GE Go EleutheraThe island, end to end
Three hundred and seventy-eight years

They wrote the constitution first, then went looking for the island.

This island is named after the Greek word for free, and it was named that before anybody landed on it. That is not a marketing line — it is the oldest fact about the place, and it explains most of the others.

1647

The Articles and Orders

A group of Puritans in Bermuda, in trouble for refusing to swear allegiance to the Crown, drafted a founding document before they sailed anywhere. It divided land communally, elected its officers, and provided for mutual aid. They called themselves the Company of Eleutheran Adventurers, from the Greek eleutheros — free.

Which meansIt is one of the earliest written constitutions in the Americas, and it was written a hundred and forty years before the one in Philadelphia. They wrote the rules first and went looking for the island second.

1648

Wrecked on the Devil's Backbone

The crossing ended on the reef off the north end — the shoal still called the Devil's Backbone. They lost the ship and most of the supplies. The survivors sheltered in a limestone cave and held services in it through the first winter.

Which meansThat cave is Preacher's Cave, and you can walk into it today, five minutes off the road in North Eleuthera. It is the founding site of the Bahamas and there is no ticket office.

1649

Corn from Massachusetts

Starving, they sent word north. The Massachusetts Bay Colony shipped provisions. The Adventurers repaid it in braziletto wood, and the proceeds of that cargo went to a small college in Cambridge.

Which meansThe money helped fund Harvard in its earliest years. A shipwrecked colony on a Bahamian reef paid its debt in timber, and the timber paid a college bill.

1845

Four hundred thousand pineapples

The soil and the rainfall here suited pineapples better than almost anywhere. In 1845 the island exported 400,000 of them to England and America.

Which meansNot a cottage industry — an export economy built on one fruit, from an island a mile wide.

1885

Over a million

By 1885 Bahamian exports had passed a million pineapples a year, and Gregory Town was the centre of it. Eleuthera stock is credited with helping start the Hawaiian pineapple industry.

Which meansThen Hawaii and canning took the market, and the island's economy fell out from under it. The Pineapple Festival in Gregory Town every June is not a themed event — it is the anniversary of what this place used to be.

1950s

Pan Am, and the Cotton Bay Club

Juan Trippe, who founded Pan American World Airways, built a club at Cotton Bay in the south. Aviation money arrived, and with it the first version of Eleuthera as a place wealthy Americans flew to rather than shipped fruit from.

Which meansThe club is long closed and the beach in front of it is one of the emptiest on the island. Cotton Bay Beach on the front page is that beach.

1960s–70s

Windermere, and the quiet years

Windermere Island became the discreet end of the market — Prince Charles and Princess Diana holidayed there, and the island's whole proposition was that nobody would bother you.

Which meansThat is still the proposition, and it is why the most valuable things here have never been on a website. The private-client route on this site exists because of it.

What the history explains about the property

Nothing here is arranged by accident. Where the settlements sit, what the houses look like, and why the law reads the way it does — all of it comes straight out of the three centuries above.

Why the settlements sit where they doEvery old settlement is on the bank side, not the Atlantic. Three hundred years of boats meant you built where you could land one — and the bank side is the lee. The Atlantic coast has the spectacular beaches and almost none of the villages.
Why Governor's Harbour looks colonialHillside houses, white picket fences and a pink library. It was the island's administrative centre when the pineapple money was moving, and the buildings are what that money built. The Haynes Library still stands and still lends books.
Why Harbour Island is differentDunmore Town was a genuine loyalist town with real streets and clapboard houses before it was anything else. It is not a resort that grew a village; it is a village that a resort economy arrived in. That is why it does not feel invented, and it is most of why it costs what it costs.
Why there is a two-acre ruleA country that was colonised, farmed out and then bought up in pieces writes its property law carefully. A non-Bahamian buying more than two acres needs government approval. It is not obstruction — it is a small country keeping hold of itself, and it is worth understanding before you make an offer.

Sourced and checked 2026-09-10. Dates are as recorded, not rounded for effect.