Chicago's Kenwood neighborhood just saw a big-money bet on vintage housing, with a 46-unit courtyard apartment building on Drexel Boulevard trading for $11.7 million after a full overhaul. The 1924 property, recently taken down to the studs and rebuilt, is changing hands again to a buyer signaling plans for more capital work. Because most residents use rental subsidies, the deal is drawing close attention from those watching how fresh investment could ripple through building operations and tenant stability.
The Deal and the Numbers
As reported by REBusinessOnline, Interra Realty brokered the $11.7 million sale of the 46-unit building at 4400 S. Drexel Blvd., which was about 91 percent occupied when it changed hands. The courtyard property is made up mostly of two-bedroom layouts and dates back to 1924. Interra's Lucas Fryman is listed as the broker who represented both the buyer and the seller in the deal.
Who Bought and Who Sold
The Real Deal reports that the sellers were brothers Raphael and Ari Lowenstein’s 312 Properties, and that Chicago-based Zeegar Properties was the buyer, at a price that comes out to roughly $250,000 per unit. “Amid significant market uncertainty in 2020, Interra guided the sale of 4400 South Drexel when it was outdated and in need of meaningful upgrades,” Fryman said, according to The Real Deal. That outlet also notes the Lowensteins paid about $6.1 million for the building in 2020.
Upgrades and Tenants
Broker listing materials show the property underwent a near-full gut rehab in 2021–22, with floor plans reworked to squeeze more livable square footage out of each unit while keeping the overall count at 46. Units were updated with new finishes, dishwashers, in-unit laundry and individual ductless HVAC systems, according to Interra Realty's listing. The marketing packet also highlights an assumable mortgage on the building and notes that apartments are occupied primarily by households using Housing Choice Vouchers administered by the Chicago Housing Authority, a setup that listing materials suggest is a key part of the property's appeal for value-add buyers.
Market Context
Beyond the simple before-and-after price jump for the sellers, the sale underscores investor interest on the South Side as money follows development activity near the University of Chicago and other projects, The Real Deal reports. At around a quarter-million dollars per door for a nearly century-old building, assets of this size and age profile continue to draw buyers looking for steady cash flow with renovation upside in comparatively affordable housing stock.
What to Watch
Brokers say the new owner plans additional capital work to further reposition units while keeping the property as an income-producing rental building. Listing details also show an existing mortgage with roughly an $8.9 million balance that may be assumed, a feature that shaped how the deal was structured. As new rounds of upgrades roll out, tenants, housing advocates and local officials are likely to keep a close eye on how the building's operations and affordability commitments evolve, given its role as largely voucher-supported housing.
