Woodside Homes for Sale
30 Homes for sale in Woodside
$3,950,000
855 Patrol Road
Woodside, CA 94062
$38,800,000
15 Hidden Valley Lane
Woodside, CA 94062
$3,195,000
1100 Old La Honda Road
Woodside, CA 94062
$4,499,000
941 High Road
Woodside, CA 94062
$2,195,000
20255 Skyline Boulevard
Woodside, CA 94062
$3,998,000
425 Summit Springs Road
Woodside, CA 94062
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Woodside Neighborhood Guide
Woodside is Silicon Valley's most rarefied residential address — a semi-rural town of roughly 5,500 on the edge of the Santa Cruz Mountains in San Mateo County, where tech founders, venture capitalists, and established wealth have built estates on forested hillsides for decades. The town has deliberately remained rural by design: no sidewalks on most roads, a single crossroads village, horse trails woven through residential streets, and some of the most extraordinary compound properties in the country. It borders Portola Valley, Atherton, and Redwood City while feeling entirely removed from Silicon Valley's intensity.
Why Buyers Love Woodside
- Land, Privacy, and Scale — Woodside's residential parcels frequently start at one acre and extend to dozens of acres, with custom estates featuring guesthouses, barns, pools, and private trails. This is where Silicon Valley's most successful go when standard luxury isn't enough.
- Equestrian Infrastructure — Woodside is one of the few Bay Area communities with a genuine equestrian culture — horse trails cross throughout the town, and many properties include stables, paddocks, and direct trail access to Windy Hill and other open space preserves.
- Woodside Elementary School District — The small, highly regarded school district serves the town through 8th grade, with a reputation for strong academics in an unusually community-oriented, low-student-count environment.
- Open Space Access — Windy Hill Open Space Preserve, Purisima Creek Redwoods, and Huddart County Park all abut or sit within minutes of residential Woodside, giving residents some of the most direct access to open space of any Peninsula community.
Neighborhoods at a Glance
Woodside Village
The historic crossroads at Woodside Road and Kings Mountain Road, with Woodside Store (California Historical Landmark), a few shops, and the social center of the community. The most walkable — if that word can apply — part of town.
Central Woodside (Canada Road Corridor)
The primary residential spine, with large estates and horse properties along Canada Road and its intersecting lanes. Mix of established ranches, modern rebuilds, and long-held family compounds.
Kings Mountain Road
The route climbing toward the ridgeline, with estate properties on heavily forested lots, extreme privacy, and views over the fog layer. For buyers who want the furthest remove from suburban Silicon Valley.
Emerald Hills (adjacent)
While technically in an unincorporated part of San Mateo County adjacent to Redwood City, this hillside neighborhood is closely associated with Woodside and offers somewhat more accessible pricing while sharing its character.
Skywood / Skylonda Area
The higher-elevation properties along Skyline Boulevard above the main Woodside residential zone, with extraordinary views, larger acreage, and a true mountain setting.
Local Amenities
Parks
Huddart County Park (redwood forest, hiking, picnic areas), Windy Hill Open Space Preserve (panoramic ridge trails), Purisima Creek Redwoods Open Space, Wunderlich County Park
Shopping
Woodside Village has a handful of specialty shops; primary shopping is in Redwood City (downtown) or along El Camino Real. Robert's Market in Woodside is a local institution.
Dining
Village Pub (Michelin-starred, Woodside's signature restaurant), Buck's of Woodside (legendary Silicon Valley deal-making spot known for tech history as much as food), Alice's Restaurant on Skyline (a decades-old biker and hiker landmark), local wine tastings along the ridgeline
Recreation
Extensive equestrian trail network throughout the town, Windy Hill hiking and mountain biking, Purisima Creek and Huddart redwood forest trails, cycling on Canada Road (closed to cars on Bicycle Sundays)
Commute Times
| Destination | Drive | Transit |
|---|---|---|
| San Francisco (Downtown) | 40–60 min | 75 min (drive to Redwood City + Caltrain) |
| Oakland (Downtown) | 50–65 min | N/A (drive-dependent) |
| Silicon Valley (Palo Alto) | 15–25 min | 35 min (drive to Menlo Park + Caltrain) |
| Redwood City (Downtown) | 10–20 min | 30 min (drive to Caltrain) |
Woodside has no transit service; the rural layout and distributed nature of the town make it fully car-dependent for residents. Most buyers here are not transit commuters — proximity to Sand Hill Road venture firms and to Highway 280 for South Bay or SF drives is the operative commute logic.
Commute times are estimates and may vary based on traffic, time of day, and route. Data is for informational purposes only.