Hillsborough, California

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+.
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Local schools include San Mateo High School, Crystal Springs Uplands School, Crocker Middle School, and South Hillsborough Elementary School.

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.

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 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.
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Families in this neighborhood are zoned for West Hillsborough Elementary, North Hillsborough Elementary, Crocker Middle School, and Burlingame High School - all A+ options.

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.
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Families in the neighborhood are zoned for North Hillsborough Elementary School, Crocker Middle School, and Burlingame High School -- all A+ rated.