Crow Holdings is back for another bite of suburban Chicago’s retail market.
Records show a real estate fund advised by Dallas-based Crow Holdings Capital, led by CEO Michael Levy, shelled out $44 million for The Overlook at Oak Brook, a shopping center that serves as a bellwether for the retail market’s resilience. The buyer may have paid all-cash as no mortgage has been tagged to the property following the Feb. 12 purchase, which would mark the property’s second consecutive all-cash purchase, according to DuPage County records.
The seller, MetLife Investment Management, walked away with a modest win. New York-based MetLife picked up the 54,000-square-foot, multi-building parcel for $41.1 million in November 2023 from GW Properties, which redeveloped the property. Selling it now for $44 million represents a roughly 7 percent appreciation in a little more than two years — a better outcome than Blackstone’s recent loss of 59 percent on a $69 million retail sale in Chicago’s northwestern suburbs.
When MetLife hired a JLL team to market the Oak Brook shopping center at 1715-1775 West 22nd Street, it was played up as a desirable offering in one of the region’s affluent shopping corridors. It’s anchored by a high-performing Amazon Fresh and features a heavy-hitting roster of national tenants, including Nordstrom Rack, Binny’s Beverage Depot and Lazy Dog Restaurant & Bar. When it hit the market in September, the property was nearly 100 percent leased with a weighted average lease term of over eight years, according to the listing.
But concerns arose about one of its main tenants, Guidepost Montessori, having recently filed for Chapter 11 bankruptcy. While Guidepost emerged from bankruptcy in December after restructuring under a new parent company, new problems have since surrounded another tenant. Amazon was reported to be closing all Amazon Fresh and Amazon Go stores in late January, to prioritize investment in Whole Foods Market.
MetLife didn’t return a request for comment on how the tenants’ actions impacted the Oak Brook property, and Crow Holdings declined to comment.
This isn’t Crow’s first big swing in the Windy City. The firm kicked off 2025 by partnering with DLC and Temerity Strategic Partners to acquire a nearly 315,000-square-foot suburban Chicago retail property in Wheaton for just under $62 million.
The Dallas player recently flexed some financial muscle to keep momentum going. In October, Crow Holdings landed a massive refinancing package for its sprawling retail portfolio, which includes 194 properties across 30 U.S. states, though the loan amount was kept under wraps. Earlier in 2025, Crow sold a 95 percent stake in an industrial portfolio for $718 million to Blackstone.
JLL’s Alex Sharrin, Moshin Mirza, Danny Kaufman, Michael Nieder, Brian Page and Danny Finkle represented MetLife in marketing the Oak Brook property.
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