One in every of San Francisco’s strangest properties simply hit the market

For $13.9 million, a house in San Francisco could be yours.
Listed this week, the peculiar mansion at 1969 California Street is unique due to its seemingly incomplete shape and storied history. The 9,000 square-foot, five-bedroom home features four levels, diamond-patterned lead windows, and a lofty 11.5′ ceiling the blurb describes as delivering “a gravitas rarely seen in today’s market.”
The historic Tobin House was built by one of the most important men in San Francisco at the time, Michael Henry de Young, and is one of the few surviving homes on the block from a century ago.
1969 California St, San Francisco.
Andrew Chamings
As a young journalist from St. Louis, de Young and his brother Charles moved to San Francisco and founded what would become the San Francisco Chronicle in 1865. In the 1910s Michael purchased two lots next to each other adjacent to his ornate Victorian mansion on California Street.
Initially planned as one of two twin homes for his daughters, Constance and Helen, de Young employed famed architect Willis Polk to design what would have then been a very modern housing complex for the time.
1969 California Street, San Francisco.
Jacob Elliott for Sotheby’s International Realty
Polk’s ambitious idea for the Tobin House (named after Constance’s husband, Joseph Tobin) and its neighbor was that they mirror each other and share an archway, which would form a tunnel leading to the giant mansion owned by Michael. But this plan would never be fully realized after Helen decided not to move to San Francisco near her sister and father, and instead remain on her estate on the Peninsula. Some old newspaper stories report on a “serious falling out” between the sisters, and this story has become part of the half-arch lore, though it’s hard to confirm.
The left side of the tall arch didn’t find its twin, leaving the striking architectural incongruity, with the half-arch slamming into the red brick wall of its modern neighbor, rendering it useless.
1969 California Street, San Francisco.
Jacob Elliott for Sotheby’s International Realty
From the street, the tall archway and roof loom large, with an almost medieval look. Its design was considered very modern at the time — the steep slate-clad Tudor style roof and a stark gray facade replacing the ornate Victorian intricacies of the era. A single gargoyle (technically a grotesque as no water runs through it) of a lion adorns the front, and the building has somehow never been painted.
The half-arch continues deep into the block with several repeated half-arches butting up against the neighbor’s home down the narrow alley that should have been a tunnel.
Michael died in 1925, and his mansion was razed in 1941, leaving the half house (now San Francisco Historic Landmark 260) as the only vestige of a time when the de Youngs’ owned the entire block.
1969 California Street, San Francisco.
Jacob Elliott for Sotheby’s International Realty
The Tobin House was purchased in the 1940s by an eccentric opera singer named Gualtiero Bartalini who reportedly hosted lavish parties there. More recently it was home to the Anthony Meier Fine Arts Gallery.
1969 California is being listed by Joe Lucier and Stacey Caen of Sotheby’s International Realty. Read our full history of the building and the block here.