Woodside | San Mateo County, CA | Where Silicon Valley Meets the Redwoods
Browse the latest MLS listings in Woodside, NY — updated daily.
Browse All ListingsPopulation: 5,600+
The Woodside Elementary School District serves K–8 students at a single, highly rated campus. High school students attend Woodside High School in the Sequoia Union HSD, known for its strong academics and scenic campus.
| School | Level | Rating |
|---|---|---|
| Woodside High School | High | A |
| Woodside Elementary School | K–8 | A+ |
| Woodside Priory School | Private 6–12 | A |
Heart of the community near Woodside Road, Buck's restaurant, Roberts Market, and the town center. A mix of ranch homes and larger properties.
Secluded mountain homes along Skyline Boulevard with towering redwoods, sweeping views, and a truly rural feel at higher elevations.
Scenic corridor with equestrian properties, rolling hills, and easy access to Portola Valley and I-280.
Prestigious address with large estates set among redwoods and oaks, offering privacy and proximity to Wunderlich Park trails.
Nearest Caltrain in Redwood City (~40 min to SF). I-280 is the primary freeway connection. Most residents drive. Winding roads and rural character define the commute experience. SFO approximately 25 minutes.
Buck's of Woodside is the legendary Silicon Valley breakfast spot where countless tech deals have been made. Roberts Market is the beloved local grocer. The Village Hub offers a cafe and gathering space. For more options, downtown Redwood City and Palo Alto are nearby.
Wunderlich County Park (25 miles of trails through redwoods), Huddart County Park, Purisima Creek Redwoods Open Space Preserve. Extensive equestrian trails throughout town. Woodside Trail Club events.
Stanford Health Care is approximately 15 minutes away. Sequoia Hospital in Redwood City is within 10 minutes. Rural setting means somewhat longer response times for emergency services.
Woodside May Day Parade and Country Fair (tradition since 1920s), Mounted Patrol horse shows, Trail Club events, and community gatherings at the Woodside Village Church.
Woodside is a rural-residential community just minutes from Silicon Valley's tech campuses. With winding roads through redwoods, equestrian trails, and properties measured in acres rather than square feet, it offers a lifestyle that feels worlds apart from the urban Peninsula. Many properties have horse facilities, and the town's Western heritage remains strong.
Woodside is true horse country. Many properties include barns, paddocks, and riding arenas. The town has miles of dedicated equestrian trails, the Woodside Mounted Patrol (active since 1940), and regular horse shows. Horseback riders share roads with cars, and equestrian easements are common in property deeds.
Buck's Restaurant is a quirky, iconic diner on Woodside Road famous as a Silicon Valley power breakfast spot. Countless venture capital deals and tech company founding stories have roots at Buck's. The eclectic decor and community atmosphere make it a Woodside landmark.
Very rural by Bay Area standards. There are no streetlights, minimal sidewalks, and many roads are narrow and winding. Mountain lions, deer, and coyotes are regular wildlife sightings. Despite this, downtown Redwood City is 10 minutes away and Stanford/Palo Alto 15 minutes — it is rural living with urban access.
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