485 Whiskey Hill Rd Woodside, California 94062 United States

Woodside Oaks
485 Whiskey Hill Rd Woodside, California 94062 United States

  • $49,000,000
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  • 12
  • 14
    Full Baths
  • 1
    Partial Bath
  • 19,000 Sq Ft.
  • 11.5 Acres
  • New Listing


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Woodside Oaks

About 485 Whiskey Hill Rd, Woodside, California

The most awe-inspiring compound in Silicon Valley is located on three knoll top level parcels totaling over 11 acres with commanding views of the Santa Cruz Mountain range and the 272-acre Horse Park at Woodside. Less than a mile away is the town center and iconic Sand Hill Road. This compound with a rich history features two main residences, three guest homes, a tennis pavilion, a strikingly handsome multi-purpose, finished barn converted to a ballroom or meeting facility, several garages, soccer field, tennis court, oversized pool, a kid’s playground “fort”, manicured grounds and much more. It is all surrounded by native specimen trees, meandering paths, and several private drives. The centerpiece of this first ever offering is the twenty-first century version of the Bernard Maybeck original that was built on this site 100 years ago. Built in 2012, it is a craftsman design like no other. Breathtaking architecture has a “live in sculpture” feel with a timeless elegance that will be admired for generations. The home is a quintessential California indoor-outdoor configuration with walk-out doors/windows on all four sides that lead to the multitude of verandas supported by impressive rough cut timber columns that create luxurious and comforting exterior living areas. The second main house has been beautifully updated with over 5100 sq. ft. of living space, five bedrooms, five baths, beamed ceilings, embellished millwork, a private office and a light filled three car garages befitting an artist studio, an oversized covered and heated pool, all overlooking Silicon Valley’s premier equestrian facility.

Architect's Introduction

Long enjoyed for its comfortable climate the knoll was chosen in 1920 as the location for a small country retreat by James J Fagan, then vice president of Crocker Bank noted Bay Area architect Bernard Maybeck was selected to design a beautiful home and guest house linked by trellises and courts incorporating the existing oaks and grounds into the building's layout. The highlight of the design was a wonderfully simple yet elegant main pavilion that served as the central gathering space functioning as an indoor-outdoor living room with the adjacent trellised courtyard. Over the years the property fell into decline and the Maybeck buildings were remodeled so carelessly that they became all but unidentifiable. With the structure literally in danger of collapse the current owners purchased the property in 2002 with the intent to restore it to its former glory. An architectural work of art is difficult to renovate in the best of circumstances. The condition of the building and a recalcitrant local planning commission was the challenge when Joel Peterson commissioned me in 2006 to design a large family home around the main pavilion. The last remaining piece of the Maybeck design that was salvageable The main pavilion was perfectly located on the property and has become the centerpiece of the new home you see today taking cues from Maybeck’s original vision the new family room and bedroom wings, connected by the new foyer and main hall seamlessly engaged the restored pavilion while embracing new outdoor spaces on all sides The hemispherical trellises replace the original at the main courtyard and pay homage to the genius of the original design by reintegrating the pavilion to its surroundings, extensively landscaping connects the new oak and acorn pavilions and ties together the barns and remainder of the property to create rich and diverse gardens Working with the Peterson family has been a wonderful experience. Design and construction are difficult processes. It also takes a large amount of patience and fortitude to accomplish something on this scale. I am as pleased to have designed this domicile as the current owners are to own it and I'm sure Mr. Maybeck would be pleased too.”

Francis Gough- Architect

Marketed By

Sotheby's International Realty - San Francisco Brokerage

117 Greenwich Street
San Francisco, California 94111 United States
Arthur Sharif & Associates
Real Estate Professional
Schedule a Showing

Property ID:PLTYMN

MLS ID:81824533


  • Barn
  • Deck
  • Gated Community
  • Granite Countertops
  • Guest House
  • Horse Facilities
  • Library
  • Security System
  • Tennis Court
  • Casita
  • Gardens
  • Hardwood Flooring
  • In-Home Fitness Center
  • Marble Countertop
  • Media Room / Home Theater
  • Screen Room
  • Stables
  • Terrace / Outdoor Space
  • Wine Cellar / Grotto
  • Outdoor Pool
  • in-law suite
  • Mountain Views
  • Country Living
  • Historic
  • Mountain
  • Privacy
  • Farm and Ranch
  • Resort
  • Suburban
  • Tennis
  • SIR Farm & Ranch
  • Equestrian