Streeterville Penthouse Condo Price Drops to $2.7 Million
The 9,280-square-foot unit has struggled to find a buyer since its initial $13 million listing back in 2015.
Updated on Oct. 28, 2026 in Commercial
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The penthouse at 415 East North Water Street in Chicago has seen its asking price drop to $2.7 million. This 9,280-square-foot Streeterville residence has remained on the market since 2015, when it was first listed for $13 million.
Why it matters
The price reduction marks a significant shift for a property that owners claimed had $14 million in total investment. It highlights the challenges of selling high-end, custom-finished luxury units that have sat on the market for over a decade.
The unit at 415 East North Water Street, Unit 3205, is now listed at approximately $290 per square foot. The 9,280-square-foot penthouse features three 500-gallon fish tanks and a 60-foot wraparound terrace.
The players
Cal Fishkin
The owner who purchased the unfinished condo in 2008 and moved the asset into a land trust.
The details
The owner, Cal Fishkin, moved the unit into a land trust after purchasing it unfinished in 2008. The property features extensive custom work including polished stone walls and a floating staircase, having previously appeared as a filming location for Empire and Chicago PD. Despite these features, the unit has undergone a cycle of repeated listings and delistings over the last decade.
Timeline
2008: Cal Fishkin purchased the unfinished penthouse.
March 2015: The unit was first listed for sale at $13 million.
2022: The property reached auction with a $2.5 million bid.
2024: The unit was re-listed for sale at $4 million.
October 2026: The current asking price was lowered to $2.7 million.
The Home Front
Luxury properties often face prolonged market stays when high-end customization limits the pool of potential buyers. This unit reflects broader trends in high-value real estate, where original investment costs frequently decouple from current market valuations.
Homeowners should note that custom, non-traditional finishes can often complicate resale value regardless of original investment. If you are planning significant high-end renovations, consult with a local real estate professional to understand how unique features may influence future marketability.
The takeaway
Large-scale luxury renovations do not always correlate with a higher resale price after years of market exposure. Prospective buyers or sellers of custom luxury units should track price-per-square-foot averages in their specific neighborhood to benchmark realistic expectations.
Further reading
For broader market insights, browse the latest listings and analysis in Chicago Commercial.
Source note: This article includes information reported by The Real Deal New York.
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