rewrite this title and make it good for SEOSelling a house for OpenAI or Anthropic stock is legal. It’s also harder than it sounds.

A growing number of sellers are seeking pre-IPO stock rather than cash for their multimillion-dollar homes. It might be expected from a home seller near Silicon Valley, but reports of listings offering to sell for Anthropic or OpenAI shares have been seen in Miami and Brooklyn, as well as more than one residence in the San Francisco Bay Area. 

That raises a basic question: Can someone buy a house with the private stock of companies soon to go public? 

It may be legal, experts say, but there is at least one hurdle that may be impossible to clear.  

Read more: Best mortgage lenders

A half-million-dollar listing discount for Anthropic stock

Tech-minded home sellers are eager to acquire pre-IPO shares in hopes of riding a wave of rapid appreciation. 

And with the expected Anthropic IPO and OpenAI IPO, investor enthusiasm to get in before the opening bell is mounting. 

One home listed for sale with a $500,000 discount for Anthropic stock is located in Sonoma County wine country. The Healdsburg vacation rental has a $2.5 million list price, but the owner will accept $2 million in the AI company’s stock.

“The deal is built for the Bay Area buyer whose net worth sits in private-company stock that is hard to spend,” the listing says. “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.”

Tax experts say that description might not be quite accurate. 

Jennifer George, a rep with tax firm PricewaterhouseCoopers, told the San Francisco Chronicle that while a home can be purchased with anything of value, including “cash, a boat, a million chickens,” a buyer using privately held stock can’t avoid capital gains taxes. 

The taxable event would likely be based on the home’s fair market value, minus the shareholder’s cost basis in the stock, George said.

Read more: What is capital gains tax? Here are strategies to reduce your bill.

Stock transfer restrictions can get in the way

Tax considerations aside, there is another possible barrier to buying a home with OpenAI or Anthropic pre-IPO stock. 

While private companies looking to go public often offer stock buybacks or tender offers that allow employees to sell their stock back to the company or to institutional investors, many of these companies have transfer restrictions that limit when and to whom company shares can be sold.

The company’s board of directors would have to approve the sale or transfer of the shares.

Another Bay Area seller seeking Anthropic stock in the sale of his $8 million home and adjacent property is aware of the possible restrictions and is willing to work a deal within the rules. 

“I’m not going to pick a fight with Anthropic,” Storm Duncan, an investment banker, told Realtor.com. “I’m not going to try to do something not legally acceptable.” Duncan said the sale of the home for stock is “a diversification play,” as he reduces his exposure to real estate while increasing his AI stake.

He already owns nearly $1 million in Anthropic stock. 

Read more: How AI is changing real estate in the U.S.

Another option: borrow against the shares

Buyers with private company stock have another option: a loan secured by the private shares as collateral. While it doesn’t fulfill the seller’s goal of gaining pre-IPO shares, it does allow the holder and potential homebuyer to retain ownership of the stock while gaining some liquidity — and delay a capital-gains-taxable sale.

A few banks offer loans made against private company stock, and some companies specialize in such financing. Generally, the loan isn’t due until the company goes public or gets sold.

However, private share lending is likely to have a higher interest rate than borrowing against publicly traded stocks and to have stricter collateral requirements. And again, transfer restrictions can also come into play.

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