$18M Vineyard Property Ranks as Napa’s Top Trade of 2023

The widow of Warren Simmons, Pier 39 mastermind and Chevy’s Fresh Mex restaurant chain founder, is the buyer of Napa’s priciest house sale this year.

A trust in the name of Caroline Simmons, who started a cranberry farm in Chile in the early 1990s with her husband that became the world’s largest producer of the fruit, purchased 1561 South Whitehall Lane for just under $18 million at the end of last month, according to public records. The vineyard property on 20 acres in St. Helena has been on and off the market since it listed at $42 million in 2017, shortly after it was completed.

The seller is Patrick Cahill, a developer who planned to use the property as a second home but then decided to sell it instead, according to media reports from when the home first listed. Listing agent Douglas Manful of Black Book International did not reply to a request for comment.

Bart Moore of Compass represented the buyer and would not confirm their identity but said when the price on the Whitehall estate dropped from its 2022 list price of $28 million to $18.75 million in February, they jumped on it, submitting an all-cash offer.

“Nothing was ever up to their standards until this property,” he said, adding that they were drawn to the modern design, two pools, tennis court, putting green, 14-acre vineyard and St. Helena location. They also liked that there was a main home and a guest home, with a total of seven bedrooms and 11 bathrooms with more than 14,000 square feet, for hosting friends and family.

Moore said that being unwilling to waver on what they wanted is typical at this upper tier of the market in wine country, where most buyers already have a primary residence elsewhere.

“A lot of times it’s just a bit of a waiting game until that property comes on the market, especially at this price point,” he said. “While we have lots of big, impressive estates in Napa, something on this level is fairly rare.”

Napa is a “fascinating luxury and estate market,” according to Patrick Carlisle, Compass chief market analyst. Its median sales price of $850,000 makes it one of the most affordable markets in the Bay Area, he said via email. But the county also has by far the highest percentage of homes priced above $5 million in the region, with one in five listed in that range.

It is also the smallest market in the Bay Area by a significant margin, he said. In the last 12 months there were only 1,000 sales at all price points, one-quarter of the volume in next-door Sonoma. Sales above $5 million are moving even more slowly, with a sales rate of about two per month over the last six months and a growing number of listings.

“That means a buyer has a very wide choice of very special properties to choose from, but with relatively little competition from other buyers,” he said. “That typically means more room to negotiate. It’s a very good time to buy a luxury home or estate in Napa County.”

Moore agreed that the market had slowed since affluent people in Bay Area cities began buying up Napa properties in the wake of shelter-in-place restrictions during hte pandemic. The market “lacked urgency” before the pandemic, he said. After two years of soaring sales followed by a big drop last year, it is now back to those same pre-pandemic conditions, though interest has picked up since the region’s big winter storms finally subsided last month, he added.

Buyers aren’t looking for a project and most vineyard homes are “a little more tired,” with many built in the 70s and 80s, he said. That was one big reason his client was so quick to make a move on Whitehall Lane, with its turn-key new construction and updated outdoor spaces.

“There’s a bit of a disconnect between the inventory that’s available and what buyers want,” Moore said.