Typical Winter Park price: about $10,500 to $16,500 for architectural shingles on about 2,000 square feet of roof surface. Measure your roof for a number based on its real size.
Roofing in Winter Park
Central Florida is mostly inland shingle country, with a large stock of homes built from the 1990s through the 2000s. Hurricanes Ian (2022) and Milton (2024) crossed the region, and insurance roof-age pressure is a common reason homeowners here replace.
- A lot of homes built before 2008 still have their second roof or an aging first roof. Those homes may qualify for My Safe Florida Home if the owner meets income rules.
- More contractors compete here than in most regions, which helps keep prices near the lower end of the state ranges.
- HOAs in many newer communities approve roof colors and materials. Check before you sign.
Winter Park is outside the High-Velocity Hurricane Zone, which covers only Miami-Dade and Broward counties.
Winter Park roof prices by material
| Material | Per square installed | 22-square roof | Lifespan |
|---|---|---|---|
| Architectural shingle | $475 – $750 | $10,500 – $16,500 | 20–25 yrs |
| Impact-resistant shingle | $600 – $925 | $13,000 – $20,500 | 20–30 yrs |
| Metal, exposed fastener (5V) | $800 – $1,200 | $17,500 – $26,500 | 30–40 yrs |
| Metal, standing seam | $1,000 – $1,800 | $22,000 – $39,500 | 40–60 yrs |
| Concrete tile | $1,000 – $1,900 | $22,000 – $42,000 | 40–50 yrs |
| Flat roof (TPO / modified) | $600 – $1,100 | $13,000 – $24,000 | 15–25 yrs |
Licensed roofing companies in Winter Park
Sunny Roofing (Sunny R&R LLC)
Featured listing. Sunny Roofing is a Florida Roof Price partner and may receive your request when you ask for quotes. See Partners.
40 roofing companies with a current, active Florida roofing license are based in Winter Park. Here are the longest-licensed. Always check a license yourself before you sign.
| Company | City | License | Licensed since |
|---|---|---|---|
| Tip Top Roofing Co Inc | Winter Park | Registered | 1981 |
| Old Mill Construction LLC | Winter Park | Certified | 1997 |
| Pro Design & Construction | Winter Park | Certified | 2005 |
| Martin Roofing Services Inc | Winter Park | Certified | 2006 |
| Winter Park Roofing, Inc. | Winter Park | Certified | 2008 |
| Fortis Enterprises LLC | Winter Park | Certified | 2010 |
| KC Construction & Maintenance Inc. | Winter Park | Certified | 2010 |
| Tyrell Enterprises, L.L.C. | Winter Park | Certified | 2012 |
| Park and Pine Homes | Winter Park | Certified | 2013 |
| JK Stevens Roofing, Inc. | Winter Park | Certified | 2014 |
See all 40 roofing companies in Winter Park →
Before you hire a roofer in Winter Park
- Get at least three written quotes that use the same square count.
- Confirm who issues the permit: the city for addresses inside city limits, Orange County for unincorporated areas.
- Check the roofer’s license at MyFloridaLicense.com.
- If your insurer sent a roof letter, read what Florida law allows first.
- Update your wind mitigation report after the job.
Get your Winter Park roof price
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Frequently asked questions
How much does a new roof cost in Winter Park, FL?
For about 2,000 square feet of roof surface (22 squares with waste), architectural shingles run roughly $10,500 to $16,500 in Winter Park. Standing seam metal and concrete tile run about $22,000 to $42,000. Measure your roof by address for a number based on its real size.
How many roofing companies are in Winter Park?
As of September 27, 2026, 40 roofing companies with a current, active Florida roofing license list a business address in Winter Park. Certified roofers based elsewhere can also work there.
Who issues roof permits in Winter Park?
If the home is inside city limits, the city’s building department usually issues the reroof permit. Otherwise Orange County does. Your roofer normally pulls it.
Nearby cities in Orange County
Orlando · Apopka · Maitland · Ocoee · Windermere · Winter Garden