Finding a qualified roofing contractor in Winter Garden, FL is an important step in protecting your home or commercial property. Whether you need a complete roof replacement, storm damage repair, or routine maintenance, working with a licensed local professional ensures the job meets Florida Building Code requirements and can withstand the region's challenging weather conditions.
The Orlando metro area's humid subtropical climate subjects roofs to intense UV exposure, heavy summer thunderstorms, and the potential for hurricane-force winds. These conditions make proper installation and quality materials essential for long-term performance. Local roofing contractors understand the specific requirements for adequate ventilation, impact-resistant shingles, and proper flashing to prevent leaks during Florida's frequent afternoon storms.
This directory currently lists 18 roofing contractors serving Winter Garden and the surrounding area. Browse listings below to compare local options and find a contractor suited to your project needs.
TruTop Roof
Florida CCC License
★ 5.0 (13 reviews)
13340 W Colonial Dr #220, Winter Garden, FL 34787
RoofingSun State Roofing LLC
Florida CCC License
★ 5.0 (19 reviews)
153 Sugar Belle Dr B #114, Winter Garden, FL 34787
RoofingLudovici Roofing & Construction
★ 5.0 (106 reviews)
127 S Dillard St, Winter Garden, FL 34787
RoofingHi Low ROOFING & SOLAR
Florida CCC License
★ 5.0 (305 reviews)
13330 W Colonial Dr Suite 110, Winter Garden, FL 34787
RoofingReliant Roofers and Restoration
Florida CCC License
★ 5.0 (82 reviews)
553 W Plant St, Winter Garden, FL 34787
RoofingEagle Roofing & Improvements
★ 5.0 (20 reviews)
14133 Jomatt Loop, Winter Garden, FL 34787
RoofingDavis Roofing & Restoration
Florida CCC License
★ 5.0 (109 reviews)
1446 9th St, Winter Garden, FL 34787
RoofingLevel Roofing
★ 5.0 (380 reviews)
1401 Beulah Rd Suite 114, Winter Garden, FL 34787
RoofingWinter Garden Roof Repair
★ 4.9 (14 reviews)
3131 Daniels Rd 119 Suite 119, Winter Garden, FL 34787
RoofingSunray Roofing and Solar
Florida CCC License
★ 4.9 (118 reviews)
861 Vineland Rd, Winter Garden, FL 34787
RoofingDeSantis Roofing Inc
Florida CCC License
★ 4.9 (32 reviews)
724 Willett Dr, Winter Garden, FL 34787
RoofingCertified Roofing Solutions, LLC
★ 4.9 (81 reviews)
1220 Winter Garden Vineland Rd #108, Winter Garden, FL 34787
RoofingKim Brothers Roof Repair
★ 4.8 (13 reviews)
15528 W Colonial Dr f a Unit F, Suite A, Winter Garden, FL 34787
RoofingMontana Roofing
Florida CCC License
★ 4.8 (39 reviews)
761 Garden Commerce Pkwy C, Winter Garden, FL 34787
RoofingSYL ROOFING SUPPLY
★ 4.8 (124 reviews)
930 Carter Rd #303, Winter Garden, FL 34787
RoofingANC Roofing, Inc.
Florida CCC License
★ 4.8 (218 reviews)
720 Business Park Blvd #10, Winter Garden, FL 34787
RoofingTalco Construction
★ 4.7 (79 reviews)
17304 C R 378, Winter Garden, FL 34787
RoofingTempest Roofing
Florida CCC License
★ 4.6 (21 reviews)
1126 E Plant St, Winter Garden, FL 34787
RoofingOcean Roofing of Florida LLC
Florida CCC License
★ 4.2 (29 reviews)
14422 Shoreside Way, Winter Garden, FL 34787
RoofingNations Roof
★ 4.2 (19 reviews)
691 Garden Commerce Pkwy #170, Winter Garden, FL 34787
RoofingWinter Garden Roof Repair
★ 1.0 (2 reviews)
RoofingWinter Garden Guys Roofing Contractors
121 Agnes St, Winter Garden, FL 34787
Hiring a roofing contractor in Winter Garden, FL
Hiring a roofing contractor in Winter Garden, FL is a high-stakes decision: Florida's heat, UV, wind-driven rain, and afternoon thunderstorms shorten the life of every roofing system, and a bad install can cost you twice — first in the redo, second in interior water damage. The directory below lists active roofing contractors so you can compare options, then verify each one's Florida license before you sign anything.
Most residential re-roofs in Winter Garden, FL are asphalt shingle, metal, or tile, and almost all require a permit pulled by a state-licensed contractor — homeowner-pulled roofing permits are heavily restricted in Florida and generally a red flag if a contractor asks you to pull one.
How to verify a roofing contractor's license in Florida
Look for license type: CCC — Certified Roofing Contractor
Go to myfloridalicense.com, the official Florida Department of Business and Professional Regulation (DBPR) portal, and use "Verify a License." Search by the contractor's business name, the qualifier's individual name, or the license number itself. Confirm the license type is "CCC — Certified Roofing Contractor," the status reads "Current, Active," the expiration date is in the future, and there is no disciplinary or complaint history attached to the record.
A "CCC" prefix on the license number means the contractor is certified to work anywhere in Florida. A "RC" prefix is a registered roofer, limited to specific local jurisdictions — make sure the license type actually covers your address.
Why verifying matters in Florida
Florida law (§ 489.127, F.S.) makes it a third-degree felony to contract without a license on a project valued at $5,000 or more, or any size project during a declared state of emergency. Verifying licensure before you sign a contract is the single most important step you can take to protect your home and your deposit. Central Florida's hurricane season runs June 1 through November 30, and unlicensed storm-chasing crews routinely move through Orange, Seminole, and Osceola counties after a major event. Confirming an active state license — and an in-state business address you can actually drive to — keeps you out of that risk pool. Roofing is the single most-impersonated trade by unlicensed operators after a storm, so this matters more here than almost anywhere else in the country.
Questions to ask before you hire
- Are you pulling the roofing permit yourself, in your company's name, with the city or county building department?
- What underlayment, drip edge, and secondary water barrier are included — and do they meet current Florida Building Code (FBC) requirements?
- What is your manufacturer warranty (material) and workmanship warranty (labor), in years, in writing?
- Will you handle the insurance claim and supplement process directly, or does that responsibility stay with me?
- Who is the actual crew on my roof — your employees or a subcontracted crew — and are they covered by your workers' compensation?
Frequently asked questions
- How long does a roof typically last in Central Florida?
- Architectural asphalt shingles in the Orlando climate typically last 15–22 years before they need replacement, metal roofs 40+ years, and concrete or clay tile 30–50 years with periodic underlayment replacement. Sun exposure, attic ventilation, and storm history all shorten those ranges.
- Do I need a permit to replace my roof?
- Yes. Every full re-roof in Orange, Seminole, and Osceola counties requires a building permit pulled by a state-licensed roofing contractor, with at least one in-progress and one final inspection. A contractor who offers to skip the permit is asking you to assume their legal liability.
- Should I file an insurance claim before or after I get estimates?
- Get an inspection from a licensed roofer first so you know what actual damage exists. If real storm damage is documented, then file the claim. Filing a claim with no documented damage can count against your policy history with no payout in return.
- Which permitting office handles roof permits in Winter Garden?
- Roof permits in Winter Garden are pulled through the building department of the city (if Winter Garden is incorporated) or the surrounding county building division. Your contractor should know exactly which office to file with — ask them to send you the permit number once it's issued so you can confirm it's open and in their name.