$2,399,000

beds

baths

2,400

square ft

20255 Skyline Boulevard

Woodside, California 94062

Name: 20255 Skyline Boulevard, Woodside, CA 94062
Price: 2399000 USD
Availability: InStock

New / MLS #82042155 / Single Family / Woodside

Listing information updated 4/8/2026 at 7:44pm

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.

See it in person

Open House

1:00pm - 4:00pm Saturday, April 11th, 2026 4/11/26

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1:00pm - 4:00pm Sunday, April 12th, 2026 4/12/26

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Full Features

Beds Above Grade:

Cooling System:

None

Heating System:

Radiant

Appliances:

Cooktop Electric, Dishwasher, Oven Built In, Refrigerator

Main Level Primary Bedroom:

Fireplace:

Pool:

Age:

63 Years

Roof Type:

Composition

Parking Type:

Garage - No Garage, Roomfor Oversized Vehicle

Square Feet:

2,400

Lot Size:

130223 SquareFeet

Acreage:

2.989

Internal Features:

High Ceiling

Taxes & Assessments

Tax Amount:

N/A

Tax Year:

N/A

Location

Zip Code:

94062

City:

Woodside

County:

San Mateo

Schools

School District(s):

La Honda Pescadero Unified

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Beds Above Grade:

Cooling System:

None

Heating System:

Radiant

Appliances:

Cooktop Electric, Dishwasher, Oven Built In, Refrigerator

Main Level Primary Bedroom:

Fireplace:

Pool:

Age:

63 Years

Roof Type:

Composition

Parking Type:

Garage - No Garage, Roomfor Oversized Vehicle

Square Feet:

2,400

Lot Size:

130223 SquareFeet

Acreage:

2.989

Internal Features:

High Ceiling

Tax Amount:

N/A

Tax Year:

N/A

Zip Code:

94062

City:

Woodside

County:

San Mateo

School District(s):

La Honda Pescadero Unified

Elementary School:

N/A

Middle School:

N/A

High School:

N/A

Listing Agent: Jennifer Paulson

Listing Office: Christie's International Real Estate Sereno

Disclaimer: The data relating to real estate for sale on this display comes in part from the Internet Data Exchange program of the MLSListings MLS system. Real estate listings held by brokerage firms other than Christie’s International Real Estate Sereno are marked with the Internet Data Exchange icon (a stylized house inside a circle) and detailed information about them includes the names of the listing brokers and listing agents. Based on information from the MLSListings MLS as of 4/8/2026 at 7:44pm (date the MLS data was obtained). 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.

20255 Skyline Boulevard

Woodside, California 94062