“When you show a property at the right time of day, when the elk are bugling or deer are bedded in the grass, buyers don’t just see a house, they see their future,” says Ashley DiPrisco, Associate Broker at Jackson Hole Sotheby’s International Realty, who has mastered the art of emotional connection in one of America’s most exclusive real estate markets.
A Family Legacy in Real Estate
DiPrisco’s journey into real estate wasn’t initially planned, despite her father being in the business since the late 1970s. “No one grows up saying ‘I want to be a realtor when I grow up,’” she jokes. “Like, career day at school, that’s not a thing.”
After her husband’s 12-year service in the Air Force took them across multiple states, DiPrisco gained firsthand experience with the buying, selling, and relocating process. This experience revealed to her “there’s actually a lot more to this than what Realtors get credit for.”
When her father extended an invitation to return to Jackson Hole and work alongside him, what once seemed unlikely became reality. Nearly a decade later, DiPrisco has established herself as a prominent broker in one of America’s most competitive luxury markets.
The Jackson Hole Market: Limited Supply, Enormous Demand
What makes Jackson Hole unique is its extremely limited supply of developable land—only about 1.5% of the total acreage is available for private ownership, with the rest protected as National Park, Forest, and Conservation Lands.
“In basic economics, that drives up the price. We have an enormous demand,” DiPrisco explains. Her team’s listings range from condos at the “low range” of $1.5 million to properties priced at $40 million. “Even if you’re in our affordable price point of a million and a half, it’s still very much a luxury market. You just can’t get around that.”
The competition is fierce among agents as well. In a town of 10-12,000 residents, approximately 600 people hold real estate licenses. “The barrier to entry is pretty low to get your real estate license here,” DiPrisco notes. “But there’s only a handful of us that actually really do it and thrive in it.”
Emotional Selling: Timing is Everything
DiPrisco’s approach to selling luxury properties focuses on creating emotional connections between buyers and properties, a strategy that has proven effective in previous market cycles.
“Before the last recession in ’07-’08, we had a little bit of emotion in the market,” she recalls. “We felt that emotion again around 2012 and 2015. When I say that, I mean when buyers truly come here and they fall in love.”
To facilitate these emotional connections, DiPrisco’s team carefully plans property showings around optimal times of day. “We tailor our showings based on the best time of the day, the early mornings, around 9-10 o’clock before it warms up, when the deer is still bedded down in the grass, or when the elk haven’t moved up the hillside.”
Evening showings offer their own magic: “We like hearing the elk bugle in the evenings. And these are even in our subdivisions, we have a fox that’ll be in the meadow just across the street.”
This strategic timing helps properties present themselves in their most natural, appealing state, a crucial factor in a market where the connection to nature is a primary selling point.
Video Marketing: Capturing Authentic Moments
Despite Jackson Hole’s sophisticated market, DiPrisco notes that surprisingly few realtors maximize the potential of video marketing, an area where her team excels.
“We were filming a new property just about 10 days ago, and we stumbled upon an elk and a baby calf that had just been born. The calf didn’t even stand up. And we’re thinking, ‘Oh my gosh, this is real.’”
These unscripted wildlife encounters perfectly embody what buyers are seeking in Jackson Hole. “That’s the vision. That’s the dream of the market,” DiPrisco explains. “People come out here to reprioritize and reconnect and reset their mind from that rat race that you experience in the cities.”
The Tax-Friendly Appeal
Beyond natural beauty, Wyoming’s favorable tax environment drives significant buyer interest, particularly from high-tax states.
“When higher tax states like California, New York, Connecticut, and even Seattle put some limits on business tax regulations, we see a bump every time,” DiPrisco explains. “Wyoming is an extremely tax-friendly state. Not only do we not have a state income tax, but we have incredible legislation for succession planning and dynasty trusts.”
This tax advantage attracts a specific clientele. “They joke and call Wyoming the offshore of the states,” DiPrisco notes. “We don’t necessarily attract the Hollywood type, they usually gravitate more towards Aspen and Vail. But we attract Fortune 500 types, the people who, whether they’ve earned it or inherited it, really want to think about their family’s financial future.”
Buyer Expectations vs. Reality
Working with sophisticated buyers presents unique challenges, as many arrive with expectations shaped by other luxury markets that don’t align with Jackson Hole’s realities.
“If they have multiple homes in other places, or if they’ve built homes elsewhere, they have a hard time finding everything on their checklist here in Jackson,” DiPrisco explains. “We have very regulated building regulations, and we have a maximum square footage that you’re allowed to have.”
These restrictions mean that despite multi-million dollar price tags, homes in Jackson Hole are more modest in size than comparable properties elsewhere. “You’re not going to get more than about 8,000 square feet of habitable space,” she notes.
This reality requires adjustment from out-of-state buyers with specific expectations. “Most of our Southern California buyers really want that dual bathroom where you have your separate closets, your separate vanities, your separate showers, but somehow you meet in the middle. We just don’t have that here. That’s not the best use of your allotted square footage.”
Similarly, requests for massive closets often need recalibration: “I’ve had multiple buyers say, ‘I want something like 700 square feet of a walk-in closet,’ and I’m like, ‘That’s bigger than my first apartment.’”
Market Dynamics: Who’s Buying and Selling
An interesting demographic shift is occurring in the market. “We are seeing a little bit of shifting in downsizing,” DiPrisco observes. “Although we’re seeing sellers wanting to downsize and stay locally, at the same time, we’re seeing younger established families move into those larger homes.”
This creates a natural cycle in the market: “It’s almost like the grandparents are downsizing and moving out and thinking about what their next 10 to 15 years looks like. But the families who can afford this price point are like, ‘Great!’”
The middle of the market—properties in the $10-15 million range—is particularly popular with empty nesters. “Those are people who have raised their families here. They don’t feel like remodeling or updating, and now they’re going to finally cash out and move into something a little easier to manage in the winters.”
Looking Ahead: Cautious Optimism
As for the future, DiPrisco expresses “cautious optimism” about the current selling season, which typically runs from July 4th through mid-October. “It’s our bread and butter season, where more than 50% of our transactions occur,” she explains.
Despite various market challenges, DiPrisco sees positive signs: “Now I think we’re adjusting and normalizing to all of this external noise that we’re hearing outside of our beautiful little bubble here, and people are finally starting to go shopping.”
For DiPrisco and her team, which includes her father and three associates, the future looks bright. “We’re in a really exciting point entering the selling season. My team alone, we have over $230 million in listings right now,” she shares. “We’ve worked really hard to get here.”
Their focus remains on their distinctive approach to marketing properties: “We do a lot of onboarding for our group, where we really want to tell the story of each property. Why is it unique? Why is it different, and why does it possibly make sense for you and your loved ones?”
In a market defined by limited supply, enormous demand, and properties that connect buyers with nature, Ashley DiPrisco has found success by focusing on what matters most: helping buyers find not just a luxury home, but a place to reconnect with what truly matters.
