The Town of Windermere has spent $637,000 on its so-far-unsuccessful battle to gain control of five wooden boathouses on the shores of Lake Butler, a town leader disclosed Tuesday — and it intends to continue fighting, at least for now.
Town Council members met in an hour-long closed-door session Tuesday evening to discuss “settlement negotiations and strategy” in the long-running legal dispute, and is asking a judge to reconsider his scathing ruling in favor of private property owners who gained use of the aging boathouses when they bought their homes.
Outside the private session, a small group of Windermere residents, including some of the boathouse owners, gathered to show their opposition to prolonging the court fight with signs written in Halloween fonts and featuring cartoon bats, ghouls, skeletons and zombies.
One read, “THE TOWN DRAINED US TO THE BONE.” Another tagged the rift as “THE LAWSUIT THAT REFUSES TO DIE.”
Roger Heinz, a Windermere resident, said he didn’t object to the town’s original court challenge of boathouse ownership, an issue that was murky and seems to be rooted in misunderstanding, but now that a court has ruled against Windermere, “We have better things to spend public money on.”
The town’s legal bill to date is more than triple the $175,000 Windermere had budgeted in the last fiscal year for legal expenses.
Other critics of the town’s stance said they weren’t sure why the town even wants the old boathouses.
And when asked by the Orlando Sentinel, the town manager wouldn’t say.
Each boathouse has three sides and a roof.
They function like a carport for storage of personal watercraft. The structures’ true value is the access each provides to Lake Butler, a popular space for boating, fishing and other water recreation and the largest of 13 interconnected lakes in southwest Orange County.
Families hold signs in protest outside Windermere Town Hall on Tuesday, Oct. 28, 2025. A judge’s recent ruling sunk the Town of Windermere’s long-held claim to ownership of the five boathouses on the north side of Lake Butler, perhaps ending a costly, taxpayer-funded property-rights dispute that dates back more than four decades. But the town seems inclined to fight on. (Stephen M. Dowell/Orlando Sentinel)
All but one of the structures, which squat over water on wooden pilings, were built before the town was incorporated in 1925 and the town has never held title to any of them, though a former mayor and a descendant of a founding family, John Palmer Luff Sr., had once owned one, maybe two.
However, the town has been insisting the users pay rent, and for years they have obliged.
Council members made no mention of the town’s strategy or intentions at its regular session which followed Tuesday’s meeting with lawyers.
Town Manager Robert Smith said he could not discuss anything related to the boathouses as the matter was still in on-going litigation. He did reveal the cost of the litigation to date, which the Sentinel had first requested three weeks ago. The town pays attorneys from a prominent private firm, GrayRobinson, for legal representation.
Attorney Charles M. Greene, co-counsel with Daniel W. Langley for boathouse owners, urged Circuit Court Judge John Jordan in a filing earlier this month to enter a final judgment in the case, citing Jordan’s findings of facts and conclusions of law in written decisions.
Greene argued there are no issues to be tried.
Langley, an attorney with Fishback Dominick, told the Orlando Sentinel earlier this month he might seek attorneys’ fees from the town for his clients, some of whom said Tuesday they had spent in excess of $700,000 in the fight to keep their titles to their boathouses.
Judge’s ruling sinks Windermere’s claim to boathouses
But lawyers for the town contend they could prove the judge’s rulings “are erroneous on the merits” if a trial were held.
In their request for a rehearing, filed last week, the lawyers argued the judge’s legal conclusions were “based on disputed issues of fact, a fundamental fallacy, or reliance on a declaration filled with speculation and hearsay making it inapplicable and in violation of Florida law.”
They want the orders vacated and reconsidered.
A key issue is whether state authorities ever conclusively determined that the ordinary high water line of Lake Butler touches the Pine Street and Third Avenue rights-of-way, a required connection for the town to have “riparian rights” to restrict access to the boathouses.
The boathouses sit on a lagoon next to the lake, not the lakeshore itself.
The town’s lawyers insist the riparian rights issue remains undecided, though the judge concluded otherwise.
Although the dispute dates back to the 1980’s, Windermere formally sought to evict the owners from their boathouse properties in 2021.
shudak@orlandosentinel.com