Is Now the Right Time to Buy or Sell on the North Shore of Chicago?

by Laurie Field

Is now the right time to buy or sell a home on the North Shore of Chicago? The honest answer: it depends on your situation, not the calendar. Market timing matters less than most people think. Personal readiness matters more.

Waiting for the "perfect" market is one of the most expensive decisions a homeowner or buyer can make. I hear some version of this question every week in Highland Park, Deerfield, Northbrook, Glenview, and across the North Shore: Should I wait? What if rates drop? What if prices fall?

The problem with waiting is that you are making a financial decision based on variables you cannot control, while ignoring the ones you can.

This post is for anyone sitting on the fence right now. I am going to give you a direct, honest framework for answering the question yourself. And I am going to back it up with real February 2026 data from four North Shore communities.

What the February 2026 Numbers Actually Show

The February 2026 statistics, compared to February 2025, tell a story that is more nuanced than most headlines will give you. Here is what the data shows across four communities.

Highland Park Median sales price: $750,000 (down 1% year-over-year). Homes closed: 21 (down 22%). Median days on market: 7 (down 53%). Homes on market: 91 (up 44%). Months of inventory: 2.7.

The headline here is the tension between more inventory and faster sales. Homes that are priced right and prepared well are still moving in one week. The homes sitting are the ones that are not.

Deerfield Median sales price: $726,000 (up 13%). Homes closed: 20 (up 82%). Median days on market: 5 (down 38%). Homes on market: 67 (up 103%). Months of inventory: 2.2.

Deerfield saw both a significant jump in closings and a sharp increase in available homes. That combination, with prices still rising and days on market shrinking, points to a market absorbing new supply quickly.

Glenview Median sales price: $675,000 (up 24%). Homes closed: 31 (up 3%). Median days on market: 7 (down 30%). Homes on market: 92 (up 42%). Months of inventory: 2.5.

A 24% median price increase year-over-year is significant. Glenview is one of the more active markets on the North Shore right now, and the data reflects consistent buyer demand.

Northbrook Median sales price: $810,000 (up 64%). Homes closed: 20 (down 29%). Median days on market: 9 (up 50%). Homes on market: 127 (up 72%). Months of inventory: 2.7.

A note on Northbrook: a 64% price increase alongside fewer closings and longer days on market typically signals a mix shift. Fewer homes sold, but the ones that sold were priced significantly higher. This fors not mean that every Northbrook home has gained 64% in value. It means the composition of what sold this February skewed higher-priced. If you own a home in Northbrook, reach out. I will be happy to talk about what the numbers mean for your property.

What ties all four towns together: Months of inventory across the board sits well below the six months and that signals a balanced market. Anything under three months favors sellers. All four of these communities are under three months.

Why "Waiting for the Right Time" Rarely Works

The North Shore and North Suburban markets do not move in dramatic crashes and surges. Inventory is structurally low in most towns along the lake, and demand from the Chicago metro continues to pull buyers north. Highland Park, Glencoe, and Winnetka rarely see the kind of price corrections buyers hope for when they say they are "waiting."

Here is the math problem with waiting on rates. If rates drop from 7% to 5.75% on a $900,000 purchase, your monthly payment falls by roughly $738. That sounds meaningful. But if home prices in your target market rise just 3% while you wait, you have added $27,000 to the purchase price, and your new loan at 5.75% on $927,000 brings your monthly payment back to about $5,411. You saved $578 per month, not $738, and you paid $27,000 more for the house.

And that assumes rates actually get to 5.75%. Rates in the 2s and low 3s were not a gift from a healthy economy. They were a response to a global crisis. Most economists do not expect to see those levels again without another significant economic shock. Nobody should be rooting for that.

The realistic range people are waiting for, somewhere in the high 5s, is possible. But nobody knows when or whether it will arrive. Buying when your life and finances are ready, then refinancing if rates drop, is a more controllable strategy than holding your move hostage to a forecast nobody can make reliably.

This does not mean you should buy regardless of conditions. It means the decision should be driven by your personal numbers, not the news cycle.

For Sellers: How to Know If Now Is the Right Time

Ask yourself these four questions before deciding to wait:

Do you have a reason to move? Life events drive most good real estate decisions. A growing family that has outgrown a home in Deerfield, empty nesters in Northbrook who no longer need four bedrooms, a job change that makes a shorter commute a priority. These are real reasons. "I might get more money if I wait six months" is rarely a sound strategy in a market where inventory is already rising year-over-year.

Do you know where you are going? Selling without a clear plan for your next home creates pressure. Most North Shore sellers are simultaneously buyers. Before you list, you need a realistic picture of what you can buy, in what towns, and at what price point. Coordinating both sides of that transaction is exactly where the work happens.

Is your home ready to compete? In Highland Park, homes that are prepared and priced correctly are selling in under a week. Homes that are not, are sitting. The data is clear on this. Preparation is not optional. If your home needs work, the question of "when" includes time to do it right.

What does your equity position look like? North Shore homeowners who bought before 2020 are sitting on substantial equity. Sitting on that equity while waiting for conditions to be "perfect" has a real opportunity cost. A conversation about your current equity position takes 20 minutes and gives you information you cannot get from a news article.

For Buyers: How to Know If Now Is the Right Time

Are you financially ready, not just pre-approved? Pre-approval is a starting point. Know your full monthly cost at the target price, including property taxes, insurance, and any HOA. North Shore property taxes are a significant line item. Make sure the numbers work at current rates, not hypothetical future ones.

Are you planning to stay at least three to five years? Real estate rewards patience. If you are buying in Glenview or Wilmette with a plan to stay through a full market cycle, short-term rate fluctuations matter very little. If you might need to sell in 18 months, the calculus is different.

Is there something available that actually fits your life? Inventory is rising in these four communities compared to last year. That is a genuine opportunity for buyers. In February 2025, there were 63 homes on the market in Highland Park. In February 2026, there were 91. More selection means more opportunity to find the right fit and negotiate more deliberately.

Have you done the rent-versus-buy math? If you are renting in Highland Park, Northbrook, or anywhere on the North Shore, you are paying someone else’s mortgage and building someone else's equity. Run the actual numbers. At current rent levels in this market, buying often makes financial sense within three to five years even at higher mortgage rates.

The Question Behind the Question

When someone asks me "Is now the right time?" they are usually asking something else: Am I going to regret this?

That is a fair concern. Real estate is the largest financial transaction most people make. It should feel like a considered decision, not a rushed one.

But it also should not be a permanently deferred one. The North Shore market has rewarded long-term owners consistently. The data from February 2026 confirms that even in a period of rising inventory and fluctuating rates, prices in Deerfield, Glenview, and Northbrook moved meaningfully higher year-over-year. Highland Park held essentially flat.

The goal of a good real estate conversation is not to tell you to buy or sell. It is to help you understand your specific situation clearly enough to make a confident decision, whether that decision is to move forward now or to prepare and wait.

Frequently Asked Questions

Is it a buyer's market or a seller's market on the North Shore right now? Based on February 2026 data, all four communities tracked here (Highland Park, Deerfield, Glenview, Northbrook) show months of inventory below three months. That range historically favors sellers. However, rising inventory compared to last year means buyers have more options than they did in 2025. The right answer depends on the specific price range and property type you are considering.

Should I wait for mortgage rates to come down before buying a home on the North Shore? Waiting for rate drops is a reasonable consideration, but it involves real risk. If prices continue rising while you wait, the savings from a lower rate may be offset by a higher purchase price. A better approach: buy when your situation is ready and refinance if rates drop meaningfully. The data in markets like Glenview (up 24% in median price year-over-year) illustrates what waiting costs.

How do I know if my home is ready to sell on the North Shore? A home is ready to sell when it is clean, decluttered, well-maintained, and priced accurately for current market conditions. In Highland Park, where the median days on market is 7, the gap between well-prepared homes and unprepared ones shows up immediately in the data. I suggest we start the conversation before you feel "ready" which gives you time to prepare properly.

If you are asking yourself whether now is the right time to buy or sell in Highland Park, Deerfield, Northbrook, Glenview, or anywhere on the Chicago North Shore, the best next step is a direct conversation about your specific situation.

Call or text Laurie Field, REALTOR® with Engel & Völkers Chicago North Shore.