How much does it cost to light up Windermere's Town Square for the holidays? Last year the answer was $35,955.27. That paid Humbug Holiday Lights to wrap 25 trees from trunk to branch tips and to light 59 light posts across downtown. This year Town Council capped the spending at $25,000. The quote that fit under that cap covered a smaller area around Town Square.
The events that made it onto Windermere's holiday calendar this year are mostly the ones other people help pay for.
Friday Night at Town Square
Light Up Windermere is Friday, November 20, at Town Square Park and Town Hall, 520 Main Street. The Town's events calendar lists it as "Food Truck Night WPD Foundation: Light Up Windermere!" That name tells you who is involved. Here is how the evening runs:
- 5:30 p.m. Gates open, with food trucks, holiday choirs, dancers and live entertainment
- 7:00 p.m. Lights on across Town Square Park
- 9:30 p.m. Event wraps
- Cost: Free
Earlier that day, the Friday Farmers Market runs from 9 a.m. to 1:30 p.m. in the same park, so Town Square is busy from morning through the evening.
Family Church of Windermere has traditionally run the activities in front of Town Hall. White Swan Academy has traditionally performed indoors and outdoors. Town Manager Robert Smith told council that both groups have done this for free, according to the Orange Observer. That volunteer work is the main reason the event survived this summer.
The July Budget Cut Light Up First
At a budget workshop on Tuesday, July 28, Smith gave council a list of possible cuts to prepare for Amendment 3. Amendment 3 was the statewide homestead exemption expansion on the November ballot. Light Up Windermere and the monthly Food Truck Nights were the two town-sponsored events proposed for elimination or suspension. The town decorations budget would drop from $35,000 to $15,000, and signage from $44,000 to $5,000.
Smith explained his reasoning to council, as the Orange Observer reported in August: "Quality of life would be having those community events, having lights, Halloween stuff, nice banners. The levels of service would be making sure our roads are in proper condition, making sure the stormwater is working, making sure the police are out protecting everybody."
The same workshop showed where Windermere's events were heading. The Easter Egg Hunt Extravaganza stayed on the calendar because the Windermere Police Department Foundation agreed to fund and organize it. The Foundation hosted that hunt in the spring, the Observer reported in April. Now the WPD Foundation's name is on the Light Up listing too.
How Light Up Got Back Into the Budget
Council Member Tom Stroup argued for restoring Light Up at the first budget hearing on September 3. "The community involvement and the community events are important to our community," he said, per the Observer's September coverage. "I think we can cut smaller item projects in order to keep our town events for our residents."
Smith said the event itself could be absorbed into the current budget. That was possible because the churches and dance academy provide the program at no cost. Council Member CT Allen asked that Light Up get its own line item, with food trucks at the event even if the separate Food Truck Night series did not return. That is why the November 20 listing combines Food Truck Night and Light Up into one evening.
The lights needed a separate vote. On September 8, council approved up to $25,000 for holiday lights by a 4-1 vote. Mayor Andy Williams also told council he had been talking with residents who were willing to contribute toward holiday festivities.
What $25,000 Buys Compared With Last Year
| 2025 season | 2026 season | |
|---|---|---|
| Approved spending | $35,955.27 Humbug Holiday Lights contract | Up to $25,000 authorized |
| Scope | 25 trees wrapped trunk to branches, 59 light posts | Humbug reduced-scope quote of $24,997 for the area around Town Square |
| Alternative quote | Not applicable | A second company quoted $49,000 and was preparing a reduced-scope quote |
| Council vote | 4-1, Oct. 28, 2025 | 4-1, Sept. 8, 2026 |
The 2025 contract was itself an upgrade. Before that, the town hired contractors only to hang its own aging lights. Public Works Director Tonya Elliott-Moore said contractors were reluctant because those old strands had become a safety liability. Humbug's contract was the first time the vendor supplied, installed and removed the lights itself, as the Observer reported last November. One year later the budget is smaller, and the lights are concentrated around the park where Friday's event takes place.
Amendment 3 Passed on November 3
Voters approved Amendment 3 with 61.98% of the vote, just above the 60% threshold, according to WUSF's results. The amendment raises the homestead exemption on non-school property taxes to the first $150,000 of assessed value next year and $250,000 the year after. It also cuts the annual cap on assessment growth for non-homestead properties from 10% to 5%. It takes effect January 1, 2027, as News 6 ClickOrlando explains.
For Windermere, Smith's July estimate is the one to watch. About 41% of the town's homes, roughly 900, have the homestead exemption. Smith projected a revenue hit of about $350,000 in the first year and more than $650,000 in the second. He told council that "we will be OK" but that recovery could take three or four years if property values keep rising. The town's adopted budget for fiscal year 2026-27 is $12,464,394.17, with the millage rate unchanged at 3.7425. The decorations, events and signage lines Smith flagged in July are the easiest places to cut next year as well.
This is general information about a statewide ballot measure, not tax advice. Homeowners should confirm how the new exemption applies to them with the Orange County Property Appraiser or a tax professional.
The Rest of the Season Follows the Same Pattern
The rest of the town's holiday calendar shows the same thing. Events with low costs or outside partners are going ahead.
- Game Night at Town Hall, Monday, November 23, 5:30 to 9 p.m. It is bring-your-own-game and potluck style, so it costs the town almost nothing beyond opening the building.
- The Friday Farmers Market continues at Town Square Park, 9 a.m. to 1:30 p.m. The Town says it is at capacity and is not accepting new vendors.
- Tennis-key and boat-ramp-pass renewals are on hold until December 1 while council considers fee changes. Current keys and codes keep working until then.
- Windermere Wine & Dine returns Saturday, February 6, 2027, hosted by the West Orange Foundation as a fundraiser for community programs.
The Craft Beer Festival, planned for October 17, was canceled, and ticket holders and sponsors received full refunds. The monthly Food Truck Nights matter beyond dinner, too. Part of their proceeds goes to the Historic Preservation Board, which is one reason council members said they kept hearing from residents who want the series back.
Dinner Before the Lights Come On
The 7 p.m. lighting leaves time to eat on Main Street first. Fresco Pizzeria is now open at 527 Main Street, with wood-fired pizza, handmade pasta and grab-and-go food, a short walk from Town Hall. A few doors away, 507 Main Street is the address of Penelope's Coffee, the Lineage Coffee and baked-goods concept from owners Leti Freitas and Joe Harris that the Orange Observer covered in October.
After that, it is a short walk back to Town Square Park, where the lights paid for by the $25,000 budget come on at 7 p.m.
At Florida 360 Group, we follow Windermere's council agendas the same way we follow its home sales, because the town's budget choices shape the town you live in. As Amendment 3 changes how homes are assessed starting in 2027, a clear picture of what your property is worth today is a useful starting point. Get Your Instant Home Valuation, and we will walk you through it before the new year.
