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The crown for Cook County’s most lucrative deals belongs to Winnetka.
Jena Radnay, with @properties Christie’s International Real Estate in Winnetka, anchored a dominant year for the firm, outpacing the competition with a $5.2 million average deal size, according to an analysis of Cook County sales records by The Real Deal.
Radnay also ranked sixth among the top residential agents and agent teams in Chicagoland by total sales dollar volume, undertaking 41 deals worth more than $213 million.
TRD analyzed closed, on-market residential transactions — condos, co-ops, two- to four-family homes, single-family homes and townhouses, filed with Cook County between October 2024 and October 2025.
Two agents from Jameson Sotheby’s International Realty rounded out the top three resi players with the highest average transaction size in 2025: Nancy Tassone, with an average deal size of $3.4 million, and Tim Salm, with an average deal size of $2.5 million.
In terms of total dollar sales volume, another @properties team — Emily Sachs Wong’s ESW Chicago — took the top ranking, with $338.3 million over 174 closed deals over the past year. The team’s average deal size worked out to $1.9 million, ranking the team fifth among the county’s top resi players.
The @properties brokerage overall also outperformed other agencies in the region. The firm, which was recently acquired by Compass, had the highest total sales dollar volume, at $7.9 billion, this year.
Brokers in the Chicago metropolitan area had to contend with tight inventory and broad macroeconomic challenges and uncertainties over the past year. Still, the top 20 agents and teams raked in $3.2 billion in sales this year, up more than 14 percent, year-over-year. This elite cohort inked 3,338 deals, about 100 fewer than last year. The average size of their transactions was a little more than $970,000.
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