I represented the buyer of 3141 N. Oakley in November 2019: a three-unit building in Roscoe Village that closed at $682,500 against a $725,000 list. Seven years later the same owner asked me what it would bring.
Turnkey three-flats in Roscoe Village rarely come up, and the owner did not want a parade of showings through occupied apartments. So the building never went live on the MLS. I priced it at $1,249,900 on the rents and the comparable sales, built the offering memorandum, and put it in front of the investor buyers I already talk to.
Three offers came in, two of them competing. It closed in August 2026 at the full asking price. Connect CRE covered the sale; the one line I gave them was that the goal from the start was to maximize the seller's price while exposing the property only to the right buyers.
What it shows
A private sale is not a discount sale. With the right buyer list and a price built on real underwriting, a building can clear at its full number without ever being public. And the same broker on both ends of an ownership, seven years apart, is the kind of relationship this work runs on.
Figures are the MLS closing record (buyer side, 11/14/2019; seller side, 08/05/2026) and the Connect CRE report, August 2026.