The Little House that Could

One of the houses that would often come up on my searches is 5056 W Winnemac Ave in Jefferson Park.

From the outside, this looked to be a decent looking 5 bedroom 3 bath house that seems to have been converted into separate apartments. Legal 3 unit building is what the description said, though I question how you can legally have 3 units in a place this size.

Three apartments in here?  But where do they put the pool?

Three apartments in here? But where do they put the pool?


The configuration would make it good for what’s known as an in-law suite which is French for *you have to take care of one set of parents anyway so you might as well get free child care out of the deal*.

It’s been on and off the market a dozen times since 2010. Over the years I’ve made appointments to see it however the day of the appointment we’d get a call from the seller’s agent explaining that the comps didn’t come through for the place so unless we were making a cash offer, there wasn’t any point of seeing it.

As I said, it would show up in my search criteria but there wasn’t anything about it that made me yearn to see it. In fact, the lack of pictures along with the no Central A/C made it really easy to scratch off the Go See It List.

The owner — most likely a stubborn Pole* — wanted a certain price, $270K IIRC. Well it just sold on May 29 for $240K so it only took 3+ years to get within 10% of Asking Price, so yay Stubborn seller!

* Being Polish I can make those comments!


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