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Paso Robles’ Windfall Farms — once owned by “Jeopardy!” host Alex Trebek — is up for auction with an opening bid of $15 million.
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Bidding for the property will culminate on until Aug. 15, a news release said, where the estate will be sold to the highest bidder as part of the RM Sotheby’s stage at Monterey Car Week, Concierge Auctions’ inaugural live real estate auction during the Pebble Beach event.
The more than 700-acre winery estate located at 4710 Flying Paster Lane was owned by Trebek for nine years, and is currently listed for $33 million through Sotheby’s International Realty.
“Windfall Farms is the rare property that will appeal to many different types of discerning buyers,” Chad Roffers, CEO and co-founder of Concierge Auctions, the company hosting the auction, said in a release. “Its celebrity history, income-producing operations, extraordinary scale, and development potential make it one of the most compelling and versatile offerings.”
Windfall Farms is known for its sustainable local agriculture and celebration of equestrian, ranch and agrarian lifestyles.
Initially developed as the only Kentucky-style thoroughbred farm in California, it is currently operated as a horse training and boarding facility with an extensive farming operation, SLOCal’s website said.
The property also hosts special events like private parties, corporate outings and weddings.
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Beside its celebrity provenance, the release said the 724-acre-property also features a singular private estate — a 10,000-square-foot home with eight bedrooms and 12 bathrooms — and has the potential for a separate destination winery or resort, a legacy vineyard operation or a curated residential community anchored by 76 already approved buildable lots.
The estate also has a working enterprise consisting of 387 acres of premium dry red varietals that are sold under contract to name-brand regional wineries.
But winery operations aren’t the only turnkey feature.
The estate has a Kentucky-style 6.5-furlong racetrack with room for a professional polo field, as well as expansive paddocks, four barns to support the full lifecycle of thoroughbred breeding and training, a training barn adjacent to the racetrack, a foaling barn, a stallion breeding barn and a yearling barn.
Sotheby Internation Realty’s Chris Atkinson said that the company’s partnership with Concierge Auctions gives the estate the attention it deserves.
“Windfall Farms is a property that truly defies category. Its operational vineyard business, equestrian heritage and the sheer scale of what is possible here creates an opportunity that simply cannot be replicated on the Central Coast,” he said in the release.
Bidding closes Aug. 15. For more information visit conciergeauctions.com.
This story was originally published August 7, 2026 at 3:45 PM.
CORRECTION: This story was updated to reflect that Alex Trebek owned Windfall Farms for nine years.
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