What’s the construction happening along Maguire Road & Main Street in Windermere?
Blog Author: Jen Durben | The Funk Collection, Brokered by eXP Realty
If you’ve driven down Maguire Road & Main Street in recent weeks and wondered what the construction is along the road, you’re not alone.
The construction marks the beginning of the Ward Trail, a new multi-modal path that will connect parts of Windermere in a whole new way. Once finished, it’s expected to make daily movement safer and more convenient.
Located near the north end of town along Maguire Road and Main Street, extending over the canal connecting Lake Down to Wauseon Bay and beyond to Lake Butler, the project is already taking shape. From dirt movement and tree removal to the early stages of a new bridge, there is a noticeable transformation underway.
A New Chapter for Windermere Trails
If you’ve been living in Windermere, Florida, you know the charm of its paths throughout downtown, and this project will further enhance the experience for bikers, dog walkers, and residents who access the path to get to and from the local elementary school.
This is not just a cosmetic improvement. It is a meaningful infrastructure upgrade that has been in the works for over 10 years. Once completed, the trail will stretch just under a mile, connecting North Drive to Park Avenue and creating a smoother, more accessible route through the heart of Windermere.
Safer, Wider, and Built for Everyday Life
One of the most noticeable improvements coming to the Windermere trails system is the redesign of the path for real, everyday use. The current pedestrian bridge along this route has long been a challenge. It is narrow, steep, and difficult for multiple people to navigate at the same time. The new design addresses those concerns directly while also improving the overall experience.
Here is what you can expect:
- A 14-foot-wide bridge replacing the existing narrow structure
- Space for pedestrians, bikes, and even golf carts to move comfortably
- A smoother, paved surface replacing sandy and uneven paths
- Addition of native landscaping like Southern Live Oaks and Saw Palmetto
- Lighting and seating areas that make the trail more usable throughout the day
Beyond safety, this is about making movement through Windermere more natural and convenient. Whether you are heading downtown, out for a walk with your dog, or navigating your daily routine, these updates are designed to support how you actually live.
What This Means for Living in Windermere, Florida
Projects like this are a strong signal of long-term investment in the community. It’s one more reason we love Windermere. Meaningful updates that have a positive impact on the community while retaining the integrity of the small town feel.
If you’ve been considering a move to Windermere, this translates to:
- Improved day-to-day convenience
- Enhanced lifestyle appeal
- More usable outdoor space
Because the trail is designed primarily for residents, it reinforces what makes Windermere unique. It is a community focused on thoughtful growth and quality of life.
Timeline: When Will The Ward Trail & Bridge Be Ready?
Construction on Phase 1 is already well underway, with major work, including bridge replacement, progressing through the coming months.
After speaking with the Town of Windermere, the project is progressing at a strong pace, with weekly status update meetings in place and Phase 1 expected to be substantially completed by mid-summer, aligning with the start of the 2026/2027 school year.
Future phases are planned to expand the trail further, depending on funding and development timelines.
Thinking About a Move to Windermere?
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If you are exploring living in Windermere Florida, having a true local expert matters.
Jeffrey Funk is not only a Team Leader of The Funk Collection brokered by eXp Realty, but he and his wife and Co-Founder, Renee, are also longtime Windermere residents who live and work right here in the community, running the eXp office on Main Street in downtown Windermere.
That local presence means you are not getting secondhand information. You are getting guidance from someone who experiences Windermere the same way you will.
Whether you are buying, selling, or simply exploring your options, Jeff can help you navigate the market with clarity and confidence.
Connect with Jeffrey Funk today to get personalized guidance on living in Windermere Florida, and finding the right opportunities for you.
Posted by Jen Durben on
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