Roofers in Winter Garden, FL

In Winter Garden and the surrounding area, we handle roof repair, roof replacement and roof inspections. Every quote is free and written out before work is booked. Send the address and a short description of the problem through the quote form and we will get someone on the roof.

A whole city of roofs reaching the same age

Winter Garden has the newest housing stock of any established town in this part of Orange County, and that is exactly why the roofing work is picking up. About 65 percent of the city's 17,300 housing units were built in 2000 or later. Only 11 percent predate 1970. A first-generation architectural shingle roof from 2004 is now twenty-plus years into a Florida climate, which means whole streets in the same subdivision come due within a couple of years of each other.

Downtown is the other Winter Garden. The Plant Street historic district went on the National Register in August 1996, covering about 100 acres and 26 historic buildings, with the oldest documented structures dating to 1912. Orange County pulled the rail line out of Plant Street in 1994 and put the West Orange Trail down the median, which is what turned the district around. Those older buildings and the houses around them are a different roofing job from a production subdivision.

Storms have not been kind lately. Winter Garden recorded the highest rainfall of anywhere in Orange County during Hurricane Milton on 9 October 2024, up to 12 inches, on a night when the county saw gusts to 87 mph and 42 tornado warnings. Back in February 1998, an F4 tornado came through with a warning that read "tornado on the ground in Winter Garden."

One thing worth knowing: a Winter Garden mailing address does not always mean a Winter Garden permit. Horizon West is unincorporated Orange County despite sharing the 34787 ZIP, so re-roofs out there go through the county, and most of those villages are HOA and CDD governed.

What we do in Winter Garden

• Repair work on lifted tabs, split boots and failed valley metal
• Architectural shingle replacement, the standard on the 2000s subdivisions
• Tile roofs on the higher-tier homes west of town
• Roof inspection reports for renewals, buyers and post-storm checks

See our Orlando base for everything else. Close by, we also handle Ocoee, roofing in Windermere and Clermont.