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Alex Trebek's $33 million SLO County estate is going to auction. Take a look inside

Alex Trebek's $33 million SLO County estate is going to auction. Take a look inside
Windfall Farms, a 700-plus acre vineyard and equestrian property in Paso Robes is going up for bid on Aug. 5, 2026. TriMotion Media

The late "Jeopardy!" host's property features a nearly 4,000-square-foot estate, an operating vineyard and a world-class equestrian park.

Paso Robles’ Windfall Farms - once owned by “Jeopardy!” host Alex Trebek - is officially up for sale and headed to auction later this summer.

The more than 700-acre winery estate located at 4710 Flying Paster Lane was owned by Trebek for 37 years, and is currently listed for $33 million through Sotheby’s International Realty.

But it’s still unclear what the property could actually sell for. On Aug. 5, Windfall Farms is headed to auction where the estate will be sold to the highest bidder with no minimum bid required.

“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 news release. “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,” he said.

Bidding is scheduled to end on Aug. 15 at Concierge Auctions’ inaugural live real estate auction at Sotheby’s stage during Monterey Car Week.

Once owned by “Jeopardy!” host Alex Trebek, Windfall Farms in Paso Robles is on the market for $33 million, and headed to bid on Aug. 5, 2026.
Once owned by Jeopardy! host Alex Trebek, Windfall Farms in Paso Robles is on the market for $33 million, and headed to bid on Aug. 5, 2026.

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.

Besides its celebrity provenance, the news 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.

This 3,900-square-foot house sits on Windfall Farms in Paso Robles, which recently went on the market for $33 million in July 2026. The more than 700-acre property also have a vineyard and equestrian park.
This 3,900-square-foot house sits on Windfall Farms in Paso Robles, which recently went on the market for $33 million in July 2026. The more than 700-acre property also have a vineyard and equestrian park.

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, the release said.

But winery operations aren’t the only turnkey feature, there’s also an equestrian legacy that remains fully intact. 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.

Windfall Farms is nestled in the rolling hills of Paso Robles and is up for sale for $33 million. The 724-acre property goes to bid on Aug. 5, 2026.
Windfall Farms is nestled in the rolling hills of Paso Robles and is up for sale for $33 million. The 724-acre property goes to bid on Aug. 5, 2026.

“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,” Sotheby Internation Realty’s Chris Atkinson said in the release. “Our partnership with Concierge Auctions allows us to introduce this remarkable estate to the highly qualified global audience it deserves.”

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