$4,379,288Average Value$1,887Average Price per Sq Ft20Homes For Sale
An exclusive pastoral oasis in San Mateo County
Surrounded by natural beauty and views of the western hills, the town of Woodside is a rural oasis near Silicon Valley. Its prime location, sprawling estates and pastoral but exclusive air have attracted tech industrialists and venture capital billionaires, making it one of the wealthiest towns in California. Located in San Mateo County, about 30 miles south of San Francisco, Woodside originated as a log-milling hub owing to its abundance of redwoods. These days, it’s a small town of around 5,000 residents hidden away in the vast greenery between the San Francisco Bay and the Pacific coastline. And while this Arcadian haven may feel remote, it’s only a short drive from nearby dining and shopping destinations in Palo Alto and Redwood City. “It’s a beautiful place and very bucolic. It’s a great, central location near San Francisco and Silicon Valley for people that are looking for more space,” says Erika Demma, a local Realtor with Compass Real Estate.
While Woodside is full of cozy ranch homes, it also has a fair amount of high end estates.
Wildflowers are abudanant in spring time in Woodside.
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Acres on acres and early 20th-century grandeur
A drive through Woodside’s winding country roads displays palatial homes shrouded in dense tree canopy on large lots up to four acres. With a mix of early 20th-century splendor, midcentury mansions and sublime contemporary dwellings, these homes are the height of California pomp. A step inside unveils light-filled kitchens, dark wood finishes, lavish master suites and French doors that open onto stone patios. Outside are flawless landscaping around backyard swimming pools and generous guest houses. “You can find some really cool, old estate properties in Woodside. But you also have parcels where the houses have been torn down and replaced with modern, contemporary homes,” Demma says. Smaller, older homes in Woodside can sell for less than $5 million, while larger homes are often priced at upwards of $15 million, capping around 31.1 million.
Up the winding hills of Woodside, CA you will find several acre lots.
Find contemporary ranch style homes in Woodside, CA.
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Woodside Elementary is No. 1
Young students living in Woodside attend one of the best schools in the state. The town’s only school, the centrally located Woodside Elementary School, is ranked the No. 1 elementary school in San Mateo County by Niche and has an A-plus rating. Its students routinely achieve above-average testing scores. “It’s a magical school. It's a great community to raise kids,” Demma says. For high school, students attend either nearby Woodside High School or Sequoia High School, both of which have A ratings. From year-round cheerleading and dance to fall football and winter wrestling, Woodside High offers a robust selection of athletics students can enrich their school days with.
Woodside Elementary School is in Woodside California.
Woodside High School in Woodside, California.
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Teague Hill, Thornewood and equestrian infrastructure
When it comes to nature and outdoor activities, Woodside residents have several exemplary parks at their front doorstep. Residents lace up their hiking boots and head over to Teague Hill Open Space Preserve, Thornewood Open Space Preserve or Wunderlich County Park, home to a maze of interconnected pathways and breathtaking views of redwood-covered ridges, open meadows and wooly canyons. For equestrian enthusiasts, Woodside’s town government maintains a network of horse trails that wind through the town. With grand homes, great schools and small-town charm, Woodside offers an idyllic, secluded retreat where residents can enjoy the countryside near all the Bay Area has to offer.
Gallop through the serene trails of Wunderlich County Park in Woodside neighborhood.
Cross the scenic bridge, a charming feature within Windy Hill Open Space.
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Shopping and dining on Woodside Road
Woodside has several convenient dining options in its small business district on Woodside Road. For a high-end experience, locals grab a table at The Village Pub, a Michelin-starred eatery serving up contemporary American cuisine with an impressive wine list. Nearby, casual cuisine is served at Buck’s of Woodside, a Silicon Valley mainstay and longtime meeting destination for dealmaking tech entrepreneurs. For a cup of coffee in a serene setting, The Village Hub Coffee Bar and Garden is a popular spot to gather and sip. Restocking the pantry can be done at Roberts Market, an upscale grocery store with a deli and excellent wine selection.
Roberts Market has all your grocery essentials in Woodside, CA.
The Village Pub is Michelin-starred eatery serving American cuisine in Woodside, CA.
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Woodside Road to Interstate 280
Woodside is quite self-contained and remote, but Woodside Road takes folks right to Interstate 280, making it quite convenient for 20-mile commutes to Silicon Valley and 34-mile trips to downtown San Francisco.
Downtown San Francisco is just a short drive from Woodside.
Highway 280 is the fastest way to get to San Francisco from Woodside.
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Written By
Micaela Willoughby
Video By
Daniel Quattro
Interested in learning more about homes in this area?
Reach out to
Carrie Davis,
an experienced agent in this area.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
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On average, homes in Woodside, CA sell after 61 days on the market compared to the national average of 52 days. The median sale price for homes in Woodside, CA over the last 12 months is $4,750,000, down 6% from the median home sale price over the previous 12 months.
Discover total serenity at this exquisite and warm family home. The home has been very thoughtfully renovated to include all the comforts one could ever need. With an open floorplan kitchen and living room, and several floor to ceiling windows. Perfect for taking in the verdant green of the surrounding forest. The home is filled with abundant natural light, benefiting from the natural clearing
Hidden gem on nearly half an acre nestled behind a private gated entry. Professionally landscaped grounds feature mature orchard trees and an abundance of flowers blooming year-round. This exceptional single-level residence blends elegance, style, and comfort in a thoughtfully remodeled, open, light-filled floor plan. The grand entry opens to a spacious living room with custom built-in cabinetry
John ShroyerGolden Gate Sotheby's International Realty
Private ~half-acre property is prime for redevelopment with an existing 3,365+/- sf house and ADU* with 5BDs and 5BAs, a carriage house with studio, paddock, two access gates and multiple outbuildings. This highly coveted location is within 0.5 mile of Woodside Village with Roberts Market, Bucks, the library, The Village Pub (Michelin starred), Village Hub and Village Bakery and Cafe, and near
Tucked into the forested hills in the Town of Woodside, this 62 acre offering spans five parcels making it a once-in-a-generation canvas for creating a world-class compound or a collection of signature estates. Here, you’re truly in the heart of Silicon Valley, be at Stanford or Sand Hill in minutes, then retreat to your own hillside sanctuary where the only noise is wind through the trees. This
Discover total serenity at this exquisite and warm family home. The home has been very thoughtfully renovated to include all the comforts one could ever need. With an open floorplan kitchen and living room, and several floor to ceiling windows. Perfect for taking in the verdant green of the surrounding forest. The home is filled with abundant natural light, benefiting from the natural clearing
Recently Updated (2023) Four Bedroom Home This wonderful home is located near the Atherton-Woodside-Redwood City borders, away from through streets and only a short walk away from the Menlo Country Club & bikable to Stanford University. Its large private courtyard provides a delightful outdoor area for entertaining that welcomes guests to your home. Recent renovations were completed in 2023 and
Welcome to this charming updated 3-bedroom, 2-bathroom home located in the beautiful city of Woodside. This inviting residence sits on a spacious 15,400 sq ft lot, offering plenty of room to enjoy the outdoors. Inside, the well-appointed updated kitchen features modern amenities including a gas cooktop, dishwasher, microwave, oven range, and refrigerator, making meal preparation a breeze. The
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