There has been a lot of discussion lately around listings, visibility, syndication, and where properties should or should not appear online.
Ironically, some of the strongest activity I have seen this year has happened quietly.
I recently represented the off market sale of a former Cubs player’s home near Fulton Market and the West Loop. The transaction marked my third off market sale already this year.
I do not believe every property should sell privately. Most should not.
For many sellers, broad market exposure remains the best strategy. Public visibility creates competition, urgency, and transparency.
But certain properties, and certain clients, operate differently.
At the higher end of the market, discretion still carries value. In some cases, sellers prioritize privacy over exposure. Buyers move more selectively. Conversations happen directly. And occasionally, the right opportunity comes together without ever truly hitting the public market.
What has become increasingly clear is that serious buyers are still very much active in Chicago despite all the recent industry noise.
The market itself has not disappeared. It has simply evolved.
Even amid recent debates surrounding Zillow, listing visibility, and syndication policies, buyer demand continues to exist for well positioned properties across the city. In fact, Zillow reversed course in Chicago almost immediately and restored listings back to the platform within a day. Markets tend to find equilibrium faster than headlines suggest.
The larger point is this:
Real estate remains deeply relationship driven.
Technology matters. Exposure matters. Marketing matters.
But relationships, trust, timing, and access still play an enormous role in how many meaningful transactions ultimately come together.
And increasingly, some of the most interesting movement is happening more quietly than people realize.
