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Haunted Chair, Haunted Choices

Haunted Choices in Today’s Chicago Real Estate Market

Current Market Conditions

Who doesn’t love a scary story during Halloween week?

My aunt on my mom’s side was the picture of success; beautiful, wealthy, married to a rich guy. They bought a grand old estate in the countryside of Geneva. It was the kind of home with character: creaky floors, towering ceilings, and that eerie kind of charm only history can give.

At the time, my aunt had one child, a baby boy named Justin.

A few months after they moved in, my aunt and a friend were having a glass of wine when a thunderous crash echoed through the house. It sounded like a massive piece of furniture had toppled over. They froze. The sound came from Justin’s room.

They ran upstairs, hearts pounding and expecting the worst. But there was Justin, standing in his crib, smiling and laughing. Nothing was out of place. No furniture had moved. Every door was closed.

They laughed it off as a strange coincidence, maybe the house settling, maybe the wine. But it didn’t stop. Over the next few months, the same thing happened again and again: the crash, the rush upstairs, Justin’s laughter echoing through the room.

Now, my family is deeply religious, especially my Granny Jo. She didn’t hesitate. “It’s something from beyond,” she said. And, believe it or not, she called an exorcist.

When the exorcist arrived, they said they could feel a spirit in the house. They followed that feeling down to the basement, where they found a small, half-hidden door. Behind it was a tiny cellar, and inside, an old wooden rocking chair.

The air was still. No wind, no draft. Yet the chair… was rocking.

They later discovered that decades earlier, a young boy had died in that home. The exorcist believed his spirit was attached to the chair, and that he’d been visiting Justin’s room to play.

The exorcist destroyed the chair, and after that, the noises stopped. Completely.

Years later, when I was about five, I stayed in that house once. I woke up from a nightmare and walked down a pitch-black hallway. The basement door was open. That night, I dreamed of a single chair under a spotlight. I didn’t even know the story yet, but I remember that dream to this day.

We all have things that haunt us.

As we head into the holidays, the housing market slows down. Fewer new listings. Fewer casual buyers. And yet, so many people are haunted by the decisions they didn’t make:

  • “I should’ve bought that one.”
  • “I should’ve offered more.”
  • “I should’ve listed earlier.”
  • “I should’ve priced it better.”

The truth? The market isn’t dead, it’s just quieter. The buyers out there right now are serious. The sellers willing to list are motivated.

So don’t let your past fears, or your missed chances, haunt you. Sometimes, like my aunt, you have to face what’s scaring you and let go of what’s holding you back.

She had to get rid of a haunted chair. You might just have to get rid of hesitation.

Let’s make sure your next move isn’t a ghost story.

With the Current

What Else Happened This Week

Demand eased again this week, marking our third consecutive weekly decline. Seasonality is kicking in, and this quieter pace will likely hold through the holidays.

Price cuts are picking up as we head into the holiday season, with existing inventory adjusting to sell before year-end.

Multiple bids remained common on well-priced new listings.

New inventory pulled back this week, with fewer homes hitting the market than we saw at the beginning of the month. Selection is tighter, but motivated buyers are still active. For sellers, lighter competition can be an advantage.

Rates were down this week, hitting a new low for the year.

The Downtown market activity stayed light this week, particularly in the luxury segment.

Market Trends

What's Trending

We typically see the highest volume of pocket listings during the holiday season. Many sellers choose to stay off the MLS to avoid racking up market time, while still wanting exposure to serious, qualified buyers. With travel plans and holiday schedules, casual showings are less convenient—expect this trend to continue through the season.

The Holiday Buyer is coming. Holiday buyers are like vampires: they come out now and only strike for a great deal. They’re a rare breed—a small slice of the market with a big appetite for value. If price, terms, or condition aren’t sharp, they’ll pass and disappear into the night.

Investor activity ramps up into year-end. Historically, we see a concentration of investment deals in November and December. Investors are disciplined, data-driven, and quick to walk away if value isn’t clear. They can be tough negotiators and often make transactions stressful, but they’re a major trend from now through the end of the year.

Checking Inventory

Single Family Homes

TREAT. Single-family homes remain red hot, with the entry-level price point drawing the most offers. Nearly all of these are selling within 48 hours. At the high end, days on market are building, but properties on larger lots or with top-tier finishes are still moving quickly, often with multiple offers. There’s no sign of a slowdown as we approach the holidays. For now, it’s a very strong seller’s market.

Lincoln Park, Lakeview, North Center, Roscoe Village

TREAT. Another week, another hot market. New listings that are priced right, show well, or sit on a highly desired street are selling well over ask. Inventory is at the lowest level of the year here. That said, homes outside those buckets are moving more slowly, some are even sitting longer than they would in the spring. Duplex-downs and townhomes remain the hottest segments. Overall, it’s a seller’s market.

West Town, Wicker Park, Bucktown, Logan Square, Avondale

TREAT. Same as above.

West Loop

TRICK. It’s still a strange market. Some units are selling quickly and over ask, while others sit with little to no activity. The homes that move are typically priced below market and show exceptionally well; the rest are slower. The luxury segment is performing the weakest locally. Overall, this remains a buyer’s market.

Old Town

TREAT. One of the hottest areas in the city right now. Inventory is very low, and every segment is moving quickly. The lowest-performing properties are high-rises without in-unit washer/dryer, yet even those are selling faster than comparable listings elsewhere. Overall, it’s a seller’s market.

South Loop

TRICK. This is one of the hardest-hit areas in the city. Even entry-level condos are feeling the pressure, with the most strain on larger units and mid-tier pricing ($550K–$800K). Overall, this remains a buyer’s market.

New East Side & The Loop

TRICK. This area continues to struggle, with activity dipping versus last week. Entry-level, move-in-ready condos are holding up—some are even moving quickly. Mid-tier condos are sitting, especially if they need work, and the luxury segment remains soft. Overall, it’s still a buyer’s market.

River North, Streeterville, Gold Coast

TRICK. The heart of the city, once the undisputed “King of Chicago,” remains soft. Entry-level condos are performing well—if priced right, move-in ready, with low HOA fees and in-unit laundry, they sell quickly. Outside of that, activity drops off. At $900K and above, the market is sluggish, and many sales are repriced significantly from prior purchases. 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.

Podcasts & VLogs

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Pressing Press

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Have a great week! Let me know if you need anything. 

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