Selling rental property in chicago
solutions for tired landlords
Selling rental property crosses your mind often in Chicago or anywhere in Chicagoland. If you’re a landlord in Illinois, you know firsthand how challenging managing rental properties can be. From dealing with demanding tenants and frequent repairs to navigating complex local regulations and rising property taxes, being a landlord can quickly become overwhelming. If you’re feeling tired, stressed, or simply ready to move on, you’re not alone. Many landlords reach a point where they realize that selling rental property is the best way to regain control of their time, finances, and peace of mind.
At Olson Home Buyers, we understand your challenges and are here to provide a compassionate, straightforward solution. This guide will help you explore whether selling your rental property is the right choice for you and how working with a cash home buyer could offer the quick, hassle-free exit you need.
We buy houses In Cook County IL in cash and on your terms. No matter what the condition your property is in, we will make you a fair offer and get the process moving fast. We buy houses directly from homeowners who want to sell without the hassles of listing the property with an agent, or paying agent fees. No middlemen. No fees or commissions. No waiting.
Pulling your hair out? You just might be a Tired Landlord.
Tired landlords are property owners who have reached a point of fatigue or frustration (and usually both!) with the responsibilities of managing their rental properties. Whether it's dealing with ahem... difficult tenants, constant maintenance, rising taxes, or the never-ending paperwork, all of that takes an emotional and financial toll.
Here are some common reasons why landlords in Illinois decide it's time to sell:
- Tenant Management Issues: Dealing with late payments, evictions, or problematic tenants can create ongoing stress.
- High Property Taxes and Costs: Illinois has some of the highest property taxes in the nation, eating into your rental income and making profitability challenging.
- Regulatory Challenges: The state’s strict tenant rights laws often make it difficult for landlords to handle disputes or evictions quickly.
- Personal Reasons: Health issues, retirement, or the desire to invest time and money elsewhere.
You're not alone if you relate to any of these scenarios. Many landlords across Illinois face similar challenges and eventually decide that selling rental property is the best way to move forward.
Selling Rental Property with Ease
Benefits of Selling to a Cash Home Buyer
Selling your rental property, especially in Illinois, can be a daunting decision. But, selling to a cash home buyer offers several advantages that can make the process much simpler and less stressful. Here’s why it might be the right option for you:
- Quick, Stress-Free Sale: Avoid the lengthy traditional sales process, which can involve months of uncertainty, showings, and negotiations.
- No Need for Repairs or Renovations: Cash home buyers purchase properties “as-is,” saving you the time, money, and effort of making repairs or updates.
- No Commissions or Hidden Fees: There are no realtor commissions or hidden costs when selling to a cash buyer, allowing you to keep more of your money.
- Certainty of Sale: Cash offers mean you won’t have to worry about financing falling through or other deal-breaking conditions.
By choosing a cash home buyer, you can alleviate the burden of managing your rental property and move forward with peace of mind and financial security.

Signs It’s Time to Consider Selling Your Rental Property
Deciding whether to sell your rental property can be tough, but there are clear signs it might be the right move:
- Frequent Tenant Turnover: If you’re constantly searching for new tenants, it could be a sign that your property is becoming more trouble than it’s worth.
- Negative Cash Flow: High maintenance costs, property taxes, and other expenses may mean you’re losing money each month.
- Personal Stress or Burnout: If managing your property has become more stressful than rewarding, it’s time to consider an exit strategy.
- Changing Market Conditions: Declining property values or a soft rental market can reduce your property’s profitability, making a quick sale more attractive.
If any of these signs resonate with you, it’s worth exploring the benefits of selling to a cash home buyer.

What Our Clients Are Saying


Carla Sanders
Jolean with Olson Home Buyers is knowledgeable, honest and hard working. It’s evident from your first conversation, her true passion is helping others find a solution.


Cecelia Riley
I had a great experience with Olson buys Homes. She was honest and tried every creative way to make a deal.


Chris Dunham
Such a easy company to deal with!They said they would buy my home and bam cash in hand! Thanks guys!

Don't leave selling your rental property to chance. seasoned investors choose us to sell one home, apartment, or even their portfolio.
The Cash Home Buying Process: A Stress-Free Exit Strategy
Selling your rental property doesn’t have to be a drawn-out, stressful ordeal. Here’s how the cash home buying process works:
- Initial Consultation and Property Evaluation: We’ll schedule a consultation to learn more about your property and understand your goals.
- Receive a Fair Cash Offer: Based on the property’s condition and market value, you’ll receive a fair cash offer within 24-48 hours.
- Quick Closing Process: If you accept the offer, we’ll handle all the paperwork and close on the date that works best for you.
- Receive Your Cash Payment: On the closing day, you’ll receive your payment in full, with no deductions for repairs or fees.
We understand landlords because we are one! We’re here to guide you every step of the way with transparency and empathy.
Discover a Smarter Way To Sell Your House
Skip the stress with our simple 3-step house-selling process.
1
Fill Out The Form To Get Started
Share some information about the property. Then, we will schedule a walkthrough.
2
Pick An Appointment Date
Then, we’ll make a fair, no-obligation, cash offer for your house in its current condition.
3
Pick A Closing Date
We offer the ability to close on your sale quickly on a schedule that works for you.
ANSWERS TO YOUR QUESTIONS
A: Yes, you can sell with tenants in place. Cash home buyers often purchase tenant-occupied properties, simplifying the process for you.
Yes. If you’re worried the house is too full of stuff or is in poor condition, we can work with that.
A: Property taxes are prorated up to the sale date. Selling can relieve you from the ongoing burden of Illinois’ high property taxes.
We can help with that, too. Our general contractors have all kinds of resources including movers.
The short answer is it can take a matter of days to a few weeks. Once we review your property, we can get you a cash offer within 24 hours. Once you sign the contract, we can close on average in 10-15 days.
Olson Home Buyers offers the most options for selling your property and the most flexibility. You're busy, but you also need return on your life's investment. We work hard to get you the price you need.
If you still have questions, we have answers. Read more on the step by step process on how to sell a house for cash. If we still didn’t address a question, reach out today and we’ll make sure you understand everything.
Want more information on how we decide on the price to offer for your house? It all comes down to a formula that we follow for each property. We don’t just pull a number from thin air. We want to offer as much as possible to make it a winning situation for both of us. Otherwise, you won’t sell to us anyway so it just makes sense.
Offering You a Way Out
We know that being a landlord isn’t easy, especially in Illinois. If you’re feeling overwhelmed, stressed, or just ready for a change, selling your rental property to a cash home buyer could be the fresh start you need. Our team is here to offer you a straightforward, empathetic solution that provides relief from the burdens of property management.
If you’re ready to explore your options, reach out to us today for a free, no-obligation cash offer. Let us help you move forward with confidence and peace of mind.

We Make It Easy To Sell Your RENTAL PROPERTY
Simplify your end-to-end selling process with our trusted pros.
Listing on the Market
Selling with Us
We Can Buy Your RENTAL PROPERTY No Matter The Situation!
Your reasons for selling do not matter to us. The only thing we care about is solving your problem by buying your house, apartment, or portfolio in cash as hassle-free as possible. No matter the reason, no matter the situation, we've seen it all, we've conquered it all.
Get An All-Cash Offer For Your rental property
If you are serious about selling your Chicago rental property, get started today! Fill out the fast response form below or call us at (312) 210-0115.