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Billionaire entrepreneur and Groupon co-founder Eric Lefkofsky in late August paid $8.25 million for a one-story, 4,272-square-foot house on Lake Michigan in Glencoe. The property adjoins one that Lefkofsky already owns.

Lefkofsky, 56, founded Tempus AI and co-founded the companies Groupon, Echo Global Logistics and InnerWorkings. He is the co-managing partner of the venture capital firm Lightbank.

In Glencoe, Lefkofsky paid $19.5 million in cash in 2014 through a Delaware limited liability company to buy a16,304-square-foot mansion and 4.3-acre lakefront property in a private transaction from former Equity Commonwealth chairman and CEO David Helfand. Lefkofsky then hired Chicago-based Studio Gang Architects to design a small addition.

The amount that Lefkofsky paid in 2014 topped every other known residential sale price in Chicago-area history at that time. Since then, however, that $19.5 million amount has been eclipsed by a handful of other higher-priced residential real estate transactions both in the city and suburbs.

Now, Lefkofsky has decided to expand his domain with another off-market deal — through that same Delaware LLC — of an adjoining house and 1.83-acre property, also along the lake. The property he purchased in late August had been owned since 1973 by the late Richard Don, who died in 2005, and his widow, Arlene.

The Dons’ son, Arthur, managed the sale on behalf of himself and his brothers. He told Elite Street in an email that after buying the lakefront property in 1973, Richard Don hired architect Stanley Tigerman to build a postmodern aluminum and glass-clad house, which was completed in 1975. He added that his mother lived in the home until the summer of 2024 and later moved to an assisted living facility before she passed away in March at age 94.

None of the Dons’ sons decided it was worth keeping the Tigerman-designed home and surrounding property in the family, Arthur Don said.

“The value of the property, coupled with the annual real estate tax and other annual costs made it very difficult for any of (my mother’s) descendants to keep the property,” Don said. “We did have a blowout family beach party last weekend to say goodbye.”

Lefkofsky did not return an email requesting a comment. Don declined to confirm that Lefkofsky was the buyer.

One thing is certain: Lefkofsky’s total property tax bill now is set to increase. In 2023, the tax bill on his existing 4.3-acre lakefront property in Glencoe was $364,482. The Dons’ former property that Lefkofsky just bought for $8.25 million had a 2023 property tax bill of $162,568, meaning that if he had owned his entire 6.1-acre lakefront spread in 2023, his tax bill would have been $527,050.

The Real Deal first reported on Lefkofsky’s purchase.

Goldsborough is a freelance reporter.