This maverick Napa Valley winery couldn’t sell. Now, it’s headed for auction — and more wineries could follow

After lingering on the market for well over a year, one of Napa Valley’s most idiosyncratic wineries will sell to the highest bidder in a May auction.

The listing for Benessere Vineyards — which focuses on Italian grape varieties and was the original home of Charles Shaw Winery, the brand behind Trader Joe’s notorious Two Buck Chuck — goes live with Concierge Auctions on Wednesday. Potential bidders can register through May 13, when the auction opens; the property will sell on May 28.

Benessere, a 43-acre St. Helena estate that includes a vineyard, winery, tasting room and two residences, originally hit the market in November 2024 for $35 million. John Benish, who owns Benessere with his mother and four siblings, said the family has put the property on the market and pulled it off a few times. It was most recently listed for $28 million, but received “no serious offers.”…

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