I Turned 42 This Week…

Current Market Conditions

I turn 42 this week.

It’s a big number. I don’t know why, but it just feels different.

Maybe it’s because everywhere I look right now, the 90s are back. You’ve probably seen it, those videos that say, “Hey mom or dad, what were you like in the 90s?” and it shows all the actors and movies we grew up on.

And it gets you thinking.

When you look back at your favorite birthdays, it’s not really about the gift you got. It’s the little things.

Running into Blockbuster and hoping your movie was still behind the box.
Grabbing way too much candy at the checkout line.
Stopping at Pizza Hut on the way home and getting that personal pan pizza in the X-Men box.

That was it.

Those were the moments.

And when you think about it, those really do feel like the best times.

The funny thing is, as you get older, you still feel like that same person. You don’t feel 42. Part of you still wants to hold on to that.

But life has a way of moving you forward whether you’re ready or not.

I remember thinking there were things I would never do.

I’d never stop hanging out with the same group of friends.
I’d never get married.
I’d never get a dog.
I’d never have kids.
I’d never move.

And one by one, all of those things change.

You grow up. You move into different stages. And even when you don’t want to leave one, eventually you do.

Not because you want to… but because it’s time.

And the funny thing is, when you look back, you realize you ended up exactly where you were supposed to be.

You don’t really want to go back. You just like remembering it.
And no matter how hard you try to hold on… sometimes it’s best to move on.

And oddly enough, that’s exactly what we’re seeing in the market right now.

A lot of sellers want to sell. They want to take advantage of the strong market.

But they’re not quite ready to leave yet.

Maybe it’s kids finishing out the school year.
Maybe it’s lining up the next home.
Maybe it’s just not knowing exactly where they’re going next.

Letting go can be hard.

So instead, they use something called a "leaseback."

They sell the home… but stay in it for a little longer.

It gives them time to figure things out.

Time to transition.

Time to move on… just not all at once.

And in this market, it’s becoming more and more common. I’m seeing it on a large percentage of deals right now.

In fact, we’re even seeing buyers give sellers 2–3 months of free rent just to make their offer more competitive.

It doesn’t always feel great from the buyer side, but it’s where the market is right now.

And if you’re a buyer, it’s something you have to factor into your offer, not just price, but timing and carrying costs as well.

This will likely continue through June as we move through the heart of the spring market.

Because just like getting older, letting go can be hard.

You don’t really want to go back. You just like remembering it.
And no matter how hard you try to hold on… sometimes it’s best to move on.

Demand was strong, but down a bit this week. With spring break over the next couple of weeks, we’ll likely see slightly lighter demand than we did a few weeks ago.

Listings were down a bit this week. We’ll still see more come on, but the bigger push will likely be after Easter.

Rates rates were up this week. They are up a lot from a few weeks ago.

Contract were up again this week.

Multiple offer in the outskirts are getting wild. Buyers are doing whatever it takes to win.

The downtown high rise market is the only part of the city where buyers are really price conscious and only making offers if they feel it’s a good deal.

Spring break is creating a window for serious buyers. The buyers out right now tend to be the most serious. There’s less traffic, but much higher intent.

We’re seeing more deals fall apart late stage. There’s been a slight uptick in contracts falling apart during attorney/inspection, mostly due to buyer fatigue and second guessing after multiple losses.

Buyers are getting more aggressive with terms, not just price. We’re seeing things like rent-backs, waived contingencies, and flexible closings being used to win.

Inventory quality still matters. Even with low inventory, buyers are still passing on properties that don’t show well or feel overpriced. The good ones go fast, the rest sit.

The gap between downtown and the outskirts continues to widen. Outskirts remain extremely competitive, while downtown buyers are still more selective and price conscious.

Single Family Homes 
Single family homes are telling a very similar story to what we’ve seen over the past few weeks. I don’t expect a big wave of new listings over the next three weeks, not because sellers aren’t there, but because many are likely hitting pause. A lot of single-family sellers have kids, and between spring break travel and the Easter holiday, many are pushing their list date until right after Easter. We should still see some homes come on, just not at full pace. The three weeks following Easter will be a key indicator for how inventory shapes up heading into the summer market. For now, entry-level properties continue to perform the strongest, and overall, this remains a seller’s market.

Lincoln Park, Lakeview, North Center, Roscoe Village
We’re seeing a bit of a mad dash from buyers right now, especially in the entry-level price points. A lot of these buyers have April and May lease expirations coming up, and it’s creating a sense of urgency that’s showing up in the offers. Quite frankly, the offers have been aggressive. Buyers are not holding back. At this point, it’s less about what a property is “worth” and more about how burned out buyers are, and what they’re willing to pay to be done with the process. I expect this to continue over the next few weeks. If you’re a seller, there’s a real opportunity to take advantage of this window before it passes. For buyers, especially those feeling fatigued, there may be some relief by June as this wave of urgency starts to ease. We’re still seeing the lowest inventory levels in townhomes and larger duplex-down units, and those segments are following a similar pattern. One trend to watch: more listings are holding showings until Saturday/Sunday, with highest and best offers due Monday. Expect that structure to continue for the next 60–75 days. Overall, this remains a strong seller’s market.

West Town, Wicker Park, Bucktown, Logan Square, Avondale
Same as above.

West Loop
Demand is starting to improve here. As the weather warms up and the neighborhood comes back to life, with restaurants and bars getting busier, buyers seem to be reconnecting with the West Loop. We’re seeing the strongest performance at the entry-level price points, along with continued demand for true trophy, high-end properties. The middle of the market is a bit softer and not moving at the same pace. Another dynamic worth noting: we’re seeing more buyers who can’t quite make West Town work financially pivot into the West Loop. It’s becoming more of a value play in comparison, with less competition and a bit more opportunity. Overall, this remains a balanced market.

Old Town
Old Town remains very hot. Walk-ups and townhomes with low HOAs are performing extremely well, driven by extremely limited inventory and strong demand, which continues to push pricing upward. Even the high-rise segment is seeing increased competition, with multiple offers becoming more common. Overall, this is a seller’s market.

South Loop
The South Loop saw another bump in demand this week. Entry-level buyers continue to be drawn here for the value it offers compared to other neighborhoods, along with a less competitive and less stressful buying environment — fewer multiple-offer situations. The luxury segment remains the most challenged, but properties with standout views or strong upgrades are still moving, assuming they’re priced appropriately.
Overall, this remains a buyer’s market, but it’s starting to inch closer toward balanced.

New East Side & The Loop
We saw another bump in activity here this week, which is great to see. A notable shift has been the return of empty nesters and out-of-state buyers, two groups we haven’t seen much of in a while. The key right now is execution. Homes that are priced well and show well are moving. If a property is overpriced or doesn’t present well, it’s sitting. There also seems to be a growing appetite for the area, driven in part by buyers who are getting priced out of other neighborhoods and are now seeing this as a value play. As a result, this has moved into more of a balanced market.

River North, Streeterville, Gold Coast
We saw demand grow again this week. Entry-level properties that are priced correctly are moving quickly, and true trophy properties — the ones with all the bells and whistles and priced aggressively — are also finding buyers. It’s the middle of the market that continues to be the most challenging. One trend to watch: the Gold Coast is seeing a noticeable push from empty nesters, a buyer group we haven’t seen active there in years. That said, buyers across the board are extremely price conscious. If a property feels even slightly overpriced, it will sit. Overall, this remains a balanced market.

The Big Picture:

• Outskirts: It remains a seller’s market across all categories, 

• Downtown Core:  Is feeling more like a balanced market.