By MAURA WEBBER SADOVI

A Florida investor recently acquired one of Miami’s best-known office addresses for $262.5 million, the biggest office deal in the city since 2008 and a gutsy bet that the city’s commercial real-estate market is on the road to recovery.

Crocker Partners acquired the marble-clad Miami Center from Sumitomo Corp. of America, a unit of Sumitomo Corp., SMFG +0.98% a Japanese global trading firm. Designed by Italian born architect Pietro Belluschi, the 34-story tower bearing Citigroup Inc.’s C +2.18% logo includes the bank among its biggest tenants. The now-defunct Stanford Financial Group also occupied several floors before its collapse in 2009.

The deal last month comes as a trickle of buyers are prowling for bargains in second-tier markets, like Miami, where office rents and vacancies have yet to recover from the recession. Analysts say they are watching if large institutional investors will follow locally based Crocker’s lead and help push up values and volume. “The market’s healing, but it’s certainly not all the way back,” said Ben Carlos Thypin, director of market analysis for Real Capital Analytics, which tracks office deals.

Nearly one-fifth of downtown Miami’s office market remains vacant, compared with 9.2% in 2007, according to Reis Inc., a real-estate research firm. The first-quarter office vacancy rate in the U.S. was 17.2%. Some market watchers say the Miami outlook could worsen before it gets better as recently completed new space is filled.

Crocker is paying about $334 a square foot, roughly the same price that the building fetched when it last traded in 2008. The price per-square-foot paid by Crocker is above last year’s $169 per-square-foot average but below the $400 range that some large trophy Miami office buildings fetched near the peak, according to Real Capital.

Thomas Crocker, founder of Crocker Partners, says he is paying a low enough price for the property, which offers water views, to compete for tenants against more-expensive and newer towers. And with fewer competitors driving up building prices he expects an initial return of about 6%, above the returns as low as 4% that investors are willing to accept for the best buildings in New York, Washington and San Francisco.

One of the city’s glitziest and largest office buildings, the 786,000-square-foot Miami Center’s early years were rocky. The property was completed by developer Theodore Gould in 1983 amid a glut of supply. By 1985 a group led by Bank of New York took ownership of the distressed center. The property’s financial and vacancy woes were briefly noted by author Joan Didion in her book “Miami” that chronicled cracks in the façade of the fast-growing city often presented “as a rich and wicked pastel boom town.”

With roughly 16% of the tower unoccupied, the building’s new owners still must find new tenants to stabilize the property, one reason Crocker got a better deal. But brokers say that may prove easier these days as employers are increasingly interested in locating near the growing number of residents chasing bargain rents or buying condos delivered during the boom, said Tere Blanca, chief executive of Blanca Commercial Real Estate. Some 23,000 condominium units built downtown during the boom are now about 94% occupied, up from 60% in 2009, according to the Miami Downtown Development Authority.

“There was a lot of pain for developers and banks with the oversupply of residential,” said Ms. Blanca said. “But in every cycle there’s also opportunity.” Downtown also is drawing new investments from developers. Swire Properties, 1972.HK -0.22% a Hong-Kong-based investor, is breaking ground on an $800 million-plus retail, condominium and hotel project called Brickell CitiCentre.

The Miami Center deal is only the latest real-estate foray for Mr. Crocker. The 59-year-old was also chief executive of CRT Properties, a publicly held real-estate investment trust that was sold to private investors in 2005. His family’s ties to the real-estate industry go back to the early 1900s, when his great grandfather arrived from Ireland and began investing in apartments in New York’s Westchester County.

Now Mr. Crocker says the Miami Center purchase is one of a flurry of five office acquisitions that his fund-management firm has completed or has put under contract in Miami and other cities, such as Houston and Dallas, over the past 20 months. Once completed, Crocker will control about 3.5 million square feet of office space that he plans to lease up, stabilize and ultimately sell. All are in so-called second-tier cities where Mr. Crocker sees less competition for assets. “I’d rather be competing with three guys [bidding on a property] than 100,” said Mr. Crocker. “That’s a better place to be.”

Write to Maura Webber Sadovi at maura.sadovi@wsj.com