Don Wilson Poised for Loss on Wicker Park Mansion

A Wicker Park mansion may end up being a loser for Chicago entrepreneur Don Wilson Jr. after recent price cuts.

The 8,250-square-foot estate at 1407 North Hoyne Avenue has been on the market since July 2023, when it was listed for $7 million. The asking price has fallen three times since then: It dropped to $6.5 million in November 2023, then $6 million in July 2024, and finally dropped to $5 million Oct. 29 this year.

The red brick Victorian mansion was originally built for beer baron John H. Raap. It is part of a popular walking tour in Wicker Park called Beer Baron Row. The home has five beds and seven bathrooms, along with offices, an exercise room, a wine room and other amenities.

Wilson, the CEO and founder of trading firm DRW Holdings as well as real estate firm Convexity Properties, bought the mansion for $4.8 million in 2021. He purchased an adjacent coach house for $1.5 million shortly after.

It’s not clear from the property listing if the asking price is for both the main building and the coach house. The 1,500-square-foot coach house is on a separate lot with a Schiller Street address, and it’s not listed for sale on public channels. The Hoyne Avenue listing only gives details about the main house.

The $5 million asking price adds up to a loss on the $6.3 million Wilson paid for both properties. If the price is for the Hoyne Avenue mansion only, Wilson would still likely take a loss after paying agent commissions and other fees.

Wilson planned to renovate the buildings, including connecting the two properties, after purchasing. He went before the Wicker Park Committee community group and the Commission on Chicago Landmarks with his plans, but it does not appear the changes were made.

Tim Salm, the Jameson Sotheby’s International Realty agent representing Wilson, did not return a request for comment.

The initial $7 million asking price was higher than any Wicker Park home had sold for before or since the listing debuted. The neighborhood record was set last November when an 8,000-square-foot mansion on North Wood Street sold for $5.3 million.