A Cook County judge has paused the sale of Crestwood Apartments, a 57-unit senior building in Chicago's Austin neighborhood, after the winning bidder disputed the property's condition and finances. The order halted a closing that had been scheduled for Sept. 21, 2026, leaving the $2.7 million receivership sale unresolved while tenants face emergency relocation.
The buyer, Crestwood CHI LLC, won a June auction with its $2.7 million bid but later sued to reduce the price rather than close as scheduled, according to The Real Deal. The company is managed by Brooklyn-based investors Boruch Zucker and Elye Neustein, the outlet reported. Judge Marian Perkins canceled the Sept. 21 closing and scheduled further proceedings.
The buyer alleges that the court-appointed receiver, Frontline Real Estate Partners, failed to disclose before the sale that the Chicago Housing Authority had suspended rent subsidies on 31 units, The Real Deal reported. Crestwood CHI LLC agreed to buy the property as is, where is, but its attorney, Thomas Emalfarb, said the company is seeking to reform the contract at a lower price. Frontline head Matt Tarshis disputed the allegations, and Mike Hopkins was identified as Frontline's attorney.
A Building Falling Apart Around Its Residents
Crestwood houses low-income seniors and has faced extensive repair problems, including plumbing failures requiring walls inside units to be opened, electrical deficiencies and an inoperable elevator. The elevator replacement estimate was $300,000 to $400,000, according to The Real Deal. The Chicago Housing Authority has declared the property uninhabitable and issued emergency relocation vouchers to tenants.
What relocation vouchers mean for tenants
HUD says tenant-protection vouchers can have different rules after displacement. Replacement vouchers may be reissued if housing assistance is preserved, while relocation vouchers generally are not reissued after the original family stops receiving them, according to HUD.
Those problems are not new. Block Club Chicago reported that Crestwood had racked up nearly a dozen failed inspections in the year before its August report and more than two dozen over the preceding decade. Residents have described sewage backups, plumbing failures, bed bugs, flooding and a lack of maintenance, and the outlet noted that tenants held a rally on July 29 to protest what organizers called dangerous living conditions and to demand immediate repairs.
Natalie Guarino said tenants have concerns about the owner's identity and the pace of ongoing repairs, per The Real Deal's reporting. Steven McKenzie said the city is concerned about whether the potential buyer is serious about making necessary repairs, according to the same report.
The Drillman Connection
The ownership dispute grew out of a defaulted loan. The entity that previously controlled Crestwood defaulted on a $5.1 million mortgage originated by Berkadia in 2020, and Fannie Mae filed a foreclosure complaint against it in 2024, according to The Real Deal. The Jane Addams Senior Caucus, which represents Crestwood tenants and intervened in the case, cited public records linking Neustein to Barry Drillman, including a shared New Jersey office address and a 2020 transfer of Mich Holdings LLC from Drillman to Neustein.
The reporting contains a discrepancy over the first name of the convicted person connected to the property. The Real Deal identified him as Barry Drillman and reported that he pleaded guilty to a $165 million federal mortgage-fraud conspiracy and received five years of probation in 2025. Block Club Chicago identified him as Boruch Drillman and likewise reported a December 2023 guilty plea and 2025 sentence. The available accounts do not resolve whether the two names refer to the same person.
Tenants and Lenders Both Want a Say
The Jane Addams Senior Caucus intervened on behalf of tenants, who are seeking to vacate the sale to Zucker and Neustein's Crestwood entity altogether. Fannie Mae and Frontline, however, have argued that the tenants lack standing to disrupt the sale, according to The Real Deal's reporting.
Fannie Mae has advanced $1 million to the receivership for necessary repairs and, along with Frontline, plans to formally object to any reduction in the purchase price. Crestwood CHI LLC was required to deposit 10 percent of the purchase price and could lose that deposit if the purchase agreement is upheld and the company still fails to close, the outlet noted. The buyer had anticipated Chicago Housing Authority subsidies as a revenue source for the property.
Judge Perkins has scheduled emergency motions from both the prospective buyer and the tenants, and Cook County's court will hold a hearing on Oct. 20 to decide whether the sale proceeds, the contract is reformed, or the property returns to the market. If the receivership sale is ultimately called off, Fannie Mae could still end up with title to the property through a traditional foreclosure sale, per The Real Deal.
