Michelle Pfeiffer’s former Woodside home sells for $33.5M 

Creekside estate on Why Worry Lane comes with 10-stall barn

Michelle Pfeiffer’s Former Woodside Estate Sells for $33.5M
Michelle Pfeiffer and 100 Why Worry Lane in Woodside (Getty, Google Maps)

A Woodside estate formerly owned by Michelle Pfeiffer sold last week for $33.5 million, according to public records, marking the third most-expensive single-family sale in the Peninsula community so far this year. 

Pfeiffer and her writer-producer husband David Kelly bought 100 Why Worry Lane for $12 million in 2004 and added an adjoining parcel for $8.6 million in 2008, according to news reports from when the couple listed the now nearly 9-acre cul-de-sac property for $29.5 million in 2018. It sold the following year for $22 million to Why Worry Properties LLC, which lists Palo Alto-based family office Rosewood Family Advisors as its mailing address in state records. 

The 1940 main home has four bedrooms and 4.5 baths with a total 6,300 square feet. There are three guest suites, an office and a gym across the front courtyard from the primary residence. The creekside grounds include a 1920s-era 10-stall barn with a paddock and riding arena, and beyond that is a pool with spa and a tennis court. There is a detached guest cottage, carport and yoga studio as well.

The property was listed at the end of May for $38 million by Shena Hurley of Golden Gate Sotheby’s International Realty. It went into contract a little more than a week before it closed on Sept. 7, indicating an all-cash deal.

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100 Why Worry Lane LLC was the buyer, with a mailing address at a UPS mailbox in downtown San Francisco, according to state records. They were represented by Alex Michas, an East Bay-based agent with KW Advisors. 

Both agents declined to comment on any specifics related to the sale. But Hurley said that, in general, affluent buyers on the Peninsula have been prioritizing lifestyle and aren’t as impacted by “economic fluctuations” as buyers at other price points. She expects the high end of the market to remain “strong and active” into the fall. 

Michas added that buyers at the highest price points, not just on the Peninsula but across the Bay Area, value both lifestyle and “absolute privacy” above all else.

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