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$2,195,000$2,399,000$204K price cut

20255 Skyline Boulevard, Woodside, CA 94062

$2.4M$2.2M$204K below original ask (9%)

45% below the Woodside median of $4.0M (21 active listings)

48% of Woodside listings have cut their price · half have been listed 87+ days

3beds
3baths
2,400sqft
$915/sqft

About this home

Spanning approximately 2.92 usable acres of gently rolling meadows with picture-postcard views, this classic horse property offers miles-away tranquility just 20 minutes from Highway 280. A palatial driveway leads to a two-story, 3-bedroom, 3-bath, open-plan residence with walls of windows capturing the rolling hill and city-light views. Almost every room has glass doors to the long, view balcony. Lawn and mini orchard. A separate charming barn captures the Old West Woodside feel with a wood-beamed ceiling, full-sized bar, and French doors to a veranda with flowering vines. Just a mile to the Thomas Fogarty Winery and 8 minutes to Alice's Restaurant.

Property details

Property type
Single Family
Year built
1963
Listed
113 days ago
MLS #
82042155
Listed by
Jennifer Paulson · Christie's International Real Estate Sereno
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Location

Approximate location based on the listing address.

Copyright 2026 MLSListings Inc. Based on information from MLSListings MLS as of 7/29/2026. All data, including all measurements and calculations of area, is obtained from various sources and has not been, and will not be, verified by broker or MLS. All information should be independently reviewed and verified for accuracy. MLS Listing #82042155. Listing courtesy of Christie's International Real Estate Sereno.