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Here’s where Chicago’s top brokerages compete for deals

City’s top residential brokerages did more deals on North Side, along Milwaukee Avenue corridor than downtown this year

Baird & Warner's Richard Druker, Coldwell Banker Realty's Ayoub Rabah, Compass' Callie Simon (Getty, Linkedin, Baird & Warner)
Baird & Warner's Richard Druker, Coldwell Banker Realty's Ayoub Rabah, Compass' Callie Simon (Getty, Linkedin, Baird & Warner)

The competition to be Chicago’s top brokerage has moved into new arenas as first-ranked firm @properties Christie’s International Real Estate and runner-up Compass expand their footprints in North and Northwest side neighborhoods.

A look into The Real Deal’s ranking of Chicago’s top brokerages by community area put numbers to what brokers have known for a while now: demand has shifted away from downtown to areas just outside the city center, North Side neighborhoods and the Milwaukee Avenue corridor.

Compass edged above @properties Christie’s International Real Estate to take the top spot along the Milwaukee Avenue corridor — a hotspot for residential real estate right now. The firm did 317 deals in Logan Square, and 589 in West Town, more than triple the number of deals as it did in the downtown area.

@properties Christie’s International Real Estate did 847 deals in this area — 302 in Logan Square and 545 in West Town, according to localized data on Cook County deals closed from July 2023 through July 2024.

Compass has beefed up its headcount in these areas, the firm’s sales manager, Callie Simon, said. Agents in other locations, like their West Loop and River North offices, have also made connections with buyers “who often reside in upscale rental condos” there, and “frequently choose Bucktown, West Town or Logan Square for their first single-family home purchase as they wish to remain in the city,” Simon said.

Buyers in these areas are often “younger people that are buying first homes, sometimes second homes,” Baird & Warner’s Richard Druker said. He’s noticed a reversal of trends in these neighborhoods where “duplex down” properties — two-floor condos with one below-ground floor that were previously not sought after — are now the first to sell.

Many top brokerages notched just as many deals — if not more — in Logan Square and West Town, along the Milwaukee Avenue corridor, than they did in the area covering the Loop and adjacent downtown neighborhoods.

@properties maintained a hearty lead on Compass in deals closed on the Near North Side, Near West Side, Lakeview and Lincoln Park — all areas where the median home values are higher than around the Milwaukee Avenue corridor. On the Near North Side, for example, @properties recorded a whopping 999 deals totaling $619.2 million in dollar volume compared to Compass’ 788 closings in the area.

In fact, @properties held onto its seat as Chicago’s top brokerage in communities across the entire North Side, according to TRD data. 

When compared to its total deals in the downtown area, @properties brokers did more than twice as many deals in Lincoln Park and more than three times as many in Lakeview. @properties’ total deals in the far North Side neighborhoods of Uptown and Edgewater also exceeded the number of deals it closed downtown for the period of July 2023 through July 2024.

A spokesperson for @properties Christie’s International Real Estate declined to comment.

The total dollar volume brought in by Chicago brokerages was also highest in these areas, according to TRD data. The Near North Side was the highest, with brokerages reporting more than $2.9 billion in dollar volume, followed by Lincoln Park with $2.1 billion and West Town with $2 billion. Lakeview came in fourth with $1.9 billion in total dollar volume, followed by the Near West Side with $1.2 billion and Logan Square with $1.1 billion. 

The total dollar volume reported for sales in the Loop was $962.5 million. 

Some of this rising appeal to the north and northwest of the Loop can be attributed to the downtown area’s population relative to other areas. The Loop has an estimated population of 41,671 residents, compared to an estimated 69,099 in Lincoln Park, for example, according to Chicago Metropolitan Agency for Planning. 

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Still, downtown luxury condos were a driving force at the top of the real estate market for many years until high-end buyers shifted their focus to other areas, leaving downtown listings to suffer price cuts or sit on the market for longer. 

@properties led the pack in the downtown area with 227 deals closed there to Compass’ 183. Berkshire Hathaway HomeServices Chicago — No. 5 in the overall ranking — came in third with 99 deals while Baird & Warner and Jameson Sotheby’s International Realty right behind at 97 and 94, respectively.

Druker of Baird & Warner said the downtown slowdown “doesn’t surprise” him as someone who lives on Pearson Street.

“This area was hit hard with tax reassessment, and I think we also get a sort of a rough reputation about crime,” he said. There are, of course, nuances to every trend, he said.

“Two of Ken Griffin’s units sold — one sold in two days — so I think there are buyers out there,” Druker said, referring to Griffin’s penthouse on the 37th floor of No. 9 Walton, which came onto the market last month and went under contract two days later at $9 million — priced for a $3.7 million loss.

Griffin sold another condo at No. 9 Walton earlier this month for $11 million – the two latest sales in a slew of Chicago properties he has been offloading over the last few years, most of them at a loss

“In certain (downtown) buildings, all of a sudden there’s a number of apartments that come on the market, and then they keep stacking up because they don’t sell, and then prices go down. So you’ve got a lot more opportunity,” Druker said.

Top firms shy from South, West Sides 

Coldwell Banker Realty — third in the overall ranking — took the lead in West Side neighborhoods like Humboldt Park, Austin and Garfield Park that, seemingly, have been less of a focus for agents of other top brokerage firms, according to the localized data. 

“We are one of the only big brokerages that has long-standing commitments to these areas by having offices, and we have been intentional about recruiting agents that are representative of those communities,” said Ayoub Rabah, regional president of Coldwell Banker Realty. 

Chicago’s two top brokerages rank considerably lower when looking at South Side neighborhoods with the exceptions of communities near the Illinois-Indiana border and gentrifying areas like Hyde Park and South Shore. 

Particularly in Southwest side neighborhoods like Lawndale, Brighton Park, Gage Park and West Englewood down to Ashburn, RE/MAX Mi Casa tops the charts, according to the localized ranking data. The brokerage ranked just shy of the top 20 on the overall ranking, coming in at No. 23. 

Keller Williams Preferred Realty is also a larger player in far South Side neighborhoods. Of the city’s top overall brokerages, Coldwell Banker Realty was the most widely present across the South Side. 

“The American dream of owning a home is strong there — people take pride in their communities,” Coldwell Banker’s Rabah said. 

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Chicago
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