Should You Buy Before You Sell on the North Shore or in the Northern Suburbs of Chicago?

by Laurie Field

Should you buy your next home before selling your current one on the North Shore or in the Northern Suburbs of Chicago?

If you can comfortably carry both housing payments for a period of time, buying first is often the less stressful path for homeowners on the North Shore and in Chicago's Northern Suburbs. You remove the biggest fear sellers have, which is not knowing where they'll go, and you shop without a deadline. If carrying two homes would strain your finances, selling first or using a home sale contingency are the safer routes.

By Laurie Field, Real Estate Advisor, Engel & Völkers Chicago North Shore | October 4, 2026

Lots of move-up sellers and downsizers ask some version of the same question when getting ready to list their home. That question is "Where am I going to go when I sell my house?"

That fear is real. For homeowners in Highland Park, Deerfield, Northbrook, Glenview, and across the North Shore and Northern Suburbs, it shapes every decision about timing.

I tell my clients if they can carry both homes for a period of time, they’re in a good position. That allows them to buy on their terms, they sell on their terms, and skip the scramble in between.

The key words are "if you can." Here's how to know, and what your options look like either way.

Why Buying First Takes the Pressure Off

When you buy first, the hardest decision is already made. You know where you're going, which changes how the entire sale feels.

You can update your new home before you move in

One of my clients bought a ranch before listing her home. Instead of sitting in her house worrying about showings and offers, she started work on the new place while she waited for her home to sell. She never had to live through construction during the new home renovation, and she was far more relaxed through the selling process because of it.

Another client did the same with a condo. They bought, made a long list of updates, and moved in once the work was done. No contractors in the kitchen at 7 a.m.

If your next home needs paint, flooring, a kitchen, or a bath, buying first gives you a window to do that work in an empty space. That's simpler to schedule and much easier to live with.

You can prepare your current home without living in it

Once you've moved, you can repair, stage, and show your current home without working around daily life. You don’t have to worry about cleaning before every showing or about packing up the dog for a few hours on a Saturday afternoon.

You shop for the right home, not just the available ones

Sellers who sell first often feel the clock ticking. I've watched clients widen their search to towns and home styles they hadn't planned on, because they'd already sold and needed to land somewhere.

Every one of them is happy where they ended up. But the process was harder and more stressful than it needed to be.

What Happens When You Sell First

Selling first is the conservative financial choice, and for many people it's the necessary one. I hear this often: "We need to be under contract before we buy. We can’t afford to be stuck with two homes."

That's a reasonable position. It also comes with tradeoffs you should plan for before you list.

Sellers in this position tend to feel a little under the gun once they're under contract. One seller I worked with had timing that didn't line up and moved into a hotel for a couple of weeks with their dog. At the time, they called it a disaster. They're very happy in their home now, but at the time, they felt very stressed.

If you sell first, ask about these tools to narrow the gap:

Post-closing possession. One option is to negotiate to stay in your home for a set period after closing. The terms are worked out between the parties and their attorneys.
A longer closing date. More time between contract and closing gives you more time to find your next home.
A plan B for housing. If you might need temporary housing, line it up in advance, not in a panic.

The Middle Path: A Home Sale Contingency

If you want to buy first but can't carry two homes, there's another option. The Illinois Multi-Board Residential Real Estate Contract 8.0, widely used in northern Illinois, offers a contingency addendum tied to the sale of the buyer's current home.

In plain terms, your purchase depends on your current home selling within a time frame both sides agree to.

The upside: you can secure the home you want without the risk of owning two.

The tradeoff: sellers generally see a sale-contingent offer as weaker than a non-contingent one. When there are multiple offers on the table, a contingent offer will almost always lose to a clean one. A seller whose home has been on the market longer may be more open to it.

Your attorney will review the exact terms during attorney review. I'll talk you through whether a contingency makes sense for the specific home you want, and how to make the rest of your offer as strong as possible if you use one.

How to Know If You Can Afford to Buy First

Work this out with your lender and financial advisor before you fall in love with a house. Every situation is different, and the right structure depends on your income, your equity, and your goals.

Start with these questions:

Can you qualify for the new mortgage while still carrying your current one? Your lender will look at both payments.
Where will your down payment come from before your current home sells? Common sources include savings, investment accounts, a home equity line of credit (which needs to be in place before you list your home), or a bridge loan. Ask your lender which options fit your situation.
What does carrying both homes cost each month? Add both mortgages, property taxes, insurance, utilities, and maintenance. Count property taxes monthly, not annually.
How many months could you carry both comfortably? Pick a number you'd be at ease with, not one you'd tolerate.
What's your plan if your home takes longer to sell than expected?
Have you talked with a tax advisor about the timing of your sale?

How long should you plan to carry both homes?

Start with market time, which measures how long a home takes to go from listing to contract. For homes that closed in September 2026, median market time ranged from 6 to 22 days across Highland Park, Deerfield, Northbrook, and Glenview.

Town	Detached	Attached
Highland Park	6 days	10 days
Deerfield	6 days	Too few sales*
Northbrook	17 days	8 days
Glenview	15 days	22 days

Only four attached homes closed in Deerfield in September, too few for a reliable median.

Source: MRED InfoSparks, September 2026 vs. September 2025, pulled October 2, 2026. Late-reported closings may adjust these figures.

Those numbers are encouraging, but they leave out three things you need for planning:

It's a median. Half of the homes that sold took longer.
It stops at the contract. You keep carrying both homes until your sale closes, which adds the weeks between contract and the closing date you negotiate.
It moves year to year. Compared to September 2025, Highland Park detached market time fell 78.6%, to 6 days. Northbrook detached market time more than doubled, to 17 days.

That's why I build a carrying-cost estimate around your specific home, not an average.

A Note for Downsizers

If you've owned your home for many years, you may have significant equity and a small mortgage, or none at all. That can make buying first more realistic than you might assume. Let’s talk or you can talk to your lender before deciding you have to sell first.

If your home holds years of belongings, buying first also gives you time to sort, donate, and move in stages, which many downsizers find helpful.

Frequently Asked Questions

Is it better to buy or sell first on the North Shore?

If you can carry both payments for a period of time, buying first usually makes the move less stressful because you already know where you're going. If two payments would strain your finances, sell first and use post-closing possession or a longer closing to bridge the gap.

What is a home sale contingency in Illinois?

It's a contract term that makes your purchase dependent on selling your current home within an agreed time frame. The Illinois Multi-Board 8.0 contract offers it as an addendum. Sellers generally view it as weaker than a non-contingent offer, especially when there are multiple offers.

Can I stay in my home after I sell it?

Often, yes. Post-closing possession lets a seller stay for an agreed period after closing, with terms negotiated between the parties and their attorneys. Raise it early so it's part of your strategy from the start.

How do I pay for a new home before selling my current one?

Common options include savings, investment assets, a home equity line of credit, or a bridge loan. Which one works depends on your finances and your lender, so get pre-approved with both payments factored in before you start touring.

What does it cost to carry two homes at once?

Add both mortgage payments, property taxes, insurance, utilities, and maintenance for each home. Your number depends on both properties, so run it with your lender before you make an offer.

Your Next Step

Buying before you sell takes the biggest fear out of the process, and it lets you move on your timeline. Selling first can work well too, with the right plan in place.

I help clients across Highland Park, Deerfield, Northbrook, Glenview, and the rest of the North Shore plan the sequence, the timing, and the numbers before they make a move. If you're weighing this decision, call or text me at 312-504-7010.

HELPING YOU MOVE FORWARD®

About Laurie Field

Laurie Field is a Real Estate Advisor with Engel & Völkers Chicago North Shore and a lifelong Highland Park resident. Licensed for more than 10 years, she has closed 76 sales totaling $58,138,091 in career sales volume, including 14 sales at or above $1 million and a career high of $3,841,145. She is a five-time recipient of the E&V Ruby Elite Award (2020, 2021, 2023, 2024, 2025), received the Onyx Elite Award in 2022, and has earned Pillar Awards for Culture of Leadership, Bespoke Experiences, and Reclaiming Luxury. Laurie works with move-up sellers, first-time buyers, luxury buyers, and downsizers, and clients describe her as knowledgeable, responsive, calm, and honest. She is a graduate of the University of Michigan.