San Mateo County · Incorporated Town Equestrian town

Woodside

Silicon Valley's equestrian enclave — horse trails, estate acreage, and intentional rurality

Median Sale
$4,260,000
April 2026 · 13 closings

Woodside Real Estate Market Snapshot

Median Sale Price
$4,260,000
+8.3% vs prior-year median
Avg. Days on Market
73
% List Price Received
99%
Months of Inventory
5.1
Homes Sold (April 2026)
13
Median price trend
2025 · $3,935,000 April 2026 · $4,260,000
List-price received
99%
90%100%120%+

As of April 2026 · Source: SAMCAR/MLSListings

Living in Woodside

Woodside is the Peninsula's equestrian and rural-residential anchor, a town of 5,300 residents spread across approximately 12 square miles of wooded hillside between Skyline Boulevard and Interstate 280. The town's character is defined by horse-keeping rights, private road easements, and one of the largest concentrations of preserved open space on the central Peninsula. The General Plan emphasizes preservation of rural scale and substantial setbacks across all R-1 zoning sub-districts.

Daily life in Woodside revolves around the Town's central village (general store, restaurants, post office) and surrounding open-space resources including Wunderlich County Park, Huddart County Park, and the Mountain Home Road equestrian trail network. Many properties are equestrian-zoned with on-site stables, riding rings, and direct trail access. The Woodside-Atherton Auxiliary serves the town's social calendar alongside private clubs.

Woodside Elementary School District (K-8) operates Woodside School at the heart of the town, with high school students attending Sequoia Union High School District (Woodside High and Menlo-Atherton High depending on attendance area). Notable private options include Woodside Priory School (independent, grades 6-12) and Crystal Springs Uplands. The combination of school access, equestrian character, and substantial open-space adjacency makes Woodside the choice for buyers prioritizing rural privacy and horse-keeping over walkability. The combination of these factors continues to position the city as a stable choice for buyers prioritizing long-term tenure.

Woodside's rural character requires buyers to think about property maintenance differently than higher-density Peninsula towns: defensible-space wildfire requirements, septic systems on certain parcels, well water on others, and private road maintenance agreements all add operating-cost considerations that flatland Peninsula buyers may not encounter. The town's limited commercial infrastructure also means most daily errands run through adjacent Menlo Park or Portola Valley.

Schools

Woodside Elementary School District operates Woodside School (K-8) at the heart of the town, with consistent state assessment performance and strong family engagement. High school students attend Sequoia Union High School District, with attendance area determining whether students go to Woodside High School or Menlo-Atherton High School. Notable private options include Woodside Priory School (independent, grades 6-12, on a 51-acre campus in adjacent Portola Valley), Crystal Springs Uplands School (independent, grades 6-12), and Sacred Heart Schools Atherton (PK-12). Many Woodside families combine public elementary and private high school, or vice versa, reflecting the town's flexibility on educational choice. Buyers and sellers in this segment of the market typically weigh school district access, lot size, and proximity to commercial amenities when narrowing target neighborhoods.

Lifestyle

Daily life centers on the Town's central village (general store, restaurants, post office, ranger station) and surrounding open-space resources. Wunderlich County Park (942 acres of redwood and oak forest) and Huddart County Park (974 acres) sit at the edges of town, with the Mountain Home Road equestrian trail network connecting them. The Woodside Country Club provides golf and swim membership, and several private equestrian clubs operate within the town. Many properties feature on-site stables, riding rings, and direct trail access. The Annual Woodside Day Parade and other town events anchor the social calendar. Buyers and sellers in this segment of the market typically weigh school district access, lot size, and proximity to commercial amenities when narrowing target neighborhoods.

Commute

Woodside is the most commute-distant of the Tier 1 cities, reflecting its rural character. Interstate 280 provides direct access to Silicon Valley in 15-25 minutes and to San Francisco in 35-45 minutes. The Menlo Park or Atherton Caltrain stations sit 10-15 minutes east via Woodside Road. Sand Hill Road's venture capital corridor is 10-15 minutes east. San Francisco International Airport is approximately 25-35 minutes north, and SJC is 25-35 minutes south. The town's location at higher elevation and away from US-101 means buyers trade direct rail access for rural privacy and substantial open-space adjacency. Buyers and sellers in this segment of the market typically weigh school district access, lot size, and proximity to commercial amenities when narrowing target neighborhoods.

Market

The Woodside Market Right Now

Woodside's first quarter of 2026 closed 3 single-family transactions in March at a median sale price of $5,750,000, with homes averaging 8 days on market and selling at 108% of list price (SAMCAR via MLSListings). Compared to the 2025 annual median of $3,935,000, March 2026 reflects approximately a 46.1% lift, consistent with the Peninsula's supply-constrained pattern in early 2026. Months of inventory ran at 6.5, and homes priced and prepared for the current market continued to clear quickly. Total March 2026 sale volume reached approximately $20 million across 3 closed transactions. Buyers preparing competitive offers should arrive with full pre-approval, condensed contingency timelines, and clear underwriting on local zoning and design review considerations. Sellers with professional staging and accurate pricing have continued to capture multiple competing offers within days, matching the broader trajectory described in the California 2026 housing market forecast for Silicon Valley. The very small March transaction count (three closings) means median figures are subject to substantial single-sale variance; longer-term trends are best read against the 2025 annual figures for proper context. Sellers preparing properties with professional staging and accurate pricing have continued to capture multiple competing offers. The combination of school district access, supply scarcity, and proximity to major employers continues to drive sustained demand. The supply-constrained pattern matches the broader Peninsula trajectory described in the California 2026 housing market forecast. Inspection windows and disclosure packages are typically more involved given the age and scale of properties in this market segment. Buyers should arrive with full pre-approval and condensed contingency timelines to remain competitive in this market.
Buildings fronting a private road or easement in Woodside must observe a 50-foot front setback measured from the centerline. — Woodside public records
Transactions

What Buyers and Sellers Should Know About Woodside

Woodside's R-1 Zone District (Town Code Chapter 153) governs single-family residential property, with development standards requiring substantial setbacks and lot coverage limits. If a building fronts a private road or easement in Woodside, the front setback shall be at least 50 feet from the centerline (Town of Woodside Zoning Code). Many Woodside properties are accessed via private roads with recorded maintenance and access easements; buyers should review title reports carefully for shared road obligations, which can include cost-sharing for maintenance, repair, and snow clearing in higher elevations. Conservation, open space, and scenic easements appear on many parcels and may restrict construction, fencing, or vegetation removal in mapped areas. Work performed in the public right of way, including infrastructure within a public easement, requires an encroachment permit from the Town. Many properties are equestrian-zoned with horse-keeping rights, on-site stables, and direct trail access. San Mateo County's base documentary transfer tax of $1.10 per $1,000 of consideration applies at recording; Woodside does not impose an additional municipal transfer tax. Standard California disclosures apply (California Civil Code §1102), with private-road and easement disclosures often substantial. Woodside's horse-keeping rights are baked into the zoning code, and many properties feature on-site stables, riding rings, or paddock infrastructure that may convey with the sale subject to negotiation. Buyers planning to keep horses should verify the parcel's current equestrian zoning, water-availability for trough infrastructure, and proximity to the Mountain Home Road trail network. Sellers without current horse-keeping who maintain the equestrian zoning typically benefit from disclosure framing that emphasizes the optional nature of the rights to broader buyer pools. Woodside's water service is provided by either California Water Service or private well infrastructure depending on the parcel's location and elevation. Buyers planning equestrian or irrigation-heavy improvements should verify water source, supply capacity, and any well-permit considerations during the inspection period.
Field Notes

Market Notes by Lisa M. Lum

Woodside's Q1 2026 figures carry the strongest sample-size caveat of any Tier 1 city: just three March closings at $5.75M median. The 6.5 months of inventory reading reflects rural and easement-laden properties where price discovery takes longer than higher-volume Peninsula markets. The 8-day DOM on the three closings is informative — when properties are accurately priced and professionally prepared in this market, buyers move quickly. The town's private-road easements, conservation overlays, and substantial title work demand careful buyer-side due diligence; experienced agents on both sides of the transaction are typically the difference between a smooth close and an extended escrow.

Updated 2026-05-03

Woodside Neighborhoods

Distinct residential areas within Woodside, each with its own character, lot patterns, and market dynamics.

  • Central Woodside

    Central Woodside surrounds the Town's village core, with proximity to the general store, post office, and elementary school. Lots typically run from one to three acres, with horse-keeping rights and direct equestrian trail access. Architecture ranges from 1920s ranch estates to substantial modern reconstructions on heavily wooded parcels.

    Explore Central Woodside →

  • Woodside Hills

    Woodside Hills sits at higher elevation in the western part of town, with elevated lots offering forested views toward the Coast Range. Lot sizes typically run from one to five acres or larger, with mature redwood and oak canopy. Many properties are accessed via private roads with recorded easements requiring careful title review at transaction time.

    Explore Woodside Hills →

  • Skyline

    Skyline neighborhoods sit along Skyline Boulevard at the highest elevations of Woodside, with substantial lots, ridge views, and direct access to the open-space preserves of the Coast Range. Many properties are accessed via private roads, and lot sizes commonly exceed five acres. The area's elevation and seclusion command premium pricing.

    Explore Skyline →

  • Family Farm

    Family Farm is a gated estate community within Woodside, offering a smaller subset of high-end properties with private security, common open space, and a controlled-access entry. The neighborhood's combination of estate scale, gated access, and Woodside character draws international and tech-equity buyers seeking maximum privacy.

    Explore Family Farm →

  • Woodside Heights

    Woodside Heights is a smaller residential pocket on the eastern side of the town with slightly more accessible lot pricing and consistent ranch-era architecture. Lot sizes typically run from one to two acres, with horse-keeping rights and a quieter neighborhood feel than Central Woodside or the upper Skyline areas.

    Explore Woodside Heights →

Frequently Asked Questions about Woodside

What is the median home price in Woodside?
In March 2026, the median single-family sale price in Woodside was $5,750,000 with homes averaging 8 days on market and selling at 108% of list price. The 2025 annual median was $3,935,000 (SAMCAR via MLSListings). Note March's 3-transaction sample is small.
What are private road easements in Woodside?
Many Woodside properties are accessed via private roads with recorded maintenance and access easements. Town code requires the front setback to be at least 50 feet from the centerline of a private road. Buyers should review title reports for shared road obligations and cost-sharing agreements.
What schools serve Woodside?
Woodside is served by Woodside Elementary School District (K-8) operating Woodside School. High school students attend Sequoia Union High School District (Woodside High School or Menlo-Atherton High). Notable private options include Woodside Priory and Crystal Springs Uplands.
Can you keep horses in Woodside?
Yes. Many Woodside properties are equestrian-zoned with horse-keeping rights, on-site stables, and direct equestrian trail access. The Mountain Home Road trail network connects Wunderlich and Huddart County Parks (Town of Woodside).
Are there sub-neighborhoods within Woodside?
Yes. Central Woodside (around the village core), Woodside Hills, Skyline (along Skyline Boulevard at higher elevations), Family Farm (gated community), and Woodside Heights each have different lot patterns and access characteristics.
What is the transfer tax in Woodside?
San Mateo County charges a base documentary transfer tax of $1.10 per $1,000 of consideration. Woodside does not impose an additional municipal transfer tax beyond the county base.
What is the transfer tax in Woodside, 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 does not impose an additional municipal transfer tax beyond the county base.
Does Woodside 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?
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?
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 home pricing.

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Last updated 2026-05-19 · By Lisa M. Lum, Realtor® · Coldwell Banker Realty · DRE 02005150