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Woodside Glens

Walkable neighborhood in the serene town of Woodside

Welcome to Woodside Glens

The town of Woodside is one of the most desirable communities in Silicon Valley, featuring spectacular residences in a serene country setting. Woodside Glens is a younger Woodside community located half a mile to the north of Central Woodside. This walkable neighborhood originally developed as a summer home community for wealthy San Francisco residents in the 1920s. Woodside Glens offers access to the great Woodside Elementary School.
Woodside Glens consists of around 180 homes covering a total area of 80 acres on the sloping terrain between Canada Road and I-280. Homes and parcels are generally smaller than those in Central Woodside, and properties here are consequently more affordable. Woodside Glens’ beautiful and spacious single-family homes offer all Woodside’s exceptional advantages of a peaceful and leafy community close to Silicon Valley tech hubs and Sand Hill Road venture capital firms.

What to Love

  • Serene country setting
  • Walkable neighborhood
  • Scenic open space preserves
  • Woodside Elementary School

People & Lifestyle

Woodside Glens’ homes lie along quiet lanes and cul-de-sacs. Properties here are within easy reach of Central Woodside businesses and the expansive greenspace of Huddart Park. Most residents commute to work in nearby Silicon Valley tech hubs such as Menlo Park, Palo Alto, and Redwood City.

Dining, Entertainment & Shopping

Homes in Woodside Glens are just half a mile away from the fine choice of businesses lining Woodside Road in Central Woodside. Buck’s of Woodside is an iconic old-school diner that has hosted many significant Silicon Valley and Sand Hill Road business deals since it opened in 1995. Surrounded by a colorful array of kitsch pop culture memorabilia, diners at Buck’s enjoy a classic menu of hearty American comfort eats. Hotmail, Netscape, PayPal, and Tesla are just a few of the major Silicon Valley tech firms to have held significant early meetings in the comfortable booths at Buck’s.
The nearby Village Pub pairs sublime high-end cuisine with an impressive selection of imported French wines. This Michelin-starred eatery is one of the finest restaurants in Silicon Valley. The Village Bakery combines a fine selection of bread and baked goods with an eclectic upscale menu of dine-in meals and drinks. Highlights include gourmet salads, pizzas, buttermilk fried chicken, and artisanal entrees prepared with high-quality ingredients. The Village Bakery also offers an extensive choice of craft beers, wines, cocktails, and specialty summer spritzes.
Roberts Market is stocked with all your grocery and outdoor essentials. This longtime Woodside institution boasts some of the area’s best meat, seafood, and deli counters. Roberts Market also carries a wide selection of outdoor goods such as horse feed, tack, garden supplies, and outdoor wear.

Things to Do

Woodside Glens is located close to some of the Santa Cruz Mountains’ most scenic open space preserves. Encompassing the area of the former Folger family ranch, Wunderlich Park is full of soaring forests, steeply sloping canyons, and trails for hikers, bikers, and horseback riders.
900-acre Huddart Park has a diverse landscape of forests, canyons, and meadows. Many trails run through Huddart Park. Huddart Park also has amenities such as a playground and barbecue pits.
Several events held each year celebrate Woodside’s strong tradition of equestrian pursuits. The Mounted Patrol of San Mateo County’s Fourth of July Celebration is an annual highlight featuring events such as the Woodside Junior Rodeo and bull riding, roping, and barrel racing contests for adults. In October, the three-day Day of the Horse involves equine-themed events, including an art show, horse show, and progressive trail rides.


Woodside Glens is served by the Woodside Elementary and Sequoia Union High school districts. A few notable local schools include:
  • Woodside Elementary, Public, K-8.
  • Woodside High, Public, 9-12.

Neighborhood Properties

Take a look at the properties for sale in this neighborhood.

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