What do you do when the same waterfront resort, same address, same 22 villas and eight suites, sells for roughly half of what it sold for two years earlier, in a market everyone keeps calling supply-constrained?

That is exactly what happened at 82779 Old Highway in the Upper Keys this summer. The Islands of Islamorada Resort changed hands in July 2026, and the number behind that sale tells a more useful story than any of the press releases that announced it. If you are comparing waterfront property anywhere along the Keys corridor, from Islamorada down through Marathon, Key Colony, and Grassy Key, this deal is worth understanding before you trust the next headline price you see.

Two Sales, One Address

In July 2024, The Wills Company bought the resort from the Frisbie Group for $72 million, with Frisbie retaining a stake in the partnership. The buyers announced plans to market the property's residences as single-family homes starting at $4.95 million, and brought in CoralTree Hospitality to run day-to-day operations.

Two years later, Mast Capital and Koch Real Estate Investments bought the same seven-acre property. CoralTree is no longer part of the picture. The new owners plan to relaunch the 22 waterfront units as condo-hotel villas, with an optional rental program, and Ocean Sotheby's International Realty handling sales. Starting price for a villa this time: $3.8 million.

Here is the part that matters more than either headline number.

The Figure the Announcement Didn't Include

When Mast Capital and Koch Real Estate Investments announced the deal, they did not disclose what they paid. That is standard practice for a lot of commercial transactions. But Monroe County deed records tell a different story than the press release did: a $38.4 million sale price, paired with a $40 million acquisition loan arranged by Berkadia Miami's Scott Wadler through lender Ardent Real Estate.

That is the lesson buried in this deal. The number a seller or buyer chooses to put in a press release and the number recorded at the county are not always the same document, and only one of them is a matter of public record you can actually check yourself. If you are underwriting a comparable sale anywhere in the Keys, the deed is worth more than the quote.

Same Address, Different Deal

Here's a side-by-side of what actually changed between the two sales:

Look at that last row again. The 2024 plan described single-family residences. The 2026 relaunch describes a condo-hotel product, a deeded interest tied to a resort operation and an optional rental pool, marketed through a luxury brokerage rather than sold as standalone homes. That is not the same asset with a lower sticker. It is a different ownership structure entirely, wearing the same villa floor plans.

The villas themselves are specific: four bedrooms, four bathrooms, three stories, roughly 4,067 total square feet split between about 3,137 square feet of interior space and 930 square feet of outdoor loggia, two-car garages with EV charging, and concrete block construction built to current hurricane code. Buyers get access to two oceanfront pools, a private beach, two pickleball courts, a beachfront bar, a fitness center, and a private marina with boat slips, paddleboards, kayaks, and sailboats. That is a real product. It just isn't the product that was announced in 2024.

What Institutional Buyers Actually Reprice

Jordan Kornberg, Mast Capital's chief investment officer, described the Keys as "one of the country's most supply-constrained hospitality markets" when the deal was announced, and he has said the same thing in nearly every release about it. That line gets repeated because it is the pitch. It is also not the whole picture. A market can be supply-constrained on land and still see a specific resort trade at less than the previous owner paid, because what actually moved here was the deal's plumbing, not the island's supply of buildable lots.

This is not the first time Mast Capital has taken this approach to a Keys asset. The firm's other Florida Keys property, Little Palm Island Resort & Spa on Little Torch Key, came into Mast's hands through a 2020 refinance after the resort's original loan went into maturity default during the pandemic. Mast partnered with RWN Management, a family office tied to Apollo Global Management co-founder Marc Rowan, to provide $30.5 million and take over a stressed capital structure at a discount. The resort has since built a strong track record, including a 2026 culinary partnership with Michelin-starred chef Curtis Duffy. The pattern across both deals is the same: buy into a complicated ownership or financing situation before it's fully resolved, then relaunch on cleaner terms.

For a buyer, that pattern is more instructive than any single price. It tells you that a lower number attached to a marquee Keys property does not automatically mean the market softened. It might mean a management contract lapsed, a partner exited, or a product got restructured into something a lender was more comfortable financing.

What This Means If You're Comparing Keys Waterfront Property

If you are weighing waterfront listings across Islamorada, Marathon, Key Colony, or Grassy Key and two properties with similar bones carry very different price tags, resist the urge to assume one is a steal and the other is overpriced. Ask instead:

• Is this a fee-simple home, or a deeded interest tied to a rental program or management agreement?
• Has the property changed hands with a partner retaining a stake, the way Frisbie Group did in 2024, or is this a clean exit?
• What does the county deed actually show, separate from what the listing sheet or press release says?
• Did a management contract just end, and does that explain a repositioning rather than a market shift?

None of those questions show up in a median price chart. All of them showed up in this one transaction, and all of them are checkable through public records before you make an offer.

FAQ

Does this mean Florida Keys property values are falling? Not on its own. This is one resort's ownership and financing history, not a market-wide price index. What it does show is that a single high-profile sale can drop significantly in headline price while the underlying real estate stays desirable, because the structure of the deal changed more than the value of the dirt and the view.

Why didn't the buyers disclose what they paid? Buyers and sellers frequently keep transaction prices out of their own announcements for competitive or strategic reasons. That's exactly why county deed records matter. In this case, the $38.4 million figure only became public because it was reviewed against Monroe County filings, not because either party volunteered it.

How is a condo-hotel villa different from buying a single-family home in the Keys? A condo-hotel structure typically ties your ownership to participation in a shared rental program and resort operations, with rules and revenue splits set by the management agreement. A single-family home gives you full control over how, or whether, you rent it out. Both can make sense depending on your goals, but they are not interchangeable products even when the price tags look comparable.

If you're weighing a waterfront purchase anywhere between Key Largo and Key West and want a second set of eyes on what a listing's price actually reflects, structure and all, Jessica Borraccino has spent 13 years reading Middle Keys deals the way this one deserves to be read. Let's connect — schedule your free consultation.