This Historic 577-Acre California Ranch, Formerly Owned by Alex Trebek, Is Back on the Market

Clue: This 11-bedroom ranch estate, previously owned by the late Jeopardy host Alex Trebek, just went on the market. And don’t worry—I’ll give you the answer: What is 535 Calf Canyon Highway.

For a cool $6,995,000, you can move into the 11-bedroom, 13-bedroom sprawling ranch estate built in 1900. The unique property boasts five houses and a private honeymoon suite, a working winery, barns, stables, and pastures and livestock pens for cattle, horses, sheep, and pigs. History buffs will also appreciate relics such as the original Highway 58 bridge and a blacksmith shop.

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“A truly unique legacy estate, 535 Calf Canyon Hwy blends family retreat with working ranch, vineyard, and winery,” says listing agent Lindsey Harn, owner of Lindsey Harn group in San Luis Obispo, California. “Surrounded by the mountains, lakes, wildlife, and open space, the property feels timeless, yet connected—offering room for 30-plus guests and generations to come.”

Trebek originally joined as a partner of Creston Manor Vineyards and Winery in 1987. He went on to buy out other partners and changed the name to Creston Vineyard and Winery, according to the Wine History Project of San Luis Obispo County. The TV legend, who died in November 2020, listed the winery in September 2000 with an asking price of $2.28 million. Harn says it sold to Simi Valley Properties LLC for $1.6 million in December 2001.

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Napa has long been synonymous with California wine country, but Paso Robles is quickly becoming the place to be for oenophiles. The estate, located in the neighboring town of Creston, is known for producing syrah, cabernet sauvignon, zinfandel, and pinot noir. In fact, wine from the property—called the 1988 Presidential Cuvée—was served as a chilled aperitif during President George H. W. Bush’s first inauguration in 1989.

Today, the winery has 22 acres of producing vineyards, a 9,700-square-foot winery building, and a 10,000-square-foot barrel room with opportunities for expansion. The sale of the entire four-parcel property would give owners access to everything—including the cows, horses, goats, and pig currently residing there. To learn more or schedule a showing, visit Harn’s listing here.