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
Price:
$2,399,000
MLS #:
ML82042155
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Neighborhood:
699notdefined
Listed Date:
Apr 8, 2026
Finished Sq Ft:
2,400
Lot Size:
130,223 sqft / 2.99 acres (approx)
Year Built:
1963
See this Listing
Schools
School District:
Other
Interior
Appliances
DW, RF, ES
Bathrooms
3 Full Bathrooms
Cooling
NO
Heating
RA
Exterior
Common Walls
NCW
Parking Spots
6
Parking Total
6
Roof
CMP
View
BA, CI, PAS
Financial
Map
Community
- Address20255 Skyline BL Woodside CA
- CityWoodside
- CountySan Mateo
- Zip Code94062
Market Summary
Current real estate data for Single Family in Woodside as of Apr 16, 2026
42
Single Family Listed
43
Avg DOM
1,569
Avg $ / SqFt
$5,393,093
Avg List Price
Property Summary
- 20255 Skyline BL Woodside CA is a Single Family for sale in Woodside, CA, 94062. It is listed for $2,399,000 and features 3 beds, 3 baths, and has approximately 2,400 square feet of living space, and was originally constructed in 1963. The current price per square foot is $1,000. The average price per square foot for Single Family listings in Woodside is $1,569. The average listing price for Single Family in Woodside is $5,393,093.
Similar Listings Nearby
Courtesy of Christie’s International Real Estate Sereno. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the California Regional Multiple Listing Service. Detailed information about real estate listings held by brokerage firms other than include the name of the listing broker. Neither the listing company nor shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. California Regional Multiple Listing Service. All rights reserved. 20255 Skyline BL
Woodside, CA