Former Trader Joe’s ‘Two-Buck Chuck’ Winery – Now a Luxury Napa Estate – Goes on the Market for $35M

A piece of Napa Valley wine history is up for grabs—at a price that’s anything but Two Dollar Chuck.

The Benessere Vineyards estate, steeped in the legacy of the original Charles Shaw winery, has gone on the market for $35 million.

The Northern California estate is where Shaw first produced his wines, including the vintage known as “Two-Buck Chuck,” so named for its $2 budget price tag at Trader Joe’s.

The wine cellar is now a feature rich.

“Embraced by vineyards and the organic landscape of the Napa River, the agrarian setting is unmatched, offering all that wine country often promises but rarely delivers,” the listing says.

St. The Helena estate is spread over 43 picturesque acres, complete with 6,300 square feet of living space, eight bedrooms and nine bathrooms.

But it’s more than just a stunning asset; it’s a nod to Napa’s past and a testament to a transformation that spanned decades.

“The desirable valley location is convenient and tucked away from well-traveled Highway 29 and the Silverado Trail, at the end of a bucolic country lane,” the listing notes.

And it’s true: Tucked away on Big Tree Road, this property feels far removed from the bustling wine trails, but is strategically located for access.

Charles F. Shaw laid the foundation for this fantastic site in 1974, producing award-winning Gamay wines before financial turmoil led to its bankruptcy in 1990.

The Benish family stepped in, buying the land – but not the brand – and named it Benessere Vineyards.

A new chapter began when Fred Franzia of Bronco Wine Co. acquired the Shaw brand for just $27,000 during bankruptcy proceedings and changed the supermarket wine landscape forever.

In 2002, the bargain basement Two-Buck Chuck debuted at Trader Joe’s, gaining a cult following and casting a long shadow over the original estate’s legacy. However, Benessere has forged its own identity since John and Ellen Benish purchased the property for $1.529 million in 1994.

With meticulous care, they revived the land, producing their first sangiovese vintage by 1995 and eventually adding a number of Italian varietals such as pinot grigio, falanghina and nero d’Avola.

According to the listing, the property is poised for a new owner to step in and continue operations, either by moving an existing wine brand or creating a new one.

The estate includes a vineyard, winery and permitted tasting room, along with single family residences.

Notably, the listing notes that the winery’s rights are “pre-WDO,” referring to the Napa County Winery Definition Ordinance of 1990; permits issued prior to this regulation are usually much less restrictive than those issued today.

Jamie Spratling and Kevin McDonald with Sotheby’s International Realty handle the listing.