The Highlands / Woodland Acres

Just south of Permanente Creek, and nestled between Foothill Expressway and Highway 280, is a small neighborhood known dually as the Highlands and Woodland Acres. Comprised of 1,000 homes, it is a relatively small community that appeals to those who place priority on privacy, a valuable commodity made even more so after the pandemic.

The tall trees lining the undulating streets speak to the rural charm and verdant beauty the Highlands has to offer. Privacy is abundant, with many of the streets gently curving, often leading into traffic-deterring cul-de-sacs. It is easy to see why the Highlands is considered the rural gem of Los Altos, with many of its two-story homes boasting magnificent views of the San Francisco Peninsula. Though it can feel somewhat remote, the sense of community is strong amongst its residents. Fun neighborhood gatherings are common and outdoor options for meetups abound in nearby Rancho San Antonio County Park, which combined with the Mid-Peninsula Regional Open Space Preserve, offer thousands of acres of trails that can be explored on foot, horseback, or mountain bike.

Adjacent to the Highlands, Woodland Acres was originally private farmland, but is now a beautiful community surrounded by towering oak trees and majestic redwoods. Typically, single-story, Ranch-style homes sit on a quarter to one-half acre lots, but recent years have shown many homeowners improving their homes with modern renovations. Like the Highlands, those who live here have the sense of being peacefully tucked away. Montclaire Park provides locals with outdoor fun and great amenities, including lighted tennis courts and a barbecue area, which plays host to an annual community picnic.

The Highlands and Woodland Acres sit close to Foothill Expressway and Highway 280, making for convenient commutes while offering homebuyers notably more affordable purchase prices relative to other parts of Los Altos. Although located within Los Altos city limits, the schools are part of the highly rated Cupertino School District (Montclaire Elementary, Cupertino Middle, and Homestead High).