You might think of Portola Valley as “discount Woodside” — same equestrian-friendly estates and easy drives to Sand Hill Road, but without the name-brand cachet, celebrity neighbors, or top-tier home sales. A recent record-breaking sale, however, may change that reputation as the mid-Peninsula luxury market continues its seemingly unstoppable upward trajectory.
“This is groundbreaking,” said Chris Iverson of Sotheby’s, the listing agent for 20 Meadow Lane, which sold this month for $56 million. “It’s the first of the really big new homes with all the trimmings at a really, really high price point to come on the market in Portola Valley.”
The sale far surpasses the previous Portola Valley record: $35 million for Sun Microsystems cofounder Scott McNealy’s 13-acre estate, decked out with a sport court, climbing wall and hockey rink, in August 2024. That property was initially listed at $100 million and took more than five years to find a buyer.
Iverson hoped to avoid such a drawn-out process for his sellers at 20 Meadow Lane, who own many homes and decided to leave their California property last fall. He declined to name his clients, but public records show they are VC investor Bandel Carano and his wife, Paula, who bought the land for $13.65 million in 2013 and completed their custom “Villa del Prato” — Prato is both a town in Tuscany and the Italian word for “lawn” or “meadow” — in 2021. The previous owners were the family of San Francisco real-estate titan Walter Shorenstein.
The 12 flat acres and newly built 12,000-square-foot main home are rarities for the area, which made pricing difficult. With $100 million seeming too high, and sales of much smaller Woodside properties at around $40 million making that price point too low, they settled on $85 million as a “trial balloon” asking price, Iverson said.
At first, Iverson kept the listing private, telling agents last fall that he had “something special” coming on the market — realtor-speak for “If you have a buyer who flies here on their own airplane and has no budget, let’s talk,” he said.
By February, he had gotten positive feedback but no offers, so he put the home on the MLS. More potential buyers started coming in, but many were tech entrepreneurs in their early 40s who didn’t see the value in the personalized upgrades the sellers had put into the property, including a 900-square-foot primary-suite closet, inspired by a Chanel boutique, which happens to double as a bomb- and bullet-resistent panic room.
“I get buyers showing up in a hoodie and their good jogger pants. They’re like, ‘Well, what do I do with that?’” he said.
Another snag: The sellers had roughed out a separate 6,500-square-foot entertainment house where they’d planned to host black-tie affairs. But it needs to be finished, likely to the tune of $10 million. Those young buyers in their joggers couldn’t wrap their minds around that kind of high-end hosting, Iverson said, let alone the time and expense of completing the project.
In mid-July, Iverson dropped the price to $65 million.
The $20-million discount caught the attention of Leslie Bauer at City Real Estate, who had been looking at “unique properties” in Atherton, Woodside, and Portola Valley with her San Jose-based clients for two years. The anonymous buyers, who purchased through an LLC, liked the combination of classic architecture and grand size with modern updates and design features.
“What mattered most to the buyers was how deeply it aligned with the life they are creating,” Bauer said.
The negotiations took about a month, Iverson said, and the last-minute possibility of a second offer helped get the deal wrapped up. Even though the second offer didn’t materialize, he said, the interest helped the buyers realize that “splitting hairs” could cost them a one-of-a-kind property.
“You could go into Woodside and buy three neighboring homes, and have 12 acres, but it’s going to cost you more like $100 million,” Iverson said.
Now that the sale has closed, the owners plan to work on finishing the entertaining house, and some renovation plans are in the works for the main home, which has a home theater, wine cellar, and 20-foot ceilings, but just four bedrooms. There’s also a 2,000-square-foot pool house with two more bedrooms.
Skipping the suburbs
Luxury properties are moving quickly in and around Portola Valley, said Bauer, who started her career two decades ago in San Francisco but added the Peninsula market as well six years ago as her clients began heading south.
There is by all accounts a lack of housing in the 4,500-person bucolic hillside community, which was bitterly divided over how to address state mandates to add homes. Interest has only been picking up of late, with young families from the city ready to skip the suburbs in favor of country life.
Iverson said he’s been flummoxed by how many San Franciscans are interested in the area. It seems like quite a lifestyle leap to go from having everything available outside your door to a sleepy spot where the nightlife is “crickets, literally.”
“‘Is it just that suburbia is so repulsive you just figure you go rural?’” he has been asking such buyers. “And people would, across the board, be like, ‘Yeah.’”