For many homeowners, deciding whether to sell before you buy is the hardest part of a move. You may be ready for a change, but what happens after your home sells?
Perhaps the house has become more than you need. Perhaps you want a different floor plan, less maintenance, or a home closer to family. You can picture the next chapter clearly enough—until you look at the homes available and wonder whether you would find the right place to go.
Selling and buying are two decisions, and both deserve a plan.
Begin With the Move You Want to Make
Before discussing a listing date, I like to understand what a client wants life to look like on the other side of the move. Do you want to remain in your current neighborhood, explore another part of Chicagoland, or consider a move farther away? Which features are essential, and where is there room to be flexible?
These questions help turn a broad search into a useful one. They also reveal whether the right next home is likely to be easy to find or whether we should allow more time.
You do not have to identify a specific property before beginning this conversation. You do need a clear understanding of what would make a move worthwhile.
Know What Your Current Home Makes Possible
The next step is a thoughtful assessment of your home’s likely market position. Its value influences your purchasing options, your timing, and how much flexibility you may have between transactions.
That assessment should consider comparable properties, condition, location, and the homes a buyer would see as alternatives to yours. As Freddie Mac explains in its guide to estimating a home’s sale price, local market conditions and genuinely comparable homes matter more than a broad estimate alone.
The wider market provides context, although it cannot tell you what your individual home will sell for. In August 2026, the number of homes for sale across the nine-county Chicago metro area was 11% lower than a year earlier, according to Illinois REALTORS®. Conditions differ considerably by neighborhood, price range, and property type.
If you are beginning to consider a move, you can explore a preliminary CB Estimate® for your home on my website. I can then help you put that starting point in context with your home’s distinctive features and current competition.
Should You Sell Before You Buy?
There is no single sequence that works for every homeowner. Some may be able to buy before selling. Others need the proceeds from their current home to purchase the next one. Some would consider a temporary move; others would rather wait than move twice.
Once we understand both sides of your move, we can evaluate the order that fits your circumstances.
If you will need financing, speaking with a lender early can help establish which paths are realistic. That gives you a clearer view of your budget and priorities before the right property appears.
Contract terms can affect timing, too. A buyer who needs to sell an existing home may consider a home sale contingency, although that condition can make an offer less attractive to a seller. Freddie Mac’s explanation of contingencies is a helpful starting point. Discuss the terms of any offer with your real estate attorney and, when applicable, your lender.
The goal is to understand your options before a decision becomes urgent.
Give Yourself the Advantage of an Early Start
An early conversation does not commit you to listing your home. It gives us time to evaluate its position, discuss what preparation would be worthwhile, and watch the market with a specific next home in mind.
A thoughtful plan can help you decide whether to sell before you buy, buy first, or wait until the right opportunity appears.
That preparation matters because the property you want may arrive at an inconvenient moment. When it does, knowing your home’s value, your priorities, and your options can help you respond with confidence.
For more than 40 years, I have helped clients navigate moves across the North Shore, Chicagoland, and beyond. My role is to look at the whole picture with you: the home you own, the life you want next, and a sensible path between them.
You do not need to have every detail settled to begin planning. If you have been thinking, “I would sell, but where would I go?”… let’s start with a confidential conversation.

Market information reflects publicly available data as of September 28, 2026. Regional trends may differ from conditions in a specific community, property type, or price range.