Hillsborough, California

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.

Hillsborough has no commercial district—no downtown to feed or entertain the locals. The city does not allow commercial buildings of this sort, so the city is largely devoid of communal energy. Of course, the amazing schools 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.

This is as pure a bedroom community as you can find. It’s only massive homes amidst the tree-lined streets. This 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. All three are beautiful open spaces for play and Vista is 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 is Crystal Springs Park, a 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.

We highly recommend visiting Hillsborough and staying in the community in a VRBO rather than a hotel to get a feel for living among the locals. You can receive discounted fares on travel via our partnership with Expedia as well.

Hillsborough is one of the highest-rated elementary school districts in the state, with an A+ rating on niche.com. There are three elementary and one middle school in the public school system, and the high school is part of the San Mateo Union High School District, another A+ rated district on niche.com. There are interesting private school options here as well. Nueva is a gifted student private school for PREK-12 that draws students from throughout the Bay Area. St. Matthews Episcopal Day School(PREK-8) and Crystal Springs Uplands School(6-12) are other excellent options.