Eric Lefkofsky’s house in Glencoe, Illinois, now spans 6.1 acres on Lake Michigan after his $8.25 million purchase of an adjoining property in August 2025. The Groupon co-founder’s combined estate includes a $19.5 million French Normandy mansion and a 4,272-square-foot postmodern home designed by architect Stanley Tigerman.
Tech billionaire Eric Lefkofsky just expanded his lakefront territory in one of Chicago’s most exclusive suburbs. The Groupon co-founder and Tempus AI founder paid $8.25 million in late August 2025 to buy the property next door to his existing Glencoe mansion. This purchase brings his total lakefront holdings to 6.1 acres and a combined investment of $27.75 million.
The move reflects a strategic expansion rather than a simple home upgrade. Lefkofsky bought land that directly adjoins his primary residence at 50 Glade Road, creating one of the largest private estates on the North Shore.
The $8.25 Million Acquisition
Lefkofsky’s latest purchase came through a private transaction in August 2025. The property at 1 Glade Road includes a one-story, 4,272-square-foot house sitting on 1.83 acres of Lake Michigan shoreline.
The home has a significant architectural pedigree. The late Richard Don commissioned renowned architect Stanley Tigerman to design a postmodern aluminum and glass-clad structure, completed in 1975. Don purchased the lakefront lot in 1973, and the home remained in the family for 52 years.
The property passed to Don’s widow, Arlene, after his death in 2005. She lived there until summer 2024 before moving to assisted living. She died in March 2025 at age 94.
Arthur Don, one of the couple’s sons, managed the sale on behalf of his family. He explained that none of the brothers wanted to keep the property due to the financial burden.
The property tax alone for the Don estate totaled $162,568 in 2023. Combined with maintenance and other costs, the family decided selling made more sense than keeping the Tigerman-designed home.
Lefkofsky purchased through the same Delaware limited liability company he used for his original 2014 acquisition. The off-market transaction kept details private, though Arthur Don confirmed the family held a final beach party before the sale closed.
The $19.5 Million Primary Estate
Lefkofsky’s main Glencoe residence sits on 4.3 acres at 50 Glade Road. He paid $19.5 million in cash for the property in 2014, buying it from former Equity Commonwealth chairman David Helfand.
The purchase set a record at the time. It topped every other known residential sale in Chicago-area history. Several higher-priced transactions have since surpassed it, both in the city and suburbs.
The centerpiece is a 16,304-square-foot mansion designed in 1917 by Howard Van Doren Shaw. The French Normandy-style estate captures the grandeur of early 20th-century lakefront architecture.
Lefkofsky didn’t leave the historic property untouched. He hired Chicago-based Studio Gang Architects to design an addition shortly after the purchase. The firm, known for its innovative approach to historic renovations, added modern elements while respecting the original design.
The property includes resort-level amenities. A swimming pool and tennis courts take advantage of the lakefront location. Large windows throughout the mansion frame views of Lake Michigan.
The Property Tax Impact
Owning 6.1 acres of prime lakefront real estate comes with substantial tax obligations. The numbers paint a clear picture of the cost.
Lefkofsky’s original 4.3-acre property carried a 2023 tax bill of $364,482. The newly acquired 1.83-acre parcel added another $162,568 in annual taxes.
His combined 2023 tax burden would have reached $527,050 if he had owned both properties that year. This total will likely increase as assessors evaluate the properties under single ownership.
These figures represent some of the highest residential property taxes on Chicago’s North Shore. Only a handful of estates carry comparable annual tax bills.
Eric Lefkofsky’s Broader Real Estate Portfolio
The Glencoe properties represent just part of Lefkofsky’s real estate holdings. The 56-year-old entrepreneur maintains homes across multiple markets.
In 2020, he purchased a $33.3 million Montecito estate from Ellen DeGeneres. The 9.3-acre compound features a Balinese-inspired design with five separate structures. The main house spans 8,200 square feet with panoramic ocean views.
The Montecito property includes a guest house, a partially subterranean gym, and a security facility. An engineering marvel swimming pool appears to cantilever over the sloped gardens. The purchase came after DeGeneres bought the property for $28.9 million and completed renovations.
Lefkofsky also owns a $30.7 million penthouse at Miami’s Four Seasons at the Surf Club. Architect Richard Meier designed the luxury development. The family maintains an Aspen ski estate as well.
Despite these holdings, the Glencoe mansion remains the family’s primary residence. Lefkofsky and his wife Liz, raised their family there.
Understanding the Glencoe Market
Glencoe ranks among the most expensive suburbs in the Chicago metropolitan area. The village of approximately 8,700 residents sits 22 miles north of downtown Chicago.
Lakefront properties command premium prices. Direct Lake Michigan access, combined with proximity to Chicago, creates strong demand among high-net-worth buyers.
The village maintains strict zoning regulations that preserve the area’s character. Large lot sizes and architectural guidelines limit density. These restrictions help maintain property values but also create scarcity.
Most lakefront estates rarely reach the open market. Private transactions between high-net-worth individuals handle many sales. This pattern keeps pricing information limited and makes comparable sales difficult to find.
Average home prices in Glencoe exceed $1.5 million. Lakefront properties typically start at several million and can reach eight figures for larger estates.
The Stanley Tigerman Architecture Connection
The newly acquired home brings significant architectural history to Lefkofsky’s estate. Stanley Tigerman designed the postmodern structure in the early 1970s.
Tigerman became one of Chicago’s most influential architects. His postmodern approach challenged the city’s dominant modernist tradition. The Glencoe house exemplifies his distinctive style from that era.
The aluminum and glass-clad design represents a bold departure from traditional lakefront architecture. Large glass panels maximize lake views while the aluminum exterior creates a striking visual statement.
Tigerman completed numerous residential and commercial projects throughout his career. He died in 2019 at age 88, leaving behind a legacy of innovative Chicago architecture.
Whether Lefkofsky plans to preserve the Tigerman house or demolish it remains unknown. Historic preservation advocates would likely prefer saving the architecturally significant structure.
What Happens Next
Lefkofsky hasn’t publicly discussed his plans for the combined estate. Several possibilities exist for the newly acquired property.
He could demolish the Tigerman house and expand the grounds of his primary estate. This would create a 6.1-acre private compound with enhanced privacy and recreational space.
Alternatively, he might preserve the house as a guest residence or facility for staff. The separate structure could serve family members or visitors while maintaining independence from the main residence.
The property could also undergo renovation to match the primary estate’s aesthetic. Modern updates might blend the postmodern structure with the French Normandy mansion.
Given Lefkofsky’s interest in architecture, demonstrated by hiring Studio Gang for his main house, he may pursue a creative solution that respects both properties’ heritage.
Lefkofsky’s Business Success
Eric Lefkofsky built his fortune through multiple successful ventures. His business career spans technology, logistics, and healthcare.
He co-founded Groupon in 2008, initially launching it as ThePoint.com. The daily deals platform grew rapidly and went public in 2011. Groupon reached a peak market value exceeding $16 billion.
His other co-founded companies include Echo Global Logistics, InnerWorkings, and Mediaocean. Each venture targeted different markets but shared a technology-driven approach.
Lefkofsky founded Tempus AI in 2015. The healthcare technology company uses artificial intelligence to personalize cancer treatment. Tempus went public in 2024 and represents his current primary focus.
He serves as co-managing partner of Lightbank, a Chicago-based venture capital firm. The firm invests in early-stage technology companies.
As of October 2024, his net worth reached approximately $4.4 billion. The majority comes from his Tempus AI stake, though his diversified investments contribute significantly.
North Shore Real Estate Trends
The Lefkofsky purchase reflects broader patterns in Chicago’s North Shore luxury market. Wealthy buyers increasingly seek privacy and space, driving demand for large estates.
Lakefront properties face a limited supply. Geographic constraints prevent new lakefront development. Existing estates rarely sell, creating intense competition when properties become available.
Prices have steadily increased over the past decade. Record-setting transactions occur regularly as wealthy buyers compete for prime locations.
Property taxes remain a significant consideration. Illinois imposes some of the nation’s highest property taxes. Wealthy homeowners factor these costs into purchase decisions.
Climate change concerns haven’t significantly impacted North Shore prices yet. Lake Michigan’s stable water levels and lower storm risk compared to ocean coastlines provide reassurance to buyers.
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