Until this August, getting from downtown Windermere to Windermere Elementary School on foot meant crossing a bridge that had seen better decades. It was narrow enough that only two people could walk it side by side, framed by a warped chain-link fence with vegetation growing through the gaps, and reached by a concrete ramp steep enough to worry any parent watching a kid on a bike take it downhill. Fourth-grader Emmett Thon and his mother Leah rode it together every school day from their home in downtown Windermere. She has described it as nerve-wracking, the kind of crossing you tolerate because there isn't another option.
On August 6, that option changed. The Town of Windermere opened the first working stretch of the Ward Trail and its new pedestrian bridge, a project that had been moving through paperwork, funding requests, and construction phases since before some of the kids using it were born.
What Opened on August 6
The new bridge spans the canal connecting Lake Down and Lake Butler, wide enough for two golf carts to cross at once, and built to handle pedestrians, cyclists, and wheelchairs without the awkward pinch point the old structure forced on everyone. The stretch that opened in August covers roughly half a mile of shared-use path, drainage improvements, and landscaping. Once every section is finished, Phase 1 of the Ward Trail will run just under a mile end to end, linking North Drive to Park Avenue. Crews are still finishing pathway sections and landscaping through the fall, but the part that matters most for daily life, the bridge itself, is open and in use.
Timing was not an accident. Town leadership set a goal to have the crossing ready before Windermere Elementary's first day back, August 11, and made it with five days to spare.
Why It Took a Decade
The delay wasn't engineering. It was land.
The trail is named for Ken and Susan Ward, whose family owned the property the town needed for the crossing. Negotiations stalled for years until the Wards died in a house fire in 2017. Their sons then agreed to the town's $250,000 appraisal for the land, and the Windermere Town Council finalized the purchase on March 13, 2018. From there, the town spent years lining up money: a $760,000 federal appropriation through the Safe Routes to School program, plus $1 million from the Florida Legislature, before construction on Phase 1 finally began in February 2026.
The bridge itself arrived by truck down Main Street on June 15, was installed the next day, and required weeks more work to level it, connect it properly, and make it ADA compliant for golf carts before anyone could use it.
"In this job, you really don't get validated that much, and just seeing the bridge, it was like a sigh of relief, saying, 'OK, I've accomplished something the residents can actually see, touch, feel and enjoy.'"
That's Windermere Town Manager Robert Smith, describing the moment the bridge showed up after a process that outlasted two mayors' worth of council meetings.
What Actually Changes Now
Before the new bridge, golf cart drivers dropping off or picking up kids at Windermere Elementary often used the main road bridge instead of squeezing onto the old pedestrian crossing. That put golf carts sharing pavement with cars on a route plenty of families use twice a day. The new bridge pulls that traffic off the main road entirely, and it does the same for cyclists and walkers who used to have to time their crossing around foot traffic on a walkway built for a different era.
The landscaping plan calls for removing close to 70 existing trees and replacing them with more than 100, including longleaf pines, firebushes, saw palmettos, and Sabal palms, along with benches and lighting along the path. The bigger structural goal, according to town officials, was connecting the older homes north of the canal to the civic core, the parks, and the boat ramps that sit south of it, without funneling everyone through the same stretch of road.
For a resident, the difference shows up in small ways: a shorter, safer walk to school, one less golf cart merging into car traffic, and a path that finally matches how people already move through town.
The Sequel Is on the Ballot
Phase 1 is done, or close enough. Phases 2 through 4 are not, and their funding is an open question tied directly to a vote happening in about six weeks.
The remaining phases are mapped out:
- Phase 2: North Drive to Sixth Avenue
- Phase 3: Sixth Avenue, from Main Street to Apopka-Vineland Road
- Phase 4: Chase Road and 12th Avenue to Sixth Avenue
Robert Smith has said future phases are uncertain because of Florida's Amendment 3, the property tax measure voters decide on November 3. If approved by at least 60 percent of voters, Amendment 3 would raise the homestead exemption for primary residences to $150,000 in 2027 and $250,000 in 2028, on top of reducing the assessment cap on non-homestead properties like second homes from 10 percent to 5 percent. New residents would need five years in the state before qualifying for the larger exemption.
Windermere's Town Council passed a resolution this July formally opposing the measure, citing concerns about local fiscal stability, bond obligations, and the town's ability to keep funding infrastructure. The numbers behind that concern are specific: the town's estimated taxable value this year is just over $1.3 billion, an increase of more than $33 million, and about 41 percent of Windermere's homes, roughly 900 properties, fall under the homestead exemption the amendment would expand. Town staff estimate the reform would cost Windermere about $350,000 in lost revenue the first year and more than $650,000 the second.
At a budget meeting in late July, Smith told council the town would be financially fine either way, but only with cuts. He drew a line between what he called needs and wants: police, fire, roads, and stormwater work stay funded no matter what. Community events and amenities, the things Smith said actually draw people to West Orange County in the first place, are first in line to be trimmed. Town-sponsored Food Truck Nights and Light Up Windermere are already on a list for possible elimination if the reform passes, and the Easter Egg Hunt Extravaganza would move from town funding to the Windermere Police Department Foundation. Council set its final budget hearing for September 16, just days before this piece published, to lock in a working number ahead of the vote.
Multimodal paths, sidewalks, and landscaping projects sit in that same "want" category Smith described. Phases 2 through 4 of the Ward Trail are exactly the kind of project that logic puts at risk.
What This Means If You Use the Trail
None of this changes what opened in August. The bridge is built, the school route is safer, and golf carts have a lane that isn't shared with cars anymore. What it does mean is that the next extensions, the ones that would eventually connect more of Windermere's neighborhoods the same way this one just connected downtown to the elementary school, depend on a ballot outcome nobody in town hall can predict yet. If you use this trail for the school run, the dog walk, or the golf cart trip to Town Square, the next few months of returns from Tallahassee will tell you more about its future than anything happening on the trail itself.
For residents who want to follow how the vote plays out locally, the Town of Windermere's own announcement and reporting from the West Orange Times & Observer are worth bookmarking, along with the state's official summary of Amendment 3 if you want the ballot language itself rather than the town's take on it.
Windermere keeps changing in ways that show up on the ground before they show up in conversation. If you're watching this town closely for reasons beyond the school run, from Butler Chain waterfront listings to what a half-finished trail phase might mean for a neighborhood a few years out, Keystone Global Real Estate tracks these local shifts as part of how we work here. Get a FREE Market Report to see what's moving in Windermere right now.
