20255 Skyline Boulevard Woodside, CA ^$ 2,399,000

20255 Skyline Boulevard

^$ 2,399,000

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Recently Listed

20255 Skyline Boulevard

Woodside, CA, 94062

^$ 2,399,000

Bedrooms3 Baths3.0 Sq 2,400

Monthly Estimate*

^$ 14,771

Listed by Christie's International Real Estate Sereno

20255 Skyline Boulevard, Woodside, CA 94062 - Image 1

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20255 Skyline Boulevard, Woodside, CA 94062 - Image 7

20255 Skyline Boulevard, Woodside, CA 94062 - Image 8

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Single Family Home for sale in Woodside, CA

for $2,399,000 with 3 bedrooms and 3 full baths. This 2,400 square foot home was built in 1963 on a lot size of 2.9895.

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.

Single Family Active

Price

^$ 2,399,000

Bedrooms

Full Bath

Property Type

Single Family

Taxes

^$ 0

Style

Lot Size

2.9895

Year Built

1963

Town/City

Woodside

County/Region

San Mateo

MLS | Web ID

ML82042155

Days on Market

Features

General

Living Area 2400

Heating Radiant

Cooling None

Possession Close Of Escrow

Roof Composition

Appliances Dishwasher Electric Cooktop Refrigerator

Zoning RM0000

Garage Spaces 0

Year Built 1963

View Bay City Lights Pasture

Property Subtype Single Family Residence

County San Mateo

New Construction false

Property Type Residential

HOA false

Attached Garage false

Garage Y/N false

Full Baths 3

Special Listing Conditions Standard

Status Active

Directions From Pagemill Rd. turn right onto Skyline Blvd. Cross Street: Hwy 84 (La Honda Rd) or Page Mill Rd

City Woodside

High School District Other

MLS Area 699 - Not Defined

Lot Size Units Square Feet

Lot Size Square Feet 130223

Carport Spaces 0

Property Attached Y/N false

Standard Status Active

Year Built Source Assessor

Virtual Tour 20255Skyline.com

Property Sub Type Additional Single Family Residence

Interior

Total Stories 2

Common Walls No Common Walls

Air Conditioning Y/N true

Heating Y/N true

Fireplace Y/N false

Total Bedrooms 3

Total Baths 3

Exterior

Parking Features Uncovered

Lot Features Horse Property

Total Parking 6

Lot Size Area 130223

Lot Size Acres 2.9895

Lot Size Source Assessor

Horse Y/N true

* Excluded Features

List By

Christie's International Real Estate Sereno

Broker

jen@sereno.com

Affordability Calculator

$14,771

Per Month

Monthly Principal & Interest: $14,771
Monthly Property Taxes: --
Monthly Home Insurance: --

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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

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Nearby

Trends
Schools

Single family listings in Woodside, CA

Average List Price ^$6,478,304

Percent of Sale Price 170%

About Woodside, CA

5,340 Population

-1% Since 2002

^$178,876 Median Income

51.89 Median Age

28% Households with Children

View more area information

Trends Information provided by ATTOM Data Solutions.

4827338 Elementary School

4827337 Middle School

Unknown High School High School

See complete school information

Pricing History

Date	Price	Price Change	Description
4/9/2026	$2,399,000		Listed Price

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20255 Skyline Boulevard, Woodside, CA, 94062 is a Single Family Home for sale at $2,399,000 with 2,400 sqft and a lot size of 2.9895. 20255 Skyline Boulevard has 3 bedrooms, 3.0 baths, and was built in 1963. The property's zip code is 94062 which is in Woodside, CA

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

Listing data provided courtesy of the Internet Data Exchange Program of the California Regional Multiple Listing Service, Inc..

Based on information from California Regional Multiple Listing Service, Inc. as of 4/25/2026. This information is for your personal, non-commercial use and may not be used for any purpose other than to identify prospective properties you may be interested in purchasing. Display of MLS data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals. Information from sources other than the Listing Agent may have been included in the MLS data. Unless otherwise specified in writing, Broker/Agent has not and will not verify any information obtained from other sources. The Broker/Agent providing the information contained herein may or may not have been the Listing and/or Selling Agent.

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20255 Skyline Boulevard

Single Family Home for sale in Woodside, CA

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