Hillsborough Highlands Homes and Neighborhood Guide
Hillsborough neighborhood guide
Hillsborough Highlands centers on Tartan Trail Road, between Crystal Springs Road and Black Mountain Road in south Hillsborough. Street names here carry a Scottish theme, and most homes were built between 1965 and 1979, which gives the neighborhood one of the more consistent eras of construction in town. Roads loop across the hillside, with homes set on large, sloping lots.
Crystal Springs Road links the area to San Mateo to the east and to the Crystal Springs watershed to the west. The Sawyer Camp segment of the Crystal Springs Regional Trail starts near Crystal Springs Dam. Vista Park is close by in Hillsborough, and Laurelwood Park and the Sugarloaf Mountain trails in San Mateo are a short drive south across Highway 92.
Hillsborough Highlands is shaded. Borders are approximate, see the Hillsborough map for the full picture.
At a glance
- Tartan Trail Road and Scottish themed street names
- Most homes built from 1965 to 1979
- Between Crystal Springs Road and Black Mountain Road
- Near the Sawyer Camp Trail trailhead at Crystal Springs Dam
Homes and Streets
Most homes in Hillsborough Highlands date from 1965 to 1979, so designs from that period are common, many since updated or rebuilt. Lots are large, often on slopes with views, and the curving streets follow the terrain. The look is more uniform than in the older parts of town, where estates from different decades sit side by side.
See current homes for sale in Hillsborough Highlands →
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
Crystal Springs Road leads east toward El Camino Real and west toward Interstate 280 and Highway 92. Hillsdale and San Mateo Caltrain stations are the nearest.
Nearby Neighborhoods
Hillsborough Highlands FAQ
Where is Hillsborough Highlands in Hillsborough?
Hillsborough Highlands centers on Tartan Trail Road, between Crystal Springs Road and Black Mountain Road in south Hillsborough. Street names here carry a Scottish theme, and most homes were built between 1965 and 1979, which gives the neighborhood one of the more consistent eras of construction in town.
What are homes like in Hillsborough Highlands?
Most homes in Hillsborough Highlands date from 1965 to 1979, so designs from that period are common, many since updated or rebuilt. Lots are large, often on slopes with views, and the curving streets follow the terrain.
What public schools are near Hillsborough Highlands?
Public schools near Hillsborough Highlands include West Hillsborough School (grades K-5), South Hillsborough School (grades K-5), William H. Crocker Middle School (grades 6-8) and San Mateo 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 Highlands?
Parks and open space near Hillsborough Highlands include Crystal Springs Regional Trail, Sawyer Camp segment, Vista Park and Laurelwood Park and Sugarloaf Mountain, San Mateo.
How do I get around from Hillsborough Highlands?
Crystal Springs Road leads east toward El Camino Real and west toward Interstate 280 and Highway 92. Hillsdale and San Mateo Caltrain stations are the nearest.
How can I find homes for sale in Hillsborough Highlands?
Browse current listings in Hillsborough Highlands 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 Highlands?
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.