Wealthy equestrian community with spectacular homes
Woodside is a wealthy equestrian community covered with towering oaks, redwoods, and Douglas fir trees in the hills above Silicon Valley. Horses are a huge part of the life and culture of this beautiful wooded town. Woodside’s spectacular real estate includes some of the grandest properties in the United States. Some of the many notable homes here include Oracle CEO Larry Ellison’s $200 million recreation of a Japanese feudal castle and rock legend Neil Young’s sprawling ranch and recording studio. Many Woodside homes are geared toward the equestrian lifestyle with barns and horse stables.
Woodside’s peaceful country lifestyle draws in many prominent families and individuals. Residents include powerful tech founders and CEOs along with famous actors, sports stars, and musicians. Steve Jobs was in the process of remodeling his Woodside home at the time of his death. Other recognizable names in the neighborhood include actress Michelle Pfeiffer and movie producer husband David E. Kelley, billionaire investor Charles E. Schwab, and CEOs and founders of companies including Apple, GoPro, Siebel Systems, Softbank, Sony, and Symantec.
Woodside’s quaint town center includes businesses such as Roberts Market, a long-serving neighborhood grocery store with gourmet produce and foodstuffs, meat and seafood counters, mouthwatering deli sandwiches, and a horse tie-up outside. The Village Bakery offers delicious freshly baked goods along with Californian farm-to-table cuisine paired with an award-winning wine list. The kitsch décor and American comfort classics at Buck’s of Woodside have made it a favorite gathering place of many Silicon Valley pioneers. Companies such as PayPal, Tesla, Hotmail, and Netscape held early meetings at Buck’s that proved pivotal to their future successes. The Michelin-starred Village Pub is another legendary Woodside restaurant. The Village Pub’s exceptional cuisine includes artisanal bread, the finest-quality charcuterie platters, and perfectly executed dishes such as lobster bisque and ricotta gnudi. The Village Pub also boasts an outstanding wine selection and indulgent desserts, including a wildly popular key lime tart.
This upscale community’s breathtaking architectural standouts include the Filoli Estate. The estate features an exquisite 1915 Georgian Revival country house designed by William Polk surrounded by a 654-acre estate with 16 acres of gorgeously landscaped gardens. Visitors can explore a collection of 17th- and 18th-century antiques inside the Filoli historic house, see art exhibitions in the gardens, and hike and horseback ride along trails throughout the surrounding nature preserve. Another Woodside cultural attraction is the three-day King’s Mountain Art Fair held each Labor Day weekend since 1963. Over 135 artists participate in the Fair’s juried art competitions. There’s also a Kids’ Hollow activity area and many food and drinks vendors. The stunning scenery around Woodside offers great hiking and horseback riding with trails running through the meadows and redwood forests of Wunderlich Park and Huddart Park.
Woodside has excellent public schools operated by the Woodside Elementary and Sequoia Union High School Districts.
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