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Shawn Bengtson

Office Broker - DRE 01236964

  • Office 760-805-7199
Questions?

20255 Skyline Boulevard, Woodside – $2,399,000

  • 3 Beds
  • 3 Baths
  • 2,400 Sqft
  • 2.99 Acres
  • 3 Beds
  • 3 Baths
  • 2,400 Sqft
  • 2.99 Acres

20255 Skyline Boulevard

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.

Essential Information

  • MLS® #ML82042155
  • Price$2,399,000
  • Bedrooms3
  • Bathrooms3.00
  • Full Baths3
  • Square Footage2,400
  • Acres2.99
  • Year Built1963
  • TypeResidential
  • Sub-TypeSingle Family Residence
  • StatusActive

Community Information

  • Address20255 Skyline Boulevard
  • Area699 - Not Defined
  • CityWoodside
  • CountySan Mateo
  • Zip Code94062

Amenities

  • Parking Spaces6
  • ParkingUncovered
  • GaragesUncovered
  • ViewBay, City Lights, Pasture

Interior

  • HeatingRadiant
  • CoolingNone
  • # of Stories2

Appliances

Dishwasher, Electric Cooktop, Refrigerator

Exterior

  • Lot DescriptionHorse Property
  • RoofComposition

School Information

  • DistrictOther

Additional Information

  • Date ListedApril 8th, 2026
  • Days on Market1
  • ZoningRM0000

Listing Details

  • AgentJennifer Paulson

Office

Christie's International Real Estate Sereno

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Jennifer Paulson, Christie's International Real Estate Sereno.

Based on information from California Regional Multiple Listing Service, Inc. as of April 9th, 2026 at 1:55pm PDT. 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.