What Baseball Taught Me About This Market

Current Market Conditions

I’ve always been a big baseball fan.

I grew up in the southwest suburbs, with my whole family rooted deep on the South Side of Chicago. Naturally, they were diehard White Sox fans. That was just how it was. It was practically part of the family tree.

But when I was about three years old, my dad took us to Wrigley Field for a Cubs game. Ryne Sandberg, Ryno, hit a home run that day. The ball landed right near me. And that was it. I was hooked. Lifelong Cubs fan from that moment on.

To this day, my dad says one of his biggest regrets is taking me to that game.

Baseball always stuck with me. I loved playing when I was young. And now my older son, Rhone, just turned seven. Little League sign-ups were this past week, so I signed him up.

I started asking other parents what to expect.

And honestly… I was surprised.

Their kids have been playing since they were three or four. Some are already on travel teams. Competing. Practicing year-round. At seven years old, it’s like the big leagues.

For a minute, I felt behind. Like I missed the window. Like I should have started him earlier.

So I did what most dads do when they feel behind, I tried to speed it up.

The good news? Kids pick things up fast. Real fast. If they practice.

I’ve been trying to teach Rhone about discipline, about waking up early and getting after it. So we booked lessons at 7:30 on a Saturday morning.

After my workout, I woke him up and we headed to the sports complex. Walking into a place with batting cages… the smell of the turf… the echo of balls hitting aluminum bats… it brought everything back.

And I realized something.

Maybe this is why dads love getting their kids into sports.

There’s no pride like watching your kid play. But it’s more than that. It’s nostalgia. It’s remembering what it felt like to be that kid. To look up and see your dad watching you.

Those are the moments you carry forever.

Now Rhone had never picked up a bat, mitt, or baseball before. But he picked it up quickly. And I told him, if you want to catch up, we’ve got to get aggressive. We’ve got to practice. A lot.

I told him, “Practice makes perfect.”

He looked at me and said, “No Dad. Practice doesn’t make perfect. Practice makes permanent. Nobody’s perfect. But you can make it permanent.”

Seven years old.

And he’s already teaching me.

Now we’re getting more aggressive with practice. And I’m not a perfect dad. Not even close. I’m still learning. Just like a lot of other dads.

And honestly?

That’s exactly where the market is right now.

We are seeing buyers get very aggressive.

A lot of leases are up in April and May. Buyers feel like their backs are against the wall. They’re looking at the calendar thinking, We should’ve started earlier.

Sound familiar?

So now when they submit offers, they’re going all in. And I mean ALL IN.

Well above ask.
Waiving contingencies.
Compressing timelines.
Doing whatever it takes to win.

When a good listing hits right now, $50K, $100K, sometimes well over $100K above ask , isn’t uncommon.

This is prime time.

And just like baseball, if you don’t know the game, it feels overwhelming. Some buyers think they can throw in $5K over and compete. But they haven’t put in the reps. They haven’t practiced. They don’t understand the speed of the game right now.

This is the last 60 days of the most competitive stretch of the season.

And here’s the thing, aggression without discipline doesn’t win games. Smart practice does.

The buyers winning right now aren’t reckless. They’re prepared. They understand value. They know when to swing and when to lay off a bad pitch.

That’s the difference.

Just like I’m learning as a dad, and just like Rhone is learning with every rep, you can’t control when you started.

But you can control how you show up today.

If your lease is coming up… if you’re thinking about making a move… if you feel like you’re behind, don’t panic.

Get a plan.
Put in the reps.
Understand the game.

Because in this market, practice doesn’t make perfect.

It makes permanent.

And the buyers who prepare now, who move with discipline and confidence, are the ones who win.

Play smart. Swing hard when it’s your pitch.


Because just like baseball, the best moments don’t come from watching. They come from stepping up to the plate.

Buyers are pouring into the market as we enter peak demand season. The next 60 days will likely be the most competitive stretch of the year. If you are on the sidelines, this is prime time.

We are in the heart of listing season. More homes are hitting the market each week, creating more options and opportunity.

Rates dropped to a new low this week.

Contract signings rose again. This is typically the busiest stretch for deals getting done.

Multiple offer remain the norm on new listings in the outskirts.

The downtown high rise market continues to struggle above $750K. It is a very different environment compared to the outskirts.

We are seeing a small but noticeable rise in empty nesters moving back into the city, and that matters. They represent a meaningful share of the high rise luxury segment, which has been waiting for momentum. If this trend continues through spring, it could help drive a turnaround. It is still early, but it is an encouraging sign.

International buyers are starting to reappear. Before the pandemic, nearly 20 percent of our business was international, and that dropped closer to 5 percent in recent years. Over the past few weeks, activity has picked up. It is not a flood, but it is noticeable. This group is critical to the high rise market, and if momentum builds, it could provide a meaningful boost where it is needed most.

The situation with Iran is still developing and markets are reacting. Oil and other assets have been volatile as investors price in geopolitical risk. So far, I have not seen a direct impact on the local housing market. Clients are asking about it, but there has been no measurable hesitation from buyers or sellers. That could change, so it is something we are watching closely in the weeks ahead.

Single Family Homes 
Single families continue to perform very well. Demand is strong and inventory remains limited, especially at the entry level where competition is the fiercest and homes are moving quickly. The luxury segment is healthy, though not everything is selling immediately. Well positioned properties are trading, but some are sitting slightly longer than entry level homes. Inventory should remain tight until around Spring Break. Most listings are launching with group showings and highest and best due Monday. This is a strong seller’s market.

Lincoln Park, Lakeview, North Center, Roscoe Village
Demand here is intense, particularly below $600K. Inventory is extremely tight, and buyers facing April and May lease expirations are submitting aggressive offers. Duplex downs and townhomes remain scarce, and when they hit the market, competition is heavy. Supply is ticking up slightly but not enough to meet demand. This remains a very strong seller’s market.

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

West Loop
Demand is picking up. While it does not have the same pre pandemic momentum, affordability and limited options in West Town are pushing more buyers here. Townhomes and larger properties are the most sought after due to low inventory. Trophy luxury homes are performing well, but dated units or those without views are sitting. For now, this is a balanced market, though momentum could shift it toward a seller’s market soon.

Old Town
Old Town is performing well, with many listings selling within days. Walk ups, townhomes, and duplexes are seeing the strongest demand. High rises without in unit laundry and with higher HOAs are lagging. Buyers continue to like the location between downtown and Lincoln Park, which supports steady demand. This remains a strong seller’s market.

South Loop
The South Loop continues to lag compared to the outskirts. Many high rises are sitting. Entry level activity has improved slightly, but overall demand remains soft. Higher HOAs and weak demand for move up properties are key challenges. Townhomes can move quickly if priced correctly. This remains a buyer’s market.

New East Side & The Loop
Activity is improving. The primary buyers are renters converting to ownership and empty nesters returning to the city, including some from out of state and the suburbs. This is helping the entry level segment. The market is not fully back, but there are clear signs of life. For now, it remains a buyer’s market.

River North, Streeterville, Gold Coast
The sub $750K segment is showing real improvement, with renewed buyer activity and sales momentum. Perception is slowly improving, which is helping demand. However, the higher end luxury market remains soft. Dated units, high HOAs, or properties lacking standout features are sitting, and inventory is building. Homes in that segment must be priced below market to move. Overall, this remains a buyer’s market.

The Big Picture:

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

• Downtown Core: Is a buyer’s market.