Woodside Highlands is a secluded hillside neighborhood in Portola Valley, offering expansive views, wooded landscapes, and a true escape from the fast pace of Silicon Valley. Tucked into the eastern slopes of the Santa Cruz Mountains, this peaceful enclave is ideal for those seeking privacy, natural surroundings, and a unique architectural mix, all just a short drive from Stanford, Menlo Park, and downtown Palo Alto.
With its rustic charm and forested setting, Woodside Highlands delivers a rare sense of tranquility without disconnecting you from the heart of the Peninsula.
Homes in Woodside Highlands are as diverse as the terrain, ranging from mid-century cabins and custom-built estates to newer constructions designed to blend with the natural landscape. Many properties are perched on hillside lots with stunning views of the Bay or forest canopy, often featuring expansive decks, large windows, and wraparound porches for seamless indoor-outdoor living.
Streets like Hillbrook Drive, Westridge Drive, and Ridgewood Drive wind through the hills and offer some of the most private and scenic home sites in all of Portola Valley.
Woodside Highlands borders Thornewood Preserve, Windy Hill Open Space Preserve, and other Midpeninsula Regional Open Space areas, offering direct access to hiking, biking, and horseback riding trails. Despite its secluded feel, the neighborhood is just minutes from Portola Road, Highway 84, and Interstate 280, providing a scenic yet efficient route to Menlo Park, Stanford University, and tech campuses across the Peninsula.
This rare combination of remoteness and reach makes Woodside Highlands especially appealing to outdoor enthusiasts and nature-minded professionals.
Homes in Woodside Highlands tend to be custom and rarely come on the market, making inventory limited and highly competitive. Properties here often include significant acreage, mature landscaping, and architectural individuality, appealing to buyers looking for one-of-a-kind living experiences in the heart of the Silicon Valley real estate market.
Whether you're looking for a hillside hideaway or planning to sell a view property, working with a Portola Valley real estate agent who understands the area’s terrain and value trends is essential. The Dana Carmel Group offers unmatched local insight and a strategic, client-first approach.
Woodside Highlands is served by the Portola Valley School District, including Ormondale School and Corte Madera School, and is also part of the Sequoia Union High School District, with access to Woodside High School. Though homes are spread out, the community has a tight-knit feel with shared stewardship of the natural surroundings.
With peaceful roads, panoramic vistas, and a deep connection to open space, Woodside Highlands offers an extraordinary lifestyle tucked into the hills of Portola Valley.
From inspections to financing, contingencies can protect your interests, but they also impact your strategy in this competitive market.
Dana Carmel
From schools and neighborhoods to investment potential, here's what luxury buyers prioritize in two of Silicon Valley’s most desirable communities.
Dana CarmelDana's extensive hands-on experience in business, marketing, and construction, led her into the world of real estate. Dana uses her strong project management and organizational skills to bring excellent service and a competitive edge to her clients.
