TED ANDERSEN December 29, 2025
As AI money flowers across the Bay Area, luxury properties are selling — and many of those homes are not going to be primary residences.
Ohana Realty President Soren Olsen told the Business Times she’s seen a welcome influx of buyers in the North Bay snapping up second, third and even fourth homes. Olsen oversees Montage Residences Healdsburg, where Ohana Realty developed 25 turnkey luxury homes; She is down to one remaining four-bedroom Harvest Home at this point, with about 30% of the purchasers coming from the Bay Area.
“I think there’s been a lot of money in the tech world of Silicon Valley and out to the East Bay with all the AI advancements, and I think anytime you have a driveto destination that services a place like that, you’re going to see spillover, you know, like Wine Country and Northern Sonoma,” Olsen said.
Wine Country is a big target for second homes that people can escape to, and a smattering of tech-money purchases have recently peppered the landscape. Since September, luxury and ultraluxury home sales in Napa and Sonoma Counties are up 58% from the same period of 2024, and there is currently the highest number of $5 million-plus listings in contract, or pending sales, than in any month in at least two years, according to Compass Chief Market Analyst Patrick Carlisle.
Among all Bay Area counties, Napa and Sonoma counties also have among the widest range of luxury and ultraluxury home, vineyard and estate listings currently on the market: 114 active listings at $5 million-plus, 31 at $10 millionplus and 8 listed at $20 million and above, according to Carlisle.
“One of the biggest differentiators of these typically spectacular Wine Country homes is the size of the acreage in which they are situated: The median lot size for homes listed in the two counties at $10 million-plus is well over 50 acres, while in the rest of the Bay Area, it is just a little above one acre,” Carlisle said. “It’s a completely different style of living for the most affluent homebuyers.”
Grace Lucero with Vanguard Properties said she’s seeing an uptick in the techie buyer profile.
“We get people who come here and want a second home just for the weekend, and I’ve got people who come here to buy when they are planning to retire, and in the meantime, they’ll just rent it out or use it themselves until they’re here full time,” Lucero said.
“I just had a young man and his wife buy a property that’s now three lots and he says, ‘Grace, I’m going to own this for over 30 years. I want a place for my friends and family to come, so I’m going to build a compound, and that’s a second home,” she told the Business Times. “I have another young man who’s just taken on an AI position and is looking for a second home, but he needs to be there for a minute before he can buy.”
Tech money has always loved Napa Valley for second homes, said Robyn Bentley, a Christie’s International Real Estate Sereno agent on the Wine Country Consultants team in St. Helena. Bentley said the tech buyers now are in their 40s and largely from San Francisco or other Bay Area cities. She said she has one AI client in that age range who is looking for a second-home site in Sonoma County.
“We are currently working with an S.F. couple in the process of purchasing 40 acres of vacant land to build their dream second-home vineyard estate located outside of Healdsburg,” she said.
Other locations in Marin County, such as Stinson Beach, have also seen an uptick in buyers driven by the AI boom, according to Compass agent Butch Haze.
Some second-home buyers in the Bay Area are looking south, though. Simona Martin of Christie’s International Real Estate Sereno in Pebble Beach and Carmel said she’s seeing action in Monterey County. Carmel, she said, is a natural fit for Bay Area tech professionals seeking a second home because it’s an easy two-hour drive for weekend escapes or hybrid work with natural beauty that offers decompression from the intensity and pressures of Silicon Valley.
“We are definitely seeing second-home buyers in the Carmel area coming primarily from the Bay Area, and many of them have ties to the tech sector, including both established Big Tech companies and people with direct or ancillary connections to AI,” Martin said. “In fact our largest sale of 2025, thus far, are buyers from an AI infrastructure company.”
In her experience, Martin said, most of these buyers are in the more established phase of their careers.
“It’s still early in the AI cycle for younger startup employees to have the kind of liquidity that typically drives second-home purchases, though we anticipate seeing more of that demographic in the coming years if the AI industry continues its momentum,” she said.
Even farther south along the Central Coast, Lindsey Harn, an agent with Christie’s International Real Estate Sereno in San Luis Obispo, said young tech secondhome buyers specifically in the AI field are descending.
“Personally we have seen quite a few and their home base tends to be Silicon Valley,” she said. “We are seeing a ton of people moving this way for second homes, to Airbnbs, to investment properties and everything in between.”
“In San Luis Obispo, we have a ton of Bay Area families who have either graduated from Cal Poly, send college students to Cal Poly or have themselves graduated and want to have a placeholder. With Avila Beach, Pismo Beach and the Paso Robles wine country, we are well positioned and a short drive or flight from the Bay Area,” Harn said. “The age range has definitely gone down — we are seeing couples as young as their early 30s getting second homes, investments or just places to retreat. They are using their funds to invest in a more peaceful lifestyle. Many of these younger buyers are in the tech industry with stock and many are paying all cash.”
And beyond California, some new Bay Area tech money is searching outside the states for second homes.
Joske Thompson, an agent with Compass who specializes in international real estate, told the Business Times that a number of Americans are buying their second homes in places like the Central American country of Panama, where he traveled for a real estate conference in early December.
“There are a lot of people looking outside of the U.S., and I think that trend is going to continue because the dollar goes really far and people just really want to diversify their assets,” Thompson said. “I do see the AI folks wanting to diversify their portfolio and take their money offshore.”
Article originally published by San Francisco Business Times.