Neighborhood

Woodside Highlands, Portola Valley, CA

Neighborhood RatingNeighborhood RatingNeighborhood RatingNeighborhood RatingNeighborhood Rating
4.3 /5
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Ranked 8th /9 in Portola Valley, CA

Neighborhood Factors

Market Conditions

  • Neighborhood Factors
    Price
    $2.82M
  • Neighborhood Factors
    Overvalued
    $463k(2)
  • Neighborhood Factors
    Appreciation
    0%(2)

(2) City data used

At a glance

Woodside Highlands is ranked #8 of 9 neighborhoods in Portola Valley with an overall score of 4.3/5. Its standout factors are safety (4.5/5, 8th of 9 in Portola Valley) and schools (4.4/5), at a median home price of $2.82M, which Houseberry currently rates as overvalued by about $92,000. The trade-off is nearby merchants (0.8/5), though prices run about 36% below the Portola Valley median.

Neighborhood Reviews & Questions

Neighborhood Review
Key Words: Scenic environment, Community-focused, Access to outdoor recreation

Woodside Highlands is a peaceful and picturesque neighborhood in Portola Valley, characterized by its natural beauty, serene atmosphere, and close-knit community. Nestled among rolling hills and lush greenery, this neighborhood offers a retreat-like environment that is ideal for those seeking tranquility while remaining connected to modern conveniences. The residential streets in Woodside Highlands are lined with charming homes, many of which feature unique architectural designs that blend seamlessly with the surrounding landscape. The properties often include mature trees and spacious yards, adding to the area’s scenic appeal. The neighborhood's winding roads and elevated terrain provide breathtaking views of the nearby valleys and hills. Residents of Woodside Highlands enjoy easy access to outdoor recreation, with numerous trails and open spaces nearby. These include Windy Hill Open Space Preserve, which offers hiking, biking, and equestrian trails, as well as opportunities to observe local wildlife and enjoy panoramic vistas. Community spirit is strong in Woodside Highlands, with local gatherings and events fostering a sense of camaraderie among neighbors. The nearby Valley Presbyterian Church and Parkside Grille serve as convenient landmarks and gathering spots for the community. Woodside Highlands is conveniently located near Portola Road, providing quick access to downtown Portola Valley and its array of shops, dining options, and services. The neighborhood's serene setting, combined with its proximity to essential amenities, makes it a highly desirable location in the area.

See City Review for: Portola Valley
Houseberry's TakeLocal InsightsQuestions

Top Neighborhoods in Portola Valley, CA

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Overall Score : 4.5
Portola Valley Ranch is a distinctive and well-regarded neighborhood in Portola ... See Full Page
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Blue Oaks is a distinguished and exclusive neighborhood located in the scenic fo... See Full Page

Neighborhood Amenities

  • Neighborhood Amenities
    Near good merchants

    0.8

  • Neighborhood Amenities
    Public Spaces

    4

  • Neighborhood Amenities
    Curb Appeal

    4

Overall Amenities score: 3.4

Neighborhood Weather

80%
of possible sunshine
Of all the daylight this spot gets in a year, 80% arrives as sunshine - clouds and fog block the rest.
Woodside Highlands ranks 4th of 9 for sunshine in Portola Valley, and it out-suns about two thirds of the Bay Area. Its warmest month is July, averaging 85° highs, and it gets about 29 inches of rain a year.
Average daily high and low temperature
90°70°50°30°JFMAMJJASONDJul 85°
Avg highAvg low
Rank in Portola Valley
4th of 9
Across the Bay Area
66th percentile
Rain per year
29 in
Warmest month
Jul 85° avg high
Summer day
52° → 84°F
Winter day
42° → 61°F
Sunshine and temperature figures are 30-year climate averages for this neighborhood's location.

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Schools serving this Neighborhood

School NameTypeGradesHouseberry School Score
Corte Madera Middle4-8
4.7/5
Woodside High High9-12
3.9/5

Click links for school listing

info at GreatSchools.org

Houseberry School Score Data

from CA Dept. of Education

Houseberry recommends using these scores as only a starting point, and conducting your own investigation into what schools fit best for your preferences. School boundaries are not guaranteed and may change. It is important to contact the appropriate school district to confirm enrollment eligibility before making any decision to move to a neighborhood.

Median Price

Woodside Highlands FAQs10 answers

Is Woodside Highlands a good place to live?

Woodside Highlands ranks 8th of 9 neighborhoods in Portola Valley with an overall Houseberry score of 4.3 out of 5. Its strongest factors are safety (4.5/5) and schools (4.4/5). The trade-off is nearby merchants (0.8/5).

Is Woodside Highlands safe?

Woodside Highlands, Portola Valley scores 4.5 out of 5 on Houseberry's Safety Score, ranking 8th of 9 neighborhoods in Portola Valley.

What do homes in Woodside Highlands cost?

The median home price in Woodside Highlands, Portola Valley is $2.82M, compared with $4.43M for Portola Valley as a whole. Houseberry currently rates it overvalued by about $92,000 against comparable neighborhoods.

Are home prices in Woodside Highlands rising or falling?

The median home price in Woodside Highlands, Portola Valley is up about 69.0% over the past 12 months, from $1.67M to $2.82M. The full 12-month history is charted in the Median Price section on this page.

Which schools serve Woodside Highlands?

Schools serving Woodside Highlands, Portola Valley include Corte Madera (4.7/5) and Woodside High (3.9/5).

What is the weather like in Woodside Highlands?

Woodside Highlands, Portola Valley receives 80% of its possible sunshine, 4th of 9 in Portola Valley. Summer days run 52° to 84°F and winter days 42° to 61°F, July is the warmest month and rainfall averages about 29 inches a year.

Is Woodside Highlands walkable to shops and restaurants?

Woodside Highlands, Portola Valley scores 0.8 out of 5 for nearby merchants and 4.0 out of 5 for public spaces. Its overall amenities score is 3.4 out of 5, 8th of 9 in Portola Valley.

What is Woodside Highlands known for?

Woodside Highlands, Portola Valley is associated with Scenic environment, Community-focused and Access to outdoor recreation. Its highest-scoring factors are safety (4.5/5) and schools (4.4/5).

How does Woodside Highlands compare to other Portola Valley neighborhoods?

Woodside Highlands ranks 8th of 9 neighborhoods in Portola Valley. It ranks 8th of 9 in Portola Valley for safety (4.5/5) and scores lowest on nearby merchants (0.8/5). The next-ranked neighborhoods in Portola Valley are Foothill Park.

What are the downsides of living in Woodside Highlands?

Woodside Highlands, Portola Valley scores lowest on nearby merchants (0.8/5).

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Top Neighborhoods in Portola Valley, CA

1st
Neighborhood Iamge
Portola Valley Ranch, Portola Valley, CA
Overall Score : 4.5
Portola Valley Ranch is a distinctive and well-regarded neighborhood in Portola ... See Full Page
2nd
Neighborhood Iamge
Westridge, Portola Valley, CA
Overall Score : 4.5
Westridge is an upscale, picturesque neighborhood in Portola Valley, celebrated ... See Full Page
3rd
Neighborhood Iamge
Blue Oaks, Portola Valley, CA
Overall Score : 4.5
Blue Oaks is a distinguished and exclusive neighborhood located in the scenic fo... See Full Page

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Contact Houseberry's 2026 Agent Pick for Woodside Highlands
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All information provided on this website including but not limited to - school ratings, safety, amenities, user opinions, and property data - is for general informational purposes only. We do not guarantee its reliability, accuracy, or completeness. Users should independently verify information and consult appropriate professionals as needed. By using this website, you agree Houseberry is not responsible for actions, decisions, or consequences arising from reliance on the information provided

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Bay East ©2025. CCAR ©2025. bridgeMLS ©2025. Information Deemed Reliable But Not Guaranteed. This information is being provided by the Bay East MLS, or CCAR MLS, or bridgeMLS. The listings presented here may or may not be listed by the Broker/Agent operating this website. This information is intended for the personal use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated at August 14, 2026 12:00 AM

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