Between the rolling hillsides and abundant greenery, Woodside Highlands lies in a serene hush, away from the hectic influences of urbanity.

Originally developed as summer cottages for affluent San Franciscans to enjoy the ideal weather and breathtaking landscape, Woodside Highlands is today a viable entry point into the Portola Valley area. Though there have been a growing number of rebuilds in the area, many homes in this neighborhood are priced well.

Narrow roads elegantly wind around this charming neighborhood, occasionally granting more of an area tour than first-comers would have originally planned. However, the close proximity to Alpine Road gives this area a convenience not found in other similarly priced homes in the hills. Though the plots of lands in Woodside Highlands are more modest in comparison with the other Portola Valley neighborhoods, they don’t come without their share of stunning vistas and nature trails.

Similar to other parts of Portola Valley, residents of Woodside Highlands have a strong sense of community. Annually, the Woodside Highlands Improvement Association organizes activities to keep residents engaged and connected, such as picnics, Easter egg hunts, road clean-ups, and visits from Santa Claus around Christmas.

Conveniently located nearby are shopping centers such as Nathhorst Triangle, Village Square, and Ladera Country Shopper. With all the available activities and amenities, Woodside Highlands is a highly desirable place to settle down and raise a family.

  • Boundaries

    • Russell Ave and Santa Maria Ave on the north
    • Portola Road on the east
    • Wayside Road on the south
    • Santa Maria Ave on the west
  • Libraries

    • Portola Valley Library- 765 Portola Road Portola Valley, CA 94028
  • Parks

    • Triangle Park- located at the intersection of Portola and Alpine Roads Portola Valley, CA 94028
    • Little People’s Park- 765 Portola Road Portola Valley, CA 94028
    • Windy Hill Open Space Preserve- Portola Valley, CA 94028
  • Public Schools

    • Ormondale School (K-3)- 200 Shawnee Pass Portola Valley, CA 94028
    • Corte Madera School (4-8)- 4575 Alpine Road Portola Valley, CA 94028 (#18 Middle School in CAlifornia)
    • Woodside High School- 199 Churchill Avenue Woodside, CA 94062