​ The Highlands A Historical Overview of Woodland Acres

Just south of Permanente Creek and nestled between Foothill Expressway and Highway 280, the Highlands—also known as Woodland Acres—is a distinctive neighborhood that offers an enviable balance of suburban charm and natural beauty. The area’s defining characteristics include tree-lined streets, architectural variety, proximity to parks and trails, and a tightly connected community. Though small in scale, with around 1,000 homes, the Highlands represent one of the most treasured and private corners of Los Altos.

A Historical Overview: From Farmland to Community Gem

Early History and Founding

The Highlands and adjacent Woodland Acres were originally private farmland dotted with orchards, groves, and open pasture. Prior to suburban development, the area was part of a broader agricultural economy that defined much of Santa Clara County in the early 20th century. Apricot orchards and orange trees dominated the terrain, and long before highways and expressways reshaped the landscape, dirt roads like Granger Avenue served as primary routes for residents and farmers alike.
In fact, Granger Avenue itself has become something of a local legend. Longtime residents recall a landowner who once used a field along the east side of the street as a makeshift airstrip to take off and land a private airplane. This anecdote reflects a time when Los Altos retained a distinctly rural character, complete with open fields and fruit groves.
During the 1930s, a few homes began to appear, often as summer retreats for affluent San Franciscans. One of the earliest properties in the Highlands is documented in a 1939 news release, pointing to the neighborhood’s gradual transformation from rustic farmland into a semi-residential outpost.

Post-War Development and Suburban Growth

The majority of homes in the Highlands were constructed in the post-World War II era, particularly during the 1950s. This period saw rapid expansion across the Peninsula, driven by the post-war housing boom and the rise of Silicon Valley. Many of the homes were built in the classic California ranch style—single-story layouts with low-pitched roofs, wide facades, and large lots.
Though urban development increased, the area maintained a sense of rural seclusion. Curved streets, natural vegetation, and an abundance of oak trees provided privacy and a natural barrier to noise and through-traffic. The addition of Foothill Expressway and Interstate 280 in the latter half of the century enhanced commuter access while preserving the sense of a tucked-away haven.

Community Development and Legacy

Over time, the Highlands distinguished itself with a unique community ethos. Residents began planting trees, organizing events, and advocating for infrastructure. One neighbor even spearheaded a petition to secure a secondary access road for safety and convenience. Others volunteered at nearby Montclaire Elementary School and participated in local planning boards, Scouts programs, and athletic leagues.
A defining moment in community history occurred after the 1989 Loma Prieta earthquake. Residents, hesitant to return indoors, gathered in the streets for an impromptu neighborhood barbecue—a gesture emblematic of the enduring camaraderie found here.

Education: A Key Driver of Neighborhood Appeal

Despite being located within Los Altos city limits, the Highlands is served by the Cupertino Union School District and Fremont Union High School District, two of the most highly regarded districts in the Bay Area.

Public Schools

• Montclaire Elementary School: Situated at the heart of the neighborhood, Montclaire is more than a school—it's a community anchor. Each morning, the sidewalks come alive with children walking or biking to school.
• Cupertino Middle School: Known for its academic excellence and strong programs in STEM and the arts.
• Homestead High School: A top-performing school with robust AP course offerings, music and arts departments, and strong college placement records.

Private School Options

Nearby private schools offer families additional academic flexibility:

• St. Simon Parish School
• Pinewood School
• St. Francis High School

Parks, Recreation, and Natural Surroundings

The Highlands offers unparalleled access to nature and recreational amenities. Residents enjoy green open space and scenic views without sacrificing accessibility to city centers.

Local Parks

• Montclaire Park: A neighborhood favorite with tennis courts, a barbecue area, picnic spaces, and three playgrounds.
• Highlands Park: Provides an open gathering space for families and children.
• Woodland Library and Park: A peaceful location perfect for quiet afternoons or small community meetups.

Regional Open Space Access

The neighborhood is bordered by some of the most expansive open spaces in the Peninsula:

• Rancho San Antonio County Park
• Midpeninsula Regional Open Space Preserve

Together, these areas offer thousands of acres of trails and open land for hiking, mountain biking, and horseback riding.

Architectural Character and Real Estate Landscape

The Highlands showcases a blend of timeless architectural styles, ranging from mid-century homes to modern rebuilds. Key characteristics include:

• Ranch-Style Homes: Most prevalent, built between the 1950s and 1970s.
• Custom Estates: Newer homes featuring contemporary designs and luxury finishes.
• Mid-Century Elements: Large windows, open floor plans, and indoor-outdoor integration.

Lots typically range from a quarter-acre to half-acre, offering generous outdoor space and privacy. Rolling hills and elevated properties offer stunning views of the Peninsula.

Real Estate Market Insights

The Highlands remains one of the most sought-after neighborhoods in Los Altos.

Current Trends

• Home Prices: Typically range from $4M to $5.5M+
• Days on Market: Properties often sell in under two weeks.
• Buyer Profile: Primarily families, tech executives, and buyers seeking a quiet yet connected lifestyle.

Renovation and modernization are common, with many homeowners investing in sustainable technologies and design-forward remodels.

Community Culture and Lifestyle

The spirit of the Highlands is rooted in neighborly connection, volunteerism, and year-round celebrations. Highlights include:

• Annual Neighborhood Picnic: Held at Montclaire Park, with participation from city officials and public safety teams.
• Seasonal Events: Halloween singalongs, holiday light displays, and summer movie nights on driveways.
• Civic Engagement: Involvement in local schools, youth programs, and city initiatives.

Residents frequently organize block parties, lend a hand to neighbors, and foster a safe, walkable environment that encourages community interaction.

Transportation and Accessibility

Though nestled in a tranquil setting, the Highlands offers excellent transportation options:

• Highway Access: Immediate access to I-280 and Foothill Expressway.
• Caltrain Proximity: Nearby stations in Sunnyvale and Mountain View.
• Cycling and Walking: Sidewalks and nearby trails support active commuting.

A Timeless Neighborhood for Modern Living

The Highlands and Woodland Acres offer more than just a place to live—they offer a lifestyle of connection, serenity, and enduring charm. From historic farmland to a community rich with legacy and involvement, the neighborhood continues to thrive through shared experiences and mutual support. It stands as a reminder that, even in Silicon Valley, true community still exists.

For more information at www.BoyengaRealEstateTeam.com