- March 18, 2026
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The Windermere Town Council voted down two offers to resolve the town’s ongoing litigation against the five titled owners of the centuries-old Third Avenue boathouses at its meeting Tuesday, March 10.
The vote came after Windermere Town Council and the residents participated in virtual mediation Wednesday, Feb. 25, before mediator and retired Circuit Judge Frederick J. Lauten.
Rachael Crews, the appellate counsel of record for the matter, presented the Town Council with the boathouse residents’ offer that asks the town to pay $500,000 to cover their fees and costs, drop the town’s appeal of the November 2025 final judgement and execute a release that makes it clear that the town will not contest the ownership of the boathouses and the underlying land on which they sit.
The town decided in December 2025 to appeal the decision to the Sixth District Court of Appeal following Ninth Circuit Court Judge John E. Jordan signing an order in October 2025 in favor of the five titled owners of the boathouses.
The appeal status is ongoing since its deadline was put on hold during the mediation process, Crews said.
Before a vote on the residents’ offer, Crews presented the counteroffer that Town Manager Robert Smith authorized.
Windermere’s counteroffer included legally determining and clarifying the ownership of the boathouses and the associated land on which the boathouses sit, recommending the town pay the residents $105,000 instead of $500,000 and offer the residents a 99-year lease with auto-renewal, which is “effectively permanent ownership,” Crews said.
Crews said one of the biggest issues with the underlying November 2025 trial court order is that it left ownership completely open: It stated the town did not sufficiently prove ownership for lease and eviction purposes and also left open who owns any portion of the lagoon.
“(With the town’s offer) both parties would walk away with legal papers where they could say ‘This is what we own and this is what you own,’” Crews said. “Under our proposal, the boathouse residents would have the boathouses in that footprint, and the town would clearly own the rest of the lagoon and the road right of ways.”
Crews said the reason for explicitly stating the town owns the roads is because of “problematic language” in the order suggesting the town never accepted the plat of Windermere, which, if true, then theoretically the town has no ownership of any of its roads or right of way.
“It’s just sloppy language,” Crews said. “I believe in the court orders that needs to be cleared up in terms of overall ownership interest.”
Included in the counteroffer also was a recommendation for Town Council to add a limitation to what could be done in the lagoon area, to coincide with the town’s efforts in keeping the historic area pristine.
“We want it to be a natural area, we don’t want to see a big monstrosity erected, or these historic boathouses torn down and something huge built,” Crews said. “We want to keep the area as it is.”
Council member Tom Stroup said he agreed with the town’s counteroffer of a 99-year lease with auto-renewal but believed the $105,000 to cover fees and costs was not a reasonable amount. Crews said the residents did not provide an official number but indicated their current legal costs are around $800,000.
The Town Council rejected the residents’ offer 4-1, with Stroup dissenting.
In the middle of the second motion to vote on approval of the town’s counteroffer, one of the boathouse owners, Jerry Fay, gave his opinion on it.
“You keep talking about a 99-year lease; you don’t own anything to lease to us,” Fay said. “You have not proven a thing that you own any of this lagoon or property or right of way or anything that you’re supposed to lease to us for 99 years. We’d be fools to take something like that.”
Town Council voted 2-3, with council members Stroup, Brandi Haines and Mandy David dissenting, failing to approve the town’s counteroffer to the boathouse residents.
With neither offer approved, the Town Council moved to schedule a shade meeting to discuss the town’s options.
The long-proposed restroom facility to be built near town hall and Windermere Library is moving forward as the Town Council unanimously approved the fourth concept iteration but not without some extra questions about measurements.
The restroom facility concept includes one additional urinal in the men’s restroom and one additional toilet stall in the women’s restroom compared to previous designs. In total, there will be four fixtures in each of the men’s and women’s restrooms. The facility also plans to include a separate family restroom with one toilet.
Haines expressed concern about the concept, though, noting that the measurements didn’t add up to her.
“The site plan that’s included in the agenda packet says 619 square feet, and that’s actually also written on the drawing for the newest option four, but when I calculated it, I’m coming up with 730 square feet,” Haines said.
Haines said the concern and reason for asking was that once the square footage returns to the 700s, it will be similar to the first concept the Town Council reviewed. She added that the bigger the concept gets, the more likely it is to harm the two historic oak trees in the construction area.
John Fitzgibbon, town consultant and civil engineer, stated the construction process is in its early stages.
“We’re at schematic level,” Fitzgibbon said. “We’re trying to figure program out, we’re trying to figure out the layout here. So I think it’s important for you guys tonight to vote on concept, and let us do our thing, and we’ll come back with a solid plan.”
Plans for the restrooms will be brought before council at 40%, 60% and 90% project completion for feedback from Town Council.
The Town Council unanimously approved phases 2 and 3 of the Windermere Town Hall rehabilitation project, which includes interior reconfiguration, accessibility improvements and proposed porch and roof modifications.
The project did not require formal review by the State Historic Preservation Office, but the town coordinated with the office to ensure the rehabilitation is sensitive to the building’s historic character.
The effort is expected to take approximately 133 hours and is projected to cost between $15,930 to $19,980.
Before moving to new business, the Town Council shook up its seating chart.
Longtime Windermere Mayor Jim O’Brien swore former Town Council Member Andy Williams into the position. Williams is the fifth generation of his family to live in Windermere and has served on Town Council since March 2018.
After taking the oath of office, Williams presented O’Brien with a key to the town, commemorating his 16 years of service to Windermere. O’Brien served as a Town Council member from 2011 to 2019 and mayor from 2019 to 2026.
“It’s fitting that finally I get the key, and we’ve changed to swipe cards,” O’Brien joked. “I just want to say what a privilege it’s been to serve each and every one of you. I want to thank my family for all the time they’ve allowed me to do this and staff for helping us all along the way. You can see that these things are not always easy, a lot of times they’re fun and easy, but a lot of times they’re not. Another thing I want to say to each and every one of you is I know that our town is in fantastic shape leadership-wise. I have full confidence in each and every one of you, and I look forward to all of your success, which is our success.”
The town plans to hold a celebration for O’Brien at town hall Friday, March 27.
Williams follows in the footsteps of his grandfather and namesake, Loren Robertson “Andy” Williams, who was a former mayor of Windermere.
Replacing Williams on the Town Council is CT Allen, a longtime resident of Windermere. She was a part of the group of seven Windermere Elementary School parents that created the Mustang Education Fund and started Windermere Wine & Dine as a fundraiser.
Town Council member Haines was sworn into her second term after she was first selected for the position in October 2023, filling the seat after the resignation of Molly Rose. Haines was reelected after she ran unopposed in March 2024.
