20255 Skyline Boulevard Woodside, CA $ 2,399,000
20255 Skyline Boulevard
$ 2,399,000
Recently Listed
Open House 4/11 1pm - 4pm
Share Save

20255 Skyline Boulevard

Woodside, CA, 94062
$ 2,399,000
Bedrooms3 Baths3.0 Sq 2,400

Monthly Estimate*

$ 14,771

20255 Skyline Boulevard, Woodside, CA 94062 - Image 1
20255 Skyline Boulevard, Woodside, CA 94062 - Image 2
20255 Skyline Boulevard, Woodside, CA 94062 - Image 3
20255 Skyline Boulevard, Woodside, CA 94062 - Image 4
20255 Skyline Boulevard, Woodside, CA 94062 - Image 5
20255 Skyline Boulevard, Woodside, CA 94062 - Image 6
20255 Skyline Boulevard, Woodside, CA 94062 - Image 7
20255 Skyline Boulevard, Woodside, CA 94062 - Image 8
20255 Skyline Boulevard, Woodside, CA 94062 - Image 9
20255 Skyline Boulevard, Woodside, CA 94062 - Image 10
20255 Skyline Boulevard, Woodside, CA 94062 - Image 11
20255 Skyline Boulevard, Woodside, CA 94062 - Image 12
20255 Skyline Boulevard, Woodside, CA 94062 - Image 13
20255 Skyline Boulevard, Woodside, CA 94062 - Image 14
20255 Skyline Boulevard, Woodside, CA 94062 - Image 15
20255 Skyline Boulevard, Woodside, CA 94062 - Image 16
20255 Skyline Boulevard, Woodside, CA 94062 - Image 17
20255 Skyline Boulevard, Woodside, CA 94062 - Image 18
20255 Skyline Boulevard, Woodside, CA 94062 - Image 19
20255 Skyline Boulevard, Woodside, CA 94062 - Image 20
20255 Skyline Boulevard, Woodside, CA 94062 - Image 21
20255 Skyline Boulevard, Woodside, CA 94062 - Image 22
20255 Skyline Boulevard, Woodside, CA 94062 - Image 23

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.

See more

Open House

4/11/2026 1:00 PM - 4:00 PM
4/12/2026 1:00 PM - 4:00 PM
20255 Skyline Boulevard Woodside, CA
* Some states or local ordinances may prohibit Open Houses at this time, please confirm with your Weichert agent or local rep to confirm

Single Family Active

Price

$ 2,399,000

Bedrooms

3

Full Bath

3

Property Type

Single Family

Taxes

$ 0

Style

Detached

Lot Size

2.9895

Year Built

1963

Town/City

Woodside

County/Region

San Mateo

MLS | Web ID

ML82042155

Features
General
Living Area 2400
Heating Radiant
Cooling None
Roof Composition Shingles
Appliances Dishwasher Electric Range Oven
Zoning RM00
Garage Spaces 0
Year Built 1963
View Bay City Lights Pasture
Stories Count 2
Levels Two Story
Property Subtype Detached
County San Mateo
Property Type Residential
HOA false
Garage Y/N false
Full Baths 3
Status Active
Directions From Pagemill Rd. turn right onto Skyline Blvd.
City Woodside
High School District La Honda-Pescadero Unified
MLS Area Listing
Lot Size Square Feet 130223
Standard Status Active
Elementary School District La Honda-Pescadero Unified
See more
Interior
Interior Amenities Family Room Storage
Air Conditioning Y/N false
Heating Y/N true
Fireplace Y/N false
Total Bedrooms 3
Kitchen Features Tile Counters Dishwasher Electric Range/Cooktop Oven Built-in
Total Baths 3
See more
Exterior
Lot Features Horses Possible
Lot Size Area 2.9895
Building Area Total 2400
Lot Size Acres 2.9895
ADU Y/N true
See more
* Excluded Features
List By
Jennifer Paulson

Listing Agent

Christie's International Real Estate Sereno

Broker

jen@sereno.com

Email

Affordability Calculator

$14,771
Per Month
100%
0%
0%
Monthly Principal & Interest
$14,771
Monthly Property Taxes
--
Monthly Home Insurance
--
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.
Learn more about how to save

Discover how much house you can afford

Your dream home may be within reach.

Learn More about how to save

The time to sell is now
THE TIME TO SELL IS NOW! What's my home worth?
Nearby
4399476 Elementary School
0 Middle School
Unknown High School High School
Pricing History
DatePricePrice ChangeDescription
4/9/2026$2,399,000 Listed Price

Map


See all

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