Pippen Buys Streeterville Condo for $2 Million
The former Bulls star's latest Chicago-area real estate purchase comes after years of moving between Highland Park, Lake Forest and the Gold Coast.
Updated on Nov. 3, 2026 in Residential
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Scottie Pippen bought a Streeterville condo for $2 million, according to the extraction of reported property records. The purchase follows his 2021 sale of a 10,500-square-foot Highland Park mansion for $1.8 million.
Why it matters
The transactions trace how a high-profile Chicago buyer has moved through the city's luxury residential market over three decades, from Highland Park and the Gold Coast to Lake Forest and now downtown. For Chicago readers, the sales offer a benchmark for upscale property values across several neighborhoods.
The Streeterville condo was bought for $2 million, while the 2021 Highland Park sale brought $1.8 million for a 10,500-square-foot home. The extraction does not specify the Streeterville unit's square footage or sale terms.
The players
Scottie Pippen
Scottie Pippen is a Hall of Fame forward who won six NBA championships with the Chicago Bulls in the 1990s alongside Michael Jordan.
The details
Pippen first bought a Highland Park mansion for $1.5 million in 1993 and later sold an 8,230-square-foot Highland Park home in 1996. The Highland Park mansion first went on the market in 2016 at just under $3.1 million, and its sale took years and multiple price cuts before closing in 2021.
Timeline
1993: Pippen bought a Highland Park mansion for $1.5 million.
1996: Pippen sold an 8,230-square-foot Highland Park home and bought a Gold Coast condo for $850,000.
1998: Pippen bought 10 acres in Lake Forest for $1.8 million.
2006: Pippen sold the Gold Coast condo.
2016: The Highland Park mansion first listed at just under $3.1 million.
Market Landscape
Pippen's moves mirror a longstanding pattern among affluent Chicago-area buyers who have alternated between suburban estates in Highland Park and Lake Forest and urban high-rises on the Gold Coast and in Streeterville. His repeated trades between these markets over three decades illustrate how the luxury segment shifts with buyers' lifestyle needs.
For Chicago homebuyers, Pippen's Streeterville purchase and his earlier Highland Park sale show the price range of high-end properties currently changing hands in the city. Buyers in the upper tier of the market can use these figures to compare asking prices across Streeterville, Highland Park and the Gold Coast.
The takeaway
Luxury property purchases in the Chicago area often move between suburban estates and downtown condos over time, so buyers and sellers should track neighborhood-level sale prices before committing. Use recent comparable sales in Streeterville, Highland Park and the Gold Coast to set realistic expectations.
Further reading
For more on the city's upscale home sales, see Residential in Chicago.
Source note: This article includes information reported by The Real Deal New York.
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