Scottie Pippen is a Chicago homeowner again. The Bulls legend closed on a three-bedroom condo in Streeterville in late May, landing a 45th-floor unit with sweeping views and a wine tower, though reporting is split on exactly what he paid for it.
The Chicago Tribune reported that Pippen paid $2.2 million for the three-bedroom unit, while The Real Deal put the price at $2 million. Yahoo Sports offered a third figure, reporting that Pippen paid nearly $2.2 million through a land trust for the three-bedroom, four-bathroom condominium. The discrepancy hasn't been resolved across the available reporting, but the broader strokes of the deal line up: a high-floor Streeterville residence changed hands in late May with Pippen as the buyer.
Whatever the final number, Pippen landed a spacious perch. The condo spans 2,400 square feet on the 45th floor of a high-rise, according to the Yahoo Sports report, with 10-foot ceilings and views stretching north, east and south. The Real Deal's account adds that the unit comes with four bathrooms, a wine tower and a primary bathroom featuring heated floors and a freestanding soaking tub.
A Possible Discount on a 2023 Sale
A search snippet from Crain's Chicago Business suggests Pippen may have bought the condo for about 9% less than what the sellers paid for it three years earlier, in 2023. That discount figure comes from a search snippet rather than the full article text, so it should be treated as preliminary rather than confirmed. Still, it fits a pattern Chicago's condo market has shown in recent years.
Back in 2023, The Real Deal characterized the city's condo market as sluggish, noting that the slow conditions were prompting a number of deconversions as investors turned their attention toward apartments instead. A discounted resale in a high-rise tower like Pippen's wouldn't be out of step with that trend, though the dossier doesn't tie the two developments together directly.
Compass Agent Brokered the Deal
Eli Masud of Compass represented Pippen in the purchase, according to The Real Deal, which previously reported on a separate, much smaller Streeterville sale: retired Bears coach Mike Ditka's condo in the Olympia Centre. That two-bedroom unit, spanning 1,900 square feet on the 39th floor, drew buyers lined up to pay just under $600,000 in 2023 — down from the $700,000 Ditka and his wife, Diana, paid for it back in 2000.
Pippen's move into the high-rise follows the sale of his sprawling suburban home. The Real Deal reported that the Hall of Famer sold a 10,500-square-foot Highland Park mansion for $1.8 million in 2021, a trade-down in square footage that mirrors his shift from a North Shore estate to a downtown tower unit.
Property transfers of this kind are typically recorded with the Cook County Clerk, whose property records search allows records to be pulled by address, PIN, grantor or grantee, with a PIN search recommended for the most reliable results.
