Alex Trebek’s former California vineyard estate has sold at auction for $16.9 million, nearly half of its original asking price. The sprawling 720-acre property in Paso Robles, known as Windfall Farms, was initially listed for $33 million in April 2025 before spending more than a year on the market.The property went under the hammer last month during Monterey Car Week, with the sale now pending, according to Concierge Auctions, which handled the transaction.
From $33 million listing to $16.9 million auction sale
The California estate was listed for $33 million in 2025 before selling at auction for $16.9 million. (Photo: Trimotion Media)
Windfall Farms was originally put on the market for $33 million in 2025. After failing to sell during its extended time on the market, the estate was offered at auction, ultimately fetching $16.9 million.The sale represents a significant drop from the original asking price, with the final figure coming in at roughly half of what the property was initially listed for.“We’re thrilled with the outcome and proud to have partnered with Concierge Auctions to introduce this remarkable property to a global audience of qualified buyers who were eager to jump at this once-in-a-generation opportunity,” Chris Atkinson of Sotheby’s International Realty said in a news release.Atkinson shared the listing with his colleague Patty Murphy.The identity of the buyer was not immediately available.
Trebek’s connection to the sprawling estate
The sprawling estate includes a Kentucky-style 6.5-furlong thoroughbred racetrack. (Photo: Trimotion Media)
While Windfall Farms is now known for its vineyards, Trebek primarily used the property for breeding and training thoroughbred racehorses.The late Jeopardy! host owned the Paso Robles estate sometime before the early 2000s and used it to pursue his passion for horse racing. His most successful colt associated with the property was Reba’s Gold.Trebek eventually parted with Windfall Farms in the early 2000s, although the exact date he acquired and sold the property could not be determined.
387 acres of vineyards
Windfall Farms features 387 acres of vineyards in Paso Robles. (Photo: Trimotion Media)
The estate includes approximately 387 acres dedicated to vineyards, producing dry red wine varietals.The property’s agricultural history has continued under its more recent ownership. Agribusiness and real estate development company Limoneira purchased Windfall Farms in 2009, according to Sotheby’s International Realty.During Limoneira’s ownership, the main residence was also used as a hospitality venue.Following the auction sale, Limoneira was offering to continue managing the vineyard and the wider property under a separate agreement, according to Concierge Auctions.
Equestrian facilities remain intact
Several of the equestrian facilities connected to Trebek’s ownership remain on the estate.Windfall Farms features a Kentucky-style 6.5-furlong racetrack, with enough space to potentially add a professional polo field. The property also has paddocks and four barns designed to support thoroughbred breeding and training.The barns include a training barn, a foaling barn, a stallion breeding barn and a yearling barn.These facilities reflect the estate’s unusual combination of luxury real estate, winemaking and professional horse breeding.
A 10,000-square-foot main house
Windfall Farms features a 10,000-square-foot main house and two manager’s residences. (Photo: Trimotion Media)
Beyond its vineyards and equestrian facilities, Windfall Farms includes a 10,000-square-foot main residence.The property also has two manager’s residences and a three-bay machine shop.The main house served as a hospitality venue during Limoneira’s ownership, adding another potential use to the sprawling property.With its vineyards, racetrack, horse-breeding facilities and expansive residences, Windfall Farms remains one of the more distinctive pieces of California real estate associated with a major television personality.After more than a year on the market at $33 million, the estate has now moved toward a sale at $16.9 million following its auction during Monterey Car Week.
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