In 1981, Charles and Diana chose a six-mile sliver of sand off the coast of Eleuthera for their honeymoon, a place reachable only by a single guarded bridge and populated almost entirely by people who already knew each other. A year later, back on the island while she was pregnant with Prince William, a photographer with a telephoto lens found her in a swimsuit on the west beach, and the image went around the world. It embarrassed a clubhouse that had spent more than a decade cultivating exactly the kind of privacy paparazzi don't respect.
Windermere Island has been managing that same tension between seclusion and access ever since, and today the ambiguity has moved from tabloids to title searches. Pull five listings on the island and you'll get five different stories about what the price actually buys. A one-bedroom apartment can list in the low six figures. A vacant beachfront lot a few hundred yards away can ask well over four million dollars for the right to build. The spread isn't really about square footage or view. It comes down to a detail that rarely makes it onto a spec sheet: on Windermere, the deed and the clubhouse membership are two separate transactions, and only one of them is guaranteed to come with the sale.
Two Gates, Not One
Windermere is governed by two distinct bodies, and conflating them is where most buyer confusion starts.
The first is the Windermere Island Owners Association, and every owner belongs to it automatically the moment they close. Dues fund the things nobody wants to think about but everyone relies on: the bridge, the roads, and the round-the-clock security that keeps the island a private enclave rather than a public thoroughfare. That bridge has real history behind it. Lord Trefgarne, the island's former owner, built it in 1960, and it's recognized as the first sea bridge constructed anywhere in the Bahamas. It's still the only way onto the island by car, and it's still manned.
The second body is the Club at Windermere, and this is where the automatic part ends. Membership is a separate arrangement, tied to individual owners rather than bundled into the deed. According to the club's own governing association, it exists for members who want dining, a pool, tennis courts, and a gym, available seasonally rather than year round. A pattern that has held for years has the dining room open from mid-November through mid-May, with the pool and courts running longer, though anyone evaluating a purchase should confirm current-season hours directly with the club rather than trust older listing copy. If you're renting a property before you buy, ask whether that specific owner is a paying Club member. Long-running guidance from residents on Windermere is blunt about this: guests are only permitted to use Club facilities if the property's owner belongs, and not every owner does.
A Club That Already Closed Once
The reason two separate systems exist traces back to a single failure.
The original Windermere Island Club opened in 1968, founded by Bahamian real estate figure Sir Harold G. Christie in partnership with businessman Harold Ley Jr. It launched with twelve private villas, ten apartments, and ten suites, and it built its reputation fast, drawing Jacques Cousteau's endorsement of the surrounding reef and a steady flow of the kind of guests who don't need their names in the paper. Christie, who reportedly scouted the island's best plots from a helicopter, once put it simply:
"I just love looking at land."
The club didn't survive the decade that followed the honeymoon photographs. Accounts differ slightly on the exact year, but they agree on the shape of the story: sometime in the early-to-mid 1990s, after outside management took over and the crowd that once justified twelve villas thinned out, the original clubhouse closed. Rather than wait for someone to revive it, Windermere's homeowners built their own. The Club at Windermere, established in 1997, is the version operating today, and it sits at the island's highest point rather than on the original site.
One more wrinkle worth flagging before you go searching online: a separate 52-lot residential subdivision project has also marketed itself under the name "Windermere Island Club," distinct from the membership club described above and distinct from the original 1968 hotel. If you're researching the island and land on materials describing a large new-construction lot program, you're likely looking at that development rather than the social club residents actually run. Confirming which entity a source is describing before you draw conclusions from it will save you a confused phone call later.
What the Spread on Paper Actually Reflects
Once the two-gate structure is on the table, the pricing on Windermere starts to make more sense.
Current listings span roughly $140,000 for a one-bedroom apartment to just under $12 million for a beachfront estate, with vacant lots priced anywhere from the high five figures to more than $4 million depending on frontage and elevation. Some of that gap is ordinary real estate variance. Beachfront versus interior, renovated versus original, two acres versus a quarter acre. But a meaningful part of it is invisible on paper: whether the specific unit carries active Club membership, whether Owners Association dues are current and what they cover beyond the basics, and whether the property sits near the newer 52-lot development or among the older, long-held family estates near the original clubhouse site.
None of this shows up as a line item in most listing sheets, which is exactly why it catches buyers off guard. Two nearly identical homes on the same stretch of beach can offer completely different day-to-day experiences depending on who held the Club membership and whether it transfers.
Before You Write an Offer
A short list worth working through with a broker who has actually called both organizations, not just read their websites:
- Does the current owner hold active Club at Windermere membership, and does it transfer with the sale or require a new application and fee?
- Are Owners Association dues current, and do they cover only the bridge, roads, and security, or additional items specific to that property's section of the island?
- If you plan to rent the property short term before committing, has the specific unit's owner confirmed Club access for your stay, in writing?
- Is the listing you're reviewing describing the membership club, or the separate 52-lot development that shares a similar name?
Long-Held, Rarely Listed
The island's other defining feature, the fact that families tend to hold Windermere property for generations rather than flip it, is a direct byproduct of everything above. When so few owners cycle through, few people have ever had to work out what the deed does and doesn't include. That's part of the charm for the people already there. For a buyer coming in from outside, it means the due diligence looks less like a standard closing checklist and more like two phone calls: one to the Owners Association, one to the Club.
Windermere sits within the broader stretch of Eleuthera and Harbour Island that continues to draw buyers looking for the kind of privacy a bridge and a gatekeeper can still provide, and it shares more in common with the brand's private island inventory than with a typical gated subdivision. The infrastructure questions are similar. Who controls access. What's mandatory. What's optional and priced separately.
Getting a straight answer on both, before an offer goes in rather than after, is the kind of groundwork The Agency Bahamas does as a matter of course, not an afterthought. If Windermere is on your list, contact the team now and we'll walk the two-gate structure with you line by line before you're deciding between a $140,000 apartment and a $4 million lot without knowing what either one actually includes.
FAQ
Is the Club at Windermere currently open? Yes, but seasonally. The dining room has historically run mid-November through mid-May, with the pool and tennis courts available longer. Confirm current-season hours directly with the club rather than relying on older listing descriptions.
Does every home on Windermere Island include Club membership automatically? No. The Windermere Island Owners Association is automatic for every owner and covers the bridge, roads, and security. Club at Windermere membership is a separate arrangement tied to the individual owner, not the title, so ask directly and get confirmation in writing before assuming pool, tennis, dining, and gym access come with the sale.
