The Little Jackson Hole That Wasn't: What a Canceled Resort Tells Pinedale Buyers

For most of 2023 and into 2024, construction lights burned through the night along Upper Hoback River Road outside Bondurant, about 25 miles from Pinedale. By day, a mountain of excavated dirt kept climbing. Crews were building a 20-unit luxury resort on a sagebrush bench above the river, complete with an underground wellness center, a European-style spa, and a 90-seat dining hall built into a basement of more than 65,000 square feet.

Then, in July 2024, it stopped. Construction crews walked off. The lights went dark. The developer ordered the site restored to something close to its original shape.

The developer was Joe Ricketts, the billionaire founder of TD Ameritrade, and the project was on his own Jackson Fork Ranch. He had a name for the address he wanted people to remember: Little Jackson Hole.

What "Little Jackson Hole" Was Supposed to Mean

Bondurant is a working ranch valley with a year-round population of roughly 100 people. Ricketts owns 1,300 acres of it, and in 2021 he got 56 of those acres rezoned from agriculture to a recreation-services designation that allowed a hotel. At a public meeting in Pinedale in May 2023, he explained why he wanted his ranch's mailing identity tied to Jackson rather than to the sleepy valley it actually sits in.

"If I advertise 'Little Jackson Hole,' everyone knows where it is."

The logic tracks. Sublette County has spent years absorbing overflow demand from a Teton County market that most buyers can't touch. A single-family home in Jackson runs several times what the same square footage costs an hour and a half south on Highway 191, and Ricketts wasn't wrong that the name recognition of Jackson does real work for marketing a remote Wyoming property to buyers in Los Angeles or New York.

What he built to match that ambition was substantial: a 20-unit resort, a private road paralleling Upper Hoback River Road so guests wouldn't add traffic past neighboring ranches, and amenities aimed squarely at the kind of visitor who already knows Jackson Hole and wants something quieter with the same polish.

Why It Stopped

The project sits inside one end of the longest known mule deer migration route in North America, and Sublette County's seasonal construction restrictions exist to protect exactly that corridor. Ricketts asked commissioners for an exemption to keep building through the restricted window. Commissioner Mack Bradley cast the deciding vote against it.

Without the exemption, his agent Steve Christensen wrote in a memo obtained by WyoFile, the added cost of working only within the permitted season would run $60 million to $100 million higher than originally planned. The memo's subject line was blunt:

"the End of the Homestead"

Christensen called the outcome a "significant economic loss" for the county, and estimated the project's collapse cost the area 100 to 150 jobs. Bradley told Cowboy State Daily he saw it as unfortunate both for the county and for the contractors who'd expected a summer of work. Some Bondurant residents, who had opposed the project from the start, wondered aloud whether the idea would resurface later under a different owner or a friendlier commission. As of now, nothing has.

The seasonal restriction that killed the Homestead didn't get created for this project and doesn't disappear because this project failed. It applies to whoever tries to build there next.

The Price Gap That Started the Idea

The instinct behind "Little Jackson Hole" wasn't invented by Ricketts. Regional coverage has used some version of that phrase for Sublette County generally, describing it as the place catching Teton County's overflow. The numbers explain why.

Pinedale's own reported median is harder to pin down than the county figure. Depending on the month and the source, it's shown up anywhere from about $510,000 to $650,000, and one recent reading put the town at only three homes sold in a single month. That kind of spread isn't a data error. It's what happens in a market where monthly sales counts are still in the single or low double digits. A buyer comparing Pinedale to Jackson on median price alone is comparing a number built on dozens of transactions to one built on a handful.

What that price gap has actually pulled toward Sublette County, according to regional coverage, isn't resort buyers. It's people who find Jackson too commercialized and are looking for standard single-family homes and acreage instead, plus a smaller group chasing large view parcels in places like Daniel, where lots with distant Teton views still trade for under $1 million.

What a Contractor's Math Shows

The cost gap between the two markets runs both directions, and a Pinedale-based builder recently put a number on it. Shane Wilson, who owns Pinedale-based Wilson Design + Build and has built mostly in and around Pinedale, bought two lots earlier this year in Porter Ranch, a new subdivision south of Jackson where lots were listing for $700,000 to $1.2 million. Asked about the cost difference between building there and building at home, Wilson told the Jackson Hole News&Guide that for roughly what it costs to build 20 homes in Sublette County, he can build four or five in Jackson.

That's the same math that killed the Homestead, working in the opposite direction. Standard construction in Sublette County is cheap relative to Jackson because the land, the labor market, and the permitting process are all lighter. Resort-scale construction in Sublette County is expensive relative to what a developer expects, because the same remoteness and wildlife protections that keep standard homebuilding affordable turn into a serious liability the moment a project needs a compressed construction season and specialized amenities.

What This Means If You're Comparing the Two Markets

The price gap between Jackson and Pinedale is real, and it isn't closing through Jackson-style development catching up to Sublette County. It's durable for the opposite reason people often assume: not because nobody has tried to build a resort here, but because someone with $7 billion tried and the seasonal wildlife protections still won.

Pinedale itself is not an empty canvas waiting for that kind of investment. It's the county seat and the commercial hub for a county of nearly 10,000 people spread across almost 4,900 square miles, with a hospital, K-12 schools, a grocery store, and established in-town subdivisions like Trails Creek, Split Diamond Meadows, and Fox Willow Park. Since 2020, the town has recorded well over 700 closed transactions across residential, land, and commercial categories, most of them ordinary homes, not luxury units.

Across the whole county, inventory stays thin: roughly 70 active residential listings, 130 land parcels, and 16 commercial properties at any given time as of mid-2026. That's a market you buy into for what it currently is, a small, functioning Wyoming town with real appreciation in its housing stock, not for a resort economy that a billionaire couldn't get built.

A Few Common Questions

Will someone try to redevelop the Homestead site? Nothing has been filed as of this writing. The seasonal construction restrictions that killed the first attempt still apply to the land, so any future proposal would face the same cost math.

Does the Jackson-Pinedale price gap mean Pinedale homes are undervalued? Not in the sense that the gap is temporary. Jackson's median reflects an established resort economy with limited land and heavy demand. Pinedale's reflects a small town with a real, if thin, housing market. They're not the same asset class, so comparing them as if one should eventually catch up to the other misreads what each market actually is.

Why do some Pinedale homes sit on the market for months while Jackson's move faster? Partly it's a smaller buyer pool trading through a smaller number of listings each month, which also explains why reported medians swing so much from one data source to the next. Price a home here against that thin-market reality rather than against a single headline number.

If you're weighing a move into Sublette County, or trying to price a home here with an accurate read on what actually drives this market, RE/MAX Elite can walk through the current listings and the local factors that shape them. Get in touch when you're ready to talk specifics.