$4,446,583Average Value$1,520Average Price per Sq Ft12Homes For Sale
A community of high-value homes that emphasize the surrounding nature
Portola Valley, nestled into the wooded hills of the Santa Cruz Mountains on the San Francisco Peninsula, is a picturesque town of spacious, multimillion-dollar homes that is known for its extensive network of protected trails that highlights the community’s natural beauty. “To stop future development and to preserve what many people felt was a very, very special place, the town was incorporated in 1964,” says Hugh Cornish, a Realtor with Coldwell Banker Realty and longtime town resident. “It’s an unusual place in the sense that it is one of the richest zip codes in the country, but the wealth is very quiet, very reserved. There’s a big emphasis on the natural environment here. We have a tremendous amount of open space.” The town also has its own school district, which features an array of top-rated schools, both public and private, and it is conveniently located on the doorstep of Silicon Valley, just west of Stanford University and adjacent to Interstate 280.
Midcentury modern designs blend into the natural environment
Quiet and reserved also applies to the town’s housing, at least in relation to surrounding communities that are known for their large, garish homes. Portola Valley features a variety of relatively understated homes on oversized lots, generally priced between $2 million and $9 million. Sleek midcentury modern designs are prominent in both established homes and new constructions. “When the area was first being developed in the 1950s and ‘60s, even before incorporation, there was a focus on contemporary architecture that was ahead of its time. It was avant-garde, but it’s never been ostentatious,” says Cornish. “It’s always been more conservative than surrounding areas because the homes seem to blend in to the natural environment very well.” Foremost among the midcentury-modern designs are Eichler homes, built by famed Bay Area developer Joseph Eichler. Ranch-style homes nestled into the mountains, sprawling contemporary custom homes in dedicated subdivisions and quaint renovations can also be found. The residential aesthetic, like the natural environment, is protected. “There are a number of restrictions in architectural styles and sizes because officials want to keep the town looking like it did 50 years ago,” says Cornish. That means the town’s newest homes can offer modern touches, but they must adhere to the restrictions and can’t stray too far from Portola Valley's signature look. “Even now, if you want to build a home in Portola Valley, the process takes a little longer.”
Portola Valley has very large modern homes.
Ranch style homes are common in Portola Valley.
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Protected trails and a popular community center provide recreation
The trail network is concentrated in the southern half of town, starting just south of Alpine Road, Portola Valley’s main thoroughfare. Part of the town’s development included an agreement with the developer that this section of Portola Valley would be preserved as open space in perpetuity so residents would always have access to the trails, which wind their way through the Coal Mine Ridge Nature Preserve. Hikers are exposed to a variety of native plants and animals along the trails, but they must stay on the designated paths at all times, and bicycles and dogs are not allowed. These rules are strictly enforced to ensure that the tranquility of the preserve is not disturbed. The Alpine Trail also can be accessed in town, and it leads to the adjacent Windy Hill Open Space Preserve. For more contemporary recreation, residents have access to the Alpine Hills Tennis and Swimming Club, which is anchored by 12 tennis courts and three pools of various sizes and includes a clubhouse, fitness center and playground. Portola Valley offers an activity-filled Town Center as well. It provides residents with a library that hosts community events including weekly family storytime, monthly Crafturday sessions and other regular activities such as Lego Club and tai chi class. The center’s community hall offers fitness classes that include yoga, aerobics and jazz dance; and recreational amenities that provide opportunities to play soccer, softball and tennis.
Russian Ridge Open Space Preserve features hiking trails in the neighborhood of
Portola Valley
Portola Valley has a wonderful library.
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A historic eatery anchors the community's dining options
The retail and dining options that can be found in town are concentrated along Alpine Road. Roberts Market offers not only groceries and sundries, but its deli is a popular place to pick up a meal for those on the go. Rossotti’s Alpine Inn is a quaint eatery that serves up comfort food classics and is known not only for its popular beer garden but also for its tavern, whose roots can be traced to 1852.
Portola Valley's Alpine Inn is a great place to go grab lunch..
Alpine Inn is a great place to grab a beer in Portola Valley.
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Students have access to highly rated public and private schooling
Portola Valley’s public school district includes Ormondale Elementary, an A-rated school by Niche, and Corte Madera, a middle school given an A-plus by Niche. Nearby Woodside High School is part of the Sequoia Union district, but don’t worry, it’s A-rated as well. For those interested in private school, the town is home to Woodside Priory, a co-ed college preparatory school for students in sixth through 12th grades, and Woodland School, an independent day school that serves special needs students in preschool through eighth grade.
Ormondale Elementary School provides education in the neighborhood of
Portola Valley
The front of Woodside High School Oak Knoll.
Woodside Priory provides private education in the neighborhood of
Portola Valley
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Main roadways provides easy work commutes to Silicon Valley
Portola Valley is just minutes from the heart of Silicon Valley and Stanford University, which results in an eclectic group of residents. “There’s an interesting mix of people and professions,” says Cornish. “Nearby is 3000 Sand Hill, known as the venture headquarters of the world, so you have residents working in venture capital, high tech, biotech. And with Stanford University nearby, there are a lot of professors and doctors. It’s a large cross-section.” Alpine Road becomes Sand Hill Road just north of town, providing convenient access to the many venture capital and tech jobs in the area. Additionally convenient is that Interstate 280 can be accessed even closer to town via Alpine Road, allowing for travel north toward San Francisco or east to San Jose.
Electric car charging is easy accessible in Portola Valley.
Cyclists and cars share the roads in Portola Valley.
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Written By
Matt Pallister
Photography Contributed By
Sean Viray
Video By
Tyler Hall
Interested in learning more about homes in this area?
Reach out to
Astha Mathur,
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 Portola Valley, CA sell after 64 days on the market compared to the national average of 57 days. The median sale price for homes in Portola Valley, CA over the last 12 months is $3,972,500, down 7% from the median home sale price over the previous 12 months.
Set on 2.8 AC, this home offers a peaceful retreat in a coveted setting. Warm, welcoming interiors span more than 3,700 SF across a multi-level floorplan, blending rustic character with an easy livability that harmonizes with the surrounding landscape. A soaring vaulted ceiling elevates the living room anchored by a fireplace and expansive windows framing views that reach toward the Stanford
On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a
Set on 2.8 AC, this home offers a peaceful retreat in a coveted setting. Warm, welcoming interiors span more than 3,700 SF across a multi-level floorplan, blending rustic character with an easy livability that harmonizes with the surrounding landscape. A soaring vaulted ceiling elevates the living room anchored by a fireplace and expansive windows framing views that reach toward the Stanford
Perched on an elevated corner lot, this spacious contemporary residence is filled with natural light and showcases marvelous Bay views. Skylights and oversized windows illuminate the dramatic two-story entry foyer, creating a bright and airy atmosphere that enhances the home's open-concept design. Expansive views serve as a stunning backdrop to the living room, primary suite, and wraparound
Welcome to 310 Old Spanish Trail in Portola Valley, a beautifully maintained custom home built in 2006 and lovingly cared for by its original owner. With gleaming floors, soaring ceilings, and expansive windows framing the natural landscape, the home feels remarkably fresh and almost brand new. Set in one of the Bay Area's most desirable communities, this property offers a rare combination of
Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.
Rarely available estate, located in the highly sought-after Westridge neighborhood of Portola Valley. This lovely home is set on 3.86 serene acres w/ majestic oaks and offers a panoramic view of the SF Bay from Stanford to Mount Diablo. Enjoy a picturesque vista from the main home and newly built, stunning ADU. A gated driveway escorts you to a light-filled home highlighted by an open concept
Perched on a knolltop within prestigious Blue Oaks, this luxurious estate epitomizes elegance and exclusivity. Set on 2.53 acres of naturally organic beauty, this residence offers unparalleled privacy and breathtaking views of the San Francisco Bay. A true sanctuary, the home seamlessly blends sophisticated design with the tranquility of its natural surroundings. The expansive living room, bathed
Build your dream home on this approx. 4.2-acre undeveloped country parcel situated adjacent to Portola Valley on Santa Clara County land just up from the Ladera Shopping Center shops and restaurants. The lot is surrounded by open space, Stanford lands and the gently flowing Los Trancos Creek and is in the Palo Alto Unified School District.
Stunning new construction Craftsman residence in the sought-after Ladera neighborhood of Portola Valley. This home features a bright, open-concept floor plan with expansive living spaces that flow to the backyard through large stacking glass sliders and a covered patio for indoor-outdoor living. The chefs kitchen includes Wolf and Sub-Zero appliances, ceiling-height cabinetry, quartz countertops
Nadine MasarwehThomas James Real Estate Services, Inc
Nearly one acre of level grounds sets the stage for this exceptional new home, defined by clean lines, sophisticated materials, and seamless indoor-outdoor living. White oak floors, soaring ceilings, and walls of glass enhance the light-filled interiors that open to the rear grounds where an infinity-edge pool and spa invite entertaining and recreational enjoyment. A tremendous great room anchors
SUNLIT GEM ON NEARLY ONE-HALF ACRE WITH PLANS TO EXPAND! Fresh, inviting, and completely sophisticated, this retreat has been transformed into a light-filled setting. Easily accessed via wide streets, the property spans nearly one-half acre of predominantly level grounds and includes plans for a future expansion. The current home, with 2 bedrooms and 2 baths, offers a streamlined scale yet the
On the market for the first time, this exceptional Craftsman home is located in prestigious Blue Oaks, an enclave of estate homes surrounded by 285 acres of open space & trails. Built by Chessler Construction in 2003, the home showcases timeless architecture, exquisite woodwork, & a flexible multi-level floor plan designed for today's lifestyle. Set on approx. 1.29 acres, the property enjoys a
Beautiful (Bonita!) very large property in upper Los Trancos Woods. Over 1.6 AC of mostly flat land with old, mostly not habitable House, Cottage, Garage and Carport, comfortably spread throughout the property. In Feb 2026, San Mateo County approved a 2 lot subdivision, and work is ongoing to complete the final map recording. The house is available prior to recording of the subdivision as a
Tucked away on a quiet cul-de-sac in one of Portola Valleys most desirable neighborhoods, this inviting fully furnished home offers privacy, comfort, and a seamless connection to its natural surroundings. Thoughtfully designed with generous living spaces, the residence is filled with natural light and framed by serene views of mature trees and landscaped grounds. The main living areas flow
Nestled in the heart of central Portola Valley, this beautifully maintained, gated residence at 169 Sausal offers the perfect blend of privacy, comfort, and convenience. Surrounded by mature trees and natural beauty, the home provides a peaceful retreat just minutes from local shopping, acclaimed schools, scenic hiking and equestrian trails, Stanford University, and Highway 280. The thoughtfully
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