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Auction of Charles Shaw’s former St. Helena estate, original home of ‘Two Buck Chuck’ wine brand, finally moves forward

The 42-acre Benessere Vineyards estate in St. Helena, once home to the Charles Shaw 'Two Buck Chuck' wine brand, is moving forward with an auction after multiple delays. The property, which had a market reserve of $9 million, is set for a final gavel drop on June 24. The estate was originally listed for $35 million in 2024 but failed to sell, leading to the auction route.

read2 min views1 publishedJun 19, 2026
Auction of Charles Shaw’s former St. Helena estate, original home of ‘Two Buck Chuck’ wine brand, finally moves forward
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Trinity Audioplayer ready...A Napa Valley winery estate that once was home to the Charles Shaw brand may finally find a buyer, after multiple attempts to sell it at auction in recent weeks.

The 42-acre Benessere Vineyards property at 1010 Big Tree Road near St. Helena was first set to be sold via Concierge Auctions starting by the end of May. Bidding was set to start May 13, but that was first postponed to early this month when the market reserve wasn’t reached. That’s determined by the highest bid received before the auction starts, which sets the price floor. The auction company had estimated bidding would start at $8 million to $12 million.

Then the opening date was moved a few times, most recently to Friday, June 12. The following Monday, June 15, Concierge said the market reserve had just been met, at $9 million. The final gavel is still set to drop this coming Wednesday, June 24, at 3 p.m. Pacific.

Charles Shaw and his wife, Lucy, purchased the property in 1977, planted vineyards and launched their namesake wine brand. The Shaws lost the estate in bankruptcy, and Fred Franzia bought rights to the brand in 1995, and it later garnered the nickname “Two Buck Chuck” from of its longtime $2 price (now $4) in the Trader Joe’s store chain. Meanwhile in 1994, John Benish, founder of Chicago-area school bus giant Cook-Illinois, and his wife, Ellen, acquired the estate and undertook extensive redevelopment, now with nearly 30 acres of vines.

The property went on the market in a conventional real estate listing 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. The listing agent, Kevin McDonald of Sotheby’s International Realty, then took the unusual route of sale at auction.

More demand for auctions of wine-related real estate prompted Concierge to launch its Global Wine & Vineyard Division with Benessere.

Jeff Quackenbush joined North Bay Business Journal in May 1999. Reach him at jeff@nbbj.news or 707-521-4256.

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