Healdsburg vacation home offered for $2 million in Anthropic shares

A Marin County homeowner and entrepreneur says he will accept $2 million in Anthropic shares in lieu of cash for his vacation property in the North Bay's wine country.

Yes, you read that right: if you happen to hold shares in the private company which helped found the AI chatbot Claude and developer tool Claude Code, you could land a deal on a vacation home in Sonoma County's Healdsburg area.

The three-bedroom, three-bath 3.25-acre estate in Healdsburg offers amenities like a pool and spa, a bocce court and a covered deck. It also boasts a detached guest suite with a second permitted septic system already in place to house guests for secondary income or an AirBnB, if desired.

It's currently listed at $2.5 million for those looking to hold a second home or earn extra income from running a vacation property, in an area where the latter is difficult to get approval for. Those who can offer the owner Anthropic shares, however, are looking at a $500,000 discount, according to the realtor.

Realtor David Hargreaves, co-founder of Bruington Hargreaves, called the property "a quintessential wine country place" on a private road near the city.

"It's one of the few places where you can get a (vacation) permit," Hargreaves said, referring to how difficult it can be to secure a vacation property permit in other high-demand areas such as Alexander Valley.

The property has been hosting vacationers this season and is eligible for a short-term-rental permit once purchased. That makes it a rarity in the area, as the pipeline to secure new permits around the city is "effectively frozen, which leaves two choices: buy an existing, income-producing property, or wait years," according to the listing.

The property has been on the market for about four weeks, Hargreaves said.

"The deal is built for the Bay Area buyer whose net worth sits in private-company stock that is hard to spend," the realtor wrote in the listing. "Rather than sell shares and trigger a taxable event to fund a second home, that buyer can put the equity directly toward a Wine Country property that earns income when it is not in personal use."

The realtor referred to owner Vijay Chattha's idea to offer his home for shares that he cannot otherwise access. As a private firm, Anthropic limits stock ownership to investors such as founders, employees and accredited wealthy investors.

That means the San Francisco company's rapidly growing value has only benefited a small eligible group of investors. Anthropic is racing against competitors OpenAI and Google's Gemini, and as of May is valued at more than $900 billion. Its revenue run rate jumped from $9 billion at the end of last year to $47 billion in May, while its biggest competitor OpenAI implied in March that its revenue run rate was about $24 billion with a total value of $730 billion.

Both companies are seeking potentially trillion-dollar IPOs – initial public offerings to transition to trading publicly on the stock exchange in order to raise billions from public-market investors.

Chattha, the founder and CEO of the strategic content and communications firm VSC, looks to get in on the AI wave while the value is riding high. And he just launched the new startup Powerlaw Funds, through which investors seek to buy shares of a fund with stakes in private companies through secondary market deals – with the goal to allow more people to potentially invest in companies like Anthropic.

Anthropic also announced Monday that it has submitted a statement to the U.S. Securities and Exchange Commission for a proposed initial public offering, which if approved would change the game for public investors.

For now, Chattha's property offer may draw interest from those who already got to invest in Anthropic. Hargreaves said in an interview May 29 that he had received more calls requesting showings that day than within the last four weeks of the property being listed.

Hargreaves said he isn't sure yet if the interest is driven by the idea of making a deal using shares, but has heard of similar deals which took place when cryptocurrency first appeared on the markets when "people were exchanging houses for crypto."

There's also a "big tax break" for those able to purchase a vacation rental, following the signing of Donald Trump's "One Big Beautiful Bill" in 2025, Hargreaves said. The realtor has already seen Bay Area tech entrepreneurs taking advantage of the change.

"We did $25 million in vacation rental purchases in the last year, and a lot of those were tech people from the Bay Area buying for the benefit of the second home and for the tax break," Hargreaves said.

Staff Writer Natalie Hanson reports on business and agriculture for The Press Democrat. She can be reached at natalie.hanson@pressdemocrat.com or at 619-665-5887.

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