Jena Radnay

Broker, @properties Christie’s International Real Estate

Radnay has been at the forefront of a renaissance on Chicago’s North Shore, driving some of the region’s biggest residential deals on the most exclusive stretch of Lake Michigan shoreline.
In 2025, she closed the two most expensive home sales in Chicagoland history, representing each side on both Winnetka deals that landed at $32.5 million and $31.3 million.
That kind of dual-agency blockbuster puts an agent under the spotlight in a business where discretion and conflicts are always part of the conversation. She’s been outspoken against the Winnetka Village Board’s controversial moves to restrict lakefront development, which have drawn lawsuits from some of Illinois’ wealthiest residents.
Radnay started her career in marketing at the firm DBB Chicago, working with high-profile clients like McDonalds. She left that job to begin selling real estate around 2010.
“I remember thinking to myself, if I don’t do this now, I’m never going to love what I’m doing,” she said of her decision to switch careers. “And I said, ‘Screw it, let’s go for it.’”
Radnay did an early stint selling parking spots in the city with brokerage Koenig & Strey, then shifted her attention north around 2016 and planted her flag in Winnetka. Radnay is the top-producing agent in Winnetka and has repeatedly shown she can move lakefront trophy stock when rates, taxes and thin inventory make buyers skittish.
Yet, the bigger question is consistency: the North Shore ultra-luxury niche throws off monster years, but it’s also volatile by nature and sensitive to a handful of listings.

— Caleb McCullough