Woodside · San Mateo County

Woodside Hills

Woodside Hills sits at higher elevation in the western part of town, with elevated lots offering forested views toward the Coast Range.

Median Sale
$5,750,000
March 2026 · 3 closings

Woodside Hills Real Estate Market Snapshot

Median Sale Price
$5,750,000
+46.1% vs prior-year median
Avg. Days on Market
8
% List Price Received
108%
Months of Inventory
6.5
Homes Sold (March 2026)
3
Median price trend
2025 · $3,935,000 March 2026 · $5,750,000
List-price received
108%
90%100%120%+

As of March 2026 · Source: SAMCAR/MLSListings

Living in Woodside Hills

Woodside Hills sits at the higher elevations of the western side of town, set apart from Central Woodside and the village core by a meaningful gain in altitude, lot scale, and tree cover. Lots typically run from one acre at the lower end to five acres or larger along the upper streets, with mature redwood and oak canopy defining the character of most parcels. Forested view orientation toward the Coast Range, mature understory, and the absence of through-traffic are the pocket's three defining features within the broader Woodside overview.

Many Woodside Hills properties are accessed via private roads with recorded maintenance and access easements, which materially shape both daily life and transaction diligence. Households here tend to prioritize privacy, mature tree canopy, and elevation over proximity to the village commercial cluster, which is several minutes downhill via winding two-lane roads.

Schools

Woodside Hills addresses fall within Woodside Elementary School District (K-8) at Woodside School, with high school assignment to Sequoia Union High School District (Woodside High or Menlo-Atherton High depending on the address) (Woodside ESD; Sequoia Union HSD). Notable private options used by Woodside Hills households include Woodside Priory School (independent, grades 6-12) on a campus in adjacent Portola Valley and Crystal Springs Uplands. Buyers should verify the specific high school attendance area at the parcel level before writing.

Lifestyle

Daily life in Woodside Hills is residential and quiet, with most errands routing downhill to the Woodside village core (general store, restaurants, post office) or east into Menlo Park along Woodside Road. Wunderlich County Park and Huddart County Park frame the eastern and northern edges of the pocket, and the Mountain Home Road equestrian trail network connects them (Town of Woodside). Many parcels carry horse-keeping rights consistent with the town's R-1 zoning and rural land-use designations.

Commute

Woodside Hills is the most commute-distant pocket in town given its elevation and western position. Interstate 280 is reached via Woodside Road or Canada Road in 10 to 15 minutes, with Silicon Valley 20 to 30 minutes south and San Francisco 35 to 45 minutes north. The Menlo Park or Atherton Caltrain stations sit roughly 15 to 20 minutes east. Sand Hill Road's venture capital corridor is 12 to 18 minutes downhill. SFO is approximately 30 to 40 minutes north and SJC is 30 to 40 minutes south.

Market

The Woodside Hills Market Right Now

Woodside's March 2026 single-family market closed 3 transactions at a median of $5,750,000 with 8-day average DOM and a 108% list-to-sale ratio (SAMCAR via MLSListings). Within the town, Woodside Hills properties typically transact at the upper end of the Woodside range when elevation, lot scale, and forested orientation align, and at a discount when private-road condition or easement complexity weighs on diligence. The 2025 Woodside annual median was $3,935,000 across 75 closed sales (SAMCAR/MLSListings 2025 annual), and the March 2026 figure reflects a meaningful lift, though a three-sale month carries significant single-transaction variance. Months of inventory ran at 6.5 townwide, longer than flatland Peninsula markets, reflecting the longer price-discovery window typical for rural and easement-laden parcels.
Transactions

What Buyers and Sellers Should Know About Woodside Hills

Woodside Hills parcels fall under Woodside's R-1 Zone District (Town Code Chapter 153), with development standards requiring substantial setbacks and lot coverage limits consistent with the town's General Plan emphasis on rural character. Where a building fronts a private road or easement, the front setback shall be at least 50 feet from the centerline (Town of Woodside Zoning Code), which materially affects buildable envelope on hillside parcels. Many Woodside Hills properties are accessed via private roads with recorded maintenance and access easements; buyers should review title reports for shared road obligations including cost-sharing for paving, drainage, and tree work. Conservation, open space, and scenic easements appear on a number of upper-elevation parcels and may restrict construction, fencing, or vegetation removal in mapped areas (Town of Woodside). Work performed in the public right of way, including infrastructure within a public easement, requires an encroachment permit from the Town. San Mateo County's documentary transfer tax of $1.10 per $1,000 of consideration applies at recording; Woodside imposes no additional municipal transfer tax (San Mateo County Assessor-Clerk-Recorder). Standard California disclosures apply, with private-road and easement disclosures often substantial on Woodside Hills transactions.
Field Notes

Market Notes by Lisa M. Lum

Recent activity in Woodside Hills tracks the townwide Q1 2026 pattern, but condition of the private road, drainage infrastructure, and any recorded conservation easements weighs more heavily in offer rounds than square footage alone. Lisa observes that prepared properties with clean title, documented road-maintenance agreements, and clear defensible-space compliance continue to clear quickly, while parcels with deferred site work or unresolved easement questions sit longer until pricing reflects the actual scope of needed diligence and improvement.

Updated 2026-05-06

Frequently Asked Questions about Woodside Hills

How does Woodside Hills compare to Central Woodside on lot size?
Woodside Hills lots typically run from one to five acres or larger, frequently exceeding the one to three acre range common around the village core. The western elevation and forested terrain support larger parcels, with mature redwood and oak canopy on many sites.
What should buyers know about private roads in Woodside Hills?
Many parcels are accessed via private roads with recorded maintenance and access easements. Buyers should review title reports for shared cost obligations, and the front setback for any building fronting a private road must be at least 50 feet from the centerline (Town of Woodside Zoning Code).
Can you keep horses on Woodside Hills properties?
Many parcels carry horse-keeping rights consistent with Woodside's R-1 zoning and the town's rural land-use designations (Town of Woodside). Buyers should verify equestrian zoning, water supply, and proximity to the Mountain Home Road trail network at the parcel level before writing.
What schools serve Woodside Hills addresses?
Woodside Elementary School District (K-8) at Woodside School, with high school in Sequoia Union HSD (Woodside High or Menlo-Atherton High depending on the address). Buyers should confirm attendance area at the parcel before writing.
What is the transfer tax in Woodside Hills, San Mateo County?
San Mateo County charges a base transfer tax of $1.10 per $1,000 of consideration, paid by the seller at close. Some cities add a local supplemental tax. Woodside Hills does not impose an additional municipal transfer tax beyond the county base.
Does Woodside Hills require a sewer lateral inspection at sale?
Several San Mateo County jurisdictions require a private sewer lateral compliance certificate before close of escrow. The requirement varies by city — confirm with your transaction coordinator early in the listing process.
What disclosures are required when selling a home in Woodside Hills?
California requires Transfer Disclosure Statement, Natural Hazard Disclosure, lead-based paint (pre-1978), water-conserving plumbing fixtures, and smoke and carbon monoxide alarm certifications. San Mateo County properties may also require sewer lateral compliance and local supplemental disclosures.
What is the difference between median and average home price in Woodside Hills?
Median price is the middle number when all sale prices are sorted — half of homes sold above, half below. It resists distortion from a few very expensive sales. Average price is the arithmetic mean and can be skewed upward by individual high-end transactions. Median is the more reliable indicator of typical Woodside Hills home pricing.

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Last updated 2026-05-06 · By Lisa M. Lum, Realtor® · Coldwell Banker Realty · DRE 02005150