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.
Ned Bonzi
The St. Helena estate of Benessere Vineyards at 1010 Big Tree Road that once housed the Charles Shaw Winery is heading to auction next month after a prolonged effort to sell it. (Daniel Wilson)
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.
The estate was once home to the Charles Shaw Winery and dates back to agricultural uses in the early 20th century. In 1977, Charles Shaw and his wife, Lucy, purchased the property, planted vineyards and launched their namesake wine brand. After financial difficulties, Shaw lost the estate in bankruptcy, and Fred Franzia bought rights to the brand in 1995. Franzia in 2002 turned it into the inexpensive “Two Buck Chuck” line that is sold exclusively at Trader Joe’s today.
AP Photo/Eric Risberg
Fred Franzia holds a bottle of Charles Shaw (“Two Buck Chuck”) chardonnay wine off the bottling line at the Bronco Wine Company facility in Napa on April 17, 2007. (AP Photo / Eric Risberg)
Meanwhile in 1994, John Benish, founder of Cook-Illinois, a Chicago-area school bus giant, and his wife, Ellen, acquired the Big Tree Road estate and undertook extensive redevelopment.
The shift of the sale of this property to an auction, while at the moment rare among current Wine Country listings, reflects broader pressures facing Napa Valley’s vineyard and winery sector, where shifting economics and weaker wine demand have complicated wine business real estate transactions.
“It’s been challenging to say the least,” McDonald said. “The economics behind a lot of these wineries and vineyards doesn’t make sense for many people. It’s tough to find comparable sales and then market these assets.”
Those challenges have been compounded by a number of North Coast vineyards and wineries, including in prime regions like Napa County, without fruit contracts and facing softer wine sales.
At the same time, the shifting economy in recent years has weighed on buyer interest.
“We came off 2021 with a strong market, with low cost of capital and an economy that was robust coming out of COVID, but then came higher costs of doing business and cost of capital, so vintners have been trying to find a balance of supply and demand. The shift started in 2022 and has slowly progressed to where it is now.”
Still, McDonald pointed to tentative signs of renewed activity, particularly through alternative sales mechanisms like auctions.
“I think we’re finally seeing some opportunities with (price) discovery like this auction,” he said. “It’s a sign that people are motivated by pricing. It’s encouraging action out there we haven’t seen in a while. We’re starting to see some light at the end of the tunnel.”
The Benessere property itself carries features that could appeal to buyers, including pre-Winery Definition Ordinance entitlements that allow for expanded production and public tastings. But even those advantages require the right match.
Ned Bonzi
The St. Helena estate of Benessere Vineyards at 1010 Big Tree Road that once housed the Charles Shaw Winery is heading to auction next month after a prolonged effort to sell it. (Daniel Wilson)
“It comes down to who is willing to pursue it,” McDonald said. “Entitlements on that property would allow significant expansion on what you can produce there. is a benefit but also have to find the right buyer who needs that much production. There is potential in the initial bid (price) range to leave room for expansion.”
Market dynamics vary widely depending on the type of buyer, McDonald said.
“On the lifestyle side, the scale of the vineyard or winery operation has to be palatable for someone interested in entering the business — but not too large or cumbersome,” he said.
Daniel Wilson
The St. Helena estate of Benessere Vineyards at 1010 Big Tree Road that once housed the Charles Shaw Winery is heading to auction next month after a prolonged effort to sell it. (Daniel Wilson)
For operating wine businesses, location and permitting are key for target properties.
“Anywhere with prime Highway 29 or Silverado Trail access is key for an existing brand that can be moved there and get traffic, or a new brand can move there for a prime location,” McDonald said.
Institutional and investment buyers, by contrast, are more focused on pricing, McDonald said.
The broader luxury real estate market in Napa Valley has also seen uneven performance.
“The last two years have been quiet,” McDonald said. “There was some pickup toward the end of last year, and then came general uncertainty in the direction of the economy. 2026 started strong, but then entering into a new war stalled out the market a bit with the uncertainty.”
Jeff Quackenbush joined North Bay Business Journal in May 1999. He covers primarily wine, construction and real estate. Reach him at jeff@nbbj.news or 707-521-4256.
Dining and Cooking