About Winnemac Properties
Winnemac Properties started in the late 1990s helping friends and family navigate Chicago real estate. What began as a favor turned into a calling—and eventually, a company built on relationships, reliability, and a genuine love for Chicago's neighborhoods.
Today, we're a full-service property management, leasing, and brokerage firm specializing in small multi-family buildings across Chicago. We manage 2-flats, 3-flats, courtyard buildings, and brownstones—the kinds of properties that give Chicago its character. Our focus is on the North Side, but our reach extends to neighborhoods across the city.
WHY WINNEMAC
Big Enough to Deliver. Small Enough to Care.
Local Team, Local Knowledge
We live and work in the neighborhoods we manage. When something needs attention, we're 15 minutes away—not in another state.
One Point of Contact
No call centers. No ticket queues. You'll have a dedicated property manager who knows your building inside and out.
Small Building Specialists
We focus on 2-flats, 3-flats, and courtyard buildings—not 300-unit high-rises. Your property won't get lost in the shuffle.
Investor Mindset
We're property owners too. We manage your building with the same care and cost-consciousness we bring to our own.
Hands-On, No Shortcuts
We're not a faceless management company. We're a local team—property owners ourselves—who believe that buildings deserve care and tenants deserve respect.
We take pride in our reputation for ethical business practices and a results-oriented approach. As long-term investors, we maintain every property we manage as if it were our own. That means no deferred maintenance, no cutting corners, and no runaround for owners or tenants.
Part of building strong communities is finding tenants who are responsible and respectful of their neighbors. We take that seriously. Every applicant goes through thorough screening, and every tenant is treated with the kind of service that makes them want to stay.
As a member of the Rogers Park Builders Group, we subscribe to their mission of encouraging responsible property investment, development, and ownership. It's not just business—it's the neighborhood we live in.
