Simon Sahi Real Estate — Real Results

Woodside, California

Woodside
Hills

Forested hillside estates west of the 280 corridor, where privacy, views and redwood groves come standard.

Explore the neighborhood Meet Simon

The neighborhood

Woodside Hills homes for sale in the western foothills.

Woodside Hills — the forested hillsides west of Highway 280 — is where Woodside's rural promise is fully kept. Winding roads climb through redwood and oak forest to estates on large, private parcels, many with canyon or hill views and room for horses, gardens and guest houses.

The 280 freeway keeps the hills connected: the village, Stanford and the Peninsula's job centers are all within a practical drive. Buyers find retreats ranging from woodland contemporaries to classic country estates; sellers offer privacy and scale that feel increasingly rare this close to Silicon Valley.

Hillside privacyLarge forested parcels west of Hwy 280
Natural settingRedwood groves, oaks and canyon views
ConnectedFast 280 access to Stanford and the Peninsula

A sense of place

Forest seclusion, freeway close.

Woodside Hills is the classic Woodside trade: come home to redwoods and quiet, then be on 280 in minutes. The roads wind, the canopy closes overhead and the estates reveal themselves one by one. It attracts buyers who want land, privacy and a genuine retreat — without a remote commute.

ArchitectureWoodland contemporaries and classic country estates.
LandscapeRedwood groves, oak forest and canyon views.
Daily lifeRetreat setting; 280 and the village minutes away.

01 / Education

Schools near Woodside Hills Woodside homes.

Public school placement is determined by the district and can change. Most Woodside addresses fall in the Woodside Elementary School District (K–8) and the Sequoia Union High School District (Woodside High School); some foothill parcels are served by neighboring districts. Confirm the exact property address directly with the district before relying on an assignment.

Representative Woodside Hills Tudor-style estate among redwoods
District resources

School resources for Woodside Hills home buyers.

Woodside Hills addresses are typically served by the Woodside Elementary School District (K–8) and Woodside High School in the Sequoia Union High School District, though some western parcels fall in neighboring districts. Confirm the exact property address directly with the district.

Woodside Elementary School District

K–8 district and enrollment resources

District

Woodside Elementary School

TK–8 campus · 3195 Woodside Road

School

Woodside High School

Sequoia Union high school · 199 Churchill Avenue

School

Woodside Priory School

Independent 6–12 school · 302 Portola Road, Portola Valley

School

02 / Parks

Forest parks in every direction.

Huddart and Wunderlich parks ring the hills with thousands of acres of redwood trails.

Redwood forest path near Woodside Hills, typical of nearby Huddart Park
01

Huddart Park

974 acres of redwood and fir forest · 1100 Kings Mountain Road

County parks
02

Wunderlich Park

942 acres with the historic Folger Stable · 4040 Woodside Road

County parks
Park hours, fees and trail access can change. Check San Mateo County Parks before visiting.

Nearby outdoors

Hiking & Trails

Explore Huddart's redwood canyons, Wunderlich's meadows or Filoli's natural lands — all minutes from the hills.

01

Huddart Park trails

Miles of trails through riparian corridors and steep hillsides with Bay views

County parks
02

Wunderlich Park trails

Hiker and equestrian trails through redwoods, madrones and open meadows

County parks
03

Filoli

16-acre formal garden plus 650+ acres of natural lands with trail loops · 86 Cañada Road

Plan a visit
Trail conditions and seasonal closures can change. Check the linked official resources before heading out.

03 / Local life

Amenities near Woodside Hills homes.

The village covers daily life; Alice's and the ridge landmarks are a scenic drive west.

Representative Woodside Hills villa with motor court and gardens
Hillside estates with canyon views
Representative Woodside Hills ranch estate at dusk with white-fenced pastures
Redwoods as the setting
Restaurants

Nearby tables

Buck's of Woodside is the classic drive-down destination, while Alice's Restaurant on Skyline makes a scenic weekend run.

Buck's
Shopping

Everyday needs

Roberts Market in Woodside Town Center covers daily groceries; Portola Valley Town Center and Stanford Shopping Center are both within an easy drive.

Outdoors

A retreat lifestyle

Huddart and Wunderlich parks put thousands of acres of trails around the neighborhood, and the hillside parcels themselves offer room for horses, gardens and guest houses.

Getting around

Getting around Woodside Hills.

Woodside Hills pairs a true retreat setting with fast 280 access to the whole Peninsula.

10

Huddart Park

10 min drive · 974 acres of redwood forest and trails

Directions
10

Woodside Town Center

10 min drive · Roberts Market, Buck's of Woodside and local shops

Directions
14

Filoli

14 min drive · Historic house and 16-acre formal garden

Directions
15

Alice's Restaurant

15 min drive · Skyline landmark at Sky Londa

Directions
20

Stanford University

20 min drive · Campus, arts and Cardinal athletics

Directions
22

Palo Alto Airport

22 min drive · General aviation nearby

Directions
32

San Jose International Airport (SJC)

32 min drive · Nearest major commercial airport

Directions
30

San Francisco International Airport (SFO)

30 min drive · International gateway

Directions
Drive times are approximate and vary by exact address, route and traffic. Confirm details for a specific property independently.

Market snapshot

Home values in Woodside Hills.

A snapshot of the market in Woodside Hills — one of Woodside’s priciest hillside pockets, with values above the town average.

$250,000+

Median household income

Citywide approx. — U.S. Census Bureau ACS 5-year estimates

$5.9M

Median home price

Median list price, Woodside Hills — Movoto, May 2026 approx.

$10M

High-end price point

Top current listing — 150 Brookwood Rd listed at $9.998M, May 2026 (neighborhood approx.)

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

Buyer guidance

Buying a home in Woodside Hills?

Woodside Hills buyers should evaluate the hillside itself: slope, drainage, sun exposure, defensible space and winter access all vary parcel by parcel. Compare architecture and condition, then consider how the retreat setting balances against the drive down to 280 and daily services.

Wells, septic and hillside insurance are common considerations here — verify them with school placement for the exact address. Local guidance can help you read hillside comparables and access questions.

Call (650) 274-1134Email Simon

Seller guidance

Selling your Woodside Hills home?

A Woodside Hills marketing plan should sell the retreat: forest photography, the privacy of the setting, room for horses and guests — balanced with the honest convenience of 280 access. The combination is the story.

Preparation starts with the specific estate, its hillside setting and relevant comparables. From pricing and presentation to launch strategy, the goal is to reach buyers seeking a redwood retreat near the valley.

Call (650) 274-1134Email Simon

Buyer & seller questions

Woodside Hills real estate FAQ.

What types of homes are found in Woodside Hills?

Woodside Hills holds woodland contemporaries and classic country estates on large, private forested parcels west of Highway 280.

Which public school districts serve Woodside Hills?

Most addresses are in the Woodside Elementary School District (K–8) and Sequoia Union High School District (Woodside High School), though some western parcels differ. Confirm the exact address with the district.

What parks and trails are near Woodside Hills homes?

Huddart and Wunderlich parks ring the hills with thousands of acres of redwood trails, and Filoli's gardens and natural lands are minutes away.

What should buyers consider in Woodside Hills?

Assess slope, drainage, sun exposure, defensible space, winter access, wells and septic — then verify school placement and property details for the exact address.

How should a Woodside Hills seller prepare for the market?

Market the retreat setting and the 280 convenience together, with hillside-specific pricing. For a tailored plan, call Simon Sahi at (650) 274-1134 or email SIMON@SPSILICONVALLEY.COM.

Continue exploring

Explore more Woodside neighborhoods.

Local guidance

Explore Woodside Hills with Simon Sahi.

For a property-specific view of Woodside Hills 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