Roofers in Winter Park, FL

We handle roof repair, roof replacement and roof inspections in Winter Park and the streets around it. Every job starts with someone on the roof and a written price, free either way. Send the address and a short description of the problem through the quote form and we will get you on the schedule.

Winter Park roofs age under an oak canopy

Winter Park has the oldest housing stock in this part of Orange County. The median home here was built in 1976, and roughly 39 percent of the city's 14,200 housing units predate 1970, with about 2,600 of them going up in the 1950s alone. Steep pitches, dormers, cut-up valleys and original detail are normal, and a re-roof has to work around all of it rather than flatten it.

Then there is the canopy. Winter Park's urban forestry division looks after around 22,000 oaks on city streets and parks, and it has been steadily removing aging laurel oaks and replanting. Shade keeps attics cooler and keeps shingles damp long after the rain stops, which is why the north slope streaks black and holds moss while the south slope looks fine. Limb wear is the other half of that bargain. Hurricane Ian in September 2022 produced 72 reports of tree damage across city parks and roads, and the city ran a curfew for flooding and debris.

Historic designation is the part homeowners get caught out by. The city's own permit checklist requires Historic Preservation Board approval for exterior alterations and re-roofs on designated properties, and it notes that the entire College Quarter neighborhood west of Rollins College is a historic district. Better to plan around that review than to discover it the morning the tear-off starts.

What we do in Winter Park

• Targeted roof repairs for lifted shingles, cracked boots and failed valley flashing
• Full roof replacement with tear-off, decking check and new underlayment
• Roof inspections for insurance renewals and pre-purchase checks on older homes
• Tile roof work on the Mediterranean revival houses around the Chain of Lakes

The rest of what we cover sits on the Orlando roofing page, and nearby we also work in Altamonte Springs, roof repair in Oviedo and Longwood roofing.