Registration for the 13th Annual Sugarloaf Showdown opened August 1, and anyone who remembers last year knew better than to wait. The 2025 tournament filled in under 48 hours, forcing a waitlist for teams chasing a shot at the bonefish, permit and barracuda that make the Lower Keys flats fishery what it is. This year's event runs November 12 through 14, with early registration reserved for Lower Keys Guides Association members through August 14 before it opens to the public on August 15, if any slots remain.
None of that is new. What's new, and what most people driving past mile marker 17 this month may not have clocked yet, is that the property where this whole tradition ends every year, the awards banquet on what the tournament's own schedule calls the "Sugarloaf Lodge grassy point," is currently listed for sale at $45 million.
That's not a rumor passed around at the tiki bar. It's a real listing, reported by The Real Deal in January and confirmed again in an April follow-up, for a 10.6-acre waterfront parcel with a 31-room hotel, a restaurant and bar, a tiki bar, a 5COP liquor license, and something rarer than any of that in Monroe County: 24 vested hotel development rights that would let a buyer build out to 55 total rooms. In a county where new hotel entitlements are almost impossible to come by, that's the real value driver behind the number, more than the aging rooms themselves.
A landmark that's always been more than a building
Sugarloaf Lodge has been the anchor of this stretch of the Overseas Highway since the late 1950s, built by the Pennsylvania mining company that first dredged and developed much of the key. Lloyd and Miriam Good bought the property in 1973 and ran it as a hands-on, live-on-site operation for over five decades. Their son John Good, who now co-owns the property, was heading off to Kenyon College around the time he got to talk with a guest at the lodge who happened to share that alma mater: Paul Newman.
Hunter S. Thompson stayed there often enough that current owner John Good has described him as "kind of part of our family for a couple of years." A dolphin named Dolly, who'd escaped a Navy program and wandered into the property's bay, was studied for her intelligence by Jacques Cousteau before the Goods removed the nets keeping her penned in and let her swim off on her own terms. That kind of texture doesn't show up in a listing sheet, but it's exactly why longtime residents talk about the Lodge as something closer to a shared institution than a commercial property.
It's also, functionally, the reason a lot of boats get in the water at all. The Lodge property includes marina access and dockage that ties directly into the daily rhythm of life on Sugarloaf Key, a place where, by most accounts, the majority of the land remains undeveloped and where a chunk of the surrounding acreage falls inside the Great White Heron National Wildlife Refuge. Development pressure here is real precisely because there's so little of it already.
The marina locals actually use
Just down the road at 17015 Overseas Highway, a separate marina address serves as the launch point for Get Up and Go Kayaking's clear-kayak tours through Sugarloaf's mangrove backcountry, the two-hour guided trips that put paddlers eye to eye with nurse sharks, stingrays and the occasional sea turtle without ever leaving sight of the highway. It's a useful reminder that "the marina" on Sugarloaf Key isn't one single thing. Between the Lodge's own dockage and the separately run bait, tackle and boat ramp operation next door, there are multiple working pieces that together keep the island's fishing guides, kayak outfitters and weekend boaters moving. A sale at the Lodge changes ownership of one piece of that puzzle, not all of it.
Still, the Lodge piece is the one carrying the most symbolic weight, because it's the piece that hosts the Showdown, and the Showdown is the closest thing Sugarloaf Key has to a shared civic calendar. Tournament director Jessyca LaBadie put it plainly when the 2026 registration opened, calling it a chance for the community to come together and celebrate the fishery that makes this stretch of the Keys worth living on. Proceeds from the tournament's silent auction benefit the Guides Trust Foundation, which has quietly helped Lower Keys guides sidelined by illness or injury cover their bills while they recover. That's not tourism marketing. That's neighbors funding a safety net for other neighbors, and it happens to unfold on lawn space attached to a listing with a nine-figure asking price.
The other constant, four miles down the road
Mangrove Mama's, the seafood spot at mile marker 20 that's been serving the Lower Keys for more than 40 years, went through its own ownership change in recent years. New owners Annie van Eller, Jeff Gagnon and Beth Connor took over with an explicit goal of winning locals back after a stretch where, in their own words, the neighborhood crowd had drifted away. Their approach has been to rebuild slowly rather than overhaul everything at once, keeping the pontoon-boat stage for live music and the outdoor tiki bar while working the menu back toward the dishes regulars actually ask for.
It's a smaller story than a $45 million listing, but it points at the same underlying pattern. The businesses that define daily life on Sugarloaf Key, whether that's a restaurant, a marina, or a fishing tournament, tend to change hands quietly and keep running much the same as before. Mangrove Mama's didn't close. It reopened under new ownership and kept the pontoon boat.
Not everything gets that second act. Perky's Bat Tower, the 1929 roadside oddity built by developer Richter Clyde Perky to lure mosquito-eating bats to his failed fishing resort, stood behind the Lodge property for nearly 90 years before Hurricane Irma toppled it in September 2017. It was never rebuilt. The bats, famously, never moved in either. Nearly a decade later, the empty lot where it stood is just part of the drive now, a landmark residents describe from memory more than from a current visit.
What actually changes this fall, and what doesn't
Nothing about the Showdown's schedule depends on who owns the Lodge on November 14. Registration windows, entry fees, and the fishing rules are all set by the Lower Keys Guides Association, not by the property's owner. Here's what residents can expect this fall regardless of the listing's status:
- Early registration for LKGA members ran August 1 through August 14
- General public registration opens August 15, if space remains, at $350 per boat
- Fishing runs Friday through Saturday, November 13 and 14, with Thursday reserved for check-in and the captains' meeting
- The awards banquet closes out the weekend on the Lodge's grassy point, per the tournament's own schedule
What's less certain is what that grassy point looks like next year, or the year after. A sale of this size, with entitlements this rare attached, tends to move slowly in the Keys. Permitting, environmental review and the practical difficulty of redeveloping waterfront property in a county that guards its growth carefully all argue against a fast turnaround. But a listing at $45 million with 24 vested hotel rights is not a listing meant to sit quietly. Someone is going to look hard at what those extra 24 rooms could become.
For residents, that's less a reason to worry about November and more a reason to pay attention to what comes after. The Showdown will happen this year the way it always has. The bat tower's absence is a small, permanent reminder that not every piece of this island's character survives every decade intact.
If you're a Sugarloaf Key homeowner curious what a listing like this could mean for property values along the corridor, or you're weighing whether now's the time to sell a home near a stretch of highway that's clearly attracting serious capital, the Karen Haack Team has spent decades reading exactly these signals in the Lower Keys. Talk to a Lower Keys real estate expert today.
