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$2,100,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,180 Sq. Ft.
  • 2 Car Garage
  • Updated 2 days ago

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Open House: 2:00 PM - 4:00 PM

Sunday 9/27 2:00 PM - 4:00 PM

20421 Skyline Blvd,Woodside, CA 94062

20421 Skyline BlvdWoodsideCA94062

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Perched high along Skyline Boulevard on 2.67 acres, this exceptional mountain retreat offers sweeping 180-degree views stretching from San Francisco to San Jose. Surrounded by the natural beauty and serenity of the Santa Cruz Mountains, its an ideal sanctuary for remote work, writing, creative projects, or simply escaping the everyday. Built in 2007, the 2,180-square-foot home features 3 bedrooms and 2.5 baths, with expansive walls of glass that flood the living spaces with natural light. Warm straight-grain fir trim and custom baseboards add timeless character throughout. The open floor plan flows onto a spacious view deck with hot tubperfect for sunset relaxation or casual entertaining. An outdoor shower makes returning from a morning hike or gardening especially refreshing. Practical amenities include a private well, backup generator, and attached 2-car garage with covered breezeway. Enjoy exceptional privacy and mountain tranquility while remaining connected to the Peninsula, with Stanford roughly 20 minutes away and easy access to Woodside, Portola Valley, and beyond.

Full Property Details for 20421 Skyline Blvd

General

  • Price: $2,100,000
  • Status: Active
  • Type: Single Family
  • Source: RE_Infolink
  • MLS ID: ML82056662
  • Updated: 9/21/2026
  • Added to Site: 2 day(s) ago

Interior

  • Rooms/Areas: Office Area
  • Interior Features: High Ceiling , Vaulted Ceiling
  • Fireplace(s): Living Room
  • Flooring: Hardwood, Slate

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1
  • Bathroom Features: Primary - Stall Shower(s), 1 Shower over Tub

Bedrooms

  • Total Bedrooms: 3
  • Bedroom Features: Ground-Floor Bedroom, Primary Suite / Retreat, Walk-In Closet

Other Rooms

  • Family Room: Separate Family Room
  • Kitchen: Stone Countertop, Dishwasher
  • Laundry: In Utility Room

Additional Information

  • Extras: Not Applicable

Parking

  • Garage Spaces: 2
  • Parking Features: Attached Garage

Location

  • Area: Skyline Area
  • County: San Mateo
  • Cross Streets: Langely Hill Road

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Radiant

Utilities

  • Sewer: Septic System Connected
  • Water: Well
  • Utility Description: Public Utilities

Structural Information

  • Architectural Style: Contemporary
  • Construction: Detached
  • Foundation: Concrete Perimeter
  • Roof: Composition
  • Square Feet: 2,180
  • Year Built: 2007

Lot Features

  • Property View: Bay, Bridge , City Lights, Mountains, Valley, Water
  • Lot Size (Acres): 2.67
  • Minimum Lot Size: 116290
  • Lot Size (Sq. Ft.): 116,290
  • Zoning: RM0000
  • Lot Description: Grade Varies

Green Features

  • Energy Efficient: Double-Pane Windows

Listed by Compass, Scott Hayes

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Listing agent

— 20421 Skyline Blvd —

  • Scott Hayes

    Compass

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 20421 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 mi
Pescadero Elementary And Middle School
620 North Street, Pescadero, CA 94060
6-810.7 mi
Pescadero High School
350 Butano Cut-Off, Pescadero, CA 94060
9-1210.3 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 20421 Skyline Blvd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/21/2026
Listed
$2,100,000
68%
MLS
6/09/2009
Sold
$1,250,000
—
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 20421 Skyline Blvd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,039
—
$1,641,886
2%
2025
$18,039
1%
$1,609,694
2%
2024
$17,789
7%
$1,578,132
2%
2023
$16,635
2%
$1,547,190
2%
2022
$16,379
2%
$1,516,854
2%
2021
$16,107
1%
$1,487,112
1%
2020
$15,894
1%
$1,471,864
2%
2019
$15,668
3%
$1,443,004
2%
2018
$15,251
3%
$1,414,710
2%
2017
$14,879
—
$1,386,972
2%
2016
$14,868
3%
$1,359,778
2%
2015
$14,411
2%
$1,339,354
2%
2014
$14,145
—
$1,313,118
—
2013
$14,093
—
$1,307,184
—
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.

Estimate the Cost for 20421 Skyline Blvd

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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 Compass, Scott Hayes

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20421 Skyline Blvd, Woodside, CA 94062 (MLS# ML82056662) is a Single Family property with 3 bedrooms, 2 full bathrooms and 1 partial bathroom. 20421 Skyline Blvd is currently listed for $2,100,000 and was received on September 21, 2026. Want to learn more about 20421 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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