An expansive 1928-era Woodside home on Olive Hill Lane that sits on 4.6-acres surrounded by dense foliage, sweeping lawns, a maze-like rose garden and an outdoor track for a mini passenger train that winds through the property's oak groves, fetched $29 million on May 9, making it among the most-expensive recorded home sales in Woodside so far this year, according to data from real estate database Multiple Listing Service. In February, a newly built 20,600-square-foot Italian-style estate on Mountain Home Road sold for $40 million. Another home on Whiskey Hill Road that sold for $44.5 million in May 2021 closed escrow this past February.

Designed by famed architect Gardner Dailey, who became internationally known for breaking new ground with his modern residential designs in the Bay Area during the 1930s, the 8,290-square-foot home includes redwood walls, five fireplaces, a library, a professional recording studio and a room for model trains, according to the property description from Compass real agents Mary and Brent Gullixson, who listed the home for sale for $38 million in March. (Due to privacy concerns, the real estate duo declined to comment or share photos from the property listing.)

The five-bedroom, seven-bath home is among Dailey's earlier, fairly traditional revival styles with a steeply pitched roof, dormers, bay windows and columns, which he designed prior to embracing modernism. Dailey often is credited for introducing modernist architecture to Northern California.

A home for 'art and tech'

For the past two decades, the property had been home to early Facebook investor, New York Times' bestselling author and rock musician Roger McNamee. Property records show that McNamee and his wife and bandmate, Ann Kosakowski McNamee, bought the property in 1999 for $6.6 million. In 2012, they purchased an adjoining 3.4-acre estate on Olive Hill Lane for $7 million, and in 2015 they extended their holdings on the block with another similarly sized property, according to the Real Deal, which reported on the property when it went on the market in March.

McNamee co-founded Silver Lake Partners, the first private equity fund focused on technology businesses. In 2004, he co-founded the venture capital firm Elevation Partners alongside U2's Bono. The firm acquired 1% of Facebook for $90 million in 2010, the Real Deal reported. After serving as an early adviser and mentor to Facebook founder Mark Zuckerberg, McNamee came out as a leading critic of the spread of misinformation on Facebook’s platform in 2016 and later wrote the book, "Zucked: Waking Up to the Facebook Catastrophe," which became a bestseller in 2019.

In the music world, McNamee is known as a bassist, guitarist and vocalist for Moonalice, which became the first band without a label to achieve one million downloads of a song from its own servers, according to a 2012 Rock and Roll Hall of Fame press release.