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Woodside Hills

Charming community in the northern part of Woodside

Welcome to Woodside Hills

Woodside Hills is a charming community offering larger lots in the northern part of the sought-after town of Woodside. Woodside Hills homes are closer to shops and restaurants than other areas of Woodside, but this community still retains a country feel. The community is within easy reach of amenities in Central Woodside and Redwood City, as well as Stanford University, Sand Hill Road venture capital firms, and numerous Silicon Valley tech hubs.
Woodside Hills’ beautiful single-family homes are located on winding country roads surrounded by lush tree cover. Lot sizes in Woodside Hills are typically a minimum of one acre. The community has a low population density with access to expansive country parks and equestrian trails. Woodside Hills’ elevated terrain provides homes with some of the peninsula’s most captivating views, stretching from the Santa Cruz Mountains in the west to the San Francisco Bay in the east.

What to Love

  • Beautiful homes on large lots
  • Peaceful country atmosphere
  • Close to shops and restaurants
  • Parks, trails, and open space preserves

People & Lifestyle

Residents of Woodside Hills include a mix of professionals, tech workers, and retirees. Woodside Hills’ proximity to Silicon Valley’s tech hubs has attracted a diverse population with residents from all corners of the globe. This relaxed rural community is the kind of place people lay down roots, and there is little turnover in homeownership here. A strong sense of community is fostered by regular social gatherings and events organized by groups such as the Woodside Hills Home Association and Woodside Hills Garden Club.

Dining, Entertainment & Shopping

Woodside Hills is located a short distance to the north of a fine selection of local businesses lining Woodside Road in Central Woodside. The Village Bakery is a combination bakery and café serving delicious fresh bread and pastries alongside a fine choice of brunch plates, salads, pizzas, and elevated American entrees. Meals at The Village Bakery are paired with West Coast craft beers, wines by the glass, and specialty cocktails and summer spritzes.
The Firehouse Bistro has transformed Woodside’s first fire station into a delightful restaurant serving chef-driven reinterpretations of classic French comfort cuisine and seafood dishes. This intimate and romantic eatery also offers a good choice of regional and international wines.
The Pioneer Saloon has been a fixture in Woodside since 1880. This laidback old-school saloon remains Woodside’s favorite watering hole well over a century later. The Pioneer Saloon hosts live music on Sundays plus regular karaoke nights.
The Little Store Restaurant is another longtime Woodside institution that has been part of the community since 1902. The Little Store’s menu includes French and Cajun entrees, half-pound Angus burgers, gourmet sandwiches, pulled pork tacos, buckwheat crepes, and a variety of soups and salads.

Things to Do

Horses are a huge part of life in Woodside and Woodside Hills. The community’s equestrian traditions come to the forefront each October during The Day of the Horse. Activities taking place during this three-day celebration include an art show, horse show, and progressive trail ride.
The Mounted Patrol of San Mateo County’s Fourth of July Celebration also showcases Woodside’s horsing heritage. Budding cowboys and cowgirls travel to Woodside from across California to participate in the event’s Woodside Junior Rodeo. Activities for older participants include barrel racing, bull riding, and roping.
The gorgeous Santa Cruz Mountains scenery around Woodside Hills provides plenty of places to explore on horseback. Equestrian, cycling, and hiking trails run through the redwood forests of Wunderlich Park. Many more trails for hiking and horseback riding traverse the diverse landscape of 900-acre Huddart Park.


Woodside Hills is served by the Redwood City elementary school district and Sequoia Union high school district. A few noteworthy local schools include:
  • Redwood City Elementary, Public, K-8
  • Sequoia High, Public, 9-12

Neighborhood Properties

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