Central Woodside & Town Center, Woodside Homes for sale, recent sales and a Property Nerd’s guide

Woodside's center grew where the lumber roads crossed. The Town's General Plan history says this land was part of Rancho Cañada de Raymundo, and that by the 1850s the redwood trade had produced small clusters of businesses at important intersections. Whiskey Hill sat on the haul road between the mills and Redwood City, and teamsters spent the night in its hotels, which is where the name comes from. The survivor is the Pioneer Hotel, built in the 1880s and now the Pioneer Saloon, a bank and offices. Andre Neuman opened a nursery and grocery on Woodside Road in 1854, and Independence Hall went up in 1884 next to the school.

When the accessible redwoods were gone, grapes took over some of the land. In 1884 Emmett H. Rixford planted the 37-acre La Questa Vineyards near the corner of Cañada and Woodside roads. The General Plan says about one acre of those vines still produces and that the stone winery has been remodeled as a residence; La Questa Way and the 1947 La Questa Acres subdivision carry the name. The 1920s added a blacksmith shop, the Neuman Brothers general store and, in 1928, a telephone exchange that brought the first direct-dial service to Woodside.

After the 1950s added 555 houses to the area, voters approved incorporation 646 to 574 on October 20, 1956, and the first Town Council met at the elementary school. The Town Center Area Plan followed in 1970. Voters have kept a short leash on the center since: Measure J (1988) fixed the line between commercial and residential land and capped buildings facing Woodside Road at 17 feet above the road's crown, and Measure A (2021), which passed by five votes, allowed limited parking and gathering space plus a gazebo or amphitheater by Town Hall. An update of the Town Center Area Plan, which will also study whether housing fits in the center, began in spring 2025 and was scheduled to wrap up by late 2026.