Email us Call us

Skyline Woodside

Rural community with gorgeous views and vistas

Welcome to Skyline Woodside

Skyline Woodside is a rural community consisting of charming homes that ascend Kings Mountain on Skyline Boulevard. Skyline Woodside homes are close to parks offering expansive areas of unspoiled natural scenery. This woodsy community is closely connected to Silicon Valley and is where Tesla is rumored to have started!
Skyline Woodside mostly consisted of rustic cabins and summer homes until the 1950s. The opening of I-280 and development of Silicon Valley tech hubs then brought many new permanent residents to the community. Skyline Woodside offers beautiful single-family homes in a tranquil setting. The elevated terrain provides homes here with mesmerizing views of the surrounding redwood forests and out to the valley and coast. Skyline Woodside feels blissfully isolated, yet the community is just a 40-minute drive from San Francisco.

What to Love

  • Mesmerizing views out to the coast
  • Isolated feel close to Silicon Valley
  • Sprawling open space preserves
  • Historic roadside restaurants 

People & Lifestyle

Skyline Woodside is one of the best options for those who want to be completely surrounded by nature without sacrificing proximity to San Francisco and Silicon Valley. Open space trails are just a few minutes’ walk from Skyline Woodside’s homes.

Dining, Entertainment & Shopping

The picturesque road of Skyline Boulevard is flanked dotted with great dining choices.
Alice’s Restaurant has served as an important stop-off for drivers, motorcyclists, and hikers since it first opened as a general store on Skyline Boulevard in the early 1900s. Alice’s Restaurant was converted into a restaurant in 1950 then renamed in honor of a famous Arlo Guthrie song in the 1960s. This local landmark prides itself on the slogan “You can get anything you want at Alice’s Restaurant.” Menu highlights include hearty gourmet burgers served with sweet potato fries, scrumptious scrambles and omelets, and delicious homemade pies. Everything on the menu at Alice’s utilizes fresh and eco-conscious locally sourced ingredients. Alice’s regularly hosts live music and also offers a fine choice of local wines and craft beers.
The Mountain House fuses American and Californian culinary traditions in an enchanting rustic cabin nestled atop a ridge amongst the redwoods. The Mountain House’s three unique areas include an elegant main dining room with a roaring fireplace, a relaxed bar and lounge, and an outdoorsy forest room. The Mountain House’s menu takes in elk and bison burgers, artisanal salads, and inventive shareable platters.
Skywood Trading Post & Deli is a dependable market, gas station, and deli at the top of the Santa Cruz Mountains. Ready-to-eat items on sale here include tasty paninis, pasta salads, and tamales. The array of rare and high-end cars and motorcycles parked outside are also an attraction by themselves.

Things to Do

Skyline Woodside is surrounded by the stunning scenery and expansive open space of the Santa Cruz Mountains.
Three miles above the town of Woodside, Skeggs Point is a scenic lookout on Skyline Boulevard with sweeping views across the El Corte de Madera Creek Open Space Preserve to the peak of Sierra Morena.
One of California’s best mountain bike tracks runs from Skeggs Point through the rugged adjacent open space preserve.
More trails for hiking and horseback riding run through the beautiful scenery of the 167-acre Thornewood Preserve.
Skyline Ridge Preserve extends over 2,143 acres of diverse scenery with miles of trails for hikers, horseback riders, and cyclists. Skyline Ridge takes in evergreen forests, grasslands, chaparrals, and the picturesque water features of Alpine Pond and Horseshoe Lake. 626-acre Teague Hill Preserve is covered with Douglas fir, oak, bay, and madrone forest. A one-mile section of the Bay Area Ridge Trail runs through Teague Hill Preserve.


Skyline Woodside is served by the Portola Valley and Sequoia Union High School school districts, as well as Cabrillo Unified School District in Half Moon Bay, dependent on street location.

Neighborhood Properties

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

Search All Homes

Work With Us

Team Cappiello is a leading Silicon Valley real estate team that emphasizes confidentiality and offers unparalleled access, creative marketing concepts, and broad market knowledge to their clients.

Follow Us