A growing number of sellers are seeking pre-IPO stock rather than cash for their multimillion-dollar homes, with listings offering to sell for Anthropic or OpenAI shares seen in Miami, Brooklyn, and the San Francisco Bay Area. While experts say it may be legal, there are hurdles. One home listed in Sonoma County wine country, a Healdsburg vacation rental with a $2.5 million list price, offers a $500,000 discount for Anthropic stock, accepting $2 million in the AI company's stock. The listing suggests the deal avoids a taxable event, but tax experts disagree. Jennifer George of PricewaterhouseCoopers told the San Francisco Chronicle that a buyer using privately held stock cannot avoid capital gains taxes, as the taxable event would likely be based on the home's fair market value minus the shareholder's cost basis. Another barrier involves stock transfer restrictions; many private companies limit when and to whom shares can be sold, requiring board approval. Storm Duncan, an investment banker selling his $8 million home and adjacent property for Anthropic stock, told Realtor.com he is aware of restrictions and will work within the rules, calling the sale "a diversification play" to reduce his real estate exposure.