Pull up two listing sheets from inside the same locked gate on Upper Matecumbe Key and you will find two different products wearing the same address. One shows a 3,609-square-foot home with a loft and a top-floor view, priced this fall at just under $3 million. The other shows a smaller, older home reduced by $80,000 to land near $1.96 million. Same community. Same monthly manager knocking on the same 31 doors. Very different deeds.
Most Pen Key Club marketing describes the community the same way: a gated, bayfront enclave near Mile Marker 83, built in a Key West architectural style with a protected boat basin, a resort-style pool, and a full-time property manager who lives on site and handles security and grounds for the whole 31-home footprint. All of that is true. What it leaves out is that "bayfront" does not mean what a buyer might assume it means once you get past the gate.
Thirty-One Homes, One Fee, Two Kinds of Water Rights
According to a recent MLS listing for one of the community's homes, Pen Key Club contains 31 properties total, and only seven of them sit directly on the open bay with their own private dock. The listing sheet for that particular parcel spells it out plainly: it is one of only seven homes in the community with direct bay frontage, carrying roughly half an acre of upland and another half acre of bay bottom that comes with the deed.
The other 24 homes are not on the water at all in the way the marketing implies. A separate current listing inside Pen Key Club lists its own waterfront description as simply "None." Its dockage field does not say private dock. It says "Assigned Dock, Dock Privileges," meaning the home's boat access runs through the shared, protected basin rather than through a private slip attached to the lot. That home still carries a $6,500 annual HOA fee, the same figure that funds the basin, the pool, and the live-in manager for every home in the community, bay lot or not.
This is the split that actually explains what a Pen Key Club price tag is buying. It is not primarily square footage. It is not primarily the build year. It is whether your particular lot is one of the seven that come with bay bottom attached, or one of the 24 that come with a line item reading "dock privileges" instead.
The Fee Doesn't Know the Difference
Here is the part that catches buyers off guard during due diligence. The $6,500-a-year HOA fee is flat across the community. It does not scale up for the seven bay-lot owners who get a private dock, and it does not scale down for the 24 interior-lot owners who share the basin. Everyone is funding the same live-in manager, the same shared pool, the same protected basin maintenance, regardless of what kind of water access their specific parcel carries.
That means the fee tells you almost nothing about what you are actually getting. Two owners can write identical HOA checks every year while one owns bay bottom and a private dock and the other owns a spot in a shared basin queue. The dues buy the community. They do not buy the water.
What the Price Gap Actually Tracks
Run the numbers on the two listings mentioned earlier and the puzzle gets sharper before it gets clearer. The larger home, at 3,609 square feet and just under $3 million, works out to roughly $830 per square foot. The smaller home, at 1,682 square feet and near $1.96 million, works out to more than $1,160 per square foot. That is not a small gap. A dramatically smaller, older home is commanding a steep premium per square foot over a much larger, newer-feeling one.
Square footage alone does not explain that inversion. Neither does age by itself. What the MLS record for that larger home does confirm is its dockage type: "Community Dockage," meaning it too draws on the shared basin rather than a private slip, despite its size and price tag. That single field is more informative than either the square footage or the asking price. It tells you the home is competing on layout, updates, and floor plan, not on being one of the seven true bay parcels.
The practical lesson for anyone comparing Pen Key Club listings is to stop asking what a home costs per square foot and start asking what the "Waterfront Description" and "Dockage" fields on the listing sheet actually say. Those two fields, more than bedroom count or year built, are doing the real work of separating one Pen Key Club home from another.
Here is the distinction as it shows up on paper:
| The Seven Bay Lots | The Other 24 Lots | |
|---|---|---|
| Waterfront description | Direct open bay | Typically listed as "None" |
| Dockage | Private dock, roughly half an acre of bay bottom included | Assigned dock or dock privileges in the shared basin |
| HOA fee | $6,500 per year | $6,500 per year |
| Shared amenities | Pool, basin, live-in manager | Pool, basin, live-in manager |
Every owner buys the same gate, the same manager, and the same maintained basin. Only seven of them buy the bay itself.
A Word for the Boater in the Buying Decision
Islamorada is a boating market first, and Pen Key Club's shared basin has its own practical detail worth knowing before you fall for a listing photo. At least one recent listing inside the community lists a control depth of five feet in the basin and flags the property's flood zone as AE, which is standard for this stretch of Upper Matecumbe Key but still worth confirming lot by lot rather than assuming it applies uniformly. If your boat draws more than that, or if your plan depends on a private slip rather than a shared assignment, the dockage field on the listing sheet matters more than almost anything else on the page.
Before You Write an Offer at Pen Key Club
If a Pen Key Club listing has caught your attention, a few questions are worth asking before the number on the sign becomes the number on a contract:
- Does the listing sheet say "Waterfront Description: Bay" or does it say "None"? That single field tells you whether you are looking at one of the seven true bay parcels or one of the 24 basin-access homes.
- Is the dockage field a private dock or "Assigned Dock, Dock Privileges"? The wording is doing real legal work, not just descriptive work.
- What is the current control depth in the basin, and does it fit the boat you actually own or plan to own?
- Has the HOA fee changed recently, and does it cover basin dredging or maintenance separately from the flat annual charge?
None of these questions show up in a scenic photo of the pool or the sunset from the dock. They show up in the listing sheet's fine print and in the deed itself.
Common Questions About Pen Key Club
How many homes in Pen Key Club actually touch the open bay? Seven of the community's 31 homes carry direct bay frontage and private dockage. The remaining 24 rely on assigned access to the shared, protected boat basin.
Does every home pay the same HOA fee regardless of water access? Yes. The community's flat $6,500 annual fee funds the same shared amenities, live-in manager, and basin maintenance for every owner, whether their lot includes bay bottom or not.
Is a larger or newer Pen Key Club home automatically on the bay? Not necessarily. One of the largest and highest-priced homes currently on the market inside the community lists its dockage as community access rather than a private dock, which shows that size and finish level do not guarantee bay frontage.
What is the fastest way to confirm which type of lot a specific Pen Key Club listing is? Check the "Waterfront Description" and "Dockage" fields on the MLS sheet directly, rather than relying on marketing language that describes the whole community as bayfront.
Pen Key Club rewards the kind of buyer who reads past the first paragraph of a listing, and that is exactly the kind of scrutiny a purchase this size deserves. Sabrina Wampler and Sarah Ewald spend their days inside these listing sheets and these deeds, translating dockage fields and bay-bottom acreage into plain answers before an offer ever gets written. If you are comparing homes inside this gate, or anywhere else along Islamorada's waterfront, The Florida Keys Sold Sisters can walk you through what a specific parcel actually buys. Start Your Island Home Search. Schedule a personal consultation today.
