Custom homes in the town often have tall masonry chimneys with multiple flues, and some houses on the Butler chain sit on open lakefront lots. That shapes where leaks here usually start.
The usual leak sources
01Flashing
- What you may notice
- Stains next to the chimney on the ceiling or wall, often after wind-driven rain.
- How it’s confirmed
- Step and counter-flashing are checked where the roof meets the chimney.
02Crown or cap
- What you may notice
- Water inside the firebox or at the top of the fireplace opening.
- How it’s confirmed
- The crown surface, the gap around the flue tile and the cap are checked from the roof.
03Chase cover
- What you may notice
- Rust streaks on the siding, water in a factory-built firebox.
- How it’s confirmed
- The cover is checked for dishing, rust and the seal at the storm collar.

What we see on Windermere roofs
Multi-flue crowns have more joints and more surface to crack, and a wide chimney needs a cricket behind it to divert water. Around Lake Butler Estates and Lake Down Estates, those two are the first places a leak is traced.
Where this page applies
This page covers the Town of Windermere. Dr. Phillips and Bay Hill are outside town limits; Dr. Phillips has its own area page.
How the entry point is found
Map the symptom
Where the water shows up, after what kind of rain, and how long after it starts.
Check inside first
Firebox, damper and, where accessible, the attic around the chimney.
Check the top and the roof line
Crown, cap or chase cover, storm collar, flashing and the masonry or siding.
Isolate if needed
Water is run on suspect areas one at a time to confirm which one leaks.
Repair that point
Then watch the next heavy rain to confirm it’s dry.
Wind-driven rain and storm season
Central Florida averages about 51.5 inches of rain a year (CurrentResults, NCEI normals), much of it in the June–September wet season (NWS Melbourne). Storms drive rain sideways into flashing gaps, crown cracks and chase seams that stay dry in gentle rain, which is why many chimneys leak only in hard storms.
Humidity doesn’t cause leaks, and storms aren’t always the cause either; they expose a weak spot that was already there. See how Florida storms find chimney leaks.
When the leak comes with damage
- Water getting in, masonry otherwise sound: leak repair, on this page
- Loose brick, cracks through the structure, storm damage: the local repair service
- Not sure what’s going on: a top-to-bottom chimney check
Leak repair across Windermere
Leak tracing and repair are available anywhere in Windermere, including Lake Down Estates. When you get in touch, say where the water shows up and in what kind of weather. For the rest of the house, see services for homes in Windermere. The same service covers service for leaking chimneys in Winter Garden, Ocoee chimney leak repair and leak diagnosis and repair in Orlando.
Related repairs that often come up: step and counter-flashing repair, crown repair, chimney waterproofing and replacing the chase cover.
For the full background, see chimney leak detection explained and storm-season chimney leaks.
References (3)
Figures for Windermere and the references used on this page.

