Hillsborough Oaks Homes and Neighborhood Guide
Hillsborough neighborhood guide
Hillsborough Oaks sits at the far north end of town, where Hillsborough meets Burlingame near Broadway. Streets such as Jackling, Armsby and Fagan Drives climb gently into wooded hills. The area is known for storybook style homes from the 1920s and 1930s, along with historic estates from the town's early decades. Like the rest of Hillsborough, it is entirely residential, with shopping just over the line in Burlingame.
Burlingame's Broadway shopping district is a short drive downhill, and Burlingame Avenue is not much farther. Because Hillsborough has very few public parks of its own, the closest public play areas and trails are in Burlingame, at Ray Park and the Mills Canyon Wildlife Area. Interstate 280 is a few minutes west via Trousdale Drive, and the trails along the Crystal Springs watershed lie beyond it.
Hillsborough Oaks is shaded. Borders are approximate, see the Hillsborough map for the full picture.
At a glance
- Storybook homes from the 1920s and 1930s
- Jackling, Armsby and Fagan Drives near Burlingame's Broadway
- Short drive to Broadway and Burlingame Avenue shops
- Ray Park and Mills Canyon trails nearby in Burlingame
Homes and Streets
Much of Hillsborough Oaks took shape in the 1920s and 1930s, and it remains one of the best places in town to see period storybook and revival homes. Historic estates mix with later houses and modern rebuilds. Lots are wooded and often sloped, streets curve with the terrain, and there are no sidewalks, which keeps the area's original country feel.
See current homes for sale in Hillsborough Oaks →
Parks and Open Space
Public Schools Nearby
School assignments follow district attendance boundaries, which can split a neighborhood and change over time. Always confirm the school for a specific address with the district, for example the Hillsborough City School District.
Getting Around
Burlingame Caltrain station is the nearest regular stop. Trousdale Drive leads to Interstate 280, and Broadway connects to El Camino Real and US 101.
Nearby Neighborhoods
Hillsborough Oaks FAQ
Where is Hillsborough Oaks in Hillsborough?
Hillsborough Oaks sits at the far north end of town, where Hillsborough meets Burlingame near Broadway. Streets such as Jackling, Armsby and Fagan Drives climb gently into wooded hills.
What are homes like in Hillsborough Oaks?
Much of Hillsborough Oaks took shape in the 1920s and 1930s, and it remains one of the best places in town to see period storybook and revival homes. Historic estates mix with later houses and modern rebuilds.
What public schools are near Hillsborough Oaks?
Public schools near Hillsborough Oaks include North Hillsborough School (grades K-5), William H. Crocker Middle School (grades 6-8) and Burlingame High School (grades 9-12). School assignments follow district attendance boundaries and can change, so confirm the school for a specific address with the Hillsborough City School District.
What parks are near Hillsborough Oaks?
Parks and open space near Hillsborough Oaks include Ray Park, Burlingame, Mills Canyon Wildlife Area, Burlingame and Washington Park, Burlingame.
How do I get around from Hillsborough Oaks?
Burlingame Caltrain station is the nearest regular stop. Trousdale Drive leads to Interstate 280, and Broadway connects to El Camino Real and US 101.
How can I find homes for sale in Hillsborough Oaks?
Browse current listings in Hillsborough Oaks on Joseph Suarez's site, or join his off-market list to hear about homes before they are listed publicly. Thinking of selling? Request a free home valuation for a local estimate based on recent nearby sales.
Thinking about Hillsborough Oaks?
Whether you are buying or selling, Joseph Suarez can walk you through recent sales, street by street pricing and what is coming up before it hits the market.
See homes for saleWhat is my home worth?Get off-market listingsContact Joseph← Back to the Hillsborough neighborhood guide or browse all Peninsula neighborhoods
Updated October 2026 by Joseph Suarez, Realtor with Coldwell Banker in Burlingame, DRE 02085594.
Sources: Wikipedia, Ed-Data. Information is believed accurate but not guaranteed.