Since July 2023, the CEO and founder of Chicago-based diversified trading firm DRW Holdings has tried to sell a prominent, five-bedroom Wicker Park mansion, which is currently listed for $5.995 million.
But that vintage mansion isn’t the only residential real estate Donald R. Wilson Jr. has tried to sell of late. Last year, Wilson sold an eight-bedroom, 10,750-square-foot mansion on Lake Michigan in Union Pier, Michigan, for $7 million.
Co-listing agent Toni Philander Morris of @properties Christie’s International Real Estate declined to comment on the seller or the home, but confirmed that that $7 million sale was a record sale for the multiple listing service in southwest Michigan’s Harbor Country, an area popular with many Chicago-area residents. At least one Harbor Country home, in nearby New Buffalo, reportedly sold for more when it changed hands in an off-market deal in 2023 for more than $8.5 million.
But in recent months, no Harbor Country home has sold for more than even $5 million, and only one has traded for more than $4 million.
Wilson currently owns and lives in a Lincoln Park mansion. He also has shown an affinity for commercial real estate, overseeing the renovations of other vintage Chicago properties, including the Three Arts Club on the Gold Coast, the Robey Hotel in Bucktown and the old Noel State Bank building in Bucktown. He has undertaken these commercial projects through DRW’s real estate arm.
The Union Pier mansion, however, is far from vintage. Built in 2007, the mansion has some 99 feet of Lake Michigan frontage, along with 6-1/2 bathrooms, one fireplace, a lower level with a wine cellar, a 12-person theater and a gym. It also has a kitchen with new Wolf appliances and a Sub-Zero refrigerator, along with a primary bedroom suite that has a walk-in closet, office space and a sitting tub.
Outside on the 0.65-acre property are a pool and a deck facing the lake.
Through a Delaware limited liability company based at DRW’s offices, Wilson paid $4.05 million in 2020 to buy the mansion from a Michigan LLC owned by Jonathan Graham, according to public records. Wilson then listed it in 2023 for $9.2 million before cutting his asking price to $8.5 million later that year. He sold the Union Pier mansion last year for $7 million to another Delaware limited liability company whose manager has homes in Palm Beach, Fla. and Oak Park, according to public records.
Meanwhile, through an opaque land trust, Wilson paid $4.8 million in 2021 in an off-market deal for the 8,250-square-foot red brick imitation castle-style Wicker Park mansion and its 0.25-acre property, and weeks later, he paid $1.475 million to a separate seller for the adjoining coach house and its 0.09-acre property, immediately to the east. Wilson then announced and ultimately completed renovations to the mansion and linked the mansion to the coach house, listing agent Tim Salm of Jameson Sotheby’s told Elite Street.
Then, in 2023, Wilson put the expanded and renovated Wicker Park mansion on the market for $6.95 million. He cut his asking price to $6.5 million later that year and then in July 2024 to $5.995 million, which is its current price.
Goldsborough is a freelance reporter.
