In feud over luxury development in Winnetka, top North Shore agent isn’t backing down
The fight has divided the village and will likely move to the courts
Winnetka is Chicago’s Malibu. Large waterfront bluffs draw elite homebuyers who stay for the scenery, small-town vibe and short train ride from the city, plus unique architectural and design possibilities of building mansions into those cliffs.
This is what @properties Christie’s International Real Estate broker Jena Radnay sells: the combination of luxury and nature. But local leaders have now pitted one against the other in a push to tighten development restrictions on all 100 or so properties on the Lake Michigan shoreline.
That’s why Radnay, last year’s top real estate dealmaker on Chicago’s competitive North Shore, has braved the Village Hall podium several times to plead her case — which, to her eye, is also her clients’ case, and the village’s, too.
The very things that make Winnetka appealing are at risk with the restriction, Radnay argued, and property values could fall by as much as 30 percent, meaning millions of dollars for many parcels.
Winnetka’s village president, Chris Rintz, didn’t like that argument much. He interrupted Radnay’s public comment last July, in a break from the standard procedure.
“We’re using facts here tonight. We’re not predicting the future,” he said, adding: “I know you’ve got a great crystal ball there, Jena.”
“No, I don’t,” she objected.
Rintz continued.
“But you know what,” he lectured, “when you make statements like that, you devalue your conversation, because that is just intended to scare people and isn’t based in any fact you can bring to this table and show this council.”
At one point, he stopped just short of calling her a liar.
“Tell the truth, please,” he said.
“I always tell the truth. That’s the problem,” Radnay replied.
Radnay insisted that the ordinance would prevent work on the bluffs and construction of high-end homes, infinity pools and cabanas in spots that best capture views, thus draining value from the village’s priciest properties. The rule increases the village’s setback for construction to 50 feet from Lake Michigan’s ordinary high-water mark, rather than 50 feet from the water’s edge, cutting the amount of land on which property owners can build.
That threatens Winnetka’s reign at the top of Chicagoland’s luxury housing market, according to Radnay and others.
Radnay is not one to back down, and so the exchange intensified, building to a climax in recent weeks as a village vote approached and Radnay sided with a group of wealthy lakefront homeowners in a fight that has divided the community and looks likely to end up in a lawsuit against the village.
Billionaire vs. millionaires
To understand how Radnay and the deals she brokers became flashpoints in a wealth-and-power town’s politics, look no further than billionaire Justin Ishbia’s lakefront compound under construction at 205 Sheridan Road.
Ishbia, founder of investment firm Shore Capital Partners and son of the founder of United Wholesale Mortgage, gained approval last year for his plan to build a 68,300-square-foot megamansion, with a total cost of $78 million — the acquisition of three homes on adjacent lots for nearly $34 million and another $44 million for construction and the demolition of the existing homes.
The project included the removal of greenery from the 3.7-acre assemblage and, to the chagrin of many Winnetkans, the leveling of lakefront bluffs. Ishbia has said the changes are temporary, and that erosion control structures will be installed to protect the beachfront.
To some in the village, this was an “ecological catastrophe,” and the new regulations sought to prevent future bluff removals. But many lakefront owners have taken exception to the suggestion that they would ever perform such extreme, permanent alterations to the steep-slope zone. Meanwhile, village leaders insist homeowners will be able to get variances for smaller-scale development activity.
“I know you’ve got a great crystal ball there, Jena.”
Some Winnetkans wondered how the village had let luxury trump nature so dramatically.
“The characterization that we were asleep at the wheel is completely wrong, and I find it very insulting,” Rintz said.
“Times are changing quickly, and I don’t think anybody in this town could have conceived of any individual assembling four, five, six parcels, multiple acres of property with a massive frontage on the lake, and then understood that he would take full advantage of the floor-area ratio yield and combine all those lots into a single parcel. We have taken steps to prevent that.”
Ishbia declined to be interviewed. His spokesperson pointed to an October letter published in the Chicago Tribune in which he correctly noted that he received all necessary approvals without variances and claimed he is “aligning our design with the broader community objectives.”
Radnay believes the village has already solved the problem of preventing such massive homes from being developed. Last year, Winnetka passed a rule that limits lot consolidation. This prevents homeowners from stacking the buildable square footage allowed on contiguous lots in order to go beyond the 25,000 square feet usually allowed on an individual parcel.
Behind the controversy over the Ishbia plan and the restriction on lakefront development lie deeper resentments. In a place where median household income is more than $250,000, the ultra-rich seem different from the merely rich.
“People don’t like people with money on the lake,” Radnay said. “They think they’re all entitled and they have too much money. This ordinance is to hurt lakefront properties, and it’s to penalize the lakefront owners. They don’t deserve this.”
Radnay doesn’t just work in Winnetka. She lives there. Her home is not on the lake, but her campaign against the blufftop regulations has left her “not well-liked,” she said. Yet she’s adamant that her perspective and voice have been used in the spirit of her “No. 1 goal,” which is to “keep Winnetka No. 1.”
“It’s an honor to work on the lake,” she said.
Although she didn’t arrange any of the deals for Ishbia’s assemblage, she thinks his move highlights Winnetka’s status.
“It only cements the value of Winnetka that someone so successful believes this town is so wonderful,” Radnay said.
Buyer’s remorse
The skirmish started in July, when the village put a moratorium in place on certain work in the steep-slope zones of lakefront properties.
That was right after two of Radnay’s lakefront deals in Winnetka went into contract: 691 Sheridan Road, which at $12.5 million became Chicagoland’s priciest sale of 2023, and 445 Sheridan, which closed at $12.3 million, a price the buyers have since said they would have reconsidered in light of village actions.
Village Council member Bridget Orsic, a fellow agent with @properties, mentioned those two deals as evidence that an ordinance wouldn’t drastically dent property values, since they closed with the moratorium in effect.
Radnay, however, said that both deals went into contract in June, weeks before the council initiated the moratorium in July. One buyer had put more than $1 million in escrow, evidence of his seriousness. (Radnay represented the sellers at 691 Sheridan and both the sellers and buyers for 445 Sheridan.)
Radnay tried to correct Orsic about this both during a public meeting and over emails written to Winnetka leaders. In an email to The Real Deal, she called it “totally terrible” that the “inaccuracy” wasn’t clarified by Orsic or the village.
Like Rintz, Orsic didn’t much like Radnay’s position.
“The personal vilification has been hard to get used to on this,” Orsic said in a Feb. 6 public meeting as Radnay sat in the audience. “In my understanding of the world, nothing is final until the closing.”
“Can I say something?” Radnay asked from the gallery.
“No,” said Rintz and Orsic.
After the meeting, Radnay said in an interview that she avoids renegotiating prices or canceling deals after coming to agreements. “I don’t do real estate like that,” she said.
Scaling up
Radnay didn’t start in luxury real estate on the North Shore, and acknowledged that she wasn’t well-received by the community at first. She had been selling Chicago homes and transitioned cautiously to the ritzy suburbs, waiting until she had a solid book of business before giving up the city. New money was heading to the North Shore’s lakefront, occasionally coming into conflict with longer-tenured residents, and initially some of those longtime residents saw Radnay as a driver of this current.
Then as now, she stood fast. She attributes the fire in her personality partly to her mother, who grew up in Cicero, an industrial suburb of Chicago. As she was guiding a reporter’s tour of the North Shore, Radnay made a left turn in front of a vehicle at a stop light without the right of way, then honked at the waiting driver. Rintz, it’s obvious to her, feels “threatened” by her.
“I always tell the truth. That’s the problem.”
Radnay keeps her ear to the ground. She lunches at local hot dog shacks, where she keeps up with the whispers from blue-collar workers about who’s building and renovating. She keeps close tabs on the New Trier Township High School, where she sends her two teenage children, as well as its feeder elementary and middle schools, and can rattle off curriculums for each grade level.
“She’s made herself the most knowledgeable” in the North Shore, said @properties Christie’s broker Emily Sachs Wong, who met her about 15 years ago.
Radnay’s mentor as she transitioned into the North Shore market was the late Barbara Mawicke, whose 2020 obituary claimed she was the first agent to reach $1 billion in career sales volume on the North Shore. Mawicke once told Radnay: “[if you’re] lucky one day, you’d be a bartender.”
“I said, ‘I don’t want to be a bartender, I want to be a Realtor,’” Radnay remembered. “Barbara said, ‘Here’s what bartenders have that Realtors don’t: They have all the inside scoop, and they just want to keep talking and talking and talking.’ Bartenders that make a lot of money, you know what they do? They have the regulars who come in, and you hear their life, and when you hear their life and open your heart to their life, you’re going to be a part of their life.”
She took the advice and has spent years cultivating relationships in the area, some of which have led to business. So she isn’t worried about losing clients for being on the lakefront owners’ side of the fight.
Losing argument
But you can’t win everything.
Lakefront owners failed to persuade the village board to give up the ordinance. In February, members voted 5-0 to enact the lakefront development rules.
Proponents pointed out that all other lakefront towns in the area have restrictions similar to those Winnetka put in place. Opponents said the fact that Winnetka didn’t have them previously is what has made its property the most valuable.
The spats between Radnay and Rintz and Orsic were far from the only testy moments with village leaders, and Radnay wasn’t alone in speaking up against the changes. Dozens of lakefront owners chimed in, claiming they had improved both the appearance and stability of their bluffs without the new rules in place.
Vijay Kotte, the CEO of GoHealth, who bought 445 Sheridan with his wife, investor Shiraz Kotte, tried to pipe up at the Feb. 6 meeting when Orsic called out Radnay’s deals, but he was also shot down, as public comment had ended. Kotte told village leaders he would have reconsidered the price he paid for the property if he had known the lakefront restrictions were coming. Kotte declined to be interviewed for this piece.
While the moratorium and the lakefront restrictions were on the table before the closings, Radnay said her buyers chose to “hope for the best” that the restrictions wouldn’t get final approval. But “the worst happened.”
A group of clients now plans to sue the village for damaging their property values, according to Mark Karasik, a lawyer with the firm Baker McKenzie who said he represents more than 30 lakefront homeowners.
Orsic declined to be interviewed, citing the threat of litigation. Rintz didn’t respond to requests for an interview.
Radnay isn’t giving up.
“I will protect the value of all Winnetka homes,” she said. “That is my job, that is my mission, that’s why I’m employed. My job is to protect their asset, maybe their biggest asset. I will continue to fight for what is right.”