Brandon Chasen, the Baltimore real estate developer whose company was once named one of the fastest growing in the area, is facing one of his most serious legal challenges yet: a foreclosure filing on the historic One Calvert Plaza building in downtown Baltimore.

Court documents made public earlier this month show Chasen Cos. was late to make payments on a nearly $34 million loan from the Maryland-based Sandy Spring Bank every month from January until its eventual default in June. The bank’s allegations mirror a pattern of similar claims made over the last year by several contractors.

Sandy Spring Trustees filed to foreclose last week on the historic skyscraper that Chasen Cos. purchased in 2022 for more than $11 million and planned to convert into an apartment building with 173 luxury units. The company agreed to strict loan terms that allow the bank to automatically enter a judgment against the debtor if it defaults on the loan terms.

The developer, who brushed off concerns about the company’s financial health in an interview with The Baltimore Banner earlier this year, was warned in advance. A July 2 letter from the bank’s lawyers includes accusations that Chasen Cos. failed to complete construction and withheld important financial information before defaulting.

This latest development could spell trouble for the firm, which has dominated in the city for the last few years. In Fells Point alone, the company has purchased about 10% of the available multifamily properties, according to a Banner data analysis of property records in June. The company controls about 2,000 residential units, mostly in Baltimore, and owns other properties in Tallahassee, Florida, and Newport News, Virginia.

Neither Chasen Cos. nor an attorney representing the company have responded to multiple requests for comment. Attorneys representing Sandy Spring declined to comment, citing the ongoing litigation.

Seydina Fall, a senior lecturer in finance at Johns Hopkins Carey Business School, is skeptical that Sandy Spring will follow through on its threat to seize the property. Banks, he said, usually prefer to restructure the loan with new terms rather than inherit an asset.

Fall said the firm may face other challenges in the short term as it attempts to fight off legal challenges and keep its daily operations going.

“It’s a situation where I think it would be a lot more difficult to borrow going forward,” he said.

Earlier this year, a steel contractor for two of Chasen Cos.’ projects in the Harbor East and Fells Point area accused the real estate company of failing to pay for its work. Patriot Steel Fabrication Inc. petitioned a judge to enter a mechanic’s lien against the firm, halting work on the historic Meyer Seed Co. warehouse and an adjacent property on Aliceanna Street. Chasen Cos. purchased the old warehouse for $10 million in 2022 and bought the Aliceanna property for $5 million that same year.

A series of additional nonpayment allegations surfaced this summer — including by a plumbing company that claims it’s owed around $48,000, a lighting supplier that says it’s out about $40,000, and a cleaning company that sued Chasen Cos. for more than $22,000 in July, and won, forcing Chasen Cos. to pay up. Emerging Concepts LLC, a Chicago company that brokered a deal between Chasen Cos. and a commercial tenant for the ground floor of the Meyer Seed project, alleges the company never paid the first installment of a $500,000 commission.

City records also show that the developer owes the city about $200,000 in unpaid water bills; Chasen Cos. has been late to pay for water at almost every address in its name. The firm said in a March email to tenants in at least one property that it planned to raise its fees for water and trash collection, though it is unclear if the increase was related to those debts.

The missteps punctuate a period of rapid gains for the company, which Chasen founded in 2017 with his best friend Paul Davis, from the prestigious Washington, D.C.-based Bullis School.

The two made waves in Baltimore for buying up more than three dozen properties, large and small, in some of the city’s most affluent neighborhoods and aggressively marketing them them as “modern,” “boutique,” and “luxury” to young professionals and families.

Privately, Chasen embodies the flashy lifestyle synonymous with the company’s brand, once counting a penthouse suite in the Four Seasons, multiple designer cars and a company jet among his personal assets. He told The Banner in May that he has since scaled down to get more in touch with his spiritual side.

From the start, the company faced backlash from tenants over matters such as security, maintenance and building quality, which many have asserted in interviews and in court records do not match the value they were paying in rent. Others have filed complaints with the Maryland Office of the Attorney General that have involved the lack of a valid rental license at some properties and what renters have described as false and misleading advertising. City code enforcers have issued citations at several properties.

Chasen’s ambitions have been tempered, in part, by a rise in interest rates that quickly increased the cost of debt to its highest level in over two decades. The interest rate on its loan from Sandy Spring climbed as high as 8.3%. He also has been frank about other challenges in the real estate market, including high materials costs and labor shortfalls.

It’s unclear whether any work has been done to refurbish One Calvert Plaza, once the city’s tallest skyscraper.

Two people, one of them donning a safety vest, were seen within the last few weeks opening the locked doors and heading inside the building.

Chasen Cos. has dubbed the project “The Plaza” and still lists the building online among the firm’s portfolio of properties. Its website, though, no longer appears to be working.