Phil Chen of Christie’s is hoping to beat out Elon Musk — when it comes to real estate, at least. 

The newly minted trillionaire had one of Hillsborough’s highest sales ever in 2021, when he sold his 16,000-square-foot mansion on 45 acres for $30 million. That 1912 chateau had been in the same family for over a century before Musk bought it in 2017.

Now Chen, an agent at Christie’s International Sereno, thinks his Hillsborough listing, a newly built nearly 14,000-square-foot home on 2.5 acres, has all the high-end bells and whistles to attract AI founders and the young VCs who fund them. Given that, and the flood of cash cascading in from secondary stock sales and soon IPOs, he’s set his asking price at just under $40 million.

“Atherton is obviously Atherton,” Chen said, referring to the wealthy enclave that’s home to the bulk of Peninsula sales at this price point but is burdened by a stodgy reputation. Palo Alto attracts a younger buyer pool, but it’s farther from San Francisco and doesn’t have homes with the square footage or privacy this group seeks.

Hillsborough, on the other hand, is the happy medium.

“A lot of those younger founders and finance and tech guys from the city are looking at Hillsborough first to find something with newer construction and bigger lots,” Chen said. 

Chen said 455 Pinehill Road — with its eight bedrooms and 13 bathrooms —ticks most of the boxes for the “low-key billionaire” founder with a young family, especially one with live-in staff.

The seller bought the estate for $7.5 million in 2023, according to public records. It was in shell condition from the original developer and has been finished at a level well above that of a typical spec home, Chen said. Everything is custom, from the marble slabs to the windows. Even the electrical outlets had to meet exacting standards. 

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“Each outlet is like $200,” he said. “Everything was just above and beyond what the developer was originally planning.”

The homeowners spent about $13 million on the bespoke upgrades, which include a 10-hole putting green complete with sand trap, indoor golf simulator, two-level movie theater, fitness center, and wine cellar with room for more than 1,600 bottles, including 60 magnums. But after living in the completed home for just a few months, they decided it was too much house for a family of three, especially since they split their time between the Bay Area and Los Angeles. They’re looking for something smaller in Hillsborough.

Since listing the home last month, Chen has given tours to about 10 groups. Most loved the views from the knoll-top mansion, though some expressed privacy concerns about the home’s visibility from the street.

“There is a planting plan for screening out some of the front of the house that we’re going to do,” Chen said, “but if you don’t want to be seen at all, this wouldn’t be the right house.” 

Even if Chen doesn’t get all the way to his $40 million asking price — he admits that he expects “some negotiation” — he thinks setting a better-than-Elon record would bring deserved attention to the town of just under 11,000. As a big, new-construction home with high-end finishes and all the amenities on an extra-large lot, the listing stands a fighting chance of bringing Hillsborough into Atherton’s sky-high pricing orbit.

“It absolutely should set a bar,” Chen said.