The Highlands: A Hidden Landscape in the Hills of Los Altos

A Landscape Woven in Time

Tucked between Foothill Expressway and the winding path of Interstate 280, The Highlands of Los Altos is more than a residential neighborhood—it’s a living chronicle of Northern California’s shifting identity. Surrounded by the ancient oaks and native grasses that once dominated the Santa Clara Valley, the Highlands is a small, tree-lined haven that whispers of its agricultural past even as modern life hums along its perimeter.

A Legacy Beneath the Trees

The Agrarian Chapter

Before the Silicon Valley tech boom, before even the suburban dreams of the 1950s, the Highlands was farmland—specifically, a patchwork of apricot orchards, vineyards, and citrus groves. The area’s gentle elevation and mineral-rich loam made it ideal for fruit cultivation, and the Highlands formed part of a thriving agricultural corridor that fed San Francisco and beyond.

The land was private and pastoral. Families who owned these plots were stewards of the land, often cultivating it by hand. Stories passed down through generations tell of morning dew rising from the orchards, children climbing trees to pick ripe fruit, and long dirt roads like Granger Avenue serving as the sole arteries into town.

Early Residents and a Quiet Frontier

By the 1930s, whispers of change began. One of the area’s earliest homes, referenced in a 1939 news release, signaled a new kind of inhabitant—wealthy San Franciscans building summer retreats among the groves. These estates were modest by today’s standards but symbolized a transition: the land’s identity was slowly evolving.

During this era, one landowner famously cleared a narrow stretch along Granger Avenue to serve as a private airstrip, using a small field to take off and land his aircraft. It was a time of eccentricity and ingenuity—a frontier still open to imagination.

Midcentury Momentum: Postwar Growth and Community Identity

Suburban Emergence

The post-WWII boom changed everything. As returning veterans looked to settle and Silicon Valley’s nascent industries emerged, the quiet fields of Los Altos were transformed. The 1950s ushered in a wave of development in the Highlands, much of it in the form of ranch-style homes—wide, low-profile, and designed to harmonize with the natural contours of the land.

Yet unlike many suburbs, The Highlands retained its sense of spaciousness and isolation. Roads curved to follow the landscape. Homes were positioned to preserve privacy. Tall pines and coast live oaks offered dappled light and insulation from the hum of the outside world.

The Evolution of Civic Life

Montclaire Elementary School opened its doors in the heart of the neighborhood and quickly became a social nucleus. Children walked or biked to school, trailed by parents and grandparents. The park next door hosted impromptu baseball games and neighborhood potlucks. Residents planted trees along the newly paved Foothill Expressway. One neighbor petitioned the city for a second road into the neighborhood. These were acts of self-definition: the neighborhood wasn’t just growing—it was shaping itself.

Even the 1989 Loma Prieta earthquake, which rattled homes and nerves, became a memory of unity. That evening, residents gathered in the street for an impromptu barbecue, cooking whatever food might spoil and finding solace in each other’s company.

A Living Landscape: Nature, Architecture, and Outdoor Life

The Ecology of a Neighborhood

Today, The Highlands remains distinct in its embrace of the natural world. Many of the original apricot trees still grow in residents’ backyards, gnarled yet fruitful. The streets are lined with tall trees, many planted by residents themselves. Deer roam the quiet cul-de-sacs. Hawks and owls patrol the skies.

Adjacent to thousands of acres of protected wilderness, including Rancho San Antonio County Park and the Midpeninsula Regional Open Space Preserve, the neighborhood offers rare access to trails for hiking, biking, and horseback riding. The land’s ecological past is not erased—it’s present, thriving, and shared.

The Built Environment

Architecturally, The Highlands resists uniformity. While ranch-style homes are the most common, newer builds reflect contemporary styles and sustainable design. Homes sit on generous lots—typically a quarter to a half acre—allowing for native landscaping, garden beds, and shaded patios that blur the line between indoors and out.

Unlike master-planned communities, The Highlands grew organically. This means homes differ in shape, style, and orientation. No two streets look alike. This architectural individuality has helped preserve the character and charm that drew the first settlers here.

Education and Local Amenities

Top-Rated Schools

The Highlands is served by the highly regarded Cupertino Union School District and Fremont Union High School District, making it a top choice for families.

Montclaire Elementary School: At the heart of the neighborhood, with strong academics and community engagement.

Cupertino Middle School: Known for its excellent STEM and arts programming.

Homestead High School: A standout for its AP offerings, college prep, and robust extracurriculars.

Nearby private school options include St. Simon Parish School, Pinewood School, St. Francis High School, and The King’s Academy.

Parks and Outdoor Recreation

Montclaire Park: Tennis courts, picnic areas, playgrounds, and a hub for community events.

Highlands Park and Woodland Library Park: Offer shaded green space and gathering areas for residents.

Rancho San Antonio Preserve: Expansive hiking and biking trails with panoramic views.

Real Estate Market Snapshot

The Highlands is one of Los Altos’ most coveted neighborhoods, blending historic charm with architectural diversity and modern upgrades.

Median home prices typically range from $3.5M to $5M+.

Lot sizes are larger than average, providing added privacy and natural surroundings.

Inventory is low due to long-term homeowners and high demand.

Buyers are drawn to the neighborhood for its unique blend of nature, community, and location—within commuting distance to major tech hubs, yet worlds away in atmosphere.

Community and Continuity

Generations of Connection

The spirit of The Highlands is not one of nostalgia, but of continuity. Block parties, holiday singalongs, and neighborhood barbecues are not formal events—they are rituals passed down like heirlooms. Families who moved in decades ago remain. New arrivals are greeted not just with a wave but with invitations.

Children play soccer at Montclaire Park, while retirees tend to succulents or swap stories on shaded porches. Even those without children participate in school and community events, reinforcing the belief that everyone has a role in the life of the neighborhood.

A Neighborhood That Remembers

It is not uncommon to meet residents who can recall the earliest days—the apricot groves, the dirt roads, the Loma Prieta quake, or the homemade landing strip. These stories are told again and again, becoming part of a living oral history. The Highlands is a place that remembers itself, even as it grows and changes.

Where Place Meets Purpose

The Highlands of Los Altos is more than a neighborhood—it is a terrain of memory, ecology, and belonging. From its agricultural origins to its modern rhythm of community life, the area represents a delicate balance between past and present, solitude and connection. It is a reminder that in the midst of innovation and expansion, there remains a place where the land and its people still speak to each other in quiet, meaningful ways.

Whether you’re searching for a family-oriented community, access to top schools, architectural charm, or proximity to nature, The Highlands offers all of this and more.

If you’re considering making The Highlands your home, the Boyenga Team at Compass offers local expertise, deep knowledge of the market, and a commitment to helping buyers and sellers find their perfect fit. As Silicon Valley’s luxury home experts, Eric and Janelle Boyenga provide strategic guidance, innovative marketing, and personalized service to ensure your success in this remarkable community.