Chicago Penthouse Price Drops to $2.7 Million

The massive Streeterville condo at 415 East North Water Street has been on the market for over a decade.

Updated on Oct. 28, 2026 in Commercial

Gouache-painted illustration of a single modern architectural tower model in muted earthy tones, representing a luxury high-rise real estate property. — A Chicago penthouse in the Streeterville neighborhood has lowered its asking price to $2.7 million after a decade of listing attempts. AI Illustration. Upload story photo >

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A high-profile penthouse in Chicago’s Streeterville neighborhood has seen its asking price slashed to $2.7 million. The 9,280-square-foot unit has been listed and delisted repeatedly since first hitting the market in 2015.

Why it matters

The property has struggled to find a buyer despite significant capital investment in its unique custom features. The price reduction marks the latest attempt to sell the unit after a failed auction attempt in 2022.

The 9,280-square-foot penthouse is currently priced at roughly $290 per square foot. The unit includes a 60-foot wraparound terrace, a floating staircase, and three 500-gallon fish tanks.

The players

Cal Fishkin

He is the owner who purchased the unfinished penthouse unit in 2008.

The details

The luxury condo, located at Unit 3205 of 415 East North Water Street, is known for its polished stone walls and appearances in television shows including Empire and Chicago PD. Cal Fishkin originally purchased the unfinished space for $5.3 million in 2008, with subsequent listings noting as much as $14 million in total investment.

Cal Fishkin purchased the unfinished unit in 2008.
The property was first listed for sale at $13 million in March 2015.
A 2022 auction listing for the unit resulted in a $2.5 million bid.
The unit was listed for sale at $4 million in 2024.
The current asking price reached $2.7 million in October 2026.

Culture Shift

The property illustrates the difficulty of moving ultra-luxury custom homes in a market that favors modernized or turnkey residential spaces. This slow turnover reflects broader shifts in how high-net-worth buyers prioritize specific architectural customization versus standardized luxury layouts.

Local buyers may view the current $2.7 million price as a significant discount from the $14 million reported investment, though the unit remains a niche asset. Prospective residents should evaluate the high maintenance costs associated with maintaining a nearly 10,000-square-foot space.

The takeaway

The persistent struggle to sell this unique unit serves as a reminder that extreme customization can sometimes limit a property's appeal in the broader real estate market. Potential investors should weigh the cost of high-end upgrades against the eventual resale value of specialized luxury features.