$4,409,765Average Value$1,787Average Price per Sq Ft24Homes 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
Susan Chong,
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.
View GreatSchools Rating Methodology
On average, homes in Woodside, CA sell after 56 days on the market compared to the national average of 58 days. The median sale price for homes in Woodside, CA over the last 12 months is $4,200,000, down 14% from the median home sale price over the previous 12 months.
Sunlit Sanctuary on 3.7 beautiful acres. Sky Hill Farm, a rare, retreat-like property that blends natural beauty, indoor-outdoor living & modern luxury minutes from the heart of Silicon Valley. This beautifully renovated home has been completely reimagined w/high-end finishes & exceptional craftsmanship, offering a lifestyle of comfort, privacy & effortless elegance. Seamlessly flowing open floor
Set upon an extraordinary 3.25-acre setting, this charming one-story home offers a rare sense of seclusion and natural beauty, further enhanced by its adjacency to a protected 6-acre parcel that ensures enduring privacy. The grounds are a true sanctuary, featuring a 40-year-old native garden that blooms nearly year-round, and a spacious rear deck overlooks this serene landscape, creating a
Tranquil Woodside Retreat Nestled within one of Woodside's most sought-after enclaves, this enchanting single-family residence offers a rare blend of privacy, natural beauty, and timeless appeal. Set on expansive, level to gently sloping grounds, the property is ideal for equestrian use, featuring serene open spaces framed by mature trees and lush, thoughtfully designed landscaping. Bathed in
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
Set on more than 2.5 acres of quintessential Woodside grounds, this spectacular estate balances timeless elegance with easy comfort. Behind gates and surrounded by mature trees and lush foliage, it conveys a quiet sense of luxurious seclusion. Inside, more than 6,400 total SF includes a dramatic foyer with columns, expansive formal rooms, a chef's kitchen, private office, theater, and five
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
Set on beautifully landscaped grounds with sweeping Bay views, this impeccably maintained Woodside residence offers privacy, scale, and resort-inspired living. Light-filled interiors feature soaring ceilings, refined millwork, and an elegant flow designed for both entertaining and everyday living. Formal living and dining rooms provide distinct gathering spaces, while the well-appointed kitchen
This home personifies tranquility. Nestled in a serene country setting just minutes from I-280 and top-rated Portola Valley schools, this beautifully updated 6-bedroom, 2- Office 3+-bathroom custom designed home perfectly balances rural privacy with modern convenience. The interior boasts an expansive, light-filled atmosphere defined by cathedral ceilings and large windows that frame the
Peter CowperthwaiteGolden Gate Sotheby's International Realty
Set beyond a gated entrance at the end of the private lane, this contemporary farmhouse is an exquisite blend of luxury and organic materials, creating a tranquil atmosphere that harmoniously blends with its natural surroundings. Completed in 2023, the approximately 10.56 acres of open landscape provide sweeping views and exceptional privacy. The architecture embodies the rural sophistication
Classic architecture & beautifully curated grounds define this inviting Woodside home set on more than one-third acre moments from the town center. Stone-clad exteriors, newly planted lawns, & a picture-perfect approach introduce interiors that are warm, welcoming, & thoughtfully designed for everyday living. Natural light fills the home through expansive windows, hardwood floors, detailed
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 your dream home on this exceptional 1.2+ acre lot in the prestigious town of Woodside. Surrounded by open space and scenic parks, the property offers direct access to miles of trails perfect for hiking, biking, and horseback riding embracing the true Woodside lifestyle. Ideally located near Interstate 280, youll enjoy convenient access north to San Francisco and south to Silicon Valley, all
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
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,
LOCATION: 683-A Old La Honda Rd, WoodsideRENTWISE PRESENTS: Escape to your private Redwood retreat in this updated 1 bedroom + loft guest cottage, just minutes from Hwy 280!PROPERTY HIGHLIGHTS:* Completely detached guest cottage - enjoy privacy and tranquility* 1 bedroom + loft -- Spacious primary suite with en-suite bathroom -- Private loft - ideal for a home office
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