San Francisco's Sea Cliff neighborhood, where Twitter CEO Jack Dorsey owns $30 million worth of homes, is a parade of oceanside mansions. Here's what it's like inside.

Katie Canales

Feb 9, 2020, 20:09 IST

San Francisco's Sea Cliff neighborhood, where Twitter CEO Jack Dorsey owns $30 million worth of homes, is a parade of oceanside mansions. Here's what it's like inside.

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Katie Canales/Business Insider

Twitter and Square CEO Jack Dorsey is just one resident in the enclave on the opposite side of downtown that features stunning, high-priced villas.

On the northwest corner of San Francisco is the exclusive neighborhood of Sea Cliff.
It was founded in 1913 as one of the city's residence parks, or makeshift suburbs.
It's become one of San Francisco's most elite residential areas housing prominent figures, including Twitter and Square founder and billionaire Jack Dorsey.
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If you need a reminder of San Francisco's multifaceted landscape, go to Sea Cliff.

As the name implies, it's a neighborhood built on, and in some parts into, a cliff overlooking the expansive Pacific Ocean. It's on the opposite side of the city center, away from the hustle and bustle - you'll get a hefty whiff of salt and brush of sea breeze by merely wandering its streets.

Sea Cliff was founded in 1913 as one of San Francisco's eight master-planned residence parks, or "garden suburbs." In the 1920s, there was a public demand for suburban-style alcoves in San Francisco that were easily accessible from downtown. These faux country-living communities provided residents with the luxuries of peace and quiet away from city life.

Fast forward to today, and it's still as peaceful as it was when it was built. But what was originally intended to be merely a reprieve from city life has transformed into one of 21st century San Francisco's most elite neighborhoods thanks in part to the proximity to the ocean.

Notable residents that have at one point owned property here include actors Robin Williams, Sharon Stone with then-husband Phil Bronstein - who was the executive editor for the San Francisco Examiner -, Cheech Marin, and Eugene Levy; musicians Paul Kantner of Jefferson Airplane and Kirk Hammett of Metallica, prominent photographer Ansel Adams, and Bay Area tech bigwigs like Twitter and Square founder and CEO and billionaire Jack Dorsey, who reportedly paid a collective $30 million for two homes next door to each other, both nestled into a cliffside overlooking the Pacific Ocean.

It's a coveted neighborhood to be apart of, Sotheby's real-estate agent Anne Herrera told Business Insider in a 2019 interview.

"It has become a place for those that have the means to do so to buy a house and still be in the city, but still be very connected to nature and all the beauty of the views of the bridge and the beach," Herrera said.

We spent a day meandering through the neighborhood's streets, down El Camino Del Mar, Sea Cliff Avenue, and into the public cove of China Beach where Jack Dorsey's home is visible.

It's a breathtaking part of San Francisco - here's what it's like inside.

Sea Cliff is a neighborhood on the northwest corner of San Francisco.

Some of the most beautiful vantage points of San Francisco, the Golden Gate Bridge, and the Pacific Ocean are in Sea Cliff.

And some of the highest-priced, coveted homes in the city are located here.

Sea Cliff itself technically covers a larger area of the city than just the main residential area. Land's End, Sutro Baths, the Legion of Honor museum, and other attractions are lumped into the neighborhood.

But many of the Sea Cliff homes are concentrated in the east part of the neighborhood.

Weaving through the streets of San Francisco's exclusive Sea Cliff neighborhood is like walking through a surreal museum of lavish homes.

We visited on a Tuesday afternoon, in the middle of a workday, so the neighborhood seemed void of all residents.

Though it seemed as though many homes haven't been occupied in a while — there were still pumpkins on display at this home, but perhaps the live-in owners are simply busy.

There was, however, no shortage of landscapers and contractors, working hard to manicure the pristine lawns and conducting renovations — some inside, some out — on the exquisite homes.

The layout of the residential streets is indeed reminiscent of suburban design — the streets and sidewalks were narrower than what you would find in a city setting, and trees were symmetrically lined along the roads.

Homes here sell on average for $3.66 million. That's well above San Francisco's median home value of $1.39 million.

The least expensive home currently for sale on the public market is a yellow house listed for $4 million. The last time it sold was in 1998 for $1.4 million.

Up the street is the most expensive home currently for sale publicly, a four-story white home built in 1915 and listed for $12 million with unobscured views of the bay and the Golden Gate Bridge.

El Camino Del Mar — Spanish for "the way or path of the sea" — is the main thoroughfare in Sea Cliff, cutting east to west from the Presidio and into Land's End.

Palm trees, Spanish tile roofing, and red-bricked porches are common sights along the road, and throughout the neighborhood.

This Spanish-style four-bedroom home on El Camino Del Mar was built in 1924 and last sold for $6 million in December 2014.

Zillow estimates that this two-story yellow home built in 1927 with 12 rooms is estimated to be worth $5 million, though it's not for sale.

A few doors down is an 18-room, rose-colored manor built in 1926 that occupies nearly half an acre on a corner lot. It's currently off the market but estimates by Zillow and Redfin value it at $6 million and $10 million, respectively.

Most of the Sea Cliff homes are of Spanish, Mediterranean, or the city's signature Victorian, design.

But some are modern — this home last sold on the public market for $3 million in 2010.

The two-story home was originally built in 1951 and has three bedrooms and three bathrooms.

There are smaller arteries branching out from El Camino Del Mar like 32nd Avenue, a street running perpendicular to the coast that might be one of the quaintest.

At the northern end along a bend in the road is a home that was once a Danish Consulate. It was owned by a Google lawyer and the founder of shoe startup Rothy's in 2016 when a driver crashed into the house.

They sold their home, which was damaged by a fire that erupted from the crash, in mid-2017 for over asking price for $3.1 million, less than a month after it was first listed. The ad came with disclaimers like "sold as is" and "buyer beware."

If you head back up to El Camino Del Mar and turn right, the street will eventually merge into Sea Cliff Avenue, a street running parallel to the coast at the northern end of residential Sea Cliff.

The homes on this street have front-row seats to the Pacific Ocean and are some of the only homes to be literally built into the cliffside.

The pink home at 224 Sea Cliff Avenue, a "fixer-upper" according to a 2019 Business Insider interview with the home's listing agent, is in serious need of some TLC and doesn't even come with photos of the interior.

And yet it's listed for sale for $13.7 million. The home has been listed since October 2019 and is currently "under contract." It comes with a winding pathway down to a secluded seaside cove.

It was once owned by Luke "Lucky Luke" Bragnara, a real-estate mogul and notorious art scammer who stashed hordes of stolen art worth a collective $11 million in the home in 2014.

A few doors down and across the street is this two-story, five-bedroom house that doesn't face the water. It last sold on the public market in 2013 for $3.2 million.

Down the street is not one but two homes next door to each other once owned by Metallica guitarist Kirk Hammett.

Walk around the corner from Hammett's previous homes and down a short path, and China Beach will begin to come into view.

It's a cove open to the public and nestled at the northern end of the residential area of Sea Cliff.

A winding staircase leads down from the street level to the beach.

The beach's history is engraved on a stone at the entrance. According to local legend, Chinese fishermen once used it as a campground while anchoring their fishing boats in the cove.

Legend or not, the plaque was erected by Chinese Americans in 1982 to honor the Chinese fisherman that contributed to the San Francisco Bay Area since the time of the Gold Rush.

Down near the beach, there's a deteriorating structure once used by lifeguards to store equipment.

Standing in the alcove of China Beach's public sand is a similarly surreal feeling to touring the neighborhood, like you're on a stage with the homes tucked away in the hillsides staring down at you.

On one side of the amphitheater are four homes, the left two once belonging to Hammett, the Metallica bassist.

Pivot in the opposite direction and there, peeking out from the foliage, is the roof of a home belonging to Twitter CEO Jack Dorsey. It's a two-bedroom, two-bathroom house clad in dark wood. Dorsey purchased it in 2012 for $10 million.

And in November 2019, he reportedly bought the two-story house right next door in an off-market sale for $21 million, perhaps for more privacy — the second house is wedged in right alongside his home of eight years, though it's difficult to catch sight of that one from the beach.

The newly-purchased home was in need of a restoration, with one building complaint claiming that the property had gone unoccupied for 15 years, according to Mansion Global.

Neither home was visible from the street, but there were workers and construction equipment and materials along the street where the entrances would be.

Dorsey reportedly is turning the two homes into a single compound.

With views like this, it's not unheard of for one of the richest men in tech — and the world — to opt for such a living situation in one of the most beautiful parts of Square and Twitter's hometown.

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