Being a landlord in Chicago can be hard. It sounds good at first. Steady rent, long-term tenants, and passive income, but when renters stop paying or start causing problems, everything changes. What once felt like a smart investment can quickly turn into a full-time headache.
Maybe you have tenants who constantly miss rent. Maybe they damage the property or won’t leave, even after the lease ends. Some landlords deal with renters who cause issues with the neighbors or bring in people who were never approved. You may be getting warnings from the city or hearing from police. Worst of all, you might be losing money every month while all this is happening.
Whether your rental is in Englewood, Avondale, Rogers Park, or anywhere else in Chicago, you’re not alone. Problem tenants are common in every neighborhood, and when things get bad, selling the property fast to a cash home buyer in Chicago might be your best option.
Common Problems Landlords Face
Some tenants are easy to work with. They pay on time, take care of the place, and follow the lease. Others do not. Some miss rent every month. Some break things and never tell you. Some refuse to leave when the lease is up, and some cause problems with the city or local code enforcement. Many landlords don’t realize how quickly costs can add up when dealing with bad tenants.
Here are some common issues we hear from landlords in Chicago:
- Late or unpaid rent
- Property damage
- Noise complaints or police calls
- Hoarding or unsafe living conditions
- Unauthorized people living in the home
- Illegal activity
- Refusing to leave after an eviction notice
These problems are stressful and expensive. They can also lead to fines, legal fees, and lost income. You might feel stuck and unsure of what to do next.
Yes, You Can Sell a Property with Tenants in It
A lot of landlords think they need to wait until the tenant moves out before they can sell. That’s not the case. We buy tenant-occupied properties all the time. It doesn’t matter if the tenant is paying rent or not, if they’re on a lease or month-to-month, or if they haven’t been following the rules at all. If you’re ready to sell, we’re ready to make you an offer.
We’ve bought properties in places like Bronzeville, Logan Square, and Belmont Cragin that still had tenants in them. Some tenants were friendly and just behind on rent. Others were hostile, uncooperative, or had damaged the home. We’ve seen it all, and we’re still ready to buy.
How the Process Works
When you reach out to us, we’ll ask a few simple questions about the home, the tenant situation, and the location. We’ll set up a time to view the property in a way that works for you. If you’re trying to avoid stirring up trouble with the tenant, we understand and can work with you on the best approach.
After we’ve seen the property, we’ll give you a fair cash offer. You don’t have to decide right away, and there’s no pressure. If you like the offer, we’ll handle all the paperwork and close on your schedule. You won’t have to worry about removing the tenant, dealing with legal steps, or cleaning anything out. Once we buy the property, we take on the responsibility.
Why Chicago Landlords Are Choosing to Sell
Owning rental property should be a source of income, not stress. But when a property is losing money, needs repairs, or has constant problems, the benefits start to disappear. You’re spending more time chasing rent, fixing damage, and dealing with complaints than actually enjoying any return.
We talk to landlords often who are ready to let go. Some live out of state and can’t keep making trips back to deal with issues. Others are trying to retire, move, or reinvest their money in something with less stress and just want peace of mind again.
If your tenant is making it hard to enjoy life, it might be time to move on. Selling your property fast for cash lets you skip the long process and get out clean.
What Types of Properties We Buy
We buy all kinds of rental properties in Chicago. That includes single-family homes, two-flats, and small apartment buildings. The condition of the property doesn’t matter. If it’s outdated, has damage, or needs work, we’re still interested. We’ve bought properties with broken plumbing, missing appliances, mold problems, hoarding issues, and more.
Even if the tenant hasn’t paid rent in months or won’t let anyone inside, we’re still open to making an offer. We’ll work with you to get the information we need and move forward in a way that works for you.
Selling When You Own More Than One Property
You might own more than one rental. Maybe a few of them are doing okay, but one of them is causing problems. Or maybe you’re ready to get out of being a landlord altogether. Either way, we can help.
We’ve worked with landlords across Chicago who wanted to sell multiple homes or a whole portfolio. Some sold all at once, while others sold one or two to free up cash. We can do either. If you want to keep some properties and let go of the ones that are stressful, we’ll help you figure out the best way to do it.
Areas We Serve
We work throughout the city and the nearby suburbs. Whether your rental is on the North Side, South Side, or West Side, we can help. We’ve bought homes in neighborhoods like Austin, Pilsen, Garfield Ridge, and Albany Park. We also buy in suburbs like Cicero, Berwyn, Dolton, Maywood, and Blue Island. If your property is in or near Chicago, we’re ready to make an offer.
What Happens After You Sell
Once you agree to our offer, we work with a trusted title company to take care of the closing. Most of the time, we can close in just seven days. If you need more time to prepare or want a specific closing date, we can work with your schedule.
You won’t owe any agent fees or closing costs. You won’t have to clean, repair, or deal with anything after the sale. Once we close, the property and the problems go with us. You walk away with cash and a clean slate.
Ready to Stop Dealing with Problem Tenants?
Being a landlord in Chicago is not always what it’s cracked up to be. If you’re tired of tenants who don’t pay, damage the home, or make your life harder, you don’t have to keep dealing with it. You can sell your Chicago house fast and move forward.
At Two Rivers Properties, we buy houses in any condition, even with tenants still living inside. We pay cash, close fast, and handle all the details. If you’re ready to get rid of a problem property, we’ll help make it simple.
Contact us today and tell us about the home. We’ll give you a fair offer and let you decide what comes next. No games. No pressure. Just a fast, easy way to move on.
