Explore Woodside Highlands (Santa Maria / Russell)

About Woodside Highlands (Santa Maria / Russell), Portola Valley

Woodside Highlands (Santa Maria / Russell) is a hillside neighborhood within the Town of Portola Valley, despite the Woodside in its name. It is generally bounded by Santa Maria Avenue and Russell Avenue to the north and west, Portola Road to the east and Wayside Road to the south. The area was subdivided in the early 20th century, and many vacation cottages were built here in the 1920s and 1930s. Woodside Highlands real estate still reflects that cabin-in-the-woods heritage.

Moving to Woodside Highlands (Santa Maria / Russell)

Moving to Woodside Highlands (Santa Maria / Russell) means settling into a wooded enclave of narrow, winding roads and homes tucked among the trees. The neighborhood has an informal, community-minded feel, with a neighborhood association that organizes seasonal events and road clean-ups. It sits just off Portola Road, close to the Town Center, library and trails. Buyers looking for older-home character and natural surroundings within Portola Valley often start their search here.

Cost of Living & Housing in Woodside Highlands (Santa Maria / Russell)

Woodside Highlands (Santa Maria / Russell) homes for sale are generally among the more attainable options in Portola Valley, largely because lots are smaller than in most of the town. Housing includes original or updated cottages and cabins from the 1920s and 1930s, mid-century homes and a growing number of modern rebuilds. Many properties sit on sloped, wooded parcels with decks that take in canyon or hillside views. Buyers should look closely at access, parking, septic and wildfire defensible-space requirements on these older hillside lots.

Getting Around Woodside Highlands (Santa Maria / Russell)

Portola Road runs along the edge of Woodside Highlands (Santa Maria / Russell), linking the neighborhood north to Woodside and south to the Portola Valley town center. Alpine Road and Sand Hill Road connect to Interstate 280 for commutes to San Francisco, San Jose and the wider Silicon Valley. Stanford, Menlo Park and Palo Alto are a short drive away. Caltrain is accessible from the Menlo Park and Palo Alto stations, while local roads are narrow and best driven with care.

Local Amenities & Things to Do in Woodside Highlands (Santa Maria / Russell)

Woodside Highlands (Santa Maria / Russell) is just down Portola Road from the Portola Valley Town Center, with its library, playing fields and community spaces. Windy Hill Open Space Preserve, with a trailhead along Portola Road, offers popular hikes with sweeping views of the bay. Small shops and cafes are located near the Alpine and Portola Road intersection, and Woodside's village center is a short drive north. The town's trail system provides plenty of options for walking and riding.

Schools & Education in Woodside Highlands (Santa Maria / Russell)

Woodside Highlands (Santa Maria / Russell) is part of the Portola Valley School District. Homes are commonly served by Ormondale School for the early grades and Corte Madera School for the upper elementary and middle grades. High school students are typically assigned to Woodside High School in the Sequoia Union High School District. Assignments can vary by address and over time, so confirm school boundaries for any specific home with the districts.

Why Buyers Choose Woodside Highlands (Santa Maria / Russell)

Buyers choose Woodside Highlands (Santa Maria / Russell) for its wooded charm, cabin heritage and relative value within Portola Valley. The neighborhood offers a strong community feel and quick access to Windy Hill, the Town Center and Portola Road. Rebuild and remodel opportunities make it attractive to buyers who want to create a custom home in a natural setting. If you are ready to buy or sell a home in Woodside Highlands (Santa Maria / Russell), contact Jessica Heredia for local guidance from start to finish.