Need to rent a property? Call me now to get your questions answered, or to get me started.

Tim Winchester / (773) 780-7048 /

I’ve rented over 500 properties for private landlords and have been recognized by the Chicago Association of Realtors as a Top Producing Leasing Agent.

I Love Landlords

Why would I love landlords?

Because my first job in real estate was calling landlords and listing their property for a team of leasing agents to rent. And I’ve been serving landlords ever since.

I know so many landlords now, from all over Chicago, all over the country, and indeed all over the world.

Landlords tend to be interesting people. They are entrepreneurial. They provide housing to people in Chicago. They pay property taxes that support the city.

There’s a lot of love about landlords.

I’ve been recognized by the Chicago Assocation of Realtors as a Top Producing Leasing Agent. I’ve rented more property in Chicago than any individual you’re likely to meet. And it remains a pleasure to serve this community.

 Devoted to Private Landlords

Of all the types of property I have rented in Chicago, I have found serving private landlords the most satisfying. Mom and pop operations, you could say. Landlords who are simply people. And I now devote all my leasing energy to this special group.

How do I Find Tenants

  1. Multiple Listing Service (MLS – Realtor’s Database)
    Just like with sales, and with the same level of professionalism, I enter my rental listings into the Multiple Listing Service. This broadcasts the property to 45,000 real estate agents in Chicagoland, and their thousands of renter clients, all of whom can now access the property with my supervision.  The vast power and sheer volume of this network of agents is all streamlined through me. I personally schedule and host every showing, screen every tenant, and take responsibility for the transaction.


  2. Websites and Platforms
    In addition to the Multiple Listing Service, I advertise the property on every website that matters, and a dozen or so that don’t matter (but I do it anyway).


  3. My Clients
    I also have my own leasing clients and place them into my listings when it’s the right fit.

My listings enjoy the broadest possible exposure to real estate agents all over Chicagoland, and apartment-seekers all over the world.


What to Expect 

If you hire me to rent your property, expect:

  1. Personal Care
    Expect me to rent your property with as much care, or more, than you would if you were renting it yourself.



  2. Ongoing Relationship
    The main reason I take such care in how I lease property for landlords is simply because that’s my nature. But it’s also good business, as I maintain relationships with my landlord clients for years and indeed decades. I’ll rent the same property any number of times over many years. I keep the photos and marketing materials I have for the property. I know the current tenants already. It all goes well. And, eventually, when a landlord decides to sell the property, I handle that for them too.

  3. No Mysteries
    I’m in touch with the market daily and have been for twenty years. Upon listing a property, I can tell you a lot about what to expect in terms of rentability. And after a week on the market, I can tell you a lot more. I can tell you if it’s going to rent, and if that’s more likely to be sooner or later. I’m data-driven, and all market data is available, so there should be no mystery as to what to expect.

  4. Getting the Details Right
    I get the details right: Utilities, amenities, move-in fees, condominium association rules, and everything else. I’ve done business in over 200 different buildings in Chicago, and if I’m not already familiar with the building, I know what I need to find out in order to properly market the property, get the lease right, and provide correct information and expectations to the tenant.

  5. Professional Screening
    I screen each tenant with income and employment verification, and credit and background checks. Importantly, I meet every tenant. I’m excellent at providing great tenants to landlords.

  6. Paperwork
    Once a tenant is selected and approved by the landlord, I arrange the lease, disclosures, and condominium documents (when applicable). These documents are sent to the landlord and tenant to easily sign online. The lease and other documents all conform to the requirements of the Residential Landlord Tenant Ordinance of Chicago.


What Does This Cost?

I have a success fee equal to one month’s rent. This is due only when I successfully find a tenant that you approve of, and all parties sign the lease. Until then, my service is free.

This Sounds Good, But Are There Any Bonuses?

There are. 


I guarantee every tenant fulfills their initial lease, or the landlord gets their money back. This is an easy guarantee to make, because given the screening process, this situation never happens.

I have developed a rider over the years that I attach to the leases. It highlights a few things I’ve learned are important to emphasize, and all but eliminates any potential misunderstandings in the tenant-landlord relationship.

Free lease renewal. If after a year you need to renew the lease, let me know, and I’ll send out a new lease to be signed online, free of charge.

My clients are clients for life. You’ll receive an informative real estate update from me once a month. And you’ll always have direct access to me for any real estate questions: leasing, sales, market conditions, home value, or anything else.