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What the Marlboro Ranch Taught Me About Today’s Market

What the Marlboro Ranch Taught Me About Today’s Market

Current Market Conditions

Smoking used to be everywhere. My parents were big smokers, especially my dad. I can still remember being a kid, sitting in the back seat with the windows rolled up, while my parents puffed away like it was the most normal thing in the world. Hard to imagine that today, right?

Back then, every restaurant had smoking and non-smoking sections. It was just a way of life. My dad was a Marlboro Red guy, through and through, and if there’s one thing he loved more than cigarettes, it was coupons. He was obsessed with his Marlboro Miles, entering contests and redeeming points for free stuff.

One year, when I was 27, I got an envelope in the mail from Marlboro. Inside was a letter saying I had won a trip to the Marlboro Ranch in Montana.

I had no idea my dad had entered me. When I asked him why, he laughed and said, “The more people I enter, the more coupons I get!” Somehow, I ended up being the lucky one.
The prize was unbelievable, an all-expenses-paid trip: flights, lodging, transportation, even custom luggage filled with clothes for the trip. They even sent $5,000 in case I owed taxes on the prize.

At first, I thought it sounded ridiculous. I didn’t smoke, I wasn’t an outdoors guy, and the whole thing felt like a gimmick. But at that point in life, I was 27, living at home, and still trying to get my business off the ground. Money was tight, and my now-wife Nicole said, “Why not? It’s free. Worst case, it’ll make a great story.”

She was right.

When we arrived, it looked like something straight out of an old Western movie, a real-life set from Tombstone. Our cabin had everything we could ever need: snow gear, boots, clothes… and about ten cartons of cigarettes (of course).

We didn’t know what to expect, but the experience was incredible. Snowmobiling through the mountains, dog sledding, ice fishing, archery, tubing, cross-country skiing, you name it. The food was amazing, too, all locally sourced from the working cattle ranch.

There was no internet, no phones, no distractions. Just people from all over the world, laughing and connecting. And even though we were non-smokers, nobody cared. Everyone was just there to have a great time.

What I thought would be the worst trip of my life turned out to be one of the best experiences I’ve ever had.

That trip reminds me a lot of what’s happening in today’s real estate market.

We’ve entered the final quadrant of the year; the Holiday Market.
And with it comes a particular type of buyer: the Holiday Buyer.

These buyers assume the worst. They think this year’s housing market was a bubble and that next year everything will crash. They’re cautious, skeptical, and only willing to buy if they can win big.

Holiday Buyers want to negotiate hard. They want to feel like they got the deal of the year, and if they don’t, they’ll walk away without hesitation.

Here are some traits we often see:

  • Irrational thinking
  • Emotional decision-making
  • A strong need to “win”
  • Demanding extra concessions after inspections
  • An all-or-nothing attitude

Normally, these buyers make deals more challenging this time of year. But this year feels different.

The market isn’t struggling like many expected. Inventory remains tight, prices are steady, and mortgage rates are stabilizing.

Many Holiday Buyers who waited for the “perfect deal” are realizing those deals just don’t exist. The market isn’t collapsing, and that’s forcing a mindset shift.

Just like I assumed the Marlboro Ranch trip would be terrible, these buyers are realizing the market isn’t as bad as they imagined. Sometimes, when you assume the worst, you end up pleasantly surprised.

The holidays bring out emotion, in people, in life, and definitely in real estate. But while some buyers are still living in fear, the market is quietly proving stronger than expected.

So if you’re buying or selling this season, remember: assumptions can mislead you. What feels like a risky trip might just turn into the best experience of your life.

With the Current

What Else Happened This Week

Demand was on par with last week. We’re still seeing qualified showings and offers, but volume is roughly 25% of what we see in the first half of the year. That slowdown is seasonal and expected, and we anticipate demand to hold at this pace through year-end.

New inventory was down this week. Seasonally, we expect lower new inventory from now through year-end, which means buyers will face fewer fresh options and sellers will see slightly less competition.

Rates held steady this week, hovering near year-lows. This stability is helping fuel the holiday market, keeping motivated buyers active even as inventory dips and the season slows. Expect this consistency to support steady demand through the rest of the year.

Multiple bids remain the norm, especially on fresh listings in the hottest neighborhoods. Well-priced, move-in-ready homes are drawing the most traffic and strongest offers within the first few days on market.

Downtown remains extremely slow, with little activity in the mid-tier to luxury segments. Buyers are selective and taking their time. For sellers, success hinges on realistic pricing and great presentation.

As we inch closer to Thanksgiving, we’re seeing price reductions on existing listings that haven’t moved. This is a classic pre-holiday pattern, as stale inventory trims pricing to re-engage buyers before year-end.

Market Trends

What's Trending

There’s a lot of chatter right now about 50-year mortgages, and while it’s still more idea than policy, it’s one worth watching closely.At the moment, 30 years is the longest standard term for traditional or FHA loans in the U.S. The FHFA, Fannie Mae, and Freddie Mac would all have to approve longer loan terms before they could become mainstream. There are 40-year options in limited cases , usually for loan modifications, not new loans. So a 50-year mortgage isn’t here yet. But if it ever did pass? It could be massive for the housing market. It could completely reshape the housing landscape. It would open the doors for millions of new buyers, push demand to new highs, and could set up 2026 as one of the hottest real estate years in modern history. Keep an eye on this one.

Deals. If there were ever a time to get a deal, it’s right now. Now, to be clear , that doesn’t mean there are tons of great deals out there. (Unless you’re buying downtown, that’s where the real opportunities are.) But across most of the market, pricing is about as low as it’s going to get. Once we roll into the new year, expect prices to start ticking back up as demand picks up and fresh inventory hits. So, if you’ve been waiting for the right moment to buy, this is it. Keep an eye out for the right property. The window for value is now, not next year.

The Shutdown. So far, the government shutdown hasn’t had a noticeable impact on the housing market. Activity and demand remain steady, and buyers are still writing offers. That said, the longer this drags on, the more likely we’ll start to see ripple effects, especially in lending, consumer confidence, and overall market sentiment. For now, it’s business as usual. But this is one to keep an eye on, because if it extends too long, it could start to weigh on both buyers and sellers heading into the new year.

Checking Inventory

Single Family Homes

This remains the city’s hottest market, especially at the lower price points where demand is outpacing limited inventory. Even though this season is typically slow for single-family homes, activity is still high. The luxury segment has cooled unless a property is truly unique or highly upgraded. Overall, it’s a big sellers market.

Lincoln Park, Lakeview, North Center, Roscoe Village

The market here is extremely hot. The best performers are move-in-ready entry-level condos, townhouses, and duplex-downs. Typically, we see more inventory and softer demand this time of year, but not now. Supply is low and demand remains high. Overall, it’s a big sellers market.

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

Same as above.

West Loop

The market has been hit or miss. Move-in-ready, well-priced entry-level condos are selling, and luxury properties that show exceptionally well are moving too. Everything else, however, is sitting longer. It’s been a challenging few months here, and overall this is a buyers market.

Old Town

The market continues to stay very hot. I’m actually surprised by how quickly the high-rise segment is still moving. The hottest properties right now are walk-ups and townhomes. Nothing is sitting for long, and market times remain low. Overall, this is a strong sellers market.

South Loop

This area is tough right now. Showings have been slow. Some well-priced, move-in-ready entry-level condos are selling relatively quickly, but most other properties aren’t. Inventory is up, demand is down, and the luxury tier is especially quiet. Overall, it’s a strong buyers market.

New East Side & The Loop

It’s been a very difficult market. We’re seeing a solid uptick in showings for entry-level condos with in-unit laundry, but mid-tier condos are slow, and luxury gets little traction unless priced well below prior purchase price. Overall, this is a big buyers market.

River North, Streeterville, Gold Coast

It’s an odd market. Entry-level condos with in-unit washer/dryers are drawing strong demand and moving quickly. The mid-tier is crawling, and luxury is basically at a standstill unless priced well under what sellers paid. Overall, this is a strong buyers market.

The Big Picture:

  • Outskirts: It remains a seller’s market across all categories, 
  • Downtown Core: Is a buyer’s market.

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

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