On a peninsula that pushes out into a chain of lakes just west of Orlando, behind a wall and a guard gate that turn most visitors around, sit some of the most expensive houses in Florida. Tiger Woods lived here through his best years. Shaquille O’Neal still does, in a place with a much-photographed bright blue roof. You can’t really see any of it from the road, and that is entirely the point.
What you’d never guess from the gate is that this ground was once named for an orange tree’s stubbornness.
A little over a century ago, two brothers from Philadelphia — Joshua and Sydney Chase — ran citrus across Central Florida, and one grove on the Butler Chain of Lakes they called the Isle of Worth. The name was really a bet. Their trees out here, ringed by water, seemed to shrug off the cold snaps that scorched groves a few miles inland — and in the Florida citrus business, surviving the cold was the entire game. A patch of ground where the fruit lived through a freeze was, quite literally, worth having.
Why an island, of all places
The lakes were the whole reason. Water holds the day’s heat and gives it back slowly after dark, so on a cold night the air over a lake stays a few degrees warmer than the air over dry land. A grove wrapped on three sides by the Butler Chain froze last, if it froze at all. The Chases built Chase & Company in 1884, and by 1886 they had assembled this one into a single large operation — a business betting that geography could beat the weather.
For a while, the bet paid. The grove shipped fruit north, the brothers’ company grew into one of the bigger names in Central Florida citrus, and the men who worked the rows had steady reason to believe the Isle of Worth was exactly what its name claimed.
The winter the bet broke
Then came the winter of 1894. On December 28, Orlando dropped to 18 degrees — a record that still stands — and groves all over the center of the state went black overnight.
What finished the industry wasn’t that one night. A warm January coaxed the surviving trees back into fresh growth, soft and vulnerable — and then a second freeze in February killed the wood itself. The state’s crop fell from more than five million boxes to about seventy-five thousand the following season. Growers who thought they were safe were ruined.
Even the Isle of Worth went down. Water buys you a few degrees, not a miracle.
The grove sat dead for years. Chase & Company didn’t grow citrus here again until 1904, when Joshua came back from a long stretch in California and started over — replanting the rows the cold had taken, and trying to defend them better this time.
Burning fire against the cold
Resilience, in a grove, was something you bought by the hour. Crews tented and fumigated the trees against pests; and on the nights the thermometer fell, they fought the cold the only way anyone knew how — with fire.
On a hard night a grove would be dotted with smudge pots — squat oil heaters burning diesel, hundreds of them, throwing just enough warmth and smoke to hold the frost off the fruit until morning. It was filthy, expensive work, and it was the difference between a crop and nothing. The lesson of 1894 had sunk in: out here, the land alone wouldn’t save you. You had to be able to make your own heat when the cold came, and you had to be able to afford it.
It worked. The replanted Isle of Worth ran as a serious citrus operation for the better part of eighty years.
The sale that changed everything
The grove stayed in the family until 1984, when Franklin Chase — Sydney’s son — sold the Isle of Worth to a golfer named Arnold Palmer.
Palmer and the architect Ed Seay laid a championship golf course over the old citrus rows; it opened in 1986. In 1993 the Tavistock Group bought the course and the land around it and began building the mansions. The citrus name stuck — the Isle of Worth became, on the gate, simply Isleworth — and the peninsula that had once grown oranges became a roughly six-hundred-acre guarded enclave on the water, home to Tiger Woods, Shaquille O’Neal, Ken Griffey Jr. and Mark O’Meara.
It stayed mostly invisible to the outside world until one night it wasn’t. At about 2:25 in the morning on November 27, 2009, Tiger Woods pulled out of his Isleworth driveway, clipped a fire hydrant and ran his SUV into a neighbor’s tree; his wife knocked out the back window with a golf club to get him out. For a few weeks, the whole country was looking at a gate that had been built so no one could.
The new thing the cold became
The threat to a place like this isn’t frost anymore. Central Florida barely grows citrus now; the groves moved south generations ago, chased by exactly the kind of freeze that took the Isle of Worth. What takes the lights out today is the hurricane.
The region runs on an overhead grid strung through one of the densest tree canopies in the state, and every big storm settles it the same way — limbs into the lines, and hundreds of thousands of people in the dark for days. Charley came straight up through the middle of the state in 2004. Irma tore down lines and trees around Windermere in 2017. Milton blew transformers across the area in 2024.
Behind the Isleworth wall, resilience is handled the way everything else is: privately, and well. Service runs underground where it can, and a standby generator — the kind that senses the outage and starts itself — is common enough that the community has rules about where you’re allowed to put one. It is, almost exactly, the smudge pot’s descendant: your own machine, your own fuel, making your own power when the world outside goes cold and dark.
The name was always a bet — that the right spot and enough money could out-engineer the weather. For the Chase brothers the weather was frost, and in 1894 it won a round. For the people behind the gate now it’s the storm and the long outage after it, and the instinct hasn’t changed at all since the nights the grovemen stood in the rows lighting fires: when the cold comes for the lights, you keep your own burning. On the Isle of Worth it just hums behind a wall now, and nobody has to strike a match.
