By Eric Ladd PUBLISHER
“If You Don’t Do It This Year, You’ll Be One Year Older When You Do.” — Warren Miller
Warren Miller’s famous line has inspired generations of skiers, adventurers and dreamers.
For the past 26 years, I’ve watched that philosophy play out not only on the mountain, but in the Big Sky real estate market.
I’ve seen people buy when others were fearful and be rewarded. I’ve watched others spend years waiting for the “perfect” moment, only to discover that perfect moments rarely exist. Markets move. Opportunities come and go. And often, the best decisions are only obvious in hindsight. Today, we find ourselves at one of those moments.
Recent data shows that Montana vacation-home purchases have fallen more than 70% from their 2021 peak, one of the steepest declines in the country. The reasons are straightforward: interest rates rose dramatically from pandemic lows, prices remained elevated and many discretionary buyers stepped to the sidelines.
Across the country, second-home mortgage originations fell from more than 257,000 purchases in 2021 to just over 88,000 in 2025.
The good news is, markets move in cycles. And what we’re experiencing today feels less like the beginning of a downturn and more like the end of one.
While interest rates have begun to ease, inventory has increased and buyers have more choices and more negotiating leverage than they’ve had in years. Most importantly, the buyers who wanted to purchase in 2022, 2023 and 2024 haven’t disappeared, they’ve just been waiting for the math to work again.
That pent-up demand is real, and we’re beginning to see signs of it returning.
It’s also important to separate national headlines from what’s actually happening here in Big Sky.
While Montana’s vacation-home market experienced a significant pullback from the extraordinary highs of 2021, Big Sky has proven far more resilient. During the winter season of 2018-2019, pre-COVOD, Big Sky recorded 168 residential sales between November and April. During the winter of 2025-2026, that number was 138 sales, a decline of approximately 18%.
That’s certainly a slowdown, but it’s far from the 70% cliff suggested by broader statewide vacation-home statistics. More importantly, values have remained remarkably strong. Median sold price per square foot increased from approximately $370 in the winter of 2018-2019 to roughly $891 this past winter, an increase of more than 140%.
Annual transaction volume tells a similar story. Big Sky recorded 366 residential sales in 2019 compared to 220 in 2025. That represents a decline in activity, but not a collapse in demand. Through the first half of 2026, we’re already seeing encouraging signs that activity may continue to improve.
What this tells me is that Big Sky didn’t experience a traditional boom-and-bust cycle, but instead, we experienced an extraordinary pandemic-driven surge, followed by a period of normalization as interest rates reset and buyers recalibrated.
The luxury segment, where Big Sky primarily plays, has remained remarkably resilient throughout the correction. While transaction volume slowed, the underlying reasons people want to own here have only become stronger. That’s what makes this cycle different.
Twenty-six years ago, Big Sky was still one of the best-kept secrets in the American West. Fast forward to today, and it is a globally recognized destination.
The arrival of Montage Big Sky and One&Only Moonlight Basin has fundamentally elevated awareness of our community. Separate from luxury resorts, they are also global marketing platforms that collectively reach millions of affluent travelers every year through their reservation systems, loyalty networks, travel advisors, luxury publications and international marketing channels.
For decades, communities like Aspen, Colorado, Jackson Hole, Wyoming, and Park City, Utah, benefited from this kind of exposure and today, Big Sky is receiving the same level of attention.
Every day, potential buyers who may never have heard of Big Sky five years ago are discovering our community through some of the most influential hospitality brands in the world. Their investment in Big Sky is a vote of confidence in our future, and their global reach continues to introduce new buyers to the region.
However, destinations are built on more than beautiful homes and luxury resorts; they are built on experiences.
One of the things I am most proud of over the last two decades is watching Big Sky evolve from a seasonal resort town into a vibrant year-round community. Events have played a major role in that transformation. The Big Sky PBR, now celebrating its 15th year and recognized 12 times as PBR Event of the Year, has become one of the premier Western sporting events in North America. Wildlands has brought world-class musicians to our backyard while raising millions of dollars for conservation. Weekly traditions like Music in the Mountains and the Big Sky Farmers Market create gathering places that strengthen the fabric of our community.
These events do more than entertain, they also create memories, build culture and support local businesses and introduce thousands of visitors to Big Sky every year. The strongest real estate markets in America have one thing in common: they become destinations first and real estate markets second.
Since Big Sky crossed that threshold, it has created opportunity for buyers. The best buying opportunities rarely occur when headlines are screaming optimism. They happen when inventory expands, uncertainty creates hesitation and buyers have leverage. Looking back over nearly three decades in this market, many of the most successful purchases were made during periods that felt very much like today.
For sellers however, today’s market requires discipline. The days of simply placing a property on the market and expecting multiple offers are largely behind us. Buyers are informed. They understand market conditions. They have access to data and more options than they have had in years.
That means pricing correctly has never been more important. A well-priced property attracts attention, generates showings, and creates competition. An overpriced property often becomes stale, forcing price reductions that ultimately leave sellers worse off than if they had priced accurately from the beginning.
I’ve often told clients that the market always wins. You can either meet it where it is today or let it bring you there over time. While the outcome is usually the same, the timeline is not making representation more important than ever.
At Outlaw Realty, one of our core beliefs is that knowledge is king. Every week, our team sits down together and reviews the market in detail. We study every meaningful sale, every new listing, pricing adjustments, inventory trends, buyer activity and emerging opportunities across Big Sky, Moonlight Basin, Spanish Peaks, Yellowstone Club, and the greater Gallatin Valley.
After 26 years in this business, I’ve learned that data alone doesn’t create great outcomes. The real value comes from combining market intelligence with local knowledge, relationships, experience and a deep understanding of what makes each property unique.
At Outlaw Realty, we challenge one another every week to understand not only where the market has been, but where it’s headed. That discipline helps our sellers price accurately, position their properties effectively, and maximize opportunity. It also helps our buyers recognize value before the broader market catches up.
In today’s environment, knowledge isn’t just power, it powers tangible results.
After 26 years in Big Sky, I believe we’re witnessing a fundamental shift—buyers have opportunities they haven’t seen in years, and sellers who price honestly and work with experienced professionals can still achieve excellent outcomes.
And the long-term fundamentals of Big Sky—from world-class recreation and conservation values to global hospitality brands, growing air service, and community-defining events—have arguably never been stronger.
None of us know exactly when the next chapter of the market begins, but I do know that the best opportunities are rarely obvious in the moment; they’re usually only obvious in the rearview mirror.
As Warren Miller famously reminded us, “If you don’t do it this year, you’ll be one year older when you do.”
That may be as true for buying real estate in Big Sky as it is for skiing a powder day.
Eric Ladd is the founder and CEO of Outlaw Partners and Outlaw Realty, and publisher of Explore Big Sky.
