$4,318,688Average Value$1,551Average Price per Sq Ft12Homes 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 54 days. The median sale price for homes in Woodside, CA over the last 12 months is $4,135,000, down 20% from the median home sale price over the previous 12 months.
Welcome to 6 Woodridge Court, an elegant residence nestled within the prestigious Woodhill Estates community, where privacy and elevated lifestyle come together. This beautiful 4-bedroom, 3-bathroom home with a 3 car garage offers a thoughtfully designed floor plan ideal for both comfortable living and stylish entertaining. Step through the grand entry foyer, where soaring ceilings and natural
Prime Woodside Plaza location meets effortless living in this 5-bedroom, 3-bathroom home. Spanning 2,600 sq ft on a low maintenance 5,944 sq ft lot, the residence has been thoughtfully updated and expanded with new floors, fresh paint, and a pristine artificial turf yard that stays green year-round. Two-car garage, abundant space for family and guests, plus the convenience of walking to Woodside
Spanning 2,670 square feet of living space, this home envelopes you with warmth and charm from the moment you enter. Sunlight filters through towering redwoods, creating a serene atmosphere throughout. Refinished hardwood floors and thoughtful modern updates blend timeless quality with everyday comfort. The spacious floor plan flows seamlessly, ideal for both daily living and entertaining. The
Hidden gem on nearly half an acre behind a private gated entry with professionally landscaped grounds, mature orchard trees, & year-round blooms. The exceptional single-level 3 bedroom, 3 bath 1,842 sqft main residence was completely renovated in 2017 & features an open, light-filled floor plan with skylights & French Oak floors throughout. The entry opens to a spacious living room with custom
John ShroyerGolden Gate Sotheby's International Realty
Discover this exceptional opportunity to own a generational estate spanning 7 acres across 3 separate parcels, each with its own APN. Through a private gate & down a long winding driveway, you're greeted by a circular motor court with incredible views of the Santa Cruz Mountains. The main residence offers 4,340 sqft featuring 6 beds & 5.5 baths, with exceptional upgrades throughout. On the east
Welcome to a residence where artistry meets architecture. Set in Emerald Hills on an expansive view lot, the home was designed for those who value quality, creativity, and originality. From the custom iron gate by Burning Man artist Bryan Tedrick to the antique Santa Fe stained-glass entry window, every detail tells a story. Soaring ceilings and dual 7×20 folding glass doors dissolve boundaries
Tranquil land. Excellent opportunity to build or ? on this sun-drenched parcel that has gentle grade for development. 3800 ft2 home plus 1000 ft2 ADU deemed possible by Lea and Braze engineers; price includes feasibility study, survey and septic perc test results. This land could be a great location for your estate home or quiet get-away. Plenty of room for horses, animals and/or hobby farm,
Kim HansenGolden Gate Sotheby's International Realty
Build up to 3615 total sq. ft. consisting of 3,175 livable & 440 garage. All public utilities including public sewers and California water service. Highland Terrace has long been one of the most desirable streets in the Woodside community of "The Glens". This lot was held for decades by the prior owner of the adjacent home. Truly a rare opportunity find a vacant parcel where you can create a new
Welcome to 6 Woodridge Court, an elegant residence nestled within the prestigious Woodhill Estates community, where privacy and elevated lifestyle come together. This beautiful 4-bedroom, 3-bathroom home with a 3 car garage offers a thoughtfully designed floor plan ideal for both comfortable living and stylish entertaining. Step through the grand entry foyer, where soaring ceilings and natural
Tucked into the tranquil forested hills of Woodside, this serene 5.64-acre parcel offers an immersive escape into nature. Surrounded by mature trees, quiet trails, and peaceful open space, the property is perfect for those seeking solitude, fresh air, and natural beauty—just minutes from the 280 freeway and an easy route to Silicon Valley. Enjoy hiking, biking, or simply relaxing beneath the
2.8 Acres of Buildable Land Next to Menlo Country Club! This exceptional 2.8-acre vacant parcel presents an extraordinary opportunity in a prestigious setting, offering endless possibilities for building. The vacant land, bordering the Menlo Country Club, offers gently rolling terrain with open meadows, wildflowers, perimeter trees, and views of the East Bay hills. With a serene landscape and
Discover a blend of charm and modern living in this beautifully updated Woodside home, nestled beneath a canopy of majestic oak trees. Originally built as a summer cottage in 1927, this 3-bedroom, 2-bathroom residence has been thoughtfully expanded and renovated while preserving its vintage character. The heart of the home features a recently remodeled kitchen designed for both everyday living
Chris IversonGolden Gate Sotheby's International Realty
Mid-century modern enthusiasts will be delighted by this truly special Woodside retreat. Nestled in The Glens and surrounded by oak trees, this home sits atop an expansive preserve with access to hiking trails. Built in 1959, the home showcases iconic mid-century modern design with floor to ceiling glass that fills the upper level with natural light and opens to an expansive 900+ sq ft deck,
Don't miss the opportunity to live in beautiful Woodside. Bright, open floor plan. Detached 3-BED, 2-BATH guest home with master bedroom. Master bath with oversize stall shower. Hallway bathroom with tub. Carpeting and closet organizers in every bedroom. High ceilings and recessed can lighting throughout. Gorgeous open concept kitchen with cook top range, built in over, dishwasher, microwave,
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