$4,314,614Average Value$1,691Average Price per Sq Ft25Homes 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
Christienne Hadley,
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 55 days on the market compared to the national average of 56 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.
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
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
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view
Jen PaulsonChristie's International Real Estate Sereno
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
Set on a beautifully landscaped setting with sweeping views, this impeccably maintained Woodside residence offers a rare blend of privacy, scale, and resort-inspired living. Spanning approximately 3,520 square feet, the 4-bedroom, 3.5-bathroom home is thoughtfully designed with a seamless balance of formal and casual spaces. A gracious entry introduces light-filled interiors with high ceilings,
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
Designer Transformation on 1.5 Acres Steps to Town! A remarkable whole-home transformation has elevated this property into a showcase of design, quality, and livability. Modern and full of sun lit spaces, the setting unfolds with park-like grounds that capture the essence of Woodside country living. Offering a stunning 4 bedroom 3.5 bath main house and a well-appointed 2 bedroom guest house with
Tucked at the end of a cul-de-sac, this meticulously maintained 2,235 sq ft modern Craftsman sits on a 7,800 ± sq ft lot framed by soaring redwoods and mature Japanese maples. Inside: vaulted ceilings, gleaming hardwood floors, two fireplaces, a chef's kitchen with BlueStar range and wine fridge, a cherry-paneled office with built-ins, and central heat and air throughout. The primary suite opens
Chris IversonGolden Gate Sotheby's International Realty
Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view
Jen PaulsonChristie's International Real Estate Sereno
Set on 2.6+ wooded acres in the hills, this warm & beautifully renovated home offers something genuinely rare on the Peninsula: complete privacy amid towering redwood trees, a profound sense of forest immersion, and less than 15 minutes to Sand Hill & 280. The updated & open floor plan kitchen flows into generous dining and living spaces, all oriented towards sweeping forest views. Natural light
Known as the High Hilltop home, you will be surprised by this move-in-ready gems breathtaking views of the Western Hills, portions of the SF Bay and colorful sunsets. Closely adjacent to Kite Hill open space trail network and within easy and safe walking distance to the acclaimed Woodside School (pre-K to 8th) and Town Center restaurants and shops, this wonderful two-story home, situated in a
This is an idyllic Woodside property on over 1 level acre, where open land, equestrian facilities, and close-in convenience come together just one-half mile from the Town Center and highly acclaimed Woodside School. The expansive, level grounds set the tone complete with a 1 bedroom and 1.5 bath guest house, barn, fenced paddocks, pool, and broad stretches of lawn that capture the true spirit of
Extraordinary residence on 5.32 acres with opulence and European inspiration at every turn. Impeccably crafted by renowned builder Markay Johnson in 2014 on a private gated lane with gated driveway and sweeping views of San Francisco Bay. Lavish beauty throughout the home with hand-selected marble from Milan, elaborate millwork, Doric columns, intricate carvings, and gilded details. All-marble
Nestled under Woodside's heritage oaks, this 1929 Woodside Glens retreat offers a rare blend of vintage character, privacy, and views. Spanning approximately 2,200 sq. ft. on a nearly 0.5 acre lot, this home features verdant scenery and a wrap-around deck to take it all in. The main level boasts a large, open-beam living room anchored by a cozy wood-burning stove, and is surrounded by windows
Stephen RumbergKeller Williams Realty-Silicon Valley
Nestled in a highly sought-after Woodside neighborhood, this single-family home offers the rare combination of privacy, space, & future potential. Situated on an expansive ~0.340.37 acre lot (15,000+ sq. ft.), the property provides generous outdoor space ideal for entertaining, expansion, or the opportunity to build your custom dream home. The residence features a remodeled kitchen & an upgraded
Nestled on a quiet tree-lined cul-de-sac this charming Craftsman-inspired single-story home sits on a level 13,746 sq ft lot in a highly desirable Central Woodside location-just a short stroll to the Village. The remodeled 3 bedroom 2 bath residence features hickory hardwood & stone flooring throughout. Vaulted ceilings & French doors create a bright open living & dining area filled with natural
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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