For more than 100 years, beginning in the 1830s, the area now called Woodside was gradually developed, first as sawmills that supplied redwood to build San Francisco, later as farms, small cattle ranches and vineyards. As early as 1852, a regular stagecoach service connected Woodside to San Francisco, and by the 1880s, prosperous San Franciscans began building country estates. Their ranks included coffee tycoon James Folger, lumber baron C.F.A. Talbot, heirs to the H.M. Newhall land and cattle fortune, and millionaire spice magnate August Schilling.
But it wasn't until the post-World War II building boom brought more than 500 new houses to the area that local residents decided to get together to protect the rural nature of their community. In 1956, the Town of Woodside was incorporated, bringing road maintenance, management, planning and zoning under local control.
2014-15 TOWN OPERATING BUDGET: $6 million
POPULATION (2010): 5,287
HOUSEHOLDS (2009-13): 2,142
SINGLE-FAMILY HOUSING (2009-13): 95 percent
MEDIAN 2014 HOME PRICE: $2,330,000
MEDIAN HOUSEHOLD INCOME (2009-13): $212,917