The Highlands: A Comprehensive Look at One of Los Altos' Most Coveted Neighborhoods
Just south of Permanente Creek and nestled between Foothill Expressway and Highway 280, the Highlands—also known as Woodland Acres—is a hidden gem in Los Altos. With approximately 1,000 homes, this tight-knit neighborhood is cherished for its privacy, community spirit, and proximity to nature. Despite its relative obscurity to passing drivers along Foothill Expressway, the Highlands is a vibrant enclave with deep historical roots and a culture of connection. This comprehensive guide explores the rich history, educational opportunities, lifestyle amenities, real estate trends, and how the Boyenga Team at Compass can help you navigate it all.
Historical Overview
From Farmland to Suburban Haven
Originally rural farmland, Woodland Acres and the Highlands began to develop in the early 20th century. One of the first homes was noted in a 1939 news release, likely owned by a wealthy San Franciscan, reflecting the area's desirability even then. Most of the neighborhood’s transformation occurred in the 1950s when apricot orchards and orange groves gave way to California ranch homes, some of which still stand today. In fact, a few original apricot trees continue to bear fruit in residents’ backyards.
Before Highway 280 and Foothill Expressway existed, Granger Avenue was a dirt road, and some remember a landowner using a narrow field for his private airplane landings. These charming tales form part of the neighborhood's unique and evolving story.
Strong Community Roots
From its inception, the Highlands has been defined by neighborly connections and community contributions. Volunteers helped plant trees that still line Foothill Expressway and Montclaire Elementary. The neighborhood continues to celebrate with block parties, Halloween singalongs, and the annual community picnic at Montclaire Park, often attended by the Los Altos Police Department, city council members, and residents from toddlers to seniors.
Education: A Pillar of the Neighborhood
Though within the Los Altos city limits, the Highlands falls under the Cupertino Union School District and Fremont Union High School District, making it a top choice for families.
Public Schools
Montclaire Elementary School – Centrally located and a cornerstone of community life. Many students walk or bike to school in the mornings, accompanied by parents and neighbors.
Cupertino Middle School – Renowned for its rigorous academics and inclusive extracurricular programs.
Homestead High School – Known for strong AP programs, outstanding arts and music departments, and its college preparatory environment.
Private Education Options
Nearby private institutions provide alternative academic options:
St. Simon Parish School
Pinewood School
St. Francis High School
The King’s Academy
Parks, Recreation, and Nature Access
Abundant Outdoor Amenities
With tall trees, curving roads, and cul-de-sacs, the Highlands offers natural privacy and abundant greenery. Outdoor lovers and families benefit from direct access to:
Montclaire Park – Offers tennis courts, a barbecue area, open lawns, and playgrounds. It's a focal point for events like the annual picnic.
Highlands Park – Central to the neighborhood with recreational amenities and open fields.
Rancho San Antonio County Park and Midpeninsula Open Space Preserve – Thousands of acres of protected land just minutes away, ideal for hiking, horseback riding, and mountain biking.
Woodland Library and Park – A serene retreat for reading, relaxation, and family gatherings.
Architecture and Home Design
The architectural identity of the Highlands is both diverse and distinctive:
Classic Ranch-Style Homes – Single-story structures on generous lots ranging from a quarter to a half-acre.
Two-Story Custom Homes – Many with panoramic views of the Peninsula and updated features.
Modern Renovations – Increasingly popular, incorporating sustainable features like solar panels, smart systems, and energy-efficient layouts.
Residents cherish the rural charm and spacious feel that larger lots afford, even as newer homes add contemporary flair.
Real Estate Market Trends
Market Characteristics
Median Home Price: Ranges from $3.5M to $5M, depending on size, condition, and views.
Inventory: Low turnover due to long-term residency.
Time on Market: Generally under 15 days for well-presented homes.
Buyer Profile: Tech professionals, executives, and families prioritizing privacy, top schools, and community.
Notable Trends
Privacy as a Premium: The pandemic accelerated demand for neighborhoods like the Highlands where space and solitude are more attainable.
Increased Investment: Renovations and rebuilds are adding luxury and tech-forward homes to the mix.
Sustainable Design: Smart home technology and green building are now common features.
Community Spirit and Events
Living Connected in the Highlands
Despite its quiet ambiance, the Highlands is anything but isolated. It’s a place where neighbors put out one another’s trash bins during vacations, host driveway movie nights, and share meals during impromptu barbecues.
Annual Picnic – A highlight event, held at Montclaire Park with attendance from local officials and public safety teams.
Seasonal Festivities – Elaborate Halloween decorations, holiday light displays, and regular game nights.
Youth Involvement – Parents volunteer with scouts, sports, arts, and school programs, building a true multi-generational sense of belonging.
Transportation and Accessibility
The Highlands offers a rural feel without sacrificing commuter convenience:
Highway Access: Immediate access to I-280 and Foothill Expressway.
Public Transit: Proximity to Caltrain stations in Sunnyvale and Mountain View.
Cycling and Walking: Trails and calm streets encourage active transportation.
A Neighborhood of Legacy and Lifestyle
More than a residential enclave, the Highlands and Woodland Acres represent a lifestyle grounded in heritage, connection, and appreciation for natural beauty. The neighborhood’s longevity and tight-knit culture are evident in every gathering, every tree planted by volunteers, and every original apricot tree still bearing fruit.
How the Boyenga Team and Compass Can Help
The Highlands is a unique micro-market within Los Altos, and it takes deep local knowledge to navigate it effectively. The Boyenga Team at Compass, led by Eric and Janelle Boyenga, brings decades of experience, strategic marketing insight, and a passion for helping clients find the perfect fit.
As Silicon Valley’s luxury home experts, they understand the Highlands’ charm, value, and market trends like few others. Whether buying, selling, or exploring your options, the Boyenga Team offers a personalized, data-driven approach to help you thrive.
Contact the Boyenga Team today for a no-obligation consultation and begin your journey in one of Los Altos’ most remarkable communities.