One developer’s fumble became another developer’s win in the Gold Coast this week.
Chicago-based R2 Companies successfully completed a buyout of all 20 units at a condo building at 127 Maple Street last week after four years of negotiations, R2 partner Zack Cupkovic confirmed.
The total purchase came out to $4.7 million or about an average of $235,000 per unit, though individual condo purchases vary based on unit size and specifics. R2 is also putting additional funding toward renovating units, Cupkovic said.
The buyout comes after another Chicago-based firm, Fifield Companies, tried to propose a 43-story apartment tower at the site in 2020. Fifield ultimately walked away from the plan after opposition from neighbors and the area’s alderman, along with rising interest rates, squashed the proposal before it could take off.
Fifiled originally proposed building a 43-story apartment tower with 406 units, and later revised the proposed tower to be 29 stories tall with 269 units. But the latter version was still too dense for the neighbors’ liking.
Triton Real Estate broker Nicole Linares started eyeing the building after Fifield walked away, knowing that many unit owners were likely still willing to sell, she said. Many were eager to offload their units because the property, built in 1886, had fallen into disrepair. It was difficult to sell them individually, however, because the majority of the condos were being rented out by the individual owners. As a result, most lenders would not underwrite mortgages for new buyers.
“The only buyers were cash buyers, which really limited the pool of potential buyers,” Cupkovic said.
Still, even with a significant number of the unit owners willing to sell, a smaller number of hold-outs made it difficult for a bulk buyer to come in and take over the property, Linares said.
Acrimony between unit owners even escalated into legal action. At least one condo owner sued the condo association, alleging it improperly agreed to a $6.7 million buyout of the building with Fifield, but that lawsuit was dismissed. The last active lawsuit between unit owners was resolved last August, public records show.
R2, led by CEO Matt Garrison, was willing to stick it out.
“Matt [Garrison] and Zack [Cupkovic] and the whole team were willing to go through this many times. We had three starts, three endings, and then finally we reached a point where we could get through it. It’s so convoluted and there are so many personalities,” Linares said. “I have to give a huge amount of credit to Matt and Zack.”
Last year, the company completed a bulk buyout of 15 of the 20 units in the building. The company closed the remaining units last week, Cupkovic confirmed. The purchase also includes a 20-spot parking lot, he said.
By the end of it, Cupkovic said he bought R2’s general counsel a pair of custom Nike sneakers embroidered with “127 Maple” on the back as a thank you for sticking it out through 20 closings.
R2, which has made a name for itself redeveloping loft office space in Chicago, has spent the last year renovating the units it already owned and renting them out. He said, unlike Fifield, they plan to keep the shell of the building the same.
The parking lot, however, could be redeveloped in the future, Cupkovic said.
Securing the prime Gold Coast land with fairly flexible zoning was worth the wait, Linares said.
And in Chicago’s hot multifamily market, deals like this are hard to come by, she added.
“It’s a great land play,” she said. “The building is really cool. It was one of the old Chicago grand dames back in the ‘20s, but it sits on a pretty decent amount of land with a large amount of zoning.”
The city’s pipeline of new development is at a historic low and is driving up leases at existing properties and fueling rapid rent growth.
New apartments completed over the past 12 months amounted to just 0.8 percent of existing inventory, and the city’s average rent hit $1,956 a month at the end of 2025, according to recent CoStar data.
In addition to office-to-residential conversions, the condo deconversion market is picking up as developers look for existing opportunities to create rental units.
“There’s a lot more of those buildings that are ripe because they’re older,” Linares said.
But no matter the size of the property, the process is often fraught.
“To [the condo owners], this is one of the biggest deals in their lives,” she said.
Another local firm, Strategic Properties of North America, has experienced those obstacles first hand over the past few years.
The condo board at 10 East Ontario Street in River North initially agreed to a $190 million bulk sale to Strategic, but after the company failed repeatedly over three years to secure the funding necessary to close the purchase of the 167-unit building, the board backed out of the deal in 2023. At the time, one condo owner called the waiting game, “hell for the past three years.”
Similarly, at 200 North Dearborn Street, the board of that 310-unit building voted to terminate a contract with Strategic in 2024 after waiting for two years for the firm to secure funding for the $95 million purchase. Since then, Strategic and an affiliate have made two subsequent offers to buy the building, the second of which is for $98 million and is currently being considered by condo owners in a building-wide vote.
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