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Windermere

Why Are So Many Roads in the Town of Windermere Still Dirt? (2026)

Written by Jared Jones
Updated November 2026
Winter Garden & Horizon West Real Estate Hub
Aerial view of a single-story lakefront home surrounded by mature oak trees and landscaped lawns in Central Florida
Lakefront homes among mature oak trees in Central Florida. In the Town of Windermere, many streets near the lakes are still unpaved.

Quick answer

By choice. Orange County says many Town of Windermere streets stay unpaved to protect the Butler Chain of Lakes, and the Town Council voted 5-0 in January 2023 against paving part of West Fifth Avenue. Maintaining the dirt roads cost about $196,000 a year as of 2019, per town documents.

$196,000Yearly dirt-road upkeep (2019)
5-02023 vote against paving West Fifth Avenue
$1.4M+Bessie and Butler streets stormwater project (2025)
3 inchesCrown kept on each dirt road (2020)
At a glance (as of November 2026)
Fact Figure
Why the streets stay unpaved (Orange County) To retain the pristine nature of the Chain of Lakes
Dirt-road maintenance, 2019 About $196,000 a year, per town documents
Cost to rebuild road crowns townwide, 2020 estimate $2 million to $4 million
Typical crown on a dirt road, 2020 3 inches, so rain runs to the sides
West Fifth Avenue paving, January 2023 Denied 5-0 by the Town Council
Bessie and Butler streets project More than $1.4 million; contract approved July 8, 2025
Funding for that project Federal Hazard Mitigation Grant Program
Projects listed for FY 2026-27 Bessie basin and Butler basin stormwater improvements

Sources: Orange County District 1, Town of Windermere page; West Orange Times & Observer (Sep 4, 2019; Jan 10, 2020; Jan 19, 2023; Aug 5, 2026); ClickOrlando (Jul 22, 2025). Dollar figures are dated to the year reported (checked Nov 12, 2026).

In this May 20, 2026 video, Jared looks at what about $1 million buys in Windermere. He says the town has dirt roads by intention, with trails and walking distance to the town square under mature oak trees, and that many homes are a short drive from a boat launch on the chain of lakes. This page explains why those roads stay unpaved and what that means day to day.

Why does the Town of Windermere keep dirt roads?

Because the town has decided to. Orange County’s Windermere page says many streets stay unpaved to help protect the Chain of Lakes. In 2019, the Town Council directed staff to study stormwater fixes for Butler and Bessie streets while keeping them dirt, per the West Orange Times and Observer.

In January 2023, the council voted 5-0 to deny paving one block of West Fifth Avenue from Forest Street to Main Street after public comment opposed it, even though staff had proposed it to improve accessibility and parking for events. The roads have become part of the town’s identity, which is why paving proposals tend to stall.

Are dirt roads actually better for the Butler Chain of Lakes?

It is debated, even inside town government. Supporters argue that permeable sand streets let stormwater soak in and protect the tree canopy that absorbs runoff. That view was voiced during public comment before the 2023 vote and matches the county’s description.

Town leaders have also pushed back on that idea. In a January 2020 Orange Observer report, then-Mayor Jim O’Brien called it a misconception that dirt roads are cheap, easy to maintain and good for the lakes, and said the original reason was that money to pave was not available when the town was built. Town Manager Robert Smith said water moves sediment into retention areas or the lakes, which the town works to prevent. The town’s approach since then has been to keep the dirt look while engineering better drainage.

How much does it cost Windermere to maintain dirt roads?

The most recent figure we found is about $196,000 a year, from town documents cited by the West Orange Times and Observer in September 2019. Treat that as a 2019 number; we did not find a current Town of Windermere budget line that isolates dirt-road upkeep.

In January 2020, the town manager told the same paper it would cost at least $200,000 a year to rebuild the roads to their proper crowned shape, and estimated a townwide rebuild at $2 million to $4 million. He also said paving would cost more up front but less in long-term maintenance. Public works staff described keeping a 3-inch crown on every dirt road with a motor grader so rain runs off to the sides.

What is Windermere doing about flooding on its dirt roads?

Rebuilding drainage without paving. In July 2025, ClickOrlando reported that the Town Council unanimously approved a construction contract on July 8 for a stormwater project of more than $1.4 million on Bessie Street and Butler Street, two of the most flood-prone roads, funded by the federal Hazard Mitigation Grant Program. Work was to begin after final FEMA approval and take about 210 days.

The town’s civil engineer said the design pitches water to the sides with swales and rain gardens, and replaces the road base with a tested material that compacts better while keeping a dirt-road look. At an August 2026 budget meeting, the Orange Observer reported, the town listed Bessie basin and Butler basin stormwater improvements among projects for fiscal year 2026-27, while noting some capital projects could be deferred.

What is it like to own a home on a dirt road in Windermere?

Expect seasonal upkeep and some mess. Town officials have described muddy roads and standing water in the rainy season, soft dry sand that can trap vehicles in the dry season, and washouts after heavy storms on low-lying segments. The town’s own engineer acknowledged dust in dry months and mud in the wet season. The 2020 report also noted the dirt roads are not lit.

For a buyer, that means checking the specific street. Ask how the road drains in front of the home, whether it is on a segment with past washouts, and whether any town stormwater project is planned nearby. Not every Windermere mailing address is inside town limits, so confirm the home is in the Town of Windermere before assuming these roads or rules apply.

Have questions about buying or selling here? Call or text 407-706-5000 or visit jaredjones.com.

Jared Jones Team, Brokered by eXp Realty.

Frequently asked questions

Are all roads in the Town of Windermere dirt?

No. Orange County says many town streets remain unpaved, not all of them, and the town has paved selectively in the past, such as part of Lake Street to reduce sediment draining into nearby lakes, according to a 2020 Orange Observer report. Check the specific street in front of any home you are considering.

Will the Town of Windermere pave my dirt road?

Do not count on it. The Town Council has repeatedly chosen to keep dirt roads, including a 5-0 vote in January 2023 against paving one block of West Fifth Avenue and a 2019 direction to design stormwater fixes on Butler and Bessie streets that keep them dirt. Recent projects improve drainage under a dirt-road look rather than adding pavement.

How much does Windermere spend on its dirt roads?

The latest figure we found is about $196,000 a year, from town documents cited by the West Orange Times and Observer in September 2019. In 2020, the town manager estimated at least $200,000 a year to rebuild the road crowns properly and $2 million to $4 million for a townwide rebuild. We did not find a current budget line for dirt-road upkeep.

Do Windermere’s dirt roads flood?

Some segments do. Town officials have described washouts several feet deep on low-lying parts of Bessie and Butler streets after heavy rain. In 2025 the town approved a stormwater project of more than $1.4 million for those two streets, funded by the federal Hazard Mitigation Grant Program, designed to move water to swales and rain gardens instead of down the road.

Why did Windermere originally have dirt roads?

According to then-Mayor Jim O’Brien in a January 2020 Orange Observer report, the main reason was that money to pave was not available when the town was built, so paving was not a priority. Over time the dirt roads became part of the town’s character, and the council has since chosen to preserve them while improving drainage.

Does a Windermere mailing address mean the home is on a dirt road?

No. Many homes with a Windermere mailing address are outside the Town of Windermere in unincorporated Orange County, where county rules apply instead. The dirt streets are a feature of the small incorporated town near Lake Butler. Confirm whether a home is inside town limits before assuming the town’s roads or rules apply.

Sources

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