Pippen Buys $2 Million Streeterville Condo

Chicago buyers of high-end condos see how long luxury suburban homes can take to sell.

Updated on Nov. 3, 2026 in Residential

Pippen Buys $2 Million Streeterville Condo

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Former Chicago Bulls star Scottie Pippen bought a Streeterville condo for $2 million, according to the extraction's core report. The purchase adds to a long record of Pippen's Chicago-area real estate deals, from a Highland Park mansion to Gold Coast and Lake Forest properties.

Why it matters

For Chicago homeowners, the deal is a reminder that high-end condo prices in Streeterville are set by a market that also includes large trade-ups and downsizing between suburbs and the city. Pippen's Highland Park history shows how long a luxury home can take to sell when asking prices are cut repeatedly.

Pippen paid $2 million for the Streeterville condo, while his 10,500-square-foot Highland Park mansion sold for $1.8 million in 2021 after first listing in 2016 at just under $3.1 million. The mansion had been bought for $1.5 million in 1993, so its sale price sat above the original purchase price.

The players

Scottie Pippen

Former Chicago Bulls star whose real estate moves across Chicago and its suburbs have drawn local attention.

The details

Pippen's Highland Park mansion sale took years and multiple price cuts, with the asking price reduced to under $2 million before it sold. Earlier moves in his record include a Gold Coast condo on Lake Shore Drive bought for $850,000 in 1996 and sold in 2006, and 10 acres in Lake Forest bought for $1.8 million in 1998 and later sold to a developer. He also listed the Highland Park mansion on Airbnb at $92 a night.

1993: Pippen bought the Highland Park mansion for $1.5 million.
1996: Pippen sold an 8,230-square-foot Highland Park home and bought the Gold Coast condo.
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 went on the market at just under $3.1 million.

The Home Front

Pippen's sequence of purchases and sales, from Gold Coast and Highland Park to Lake Forest and now Streeterville, traces a pattern of luxury buyers shifting between city condos and suburban estates. The 2016-to-2021 Highland Park sale shows that high-end suburban homes can take years to close even at reduced prices.

If you are planning to sell a large suburban home, check recent sale prices and days-on-market for comparable properties before setting an asking price. Consider consulting a licensed local agent about how long a luxury listing may take and whether staged price reductions are likely.

The takeaway

Long listing histories and repeated price cuts are normal at the luxury end of the Chicago market, so set expectations accordingly. Keep records of your purchase price and improvements, since those figures shape your gain or loss when you sell.