One of my favorite books about my beloved home is by the great Nelson Algren. It’s called Chicago: City on the Make, and is a raucous, sharp, and oftentimes brilliantly funny book on this city. Everyone in it is working hard to make something of their lives. It’s always inspired me—in this muscular city, you’ve got to work to get ahead. That’s especially true in real estate investing. 

What do I mean by that? I mean that if you want to get the best leads, close deals, and be successful, you have to be smart and fast. You have to look for houses before other investors see them. You have to know where to find off-market properties in Chicago so that you can strike the right deal. 

Of course, everyone wants the best deal. So, most people in this business are looking for off market properties in Chicago. You’re gonna have to work extra hard to get ahead. 

Well, here’s how to make that happen.  

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Understanding Off-Market Properties

Before we get into that, we need to understand what is meant by off-market properties. Basically, these are homes that are for sale that aren’t listed with the Multiple Listing Service (MLS). Listing with the MLS is the ‘go-to’ strategy that many homeowners take when selling but it is far from a given. 

The question is: why do homeowners try to sell off market? Some think it is more hassle. Some want to serve as their own real estate agents. Some aren’t technically for sale yet, but the owner is testing the market. But, all are looking to sell. 

Getting a lead on an off market house can be a huge boon for your real estate investing business. There is generally less competition. Prices don’t get jacked up as much. And you have a better chance at establishing a one-on-one connection with the seller, which goes such a long way toward building that needed trust. 

So, in a city as big and diverse as Chicago, how do you find these listings? Here are some of the ways that many people find that works. 

Finding Off-Market Properties in Chicago

A long time ago, when I started real estate investing, old-timers told me that the best way to find properties was to walk around, especially in areas that had a lot of foreclosures, and knock on doors. That was good back then, and still can be effective, but there’s some problems. 

For one thing, Chicago is huge. I live in South Shore. I do business everywhere from Rogers Park to Canaryville and even the suburbs. Now, I like walking, but that’s pretty limiting. So, I needed some new methods. 

Here are some options for you. 

Retain a real estate agent

This is something that I know a lot of investors do. Real estate agents tend to know every listing and even the ones that aren’t on the market yet. They are usually happy to work with a pro and talk to you about other potential sales they’ve heard of. 

For a fee, of course—on top of the other fees. It’s a decent shortcut, but it is going to cost you. 

Advertise online

There are a lot of places where you can advertise your business online. I know some investors who try to make deals on Craigslist Chicago. And, this can work. After all, people who are looking to sell their house will sometimes just google “sell my house fast” or something similar. 

But, when you are online, you have a lot of competition and there is no way to make a personal connection. How do you come across as professional, not cheesy, pushy, or untrustworthy? How do you cut through the clutter? How do you stand out? You can boost your signal by paying more, but then you’re paying a lot more with zero guarantees. 

Talk to your network

Here’s a free way to try to get leads: talk to friends. Talk to the Chicago real estate investing groups you belong to. Get active in online forums or social media groups If you have groups with wholesalers, you might be able to make a deal with them to buy one of their properties to fix and flip. 

Of course, there is going to be competition in those networks. You usually won’t have sole access to a deal. And, you might be waiting for a long time. It might not be worth your time at all. 

Use a paid site

One of my favorite sites on the internet way back when was a Chicago Burrito Bracket, which a local kid ran to rank his favorite burritos in the city (Side note: that local kid was Nate Silver, of 538 fame). The point is, you can find anything online. And there are paid services which list every house, including those not listed on MLS. 

The problem, again, is that you aren’t paying for exclusive rights. And, not every property is going to be listed on it. It’s money spent without any guarantees of a solid lead. 

So what is the best way? Well, I’ll tell you what’s worked for me. 

The Best Way To Find Off-Market Houses in Chicago

I’ve tried all of these. I’ve done everything from knocking on doors to direct mail to direct social media bursts. But, nothing has supercharged my business like becoming an independently owned and operated HomeVestors® franchisee. 

HomeVestors® has been around since 1996. You know them. You know the “We Buy Ugly Houses®” ads. Everyone in Chicago knows those television and social media ads—and the nationwide billboards and direct mail letters that bring qualified leads directly to local HomeVestors® franchisees. 

And when they do, I get a qualified lead on a house that can be 100% off market. It hasn’t been listed yet. The people want to sell fast without going through all the trouble of an agent or all the other hassles. They may want to sell it themselves, with true Chicago spirit, to someone they can trust. I’m proud when that can be me.

In that book I mentioned, Algren said that Chicago might not be traditionally lovely, but there was “never a lovely so real.” I believe that. I believe we help each other. I’m proud to be part of the solution, helping people, and finding great houses off market. 

If you want to be part of that solution, request information about becoming a franchisee today


Each franchise office is independently owned and operated.


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