Iconic Chicago Old Town apartment community trades for $88.25M

CHICAGO, Mar. 6, 2025 – JLL Capital Markets announced today that it has secured the $88.25 million sale of  Cobbler Square, a historic 292-unit apartment community located in Chicago's highly sought-after Old Town neighborhood.

JLL represented the seller. The buyers were JDL Development, LLC and Centaur Capital Partners.

Cobbler Square is strategically located at 1350 N Wells St., occupying an entire city block in the heart of Old Town. This prime location provides residents with easy access to Chicago's best attractions, including restaurants, entertainment venues, North Avenue Beach and Lincoln Park. The property boasts an exceptional 99 Walk Score, reflecting its highly walkable urban setting.

Originally built in 1889 as the Dr. Scholl's shoe factory, Cobbler Square was converted to residential use in 1985. The community offers a unique mix of studios, one- and two-bedroom loft-style apartments with 12-18 foot ceilings, appealing to a wide demographic of tenants. The property also features approximately 19,038 square feet of fully leased retail space.

Cobbler Square presents significant value-add potential for the new owner, with opportunities to continue the programmatic renovation plan for unit interiors. Additionally, the property offers two exciting development opportunities: potential construction on an adjacent parking lot and the possibility of adding units above an existing parking garage.

Chicago is the third-largest city in the United States, with a metropolitan population of over 9.4 million. The city boasts a diverse economy, world-class cultural institutions, and a growing tech sector, making it an attractive destination for both businesses and residents.

JLL Capital Market’s Investment and Sales Advisory team representing the seller was led by Managing Directors Mark Stern and Kevin Girard, Director Zach Kaufman and Senior Analyst Sam Grohe.

"The sale of Cobbler Square demonstrates the continued investor interest in well-located multifamily assets with value-add potential in dynamic urban markets like Chicago," Stern commented. "The property's iconic status, prime location in Old Town, and its redevelopment possibilities make it an attractive acquisition for the JDL Development and Centaur Capital Partners venture."

JLL Capital Markets is a full-service global provider of capital solutions for real estate investors and occupiers. The firm's in-depth local market and global investor knowledge delivers the best-in-class solutions for clients — whether investment sales and advisory, debt advisory, equity advisory or a recapitalization. The firm has more than 3,000 Capital Markets specialists worldwide with offices in nearly 50 countries.

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JDL, founded in 1993 by Jim Letchinger, has established itself as Chicago's premier residential developer known for creating dynamic luxury developments that exceed expectations. With a focus on residential and mixed-use projects, JDL has delivered iconic properties like No 9 Walton, One Chicago and the upcoming North Union, all of which have significantly impacted Chicago's real estate landscape and skyline.