City records show the Block co-founder filed this summer to restart and finish earlier work on his Sea Cliff homes, as building fills the enclave.
Jack Dorsey has built a reputation for restraint. The co-founder of Twitter and the payments company Block is known for spare clothing, minimalist design and, by his own account, long fasts. His house in Sea Cliff has been a slower, more elaborate undertaking.
Work on the property, which Dorsey bought in 2012, has continued in one form or another for nearly 14 years, SFGATE reported this month in a long look at the construction that now fills much of the neighborhood. The New York Post and Hoodline followed with their own accounts.
City records reviewed by The Inquirer show that the project entered a new administrative phase this summer. On June 16, four permit applications were filed for Dorsey’s original property, each described in the city’s building permit database as “recommencement and completion of work” under an earlier permit. The four cover the main redevelopment permit first filed in 2013, the 2020 redesign of that project, and permits from 2021 and 2022. The city issued all four on June 25.
Two houses, one long project
Dorsey bought the first house through a limited liability company in February 2012 for $9.99 million, according to SFGATE. The modernist home, built in 1965, had moved on and off the luxury market for years, SFGATE reported, including a $15 million listing in 2009. After the purchase, Dorsey posted on Twitter: “I need the sea because it teaches me.”
The main redevelopment application arrived in December 2013, with proposed work valued at $3.7 million that included seismic strengthening and an expansion of the house, SFGATE reported. The city issued that permit in June 2017. A substantial redesign was filed in February 2020 and issued in July 2022.
In November 2018, six years into the project, Dorsey bought the house next door for $21.9 million, SFGATE and the Post reported. Together, the two properties cost about $31.9 million and cover roughly 1.21 acres. The purchase drew comparisons at the time with the compounds other technology founders have assembled, but SFGATE wrote that the architectural plans it viewed “do not show the houses being joined into a single structure.”
Smaller permits have filled in the years between. City records show landscape retaining walls, valued at $250,000, approved in August 2025, and a final inspection in March of this year on landscaping work at the second property under a permit first issued in 2019.
A style closer to the cypress than the villa
Little of Dorsey’s house can be seen from the street, according to SFGATE, which described the visible part as a planted “living roof” rising behind new redwood gates. The paper wrote that the dark timber, stone and planted roofs place the house “closer to Northern California modernism, with a Japanese influence” than the white villas and Mediterranean mansions elsewhere along the cliff.
That would fit what Dorsey has said about his tastes. A 2013 New Yorker profile, cited by SFGATE, described his interest in botanical illustration and in wabi-sabi, the Japanese aesthetic that finds beauty in imperfection and impermanence.
A neighborhood under scaffolding
Dorsey’s project is far from the only one on his street. Sea Cliff was laid out more than a century ago as a residential park, its curving streets and large lots set between the ocean and the Presidio, SFGATE noted. Over the years its residents have included Robin Williams, Ansel Adams and Sharon Stone; Salesforce co-founder Marc Benioff and the investor and former presidential candidate Tom Steyer also have homes there, SFGATE reported.
These days, the soundtrack is more cement mixer than surf. SFGATE’s review of planning documents found that “no fewer than 24 homes have filed building permits since the beginning of 2025” along the street where Dorsey lives. An Inquirer review of the city’s building permit data, current through Oct. 24, found 51 permit applications filed for 23 addresses on that street since Jan. 1, 2025, with declared estimated construction costs totaling about $8.3 million. Estimated costs on permit applications are supplied by applicants and can differ from what projects ultimately cost.
The Inquirer also reported this week that the city is moving to auction a Sea Cliff house at the center of a deed-fraud lawsuit, a reminder that the neighborhood’s real estate draws attention for more than its views.
The fortune behind the gates
Dorsey, 49, co-founded Twitter in 2006 and served twice as its chief executive, most recently from 2015 to 2021; he left its board in 2022. He co-founded Square, now Block, which runs the Square payments business and Cash App, and he leads the company today.
Forbes’ real-time ranking estimated his net worth at $7.41 billion as of the market close on Friday, Oct. 23. Forbes reports that his holdings include a stake of about 0.14 percent in SpaceX, which merged with X, the former Twitter, and went public this year.
In 2020, Dorsey pledged $1 billion of his Square equity to Start Small, a philanthropic initiative he created to fund pandemic relief and, later, other causes. Forbes reports that the effort has distributed about $807 million so far.
The Inquirer’s survey of the 100 families who hold San Francisco’s wealth, published Friday, counts Dorsey among the city’s most prominent residents. For a famously private executive, the city’s permit files offer one of the few public windows into how he lives.
The Post wrote that it had sought comment from representatives for Dorsey; its article did not include a response.
Pilar Ashcombe covers San Francisco society and the public lives of its billionaires, from galas, museum and opera boards and art collections to landmark homes and the city’s old and new fortunes, for the Inquirer’s Billionaires desk. More from Pilar Ashcombe
