Simon Sahi Real Estate — Real Results

Portola Valley, California

Woodside
Highlands

Foothill streets off Portola Road, where homes back to open slopes with redwoods, meadows and long western views.

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The neighborhood

Woodside Highlands Portola Valley homes for sale in a singular setting.

Set in the foothills off Portola Road near Portola Valley’s northern edge, Woodside Highlands is a hillside enclave of homes on generous, often sloping lots. Redwoods and oaks frame the streets, and many properties look west over meadows toward the Santa Cruz Mountains.

Buyers are drawn to the Highlands’ combination of elevation, privacy and proximity: Windy Hill’s trailheads are minutes south, Filoli and Huddart Park are a short drive north, and Stanford, Sand Hill Road and Highway 280 are all within easy reach. For sellers, setting and outlook carry the listing.

Foothill settingSloping lots with redwoods and meadow views
Trail accessWindy Hill trailheads minutes south
ConnectedQuick to Stanford, Sand Hill and 280

A sense of place

Foothills, forest edge and big skies.

Woodside Highlands feels like the meeting point of town and wild. Streets climb through mixed evergreen forest, homes perch to catch the view, and the evening light rakes across the western meadows. It is quiet and private, yet the Town Center and the Woodside village are both a short drive.

ArchitectureHillside homes and updated ranches angled toward the view.
LandscapeRedwoods, oaks, meadows and long western outlooks.
Daily lifeTrail mornings, garden afternoons and sunset decks.

01 / Education

Schools near Woodside Highlands Portola Valley homes.

Public school placement is determined by the local districts and can change. Confirm the exact property address directly with the district before relying on an assignment.

California elementary school campus building
District resources

District and campus resources for Highlands buyers.

Woodside Highlands is served by the area’s highly regarded public school districts — Portola Valley School District for kindergarten through eighth grade in much of the area, with high school through the Sequoia Union High School District. Confirm the exact property address directly with each district before relying on an assignment.

Portola Valley School District

Official district and enrollment resources

Official site

Ormondale School

Grades K–3 · 200 Shawnee Pass, Portola Valley

Official site

Corte Madera School

Grades 4–8 · 4575 Alpine Road, Portola Valley

Official site

02 / Parks

Preserves in both directions.

Windy Hill’s summit trails lie minutes south on Portola Road, while Huddart Park’s redwoods and Filoli’s gardens wait a short drive north.

Redwood forest hiking trail near Portola Valley
01

Windy Hill Open Space Preserve

1,335-acre preserve · 555 Portola Road · summit views

Official site
02

Huddart Park

Redwood groves and meadows in nearby Woodside

03

Filoli

Historic house and 16 acres of formal gardens in Woodside

Facilities and access conditions can change. Review the official preserve and town listings before visiting.

Nearby outdoors

Hiking & Trails

Highlands residents split their trail time between Windy Hill’s open ridges and the redwood canyons to the north.

01

Windy Hill trails

Spring Ridge Trail to the 1,900-foot summit.

Official site
02

Huddart Park trails

Redwood-lined routes a short drive north.

03

Portola Road cycling

Valley-floor riding toward the Town Center and Alpine Road.

Trail conditions, seasonal closures and access rules can change. Check the linked official resources before heading out.

03 / Local life

Amenities near Woodside Highlands.

The Town Center and Woodside village split daily needs; the Alpine Inn, Stanford and Palo Alto cover dining and shopping.

Luxury home exterior at dusk in the Portola Valley foothills
Foothill home with redwoods and meadow views
Home terrace with mountain views in Portola Valley
Outdoor living at the forest edge
Dining

Alpine Inn & Woodside tables

Alpine Inn’s 1852 beer garden is minutes south, while Woodside’s village restaurants and Palo Alto dining are a short drive.

Shopping

Town Center & Stanford

The Thursday farmers’ market at 765 Portola Road and Stanford Shopping Center handle weekly shopping.

Everyday

Groceries & services

Roberts Market in Woodside and Bianchini’s Market in Ladera cover daily groceries within a short drive.

Map & getting around

Getting around Woodside Highlands.

Woodside Highlands sits in the foothills off Portola Road near Portola Valley’s northern edge. These are the everyday destinations Highlands residents drive to most.

8 min

Windy Hill Open Space Preserve

8 min drive · Portola Valley area

Directions
5 min

Portola Valley Town Center

5 min drive · Portola Valley area

Directions
10 min

Filoli

10 min drive · Portola Valley area

Directions
12 min

Huddart Park

12 min drive · Portola Valley area

Directions
15 min

Stanford University

15 min drive · Portola Valley area

Directions
16 min

Downtown Palo Alto

16 min drive · Portola Valley area

Directions
28 min

San Francisco International Airport

28 min drive · Portola Valley area

Directions
Drive times are approximate and vary with traffic. Tap Directions for live routing.

Market snapshot

Home values in Woodside Highlands.

Portola Valley commands some of the Peninsula’s strongest home values. Here’s a quick snapshot of the market around Woodside Highlands.

$250K+

Median household income

Citywide approx. · U.S. Census ACS 5-year

$4.0M

Median home price

Citywide approx. · Zillow & Redfin market data

$20M+

High-end price point

Citywide approx. · recent top sale $56M, Nov 2025

Figures are approximate as of Sept 2026. Sources: U.S. Census Bureau (ACS), Zillow/Redfin market data.

Buyer guidance

Buying a home in Woodside Highlands?

Highlands homes reward a property-by-property approach. Compare view, usable hillside land, privacy, improvements and access, then consider how each address connects to Portola Road, Windy Hill trailheads and town services.

School assignments and property details — including hillside and district-boundary considerations — should be verified for the exact address. Local guidance can help you evaluate comparable sales and understand how each home fits the foothills.

Call (650) 274-1134Email Simon

Seller guidance

Selling your Woodside Highlands home?

A Highlands marketing plan should lead with setting. Redwood framing, meadow views, sunset outlooks and foothill privacy all shape how the home is presented.

Thoughtful preparation starts with the specific home, its outlook and relevant comparable sales. From pricing and presentation to launch strategy, the goal is to connect the property with buyers who want the foothill edge.

Call (650) 274-1134Email Simon

Buyer & seller questions

Woodside Highlands real estate FAQ.

What types of homes are found in Woodside Highlands?

Woodside Highlands includes hillside homes and updated ranches on generous, often sloping lots in the foothills off Portola Road, many with western meadow and mountain views.

Which public school districts serve Woodside Highlands?

Much of the area is served by the Portola Valley School District for grades K–8 and the Sequoia Union High School District for high school, though boundaries can vary — buyers should confirm the exact address directly with each district.

What parks are near Woodside Highlands homes?

Windy Hill Open Space Preserve’s summit trails are minutes south, Huddart Park’s redwoods are a short drive north, and Filoli’s gardens are nearby in Woodside.

What should buyers consider when comparing Highlands homes?

Compare the view, usable land, privacy, improvements and hillside access, then independently verify school placement and property-specific details before making a decision.

How should a Highlands seller prepare for the market?

A strong plan should present the home’s setting, views and improvements clearly, supported by property-specific pricing and marketing guidance from a local specialist.

Continue exploring

Explore more Portola Valley neighborhoods.

Local guidance

Explore Woodside Highlands with Simon Sahi.

For a property-specific view of Woodside Highlands homes, school placement, neighborhood edges and nearby amenities, begin with the exact address and a thoughtful local conversation.

Simon Sahi
Visit SimonSahi.com(650) 274-1134SIMON@SPSILICONVALLEY.COMCA DRE #01953287