Clint Reilly doesn't usually sell. The longtime San Francisco investor is known for holding real estate for decades. But this week, he made another exception - his third sale in two years.

Public records show Reilly, who owns the San Francisco Examiner and other local media companies, sold his 18,300-square-foot office-and-retail building at 360 Pine St. for $9.2 million - just over $500 per square foot - after owning it for about 20 years. In a downtown market still struggling with high vacancy, the price defies the broader market slump.

Roughly one-third of San Francisco office space remains empty years after the pandemic reshaped workplace demand, pushing many large towers that are now worth less than the debt that is owed for them to trade at steep discounts - often around $300 to $350 per square foot. Smaller, well-located properties and so-called "trophy" buildings, however, continue to attract stronger pricing.

The 360 Pine sale sits in that divide. A larger, 50,000-square-foot building nearby at 200 Pine St. sold late last year for about $263 per square foot - roughly half the price on a per-foot basis.

Meanwhile, last week, a 360,000-square-foot nearly vacant tower at 123 Mission St. in the South Financial District, purchased for $400 million by e-cigarette maker Juul in 2019, traded hands through a loan sale for less than $300 per square foot.

Reilly, whose real estate portfolio includes the Merchants Exchange Building at 465 California St. and a 25-story office tower at 235 Pine St., bought 360 Pine in 2006 for $5.1 million. Reilly did not immediately respond to an inquiry from the Chronicle seeking comment on the deal.

Its most recent buyer is an entity tied to Matt Fisher, president of Hayward-based Fordere Cornice Works, a historic architectural metal company founded in 1875. The company already owns a roughly 50,000-square-foot industrial building in the city, at 269 Potrero Ave. The Chronicle reached out to Fisher for comment on the sale but did not hear back.

"This deal shows that local families are reinvesting in San Francisco and excited about downtown," said Zach Haupert, a broker with Touchstone Commercial Partners. Working alongside Michael Sanberg and Christian Diggs, also of Touchstone, he represented Reilly in the transaction, while Will Cliff of brokerage Colliers represented the buyer.

The Pine Street sale follows other recent real estate moves by Reilly. In 2024, he sold the former Little Fox Theater in Jackson Square to famed iPhone designer Jony Ive for $56.7 million, which is located on a block where Ive paid above market prices to assemble a group of buildings to serve as the headquarters for his design firm, LoveFrom. Reilly separately sold a Sea Cliff mansion for $14.5 million that same year.

Real estate insiders say deals like 360 Pine often involve owner-users willing to pay a premium to secure long-term space without leasing risk.

"Owner-users often pay the high purchase prices: This results from the elimination of leasing downtime and commission, as well as a reduction of required tenant improvements, when these occasional buyers lock in their long-term occupancy costs during temporary market downturns," said local commercial broker Charlie McCabe.

The 360 Pine building's office space is largely leased, according to Haupert, and has a new restaurant tenant lined up, replacing Credo, a longtime Italian spot that closed early last year after operating for 15 years at 360 Pine, and was also owned by Reilly.

For downtown San Francisco, the takeaway is mixed: The broader office market remains under pressure, but select properties are still commanding top dollar.

This article originally published at Even in a weak S.F. office market, one Financial District building fetches top dollar.