At a glance
- Where it is: the hills between Redwood City and the Santa Cruz Mountains.
- Known for: large parcels, equestrian properties, and one of the densest trail networks on the Peninsula.
- The environment: wooded, hilly, and low-density, with a small town center.
- What sets it apart: horses are a genuine part of daily life here, with dedicated trails and crossings throughout the town.
Housing character
- Large single-family homes on acreage.
- Equestrian properties with barns, paddocks, and riding arenas.
- Wooded and hillside parcels, some with significant grade.
- Well and septic systems on a number of properties rather than municipal utilities.
Places within Woodside
- Woodside Heights
- Neighborhood near the town center with somewhat smaller parcels.
- Mountain Home Road
- Established corridor with large wooded estates.
- Skyline / Kings Mountain
- Higher-elevation area along Skyline Boulevard with forested parcels.
- Emerald Hills edge
- Eastern area adjoining Redwood City with more compact lots.
Around town
- Woodside Town Center with a general store, bakery, and a handful of businesses.
- Wunderlich and Huddart county parks, both with extensive trails.
- Skyline Boulevard and the ridge open-space preserves.
- The Filoli historic estate and gardens nearby.
- A long-running equestrian community with events at the Horse Park.
Getting around
- Interstate 280 is the main access route.
- State Route 84 (Woodside Road) connects east to Redwood City and west over the hills to the coast.
- No rail service in town — Redwood City Caltrain is the closest station.
- The town is entirely car-dependent.
What to check
- Wildfire risk in hillside and wooded areas significantly affects insurance availability and cost — investigate this before anything else.
- Well and septic systems on some properties require separate inspections and ongoing maintenance.
- Winding roads and longer drives to shopping, schools, and services.
- Power outages during storms and public safety power shutoffs are a recurring reality.
- Tree, grading, and creek ordinances materially affect what you can build.
- Verify current transportation service, school assignment, permit requirements, hazard information, and total housing costs for the specific address.