Hillsborough Hills

Hillsborough Hills is one of the most majestic neighborhoods in Hillsborough

Hillsborough Hills has an accurate name. It is the westernmost district in upper Hillsborough, offering gracious homes on wooded lots, many with San Francisco Bay views. Located at Hillsborough’s north and west boundaries, its borders are Skyline Drive, Skyfarm, Oaksbridge and the Burlingame Hills, and it is one of the smallest neighborhoods in Hillsborough by area.

Along with some of Hillsborough’s trademark neatly-landscaped streets lined with sprawling 1950s California ranch-style homes, parts of Hillsborough Hills offer stretches of majestic trees, including oaks and California Redwoods, and enough greenery to obscure the grand homes hidden behind. With a population of around 1,300 and a total area of just under 0.6 of a mile, Hillsborough Hills’ population density is 2,176 people per square mile, approximately two-thirds that of Hillsborough as a whole.

After logging five sales during the second half of 2021, activity in Hillsborough Hills slowed to a near halt last year. Only two homes sold in 2022, making any sort of data-driven comparison to 2021 challenging. For example, how seriously do we take Hillsborough Hills’ 40% increase in average sale price (up to $6.49 million) in 2022?  Or it’s 72% drop in average DOM?  Hillsborough Hills’ small sample size makes almost every data point irrelevant for our purposes, though I will note that the neighborhood’s average price per square foot ($1,297) was similar to 2021’s average ($1,251), and that its two buyers paid an average of 95.6% of asking price, significantly lower than 2021’s 117.8% sale-to-list price percentage.


  • Gracious homes on wooded lots with many views of San Francisco Bay

  • Smallest neighborhood in Hillsborough by area

  • Neatly landscaped with stretches of majestic trees, including oak and California Redwoods

  • Wide range of home options, from subdivision properties to ranch-style homes


  • Real estate tends to vary

  • Only a handful of homes sell each year

  • 149


  • $6.5M

    Median Sale Price

  • $6.5M

    Average Sale Price

Pricing data based on single-family homes

Hillsborough Hills on the Map

Hillsborough Real Estate Market Review

In my 12th annual review of the Hillsborough residential real estate market, I examine 2023 market trends and relevant sales statistics. You'll learn first-hand what’s happening in your neighborhood.

Schools & History


Hillsborough Hills is primarily served by West Hillsborough Elementary, located in Carolands neighborhood. It’s about a 7 minute drive from Hillsborough Hills. Part of the neighborhood attends North Hillsborough Elementary School, located in the Country Manor neighborhood on Eucalyptus Avenue. It’s about a 7-9 minute drive from Hillsborough Hills.

There is one public middle school in Hillsborough, Crocker Middle School, which is located in the Country Club Manor neighborhood on Ralston Avenue. It’s an 8 minute drive from Hillsborough Hills and located next to North Elementary School.

Hillsborough does not have its own public high school. Most of the residents in the neighborhood attend Burlingame High School, located in Burlingame on Mangini Way. To search a high school by a specific address using a School Locator, click here.


Old-timers will tell you that Hillsborough’s “golden era” ended with World War II. Following the war, the town added “workmen” – physicians, dentists, lawyers – to its population as the original, ultra-wealthy residents began selling off pieces of their grand estates. Hillsborough Hills is a product of this transformation. Its original inventory of single-story homes are a reflection of the town’s move toward inclusiveness, and its new properties evidence of Hillsborough’s continuing appeal to high-end buyers.

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