Grandpa George Webb started in 1922 subleasing 40 acres from Stanford University to be closer to San Francisco produce markets. Prior to 1922, the Webb's started in Watsonville (1917) with strawberries. In 1929, Grandpa George moved the family to Portola Valley and leased the full 285 acres at that time. Originally, ranch-grown produce was delivered to Purity Markets and a berry co-op.

In 1950, Stanley Webb, the youngest of 4 brothers, took over the farm. He continued the tradition growing strawberries until 1963, when he opened the Alpine Road Fruit Stand to offer fresh-picked seasonal produce for direct sale to consumers. That move started the diversity of growing multiple crops like corn, tomatoes, string beans, squash, etc.

In the 1980s, the  major change was when switching 90 acres of farming from flood irrigating to a drip irrigation (saving 75% water) this was a three year process. 

In the 1990s, Webb Ranch formed a union (with health and dental) to provide the best working conditions for the farm workers. Some farm workers have been with the Webb's for over 25 years.

In the 2000s, U-Pick berry operations began and has become a popular family event, with pony rides, picnic tables, ranch tours, and fresh berries in June and July, weather permitting. This is run by the fourth generation of Webb's.

In 2013, Webb Ranch focused 100% of its farming resources on growing and marketing its California Certified Organic Farmer (CCOF) produce through various outlets. The Farmers Market at Hwy 280 @ Alpine Road stopped offering produce on a daily basis. Webb Ranch went “Back to the Future,” to once again provide produce to local farmers markets, grocery stores, and select restaurants.