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Bill Maddox, DRE#01972575, REALTOR®
(805) 215-0729
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20255 Skyline Boulevard, Woodside, CA 94062

$2,399,000
  • 20255 Skyline Boulevard, Woodside, CA 94062 Main Photo

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Active
BEDS3 BATHS3 full SQUARE FEET2,400 MLS#ML82042155
STATUSActive PROPERTY TYPEResidential - Single Family SCHOOLOther

Listing Courtesy of: Christie's International Real Estate Sereno
Agency Phone: (650) 947-2900
Associate Name: Jennifer Paulson
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Listing Shown by: Farrell Smyth, Inc.
Associate Name: Bill Maddox, DRE#01972575, REALTOR®


Property Description

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.

20255 Skyline Boulevard | MLS# ML82042155

This single family home located at 20255 Skyline Boulevard, Woodside, CA 94062 is currently listed for sale with an asking price of $2,399,000. This property was built in 1963 and has 3 bedrooms and 3 full baths with 2400 sq. ft. Skyline Boulevard is located within the Other school district. Search Woodside real estate on billmaddox.farrellsmyth.com today.

Property Features

Property Type: Residential - Single Family
Cooling: None
Heating: Radiant
Lot Size: 2.99 Acres
Roof Type: Composition
Stories: 2.0
Year Built: 1963

Feature Descriptions

Appliances: Dishwasher, ElectricCooktop, Refrigerator
Days on Site: 10
Lot: HorseProperty
Parcel#: 080110100
Parking: Uncovered
Parking Notes: Uncovered
Special View Info: Bay, CityLights, Pasture

Local Schools

School District: Other

Listed By / Shown By

Listed By

Agency Name: Christie's International Real Estate Sereno
Agency Phone: (650) 947-2900
Agent Name: Jennifer Paulson

agent picture

Shown By

Agent Name: Bill Maddox, DRE#01972575, REALTOR®
Agent Phone: (805) 215-0729
Agency Title: Farrell Smyth, Inc.

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Estimate Your Payment

Estimated Payment

$ 6,038.84 per month $5,339.13 Principal & Interest $0.00 Property Tax (data not provided by mls) $699.71 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 04/19/2026. The listing information on this page last changed on 04/19/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 04/19/2026 12:00:38 AM EST) or CRMLS (last updated Sat 04/18/2026 11:50:03 PM EST). Real estate listings held by brokerage firms other than Farrell Smyth, Inc. may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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