Hunter S. Thompson spent enough time around Sugarloaf Lodge in the 1970s and 80s that John Good, whose parents ran the place, once described him as "kind of part of our family for a couple of years." Paul Newman used to sit at the bar and talk about Kenyon College. A dolphin named Dolly, who'd slipped away from a U.S. Navy program, took up residence in the bay behind the lodge long enough for Jacques Cousteau to study her before the Good family took the nets down and let her swim off for good. Her tankmate, Sugar, stuck around performing for guests until she died in 1997.
That history matters here because Sugarloaf Lodge & Marina, the low mid-century property at Mile Marker 17 where most of us have eaten at South of the Seven or watched a sunset from the tiki bar, went up for sale in January 2026 for $45 million. The listing is being handled by Lisa Swanson of The Agency Florida Keys, working alongside Jamie Bederak of The Agency Miami. If you've heard people at the marina talking about the number, the number isn't really the story. What's actually attached to that sale is more interesting, and it's the part you can't see from the highway.
What's Actually Listed on the Deed
The physical property is straightforward enough. The 10.6-acre site includes:
- 31 hotel rooms, still carrying much of their original mid-century modern decor
- A 5,300-square-foot restaurant space leased to South of the Seven
- A tiki bar and events venue overlooking Sugarloaf Sound
- Marinas, a pool, and tennis courts
- Office space leased to kayak and boat rental operators and a solar energy company
- An apartment unit
Run the math on the asking price against the existing 31 rooms and you land close to $1.45 million per hotel key, a steep number for a set of rooms built in the late 1950s and expanded in the 1960s. That price only makes sense once you understand what else comes bundled with the buildings.
The Right That Doesn't Show Up When You Drive By
Hurricane Wilma hit in 2005 and took out part of the original room count. The lodge never rebuilt those units, but the legal right to do so never went away. It's what's called a vested right, meaning it runs with the land rather than with any particular owner. Whoever eventually buys this property inherits the ability to construct 24 additional hotel rooms without having to win new development allocation from Monroe County, a process that's notoriously scarce and slow anywhere else in the Lower Keys.
That's the real asset here. A buyer isn't just purchasing 31 rooms, a restaurant lease, and a marina. They're purchasing a path to nearly double the room count to something close to 55, using an entitlement that's already sitting on the property from a storm two decades gone. For a stretch of shoreline where new hotel density is otherwise almost impossible to come by, that's worth more than the tennis courts.
Same Footprint, Different Rules
Here's where it gets complicated for anyone picturing what a rebuilt lodge might look like. The property can be redeveloped, but current construction regulations require larger setbacks from the bay than existed when the original buildings went up. That matters most for the restaurant, which today sits on stilts jutting out over the water. A full rebuild large enough to use those 24 banked rooms would likely need to sit further back from the shoreline than what's there now.
Height is the other constraint. Monroe County currently caps building height at 38 feet, though county officials have been weighing a change that would raise the limit to 42 feet for residential construction. Neither number allows for anything resembling a high-rise, but the four-foot difference matters when a builder is trying to fit more rooms onto a footprint that's being pushed back from the water at the same time.
Put together, any version of this property that actually uses its full development rights would look different from what's there today. Lower, set back, and built to a different waterline than the one South of the Seven currently overlooks.
A Fourth Owner Isn't a Crisis
Lloyd and Miriam Good bought Sugarloaf Lodge in 1973 and moved down to run it with their four children. That's 53 years of one family's name attached to the property, which is unusual for a commercial resort anywhere in the Keys. Today the entity behind the sale is Miriam BG, led by John Good and Caren Ward, the Goods' children, along with nieces Jessica Duncan Wex and Katchen Elizabeth Duncan.
A sale after more than five decades under one family reads as a planned exit, not a distress signal. Properties like this can sit on the market for a long stretch before a deal closes, and even after a sale, permitting and construction on something this size takes years. Nothing about South of the Seven's dinner service or the tiki bar's sunset crowd changes because a listing went live.
Not the Only Legacy Name on the Market This Year
Sugarloaf Lodge isn't operating in isolation. In April 2026, Islamorada's Cheeca Lodge & Spa, a 27-acre resort with a history tied to President George H.W. Bush's annual bonefish tournament, hit the market for an asking price of $300 million. Different scale, different ownership structure, but the same underlying pattern: a long-held, storied Keys hospitality property testing what buyers will pay in a year when luxury lodging performance has been strong across the country.
Two legacy properties surfacing within a few months of each other says something about timing more than it says anything specific about either deal. Owners of properties like these tend to watch each other's moves closely, and a strong asking price on one can pull another off the sidelines. Whether that turns into two closed transactions or two long listings is impossible to know yet, but for anyone who's spent years driving past Sugarloaf Lodge on the way into Key West, it's worth knowing this stretch of Overseas Highway is part of a bigger moment for old Keys resort names, not an isolated local story.
For now, the lodge keeps running the way it always has. The rooms still carry their original character, the marina still rents kayaks, and the tiki bar still fills up around sunset. What changes, if anything does, will take years to show up in the skyline at Mile Marker 17. But the next time someone mentions the sale at the bait shop, you'll know the number that matters isn't $45 million. It's 24.
If you're curious how a sale like this could eventually ripple into property values or the character of Sugarloaf Sound, or you just want to talk through what you've heard around the island, Anneliese Dietrick is always happy to talk it over. Let's Connect.
