Windfall Farms, once owned by Alex Trebek, headed to auction

By Staff Report · Thu Jul 23 2026

PASO ROBLES — Windfall Farms, a sprawling 724-acre Paso Robles estate once owned by longtime "Jeopardy!" host Alex Trebek, is headed to auction next month, with bidding opening Aug. 5 and closing Aug. 15 during Monterey Car Week.

The property, listed for $33 million, is being sold through Concierge Auctions in cooperation with Sotheby's International Realty. The auction will have no minimum bid, meaning the highest bidder will take ownership regardless of the final sale price.

Located within the Paso Robles American Viticultural Area (AVA), the estate encompasses 723.92 acres and includes 387 acres of producing vineyards, equestrian facilities, multiple residences and approved development opportunities. The vineyards are currently under contract with regional wineries and are managed by Limoneira, which has offered to continue managing the property following the sale.

Windfall Farms was owned by Trebek until the early 2000s, serving as a private retreat during his decades-long tenure as host of "Jeopardy!" The ranch retains its equestrian roots with a Kentucky-style 6.5-furlong racetrack, four specialized horse barns, paddocks and facilities for Thoroughbred breeding and training.

The estate also features an approximately 10,000-square-foot main residence that currently serves as hospitality lodging for visitors and management. The home could potentially be converted into a clubhouse, bed-and-breakfast or resort amenity. Additional improvements include two manager's homes, a three-bay machine shop, extensive water infrastructure with seven wells and more than four miles of paved internal roads.

The property also includes 76 approved buildable lots, offering potential for future residential development in addition to its agricultural and hospitality uses.

"Windfall Farms is the rare property that will appeal to many different types of discerning buyers," said Chad Roffers, CEO and Co-Founder of Concierge Auctions. "Its celebrity history, income-producing operations, extraordinary scale, and development potential make it one of the most compelling and versatile offerings. By selling with no minimum bid required, we are creating the most competitive and transparent environment possible to determine true market value for this one-of-a-kind asset."

Chris Atkinson of Sotheby's International Realty said the estate's combination of a working vineyard, equestrian facilities and development opportunities makes it a unique offering on the Central Coast.

The sale is part of Concierge Auctions' Global Wine & Vineyard Division, which specializes in winery and vineyard properties worldwide.

Paso Robles is home to more than 200 wineries spread across 11 distinct wine-growing districts, making it one of California's premier wine destinations.

For more information, visit windfallfarmspaso.com

Feature Image courtesy of windfallfarmspaso.com