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$2,399,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 2,400 Sq. Ft.
  • Updated 1 day ago

Next open house:

Open House: 1:00 PM - 4:00 PM

Saturday 4/11 1:00 PM - 4:00 PM

20255 Skyline Blvd,Woodside, CA 94062

20255 Skyline BlvdWoodsideCA94062

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Join us at 20255 Skyline Blvd on:

  • Open House: 1:00 PM - 4:00 PM

    Sunday 4/12 1:00 PM - 4:00 PM

    20255 Skyline Blvd,Woodside, CA 94062
    20255 Skyline BlvdWoodsideCA94062
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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.

Full Property Details for 20255 Skyline Blvd

General

  • Price: $2,399,000
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82042155
  • Updated: 4/8/2026
  • Added to Site: 1 day(s) ago

Interior

  • Rooms/Areas: Storage
  • Interior Features: High Ceiling

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3
  • Bathroom Features: Full on Ground Floor, Shower and Tub, 1 Shower over Tub, Stall Shower, Updated Bath

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Family Room: Separate Family Room
  • Kitchen: Electric Cooktop, Tile Countertop, Dishwasher, Built-In Oven, Refrigerator
  • Laundry: In Utility Room, Inside
  • Guest Quarters: Barn

Additional Information

  • Extras: Not Applicable

Parking

  • Parking Features: No Garage, Room for Oversized Vehicle, Uncovered Parking

Location

  • Area: Skyline Area
  • County: San Mateo
  • Cross Streets: Hwy 84 (La Honda Rd) or Page Mill Rd

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Radiant

Utilities

  • Sewer: Existing Septic System
  • Water: Domestic Well
  • Utility Description: Propane on Site

Structural Information

  • Construction: Detached
  • Foundation: Concrete Perimeter and Slab
  • Roof: Composition
  • Square Feet: 2,400
  • Year Built: 1963

Lot Features

  • Property View: Bay, Pasture, City Lights
  • Lot Size (Acres): 2.9895
  • Minimum Lot Size: 130223
  • Lot Size (Sq. Ft.): 130,223
  • Zoning: RM0000
  • Lot Description: Gently Sloped
  • Fencing (Description): Horse Fencing

Horse Property

  • Horse Property: Yes
  • Horse Facility Desc.: Pasture, Fenced

Listed by Christie's International Real Estate Sereno, Jennifer Paulson

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Listing agent

— 20255 Skyline Blvd —

  • Jennifer Paulson

    Christie's International Real Estate Sereno

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 20255 Skyline Blvd

School District:La Honda-Pescadero Unified School District
NameGradesDistance
La Honda Elementary School
450 Sears Ranch Road, La Honda, CA 94020
PK-54.2 mi
Pescadero Elementary And Middle School
620 North Street, Pescadero, CA 94060
6-810.8 mi
Pescadero High School
350 Butano Cut-Off, Pescadero, CA 94060
9-1210.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20255 Skyline Blvd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/08/2026
Listed
$2,399,000
27.95%
MLS
11/06/2019
Sold
$1,875,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 20255 Skyline Blvd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$22,953
1%
$2,050,580
2%
2024
$22,635
7%
$2,010,374
2%
2023
$21,165
2%
$1,970,956
2%
2022
$20,839
2%
$1,932,311
2%
2021
$20,493
1%
$1,894,424
1%
2020
$20,222
-3%
$1,875,000
-2%
2019
$20,821
49%
$1,912,500
48%
2018
$13,929
3%
$1,291,568
2%
2017
$13,589
—
$1,266,244
2%
2016
$13,578
3%
$1,241,416
2%
2015
$13,161
2%
$1,222,770
2%
2014
$12,918
—
$1,198,818
—
2013
$12,874
—
$1,193,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Christie's International Real Estate Sereno, Jennifer Paulson

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20255 Skyline Blvd, Woodside, CA 94062 (MLS# ML82042155) is a Single Family property with 3 bedrooms and 3 full bathrooms. 20255 Skyline Blvd is currently listed for $2,399,000 and was received on April 08, 2026. Want to learn more about 20255 Skyline Blvd? Do you have questions about finding other Single Family real estate for sale in Woodside? You can browse all Woodside real estate or contact a Coldwell Banker agent to request more information.

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