$4,378,319Average Value$1,541Average Price per Sq Ft22Homes 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
Lyn Cobb,
an experienced agent in this area.
On average, homes in Woodside, CA sell after 74 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 $4,540,000, down 6% from the median home sale price over the previous 12 months.
Step into a stunning Woodside Plaza gem, nestled in the heart of Silicon Valley, just minutes from Hwy 280, Stanford, Meta, Google & other top employers! This meticulously upgraded home blends modern flair w/ timeless comfort. An open-concept layout seamlessly connects the kitchen, dining & living areas, perfect for entertaining or cozy nights in. The spacious family room invites relaxation,
Peaceful Woodside Retreat with Sweeping Bay Views Welcome to 168 Sunrise Drive, a serene retreat in the heart of Skywood Acres where you'll enjoy breathtaking panoramic views of the Bay, stretching from San Carlos to San Jose. Set on a spacious 53,577A± sq. ft. lot, this home offers both privacy and connection to nature. A long driveway leads you to the inviting residence, surrounded by mature
Step into a stunning Woodside Plaza gem, nestled in the heart of Silicon Valley, just minutes from Hwy 280, Stanford, Meta, Google & other top employers! This meticulously upgraded home blends modern flair w/ timeless comfort. An open-concept layout seamlessly connects the kitchen, dining & living areas, perfect for entertaining or cozy nights in. The spacious family room invites relaxation,
Outstanding opportunity to improve the current home or rebuild your dream home on one of the most desirable lots in all of Emerald Hills. Situated on an almost 15,000 square foot level lot with no immediate rear neighbor, this property offers endless possibilities. The current home offers three bedrooms, two bathrooms, an oversized living room, formal dining, open kitchen and a sun room. The
Bob BredelChristie's International Real Estate Sereno
Live in the heart of Woodside: * Steps from the Woodside School (Ranked #1 Best Public Elementary School in SF Bay Area, preschool - 8th grade)* Minutes stroll to coffee, dining, shopping, and groceries (Woodside Town Center)* Minutes drive to Hwy 280 for a quick commute to Silicon Valley or SF* Stroll the lush landscaping and enjoy a wide variety of fruits and
Discover the charm and serenity of this beautifully updated 2-bedroom, 2-bathroom home, nestled on an expansive 15,400 sq ft lot in the highly desirable city of Woodside. Designed for both comfort and functionality, this residence provides a rare combination of privacy, outdoor space, and modern convenience, including an office. Inside, the thoughtfully remodeled kitchen is equipped with premium
Property Id: 2117159Home Road, Woodside, CA 94062, right off Portola Road on the way to PV.This very private 2 bedroom, 2 bath home (not an ADU) features a living room and dining room combination with fireplace, full kitchen, laundry room with washer and dryer. New baths and laundry room- recently updated. Wonderful private location on approximately 1/3 acre with great yard and
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