A new Hillsborough mansion at 455 Pinehill Road hit the market last month at just under $40 million — which would set a new local sales record — with listing agent Phil Chen of Christie's explicitly targeting AI founders and VCs flush with secondary-market and pre-IPO cash.

A newly built mansion in Hillsborough's Pinehill Road went on the market last month at just under $40 million, a figure that would set a new sales record for the Peninsula town if it closes — and, the listing agent says, one sized to capture Bay Area AI wealth before it finds somewhere else to land.

The property, at 455 Pinehill Road, spans nearly 14,000 square feet on 2.5 acres and carries eight bedrooms, 13 bathrooms, a 10-hole putting green with sand trap, an indoor golf simulator, a two-level home theater, and a wine cellar built for more than 1,600 bottles. A glass bridge connects the main house to a guest ADU housing a gym and additional amenities. Listing agent Phil Chen of Christie's International Sereno, in coverage published Thursday by the SF Standard, said the seller purchased the property in shell condition for $7.5 million in 2023 — a figure supported by public records — then poured roughly $13 million into bespoke finishes, down to $200-apiece electrical outlets.

The arithmetic: approximately $20.5 million in documented-and-claimed combined costs against a $40 million ask. Chen is pricing the spread on AI-era demand. He's positioning Hillsborough as the emerging alternative to Atherton — newer construction, larger lots, shorter commute from San Francisco — and explicitly pitching the home at younger founders and VCs flush with secondary-stock proceeds and anticipated IPO liquidity. That's a read on the market, not a documented capital flow.

The bar this ask is trying to clear: Elon Musk's $30 million sale of a 16,000-square-foot Hillsborough chateau on 45 acres in 2021. Chen's listing, on a considerably smaller 2.5-acre lot, would need to close above that number to set a new local benchmark. He has acknowledged he expects "some negotiation" on price.

About 10 groups have toured since listing. Some prospective buyers flagged visibility from the street — Chen says screening landscaping is planned, while conceding that full privacy isn't what this home delivers. The $13 million upgrade figure is the seller's claim, reported by the Standard, and has not been independently verified. As of Thursday, the property had not gone into contract.

What to watch: whether a named buyer from the AI or VC world materializes — or whether the secondary-liquidity narrative that has been bidding up Peninsula luxury simply finds its ceiling here.