Billionaire Groupon co-founder Eric Lefkofsky spent nearly $8.3 million buying the house next to his record-setting estate in Glencoe in late August, The Real Deal has learned.
An LLC tied to Lefkofsky bought 1 Glade Road, a house on a 1.83-acre lot adjacent to 50 Glade Road, the home Lefkofsky bought for $19.5 million in 2014. At the time, that was the most expensive home purchase in Chicagoland’s history.
The buyer of 1 Glade Road is listed as 50 Glade LLC, the same entity that purchased 50 Glade Road and was later identified as Lefkofsky’s company, according to Cook County property records. Lefkofsky purchased the property on Aug. 27, property records show. The sale was made without being publicly listed, so property records don’t list the agents that represented the buyer and seller.
At 1 Glade Road is a 4,300 square-foot house with 4 bedrooms and 6.5 bathrooms. Lefkofsky’s existing house at 50 Glade Road spans 15,800 square feet and has 8 bedrooms and 6.5 bathrooms. It includes a tennis court and a swimming pool.
The house at 1 Glade Road was previously owned by the late Richard and Arlene Don. Their son, Arthur Don, senior counsel at Greenberg Traurig, helped manage the estate sale after Arlene’s death this year. He did not confirm the buyer.
Don said his father bought the Stanley Tigerman-designed lakefront property for $150,000 in 1973. His mother lived in the house until shortly before she died, he said.
“We received offers from people for years, and we said we’re not going to sell as long as my mother is alive,” he said.
Lefkofsky’s plans for the Dons’ property are not yet known. Groupon did not immediately respond to a request for comment.
The entrepreneur is worth an estimated $6.4 billion, ranking him 598th richest in the world, according to Forbes. In addition to co-founding the daily retail deals website Groupon, he has invested in five other unicorns, including healthcare startup Tempus.
His purchase of the Dons’ property extends a trend of elite buyers absorbing multiple adjacent waterfront properties with large compounds in mind within wealthy enclaves. Fellow billionaire Justin Isbhia’s waterfront Winnetka estate that’s under construction at an estimated total cost of more than $70 million, including more than $30 million in land assemblage through the purchase of multiple lakefront properties, sparked controversy and new limits on lakefront development in that North Shore power town.
Similarly, Glencoe in August began considering new incentives to help homeowners preserve historic properties amid growing threats of teardowns to make way for new construction. It’s unclear whether Lefkofsky’s latest real estate purchase played a role in prompting the discussion. But the village is looking at whether to offer tax breaks and zoning relief aimed at offsetting the costs of maintaining landmark homes to boost the appeal of preservation as compared to demolition.
Far bigger purchases have been made on coastal markets by wealthy buyers seeking to create mega-estates by adjoining multiple properties. In Miami, the pandemic attracted a surge of buyers from other regions, significantly boosting waterfront luxury markets with unparalleled demand and skyrocketing prices as land assemblage ramped up in recent years.
The sale also adds to the banner year Chicago’s luxury market is seeing so far, especially in the wealthy North Shore towns. By mid-September, the number of Chicago-area homes sold for more than $4 million surpassed the number sold in all of 2024. Winnetka, just south of Glencoe, has been the site of much of the action, including a record-breaking $31 million deal that closed in August.
The $8.25 million price tag for 1 Glade Road makes it one of the most expensive home sales in Glencoe history, after Lefkofsky’s record-setting $19.5 million transaction. At least two other properties have sold for more: A property on Lakewood Drive sold earlier this year for $9.2 million, and a Longwood Avenue estate brought in $8.7 million in 2021.
The Dons’ property was tagged with a $6.7 million valuation in the most recent look by Cook County tax officials, which translated to a property tax bill of just under $163,000 in 2023, public records show. Lefkofsky’s home at 50 Glade Road was most recently assessed at $16.2 million, with a tax bill of over $364,000 in 2023.
Editor’s note: A previous version of this story referred to Lefkofsky as Groupon’s chairman. He was formerly its chairman, and the story has been updated to correct his title to co-founder.