Charles Shaw’s former St. Helena estate, original home of ‘Two Buck Chuck’ wine brand, goes to auction

A St. Helena winery estate with deep roots in Napa Valley history, including a stint as the home of the Charles Shaw brand, is heading to auction next month after a prolonged effort to sell it the conventional way amid ongoing challenges for the North Coast wine business.

The 42-acre property at 1010 Big Tree Road first went on the market in November 2024 at $35 million, came off at the end of 2024, was relisted in February of last year at a 20% discount ($28 million) then was removed from the market in February of this year.

Now, it’s set to sell by the end of next month on Concierge Auctions. Bidding is set to start May 13, with a final gavel May 28. The expected opening bid is $8 million to $12 million.

“The sellers are finally at a point they know they need to move on,” said Kevin McDonald, the Sotheby’s International Realty agent who has been listing the property…

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