Woodside Highlands Portola Valley Homes and Neighborhood Guide
Also known as Santa Maria / Russell Area
Portola Valley neighborhood guide
Woodside Highlands sits in the northwest corner of Portola Valley, around Santa Maria Avenue and Russell Avenue near Portola Road and the Woodside border. Despite the name, it is one of the town's own subdivisions, and homes carry Portola Valley addresses.
Like Brookside Park and Los Trancos Woods, Woodside Highlands was laid out in the 1920s and 1930s, when many lots held weekend and vacation cottages in the woods.
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Woodside Highlands is shaded. Borders follow MLSListings area lines. Zoom in for street detail, or see the Portola Valley map for the full picture.
At a glance
- Northwest Portola Valley near Portola Road
- Around Santa Maria and Russell avenues
- Subdivided in the 1920s and 1930s as vacation cottages
- Smaller wooded lots than most of town
- Short drive to Woodside's town center
- MLSListings area 265
Woodside Highlands market report
A monthly email with new listings, recent sales and prices in Woodside Highlands.
Get the monthly reportHomes and Streets
Lots are smaller and more wooded than in much of Portola Valley, and the homes range from expanded early cottages to newer custom houses. Streets are narrow and winding, with many homes set into the slope.
Many homeowners here are close to both Portola Valley and Woodside amenities.
See current homes for sale in Portola Valley →
Videos: Woodside Highlands
Tours and local stories I have filmed around Woodside Highlands and Portola Valley.
Available for the first time in 25 years
A Portola Valley home tourWatch on Instagram
A single level home in Portola Valley Ranch
Tour of a Ranch homeWatch on Instagram
An architectural retreat on 1.5 acres
Near the Alpine InnWatch on Instagram
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.
Nearby Neighborhoods
Woodside Highlands FAQ
Is Woodside Highlands in Woodside or Portola Valley?
It is one of Portola Valley's subdivisions, and homes use Portola Valley 94028 addresses. It sits near the Woodside border, so confirm the jurisdiction for any specific parcel.
When was it built?
Woodside Highlands was subdivided in the 1920s and 1930s, when many lots held vacation cottages.
What is MLSListings area 265?
It is the Santa Maria and Russell area, the MLS area that covers Woodside Highlands.
How can I find homes for sale in Woodside Highlands?
Browse current listings in Portola Valley 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 Woodside 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 Portola Valley neighborhood guide or browse all Peninsula neighborhoods
Updated November 2026 by Joseph Suarez, Realtor with Coldwell Banker in Burlingame, DRE 02085594.
Sources: Town of Portola Valley, General Plan historic element (2014), Wikipedia, Portola Valley, California, Town of Portola Valley, local schools. Information is believed accurate but not guaranteed.