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The low-key SF neighborhood where Airbnb and Instagram founders live

Airbnb CEO Brian Chesky in 2022 | Getty Images

When Airbnb CEO and founder Brian Chesky listed his home on Airbnb in November, the entrepreneur, who’s worth $7 billion, disclosed the San Francisco neighborhood he lives in. And it’s not anywhere near Billionaires’ Row in Pac Heights, known for its A-list of tech and old money residents, from the Getty family to Larry Ellison.

Chesky’s neighborhood? Dolores Heights or, in Chesky’s words, a residential neighborhood “near the Mission, Castro and Noe Valley neighborhoods with plenty of great boutiques, restaurants, and coffee shops.”

If that sounds to you like a fairly regular neighborhood, it’s true. With rows of Victorians squeezed shoulder-to-shoulder, it’s a far cry from the megamansions on oversized lots in Pacific Heights.

The Dolores Heights neighborhood | Camille Cohen/The Standard

The inside of Chesky’s home is nice, but it’s no Birch Castle, the home of tech entrepreneurs Michael and Xochi Birch, whose luxe and lacquered Pac Heights mansion features a bar reclaimed from a decommissioned British pub. Instead, it has the light, airy West Elm-chic look that Airbnb helped make ubiquitous. There’s a normal-sized kitchen and his golden retriever is allowed to sit on his squishy-looking gray couch. According to the Airbnb listing, you even have to share a bathroom.

Other technorati live nearby. Until he sold his home for $31 million earlier this year, Mark Zuckerberg’s pied-à-terre was in Dolores Heights. 

Instagram founder Mike Krieger and his family also live in the neighborhood, as well as a coterie of other early Facebook employees.

Zuckerberg’s entrance into the neighborhood 15 years ago was a turning point, said Bernie Katzmann, a real estate agent who has lived in Dolores Heights for 25 years. He personally knows of several billionaires in the neighborhood, though he won’t name names.

“The changes really started when Zuckerberg bought his house,” he said. “A lot of people suddenly started recognizing that it’s a beautiful area. That’s what really started the migration to the area, and it’s become a much wealthier area than it was.”

Prior to that, Dolores Heights was a family-friendly and modest neighborhood, recalls Carolyn Kenady, who chairs the Dolores Heights Improvement Club, the area’s neighborhood association.

"The original houses here were quite small,” she said. "On top of the hill, there were farmhouses, with milk cows and dairy.”

Camille Cohen/The Standard

That’s because the neighborhood was originally built for the working class. Many of the area’s homes were built by Fernando Nelson, one of San Francisco’s most prolific Victorian builders, who specialized in "modest” homes for “working-class families”.

But that was before the tech workers got wind of Dolores Heights. The neighborhood’s proximity to the freeway and its location on the south side of the city made it attractive to Silicon Valley workers, Katzmann said.

Additionally, the area has exceptionally steep hills, which means many streets have stunning city views and offer privacy. In particular, Cumberland Street is tucked away and difficult to access except via stairs making it a favorite for privacy seekers. It was also one of the first streets with underground electrical wiring, as a former PG&E executive used to live there and advocated for it, Katzmann said.

Since the neighborhood became a high-status enclave, the longtime residents and the newcomers have often clashed.

Homes in Dolores Heights | Camille Cohen/The Standard | Source: Camille Cohen/The Standard

The neighborhood went wild when a couple who were both early Facebook employees proposed tearing down an 877-square-foot cottage on Cumblerand Street and instead building a 8,300-square-foot mansion merging the lots on Cumberland Street spanning two lots.

"The project is tremendously excessive. It is especially offensive when placed between two modest cottages,” wrote one resident. Dozens of neighbors, many longtime residents, wrote impassioned letters expressing opposition. Dozens of other neighbors, many of whom were tech executives, wrote letters in support.

The home was eventually built.

Kenady says she’s not opposed to all development, but that in a city with a notorious housing problem, she sees a lot of vacant mansions.

"I’m saddened that this neighborhood has too much vacant housing; it’s a second home for people,” she said.

Chesky says he’s not one of those tech execs.

“I live here, so I’ll be here,” he said in a video posted on the Airbnb site.

And yes, Dolores Heights might just be the perfect place for a tech billionaire who needs privacy, but also dreams of being able to walk to a neighborhood bar and meet up with buddies.