Woodside Real Estate

Find luxury property, land, condos, houses & homes for sale in Woodside with real estate agent & Realtor, Chris Iverson.

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Woodside Real Estate

 

Redwoods, Horses, & Absolute Privacy: 94062

View 2025 Inventory

2025 Market Snapshot

$4.5M - $15M+

Median Home Price

30-60 Days

Avg Days on Market

3 Acres

Common Estate Size

Varied

Market Velocity

The Woodside Way

Woodside is the antidote to Silicon Valley's frenetic pace. It is a town of unmarked roads, towering redwoods, and world-class equestrian facilities. Here, privacy is not just a feature; it is the culture.

The Micro-Markets

Central Woodside

The Estate Zone

Home to the largest flat lots (3+ acres) and the most valuable estates. Walking distance to Roberts Market and The Village Pub.

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Woodside Glens

The Village Feel

A tight-knit community of smaller lots and charming homes carved into the hillside. Known for neighborly vibes and lower entry prices.

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Mountain Home Road

Billionaire's Row

The most prestigious corridor in the town. Massive, gated compounds set back from the road, offering the ultimate in seclusion.

View Luxury Estates →

Woodside vs. The Competition

Neighborhood Vibe vs. Woodside The Trade-off
Atherton Manicured Luxury. Flat, open, less tree cover. Environment. Atherton is suburban; Woodside is rural. You trade "lawns" for "forests."
Portola Valley Rustic Views. Hillside homes with valley vistas. The Canopy. PV is sunnier and more open. Woodside is darker, cooler, and more private.
Los Altos Hills New Money Modern. Tech-centric, fewer trees. History. Woodside has deep historic roots (1800s); LAH feels newer and more developed.

Schools & Lifestyle

Education

Woodside operates as a single-school district, creating an incredibly bonded community.

  • Woodside Elementary (K-8): A "Private School in a Public District." Massive endowment, organic garden, and unrivaled resources.
  • Woodside High School: The assigned public high school (located in Redwood City).
  • Private Options: Woodside Priory (6-12) is located directly in town.

The Equestrian Life

Woodside is the equestrian capital of the Peninsula.

  • The Horse Park: 272 acres of competition arenas and cross-country courses.
  • Trail System: Hundreds of miles of dedicated horse trails connecting Huddart and Wunderlich Parks.
  • The Village Pub: The Michelin-starred "local canteen" for the elite.

Exclusive Woodside Inventory

Woodside is a "pocket listing" market. Many of the finest estates on Mountain Home and Cañada Road never hit the MLS.

Woodside Real Estate

Silicon Valley's Most Exclusive Luxury Home Market

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Woodside Real Estate Market Overview

$3.8M

Median Home Price

27

Days on Market (Avg)

97%

List-to-Sale Price Ratio

+6.2%

Year-over-Year Appreciation

Woodside Community Highlights

Woodside is renowned as one of the most exclusive communities in Silicon Valley, offering:

  • Minimum 1-acre lot sizes (most 2+ acres)
  • Equestrian-friendly community with riding trails
  • 20 minutes to Stanford University
  • 30 minutes to San Francisco International Airport
  • Private security through Woodside Patrol
  • Historic downtown with Michelin-starred restaurants

The Woodside real estate market remains one of the most stable luxury markets in the nation, with properties often selling off-market to preserve privacy for high-profile residents.

Exclusive Woodside Neighborhoods

 

Devonshire

Woodside's most prestigious enclave featuring grand estates on 2+ acre parcels with panoramic views.

Median Price

$4.2M

Avg Lot Size

2.3 acres

Inventory

3-5 homes

Explore Devonshire →
 

Woodside Hills

Private, wooded properties with architectural diversity and excellent school access.

Median Price

$3.6M

Avg Lot Size

1.5 acres

Inventory

8-12 homes

Explore Woodside Hills →
 

Skywood

Mountain retreats with spectacular views and privacy near the famous Skylonda area.

Median Price

$3.9M

Avg Lot Size

3.1 acres

Inventory

4-6 homes

Explore Skywood →

Top-Rated Schools in Woodside

Woodside Elementary School

Grades K-8 | Public

10

GreatSchools Rating

#1 in San Mateo County

Address: 3195 Woodside Rd, Woodside, CA 94062

Notable: Spanish immersion program, STEM focus

Menlo-Atherton High School

Grades 9-12 | Public

9

GreatSchools Rating

Top 5% in California

Address: 555 Middlefield Rd, Atherton, CA 94027

Notable: 95% college attendance rate

Woodside Priory School

Grades 6-12 | Private

A+

Niche Rating

#2 Private HS in Bay Area

Address: 302 Portola Rd, Portola Valley, CA 94028

Notable: Benedictine college prep, 8:1 student ratio

Exclusive Woodside Listings

Discover the finest luxury properties currently available in Woodside. Contact us for private showings and off-market opportunities.

 

125 Mountain Home Rd

$7,250,000

  • 5 Beds
  • 5.5 Baths
  • 6,500 Sq Ft
  • 2.1 Acres

Stunning contemporary estate with panoramic views, smart home technology, and resort-style pool and spa.

View Details
 

18 Canyon Trail

$12,995,000

  • 6 Beds
  • 7 Baths
  • 9,200 Sq Ft
  • 4.5 Acres

Architectural masterpiece with equestrian facilities, guest house, and vineyard.

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42 Skyline Blvd

$9,750,000

  • 5 Beds
  • 6.5 Baths
  • 7,800 Sq Ft
  • 3.2 Acres

Modern farmhouse with panoramic Bay views, infinity pool, and organic garden.

View Details

Woodside Lifestyle & Amenities

 

Equestrian

World-class equestrian facilities including Webb Ranch and Horse Park

 

Private Clubs

Exclusive access to The Village Club and Woodside Golf & Country Club

 

Nature

Adjacent to 1,400+ acres of open space at Huddart and Wunderlich Parks

 

Security

24/7 private patrol service and gated community options

Work With Me

Chris Iverson has worked in the real estate industry for over 18 years and has amassed a renowned class of clientele and unmatched experience.