Oakland’s early 20th century Tribune Tower is for sale for the second time in less than two years.

The 95,000-square-foot, 22-story tower could be sold for up to $50 million, or over $500 per square foot, according to Kathryn Collins of Harvest Properties of Emeryville, the building’s owner. Oakland’s property values have jumped in the past few years, but still lag behind San Francisco, where the most lucrative office sales have surpassed $1,200 per square foot.

The building has a storied past. In 1923, the year the tower portion was completed, magician Harry Houdini managed to free himself from a straitjacket while suspended from the ninth floor. The building housed the Oakland Tribune until 2007.

The building at 409 13th St. has been renovated by Harvest, which bought it two years ago, mostly empty, for $20.4 million, according to property records. Its website advertises “creative office space.” Occupancy has increased, according to Harvest, and current tenants include visual intelligence company Zorroa, mental health company Two Chairs and digital marketing agency Ayima.

“Most tenants now prefer not to be in your typical, class-A high rise. They want to be in a cool, creative, historical building that has character,” said Dane Hooks of Cushman & Wakefield, the building’s leasing broker. “There’s been a huge demand for that type of creative space in the last couple of years; that’s leading the market now in terms of demand and rental rates.”

Harvest invested about $13 million for improvements to the building. The biggest capital expense was $5 million in seismic retrofitting, according to Collins. She said that Harvest Properties bought the building planning to significantly renovate the tower, lease the space to businesses and eventually sell — though not necessarily this soon.

“We thought it was an appropriate time to market the building now that we’ve taken care of deferred maintenance and base building deficiencies,” Collins said.

The sale follows a trend of high-rise properties being flipped and resold for a profit in Oakland, as more investors have flocked to the city. Last year, Harvest Properties and KKR, the private equity giant, bought 180 Grand Ave. near Lake Merritt. The building was previously sold in 2014. One of the city’s most high-profile buildings, Uptown Station, was sold to Uber in 2015; the ride-hailing company sold it to CIM Group last year after abandoning plans for an office in Oakland.

Despite Uber’s decision, more businesses are opting for Oakland over San Francisco, which Robert Ogilvie of SPUR, an urban planning think tank, attributes to the East Bay city’s relative affordability.

“Unless you’re tech, San Francisco is hard to afford … there are a lot of businesses that cannot compete in terms of the rent they can pay, so downtown Oakland is a great alternative,” Ogilvie said. He notes BART access as a major selling point for workers commuting from both the East Bay and San Francisco.

San Francisco Chronicle staff writer Roland Li contributed to this report.

Rebecca Aydin is a San Francisco Chronicle

staff writer. Email: rebecca.aydin@sfchronicle.com Twitter: @RebeccaAydin