Light Up Windermere Made It Through the Budget Cuts. Volunteers Are Doing Most of the Work.

Last holiday season, the Town of Windermere paid Humbug Holiday Lights $35,955.27 to bring in lights, put them up, take them down and maintain them. This year the Town Council has approved up to $25,000. Humbug's quote at roughly that price, $24,997, covers a smaller display around Town Square.

Light Up Windermere is still set for Friday, Nov. 20. It almost didn't make the budget. It got back in because a church and a performing arts academy already provide most of the evening for free, and the same is true of nearly every event between now and Thanksgiving. The events that held on are mostly the ones a church, a civic club or a volunteer group already runs at no cost to the town. The events that needed town money and town staff are the ones that got cut back.

How Light Up Windermere got back into the budget

The West Orange Times & Observer reported that at a July 28 budget workshop, staff proposed eliminating or suspending two town-sponsored events, Light Up Windermere and Food Truck Nights. The cuts were meant to prepare the town in case Amendment 3, the property tax measure on the November ballot, passes.

At the first budget hearing on Sept. 3, Council Member Tom Stroup argued to put the holiday event back in. The Observer quoted him:

"The community involvement and the community events are important to our community, and I think in this case, we need to do all we can within the budget to continue to maintain those events, especially some of the more historic ones we've had (for) quite a while."

Town Manager Robert Smith's answer is what made it work. He said Family Church of Windermere usually runs the activities in front of Town Hall, and White Swan Academy performs indoors and outdoors, all at no charge. He said the town could absorb the cost of hosting the event within the current budget. Council Member CT Allen asked that Light Up Windermere get its own line item, so its fate would not be tied to Food Truck Nights. She also suggested food trucks could still come to the holiday evening even if the monthly series ended.

That left the lights, the one large cost the volunteers could not cover. The proposed FY2027 budget had dropped them entirely. On Sept. 8, council voted 4-1, with Council Member Brandi Haines voting no, to let staff spend up to $25,000. Public Works Director Tonya Elliott-Moore got Humbug's two quotes, about $35,000 for last year's display and $24,997 for the Town Square area only. A second company quoted $49,000 and was working on a smaller quote. Mayor Andy Williams said he has been talking with residents who are willing to help pay for the holiday festivities.

The town's Oct. 12 announcement promises food, live performances and holiday festivities, with more details to come.

Food Truck Nights needed the one thing volunteers can't supply

Food Truck Nights went the other way, and the reason is staff time. When council members asked about bringing the series back, Mayor Williams said they should first get "hard numbers" on the cost and on how much work it takes from town staff. The Observer quoted his conclusion: "the bottom line is, we still have to cut something else to bring it back."

The town's Food Truck Nights page now has a "suspended until further notice" banner. The events calendar lists the Oct. 23 Halloween Special at Town Square as canceled. Staff had proposed either suspending or eliminating the series, and for now the town lists it as suspended. Stroup asked council to discuss offering Food Truck Nights again at a future meeting. Haines said parents of school-age children had told her they don't care whether there is a band or DJ, because they simply want a community event to gather at. One resident suggested playing an approved playlist on a speaker instead.

The suspension also hits a town board. Smith said that before the Historic Preservation Board started getting money from Food Truck Nights proceeds, it had to raise its own funds. Haines objected that the Historic Preservation Board and the Windermere Tree Board were taking cuts while other line items were being added back. She said that if the town is cutting 10%, the cut should be 10% across the board.

The rest of the budget, line by line

Council unanimously adopted the FY2026-27 budget on Sept. 16, with an operating millage of 3.7425 and total spending of $12,464,394.17. Here are the smaller changes residents are likely to see around town.

Smith described the choices as "needs versus wants." Under the new budget, the town will maintain the sidewalks it already has and plan no extensions until it knows how Amendment 3 turns out. Signs that are falling down or don't meet standards will still be replaced, but no new signs will be added. About the smaller Arbor Day trees, he said, "it might not be what the residents want, but it's what we can afford at this time."

The Florida Division of Elections summary gives the background. The amendment would raise the homestead exemption for all non-school taxes to $150,000 in 2027 and $250,000 in 2028, then adjust it for inflation. It would lower the annual cap on assessment increases for non-homestead property from 10% to 5%, and it would require counties and cities to use property taxes for listed categories such as public safety, infrastructure and operations. Other spending could still be approved by county officers or local governing bodies unless general law prohibits it. If approved, it takes effect Jan. 1, 2027. The Orange County Supervisor of Elections lists the general election for Tuesday, Nov. 3, with polls open 7 a.m. to 7 p.m. Smith called the budget "a living and breathing thing" and said council could reconsider it in April.

Who is running each event from Halloween to Thanksgiving

The calendar from here to Thanksgiving is still full. Most of it is hosted by community groups, with the town providing the venue.

The bunk bed build is still taking volunteers, and it needs new twin-size bedding. You can drop bedding off in the Windermere PD lobby or at Flippers Pizza Co. on Old Brick Road, which the foundation thanked for partnering on the drive. Meals on Wheels will deliver the Smiles for Seniors bags, filled with essentials and holiday treats, in time for the holidays. Volunteers can sign up through the Rotary's community service contact. The next big fundraiser is the West Orange Foundation's Windermere Wine & Dine on Feb. 6, 2027, and ticket sales open Saturday, Oct. 24.

There is also a new business coming to Main Street. The Observer reported on Oct. 2 that renovations were nearly finished at 507 Main St. for Penelope's Coffee, which will serve coffee and baked goods and plans to open this fall. No opening day had been set.

On Dec. 1, the tennis pass doubles

The same approach shows up at the town courts. On Oct. 13, council unanimously approved raising the tennis pass from $25 to $50, effective Dec. 1. The boat ramp pass stays at $35, the Observer reported.

A staff cost analysis puts the tennis facilities at about $19,200 a year and the boat ramp facilities at $9,120 a year. There are 232 tennis passes and 158 boat ramp passes in use. To cover the full cost, the tennis pass would have to be about $82.78 and the boat ramp pass about $57.72. At $50, the tennis pass brings in about $11,600 in additional revenue and covers 60% of the cost, the same share the boat ramp pass already covers.

Dena O'Malley, who chairs the Windermere Parks and Recreation Committee, put the old fee in context. At $25, the pass works out to about $2 a month. A single one-hour court rental at a comparable Orange County facility costs $4 to $6. She said the committee relies on fundraising for court improvements, including the roughly $300,000 it will take to rebuild the Main Street courts. A recent resurfacing cost $27,385. The town has put tennis key and boat ramp pass renewals on hold until Dec. 1, so current pass holders keep access until then at no extra charge.

The figures in this post on town fees and the ballot measure are general information, not legal, tax or financial advice. Please check how they apply to you with the right professional.

If you want to talk about what Windermere's town budget and amenity fees mean for your own home plans, Mary Rossi would be glad to help. We'll take the time to go through the details with you, with no pressure. Get in Touch.