Last November 21, a crowd gathered outside Town Hall at 520 Main St. Family Church choirs sang, and White Swan Academy ballerinas performed. Around 7:15 p.m. the mayor led a countdown and the holiday lights came on, followed by glow-in-the-dark bubbles and a DJ.
This summer that evening was on a list of things the town could stop paying for. It is back in the budget now, with a lower spending limit for the lights. Windermere's FY2026-27 budget keeps a tradition when its cost can be moved off general town revenue and onto volunteers, private donors, a foundation, or the residents who use the amenity. Light Up Windermere, the Easter Egg Hunt and the boat ramps are each being handled that way. Food Truck Nights have no other source of funding yet, and they are the one tradition currently suspended.
The Line the Town Manager Drew in July
At a budget workshop on July 28, Town Manager Robert Smith recommended which events and projects to cut or defer if a statewide property tax measure passes on Nov. 3. He told the council the town would be fine either way, and he described the standard he used to choose.
"Quality of life is one thing, the level of service is another. 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 measure is Amendment 3. According to the Florida Division of Elections summary, it would raise the homestead exemption on non-school property taxes to $150,000 in 2027 and $250,000 in 2028, then adjust it for inflation. It would also lower the cap on assessment growth for non-homestead property from 10% to 5%. The Pinellas County Property Appraiser notes that Florida amendments need 60% approval, and that if this one passes it takes effect Jan. 1, 2027.
For Windermere, the effect is easy to estimate. About 900 town homes, roughly 41%, would fall under the expanded exemption. Smith projected revenue losses of about $350,000 in the first year and more than $650,000 in the second. The council kept the millage rate at 3.7425, where it has been since 2018. On Sept. 16 it adopted a total budget of $12,464,394.17.
Smith also recommended giving back about $800,000 in unspent state money for the Potable Water Central Phase project. State reimbursements arrive eight to 12 months after the town spends, and the town was still waiting on at least $5.8 million it is owed. The same budget makes a similar call for events and amenities on a much smaller scale.
The Easter Egg Hunt Was Covered First
The Easter Egg Hunt Extravaganza was the first event moved off the town's books. Smith reported that it will continue, with the Windermere Police Department Foundation funding and organizing it. No council debate was needed. Another organization took on the cost and the event stayed.
Light Up Windermere followed the same path in September. Council Member Tom Stroup argued at the Sept. 3 budget hearing for keeping the town's long-running events, even if smaller projects had to be cut to pay for them. Smith said the event itself could fit in the current budget because most of its program already costs the town nothing. Family Church of Windermere usually provides the activities in front of Town Hall, and White Swan Academy performs inside and outside at no charge.
The lights were harder to keep.
What It Costs to Light Town Square
The FY2027 proposal had dropped the lighting entirely. These are the figures the council worked from:
| Lighting option | Cost |
|---|---|
| 2025 Humbug Holiday Lights contract: install, removal, maintenance | $35,955.27 |
| Humbug quote for a similar display in 2026 | about $35,000 |
| Humbug quote for a reduced scope around Town Square | $24,997 |
| Second company, full scope | $49,000 |
| Council spending authorization, Sept. 8 vote of 4-1 | up to $25,000 |
The $25,000 cap is $3 above the reduced Humbug quote and about $11,000 below what last year's display cost. The authorization sets a spending limit. It does not pick a vendor or a scope. Public Works Director Tonya Elliott-Moore said the second company was preparing its own reduced-scope quote.
Private money could fill the gap. Mayor Andy Williams said he has been talking with residents who are willing to help pay for the holiday festivities. He also said he would rather hire a vendor with a track record than save money on an unproven crew.
As of Oct. 10, neither the town nor the Orange Observer has announced a 2026 date, time or program for Light Up Windermere, or reported that a lighting contract was awarded. The town's online event calendar runs through Oct. 31 and does not list it. Last year's event was on the Friday before Thanksgiving. That gives an idea of the usual timing, but the town has not confirmed a date.
Food Truck Nights Had No Outside Funder
Food Truck Nights were the other event proposed for elimination, and they have not come back. The town's Food Truck Nights page shows a banner saying the event is "suspended until further notice." The town calendar marks the Oct. 23 Halloween Food Truck Night, scheduled for 5 to 10 p.m. at Town Square, as "Canceled Until Further Notice." Lower on the same page, older text still says the event runs on the fourth Friday of every month. The suspension notice is the current information.
The two events used to happen together, so splitting them was a real choice. Council member CT Allen asked that Light Up be budgeted as its own line item. She suggested food trucks could still come to Light Up even if the monthly nights end, so residents get the same evening as in past years.
The suspension also affects another part of the budget. Food Truck Night proceeds help fund the Historic Preservation Board. During the hearing, a council member raised concerns that the cuts landed on events that support that board and the Windermere Tree Board.
The Ramp Pass Gets a Cost-Recovery Price
The boat ramps are where the town is applying this approach most directly. Windermere has two resident-only ramps: Fernwood Park on Lake Butler and the Lake Bessie ramp. The public Orange County ramp onto Lake Down, at E. 6th Avenue and Conroy, is separate. For Fernwood, at W. 7th Avenue and Butler Street, the town recommends driving in from Butler Street.
Passes and tennis keys normally renew on Oct. 1. This year the town has put both renewals on hold until Dec. 1, and current keys and codes keep working until then at no extra charge. The Parks and Recreation Committee first recommended raising the boat pass from $35 to $50 and the tennis key from $25 to $50. On Sept. 8 the council tabled those increases and asked for five years of actual spending.
That data went into a memo for the Sept. 22 workshop. Over five fiscal years, the boat ramps averaged $9,120.20 a year in costs, including gate and access-control work, fencing, locks, security improvements and grounds work. The town has 158 ramp passes and 232 tennis keys outstanding.
| Annual boat ramp pass | Share of average cost covered by pass fees |
|---|---|
| $35, current | 60.6% |
| $45 | 78.0% |
| $55 | 95.3% |
| $57.72, break-even | 100% |
| $60 | 103.9% |
The tennis courts have a bigger gap. At $25 per key, user fees cover 30.2% of the courts' average annual cost of $19,204.76, and the break-even fee would be $82.78. The memo says the council does not have to recover the full cost. Residents and property owners already support these facilities through general town revenue, and the tables are meant to help the council decide how much users should pay. No vote was taken at the workshop. Revised fee resolutions could come up at the Oct. 13 council meeting.
The town's park page says ramp passes are sold to residents of the incorporated town. The draft resolution refers to eligible residents and property owners. If eligibility matters to you, Town Administration can confirm it.
What Runs on Its Own
Some events never needed a decision. The rest of the October calendar is still set:
- Windermere Beer Fest, Oct. 17
- Halloween Hayride Parade, Oct. 24
- Pumpkin-carving potluck, residents only, Oct. 25
- Bunk-bed build, Oct. 31
- Windermere Farmers Market, Fridays from 9 a.m. to 1:30 p.m. at Town Square Park, 520 Main Street
On Main Street, Penelope's Coffee is getting ready to open at 507 Main St. As of Oct. 2, the Orange Observer reported that renovations were nearly done and the shop expected to open this fall, with no exact date announced.
Parts of Ward Trail and its new pedestrian bridge opened before the school year began. The trail is about half a mile long and crosses the canal on a bridge for pedestrians, bicycles and golf carts. In its Aug. 6 update, the town said final path sections and landscaping were still being finished and expected the full opening in fall or winter. Ward Trail Phase 1 is on the FY2026-27 project list along with the Windermere Road and Main Street intersection improvements. Smith said design money is already committed, but construction can wait until cash flow allows it.
The Dates Still Open
- Oct. 13: the Town Council may consider revised boat ramp and tennis fee resolutions.
- Nov. 3: Amendment 3 is on the general election ballot.
- Dec. 1: current ramp passes and tennis keys stop working without a renewal.
- To be announced: the Light Up Windermere date, the lighting vendor, and whether food trucks will be part of the evening.
Smith also said the town may hold off on some capital projects until after Nov. 3, when the 2027 and 2028 property values are known.
At Danholm Collection, we follow Windermere's council decisions because they shape how the town works for the people who live in it. If you would like to talk through what this year's budget means for your property or a home you're considering, book your strategy consultation.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
