One of the most common questions I hear from homeowners planning their next move is:
Should I sell my current home first, or buy the next one first?
There isn’t one right answer. In Chicago, it depends on your finances, your current home, whether you’re working from home, what you’re hoping to buy, and how competitive the market is.
Selling First
Selling first gives you certainty.
You know exactly how much equity you have available for your next purchase, and your offer may be stronger because it isn’t dependent on selling another property. In our experience, sellers do not like to accept any offers that contain a home-to-close contingency unless the home is almost closed or other terms, such as price, are outstanding.
The downside is timing. If you haven’t found your next home yet, you may need temporary housing or could end up moving twice. Our clients have had good luck finding homes through Airbnb or VRBO. Occasionally, they have a second home they could stay at, or friends or family in town who could let them stay temporarily.
Sometimes we can create more flexibility with a later closing date or post-closing possession so you aren’t forced to rush into your next purchase. With low inventory, buyers are letting sellers rent back for free, a term that can be negotiated in the sales contract. This always makes our sellers very happy!
Buying First
Buying first gives you more time to wait for the right home.
It can also make the move easier because you can move out before preparing your current home for photos, showings, and the market. This is very valuable, not only from a logistics side but also for peace of mind. You will not have to leave the home for every showing and make sure that it is clean, picked up, smells nice, and more. This can be especially hard with pets and guests. Many of our buyers like to move out and stage the property, which is always the best-case scenario.
The biggest question is financial: can you comfortably carry both properties if your current home doesn’t sell immediately?
That’s why I always recommend talking with your lender before deciding on this strategy.
What About a Home Sale Contingency?
You can also make an offer contingent on the sale of your current home.
That reduces some financial risk, but it can make your offer less competitive—especially if you’re trying to buy a home with multiple interested buyers.
This is where Chicago gets very specific.
Your home may be in a neighborhood with very little inventory and strong demand, while the single-family home you’re trying to buy may be in a completely different market.
Can You Close on Both Homes the Same Day?
Yes.
The proceeds from your sale can often be used toward your next purchase, but same-day closings require careful coordination between your agents, lender, attorneys and title companies.
Whenever possible, I prefer to build some flexibility into the plan rather than relying on everything happening perfectly within a few hours.
In my own personal experience, I don’t recommend closing on the same day. If anything goes wrong with the loan, the title company, the final walkthrough on either the buy or sell side, relying on the sellers being out of the home you are buying and moving into, and much more. At my closing, our new-construction home was months delayed. We thought we built in enough buffer but literally made it by one day. This meant we found ourselves painting while we were in the home, rather than having it all done before we moved in. If I ever move again, I would sell, get my money and take my time finding what my purchase will be without the constraints of a sale and/or closing contingency.
Start Planning Early
You don’t need to be ready to list your home to start the conversation.
Before deciding which comes first, I usually want to know:
What could your current home realistically sell for?
How quickly is it likely to sell?
What are you hoping to buy?
Which side of the transaction is likely to be more competitive?
Once we understand those pieces, the best strategy usually becomes much clearer.
