5.0
180+ reviews
Roofing Contractor in Kissimmee, FL Specializing in Metal Roofing
Fiddler’s Roofing provides residential and commercial roofing services for homes, businesses, and other properties in Kissimmee, FL. Our Kissimmee roofing team handles roof inspections, roof repair, roof replacement, metal roofing, shingle roofing, tile roof repair, and commercial roofing systems.
Metal roofing is our featured specialty. We install QueenTile stone-coated steel and standing seam systems using steel supplied through Metal Alliance, while continuing to serve customers who need GAF shingles or another appropriate roofing solution.
Book An Inspection Now
- Florida Certified Roofing Contractor
- License CCC1333004
- Serving Central Florida Since 2003
- Financing Available







Residential Roofing Services in Kissimmee
Our residential roofing services are planned around the house, existing roof condition, architecture, budget, and ownership goals. Available services include:
- Free roof inspections
- Roof leak diagnosis and repair services
- Full roof replacement
- New roof installation
- Residential metal roofing
- GAF asphalt shingles
- Tile roof repair
- Low-slope roofing solutions
- Roof coatings for eligible surfaces
- Storm damage assessments
- Roof financing for qualified applicants
The right roofing material depends on the property. We compare roofing systems, explain material and workmanship warranties, and provide a written scope before professional installation begins.
EXCELLENT Based on 186 reviews Posted on Google Brent WintersTrustindex verifies that the original source of the review is Google. These guys did a fantastic job w/our new roof install. They worked late to get our large home finished in 2 days. And they were the only roofer of the top 5 on Google I received quotes from that didn't have a contract heavily weighted to the contractor. Other agreements said they might destroy my gutters, or damage my AC, or other things and I would have to pay for it. Read the fine print! One roofer said outright every company is going to tear up your gutters and that's the way it is, but Fiddler replaced our drip edge and put the gutters back with no problem. The owner, Kevin, strikes me as a straight shooter trying to do right by the customer --- increasingly rare today.Posted on Google Eliana GonzalezTrustindex verifies that the original source of the review is Google. Very nice person to work with very polite and responsible. I would recommend it to everybody.Posted on Google Nesa DownardTrustindex verifies that the original source of the review is Google. Found Fiddler’s after doing some searches and reading reviews, we got a good amount of quotes from other companies. Was looking for an entire new roof and gutters instillation . We decided to use Fiddler’s based on their reviews and how they approached getting our business. Kevin (the owner) came out to look at our very old roof and was very friendly and told me how they go about their process, he even gave me recommendations on things I should consider doing even if I don’t use them. With other roofing companies I met with, all they did was bad mouth other companies and how they were so much better. Fiddlers just focused on what they could/would do for us. I liked that they are a family owned business and they also use a family owned business for their gutters. The quote we received was a very good one with detailed options for us to choose from. Once we signed with them the process was quick, they came out shorty after and got started. The crew and Forman (David) were great, they answered any questions we had, and were so friendly. My roof was crazy old and as they removed the old roof they discovered some problems that they quickly assessed and handled. Our roof was done in two days and it looks beautiful. With the thousands of roofing companies here in Florida you never know who you can trust and what type of quality you will get. I’m so grateful we found Fiddlers. You can definitely trust them to do right by you and give you a quality roof. Highly recommend!Posted on Google peggy fraserTrustindex verifies that the original source of the review is Google. Kevin and his team did a great job repairing my roof. They pay attention to detail and got the job done quickly. I wouldn’t call anyone else but Fiddler Roofing. They are outstanding!Posted on Google Pat CastellanoTrustindex verifies that the original source of the review is Google. Kevin and company came recommended to us as new Floridians. He came as quickly as asked, provided his assessment and the work done by his team was neat, on schedule and with professionalism. The solar fan looks great and will help maintain the roof and cool the attic during those hot Florida days. Thank you Kevin and team.Posted on Google Clarence MillsTrustindex verifies that the original source of the review is Google. Kevin and the team at Fiddlers Roofing did an outstanding job! From start to finish, the process was smooth, professional, and stress-free. Kevin was knowledgeable, honest, and took the time to explain everything clearly. The crew worked efficiently, kept the area clean, and completed the job on time. The quality of the workmanship is excellent, and the new roof looks fantastic. I truly appreciate the attention to detail and the great customer service. I highly recommend Kevin and Fiddlers Roofing to anyone looking for reliable and high-quality roofing work!Posted on Google Sue HauseTrustindex verifies that the original source of the review is Google. I am very pleased with my new roof and the guys and the forman Mike were very efficient. Kevin the owner helped me decide on the color and proper shingles and gutters . great choice! the cleanup was done very nicely and all inspection was smooth. Thank you all who made this experience rewarding!!!!! Sue HausePosted on Google Jennie AyersTrustindex verifies that the original source of the review is Google. 1000% satisfied. I had a very tough flat roof that had been abused for decades. They did a great job, and spent over a week with no change in cost to make sure the entire roof went well. Would recommend to any and all customers!!Posted on Google Dennis ThurmonTrustindex verifies that the original source of the review is Google. Excellent experience! The team kept me fully informed during the entire process, sending real time messages with pictures of before and after work. They were able to replace my entire roof in two days. Very happy with my new roof; thanks again!Posted on Google JoeTrustindex verifies that the original source of the review is Google. Kevin, the owner, spent 11 months working with me and walking me through the unbearable hoops with my insurance claim from a hurricane last year. He went above and beyond and helped me by referring an AMAZING public adjuster and another contractor to do some other work. The staff, including Alexis and Ruben were fantastic as well. And the finished product? Absolutely amazing! Not only does my house look beautiful again, Ruben helped make it safer by pointing out where my roof needed improvement. Even if it were just Kevin, I would wholeheartedly recommend Fiddler’s Roofing to everyone, but with his top notch team, it’s a no brainer. Kevin also helped my sister get her roof fixed after the same storm, thankfully, her roof was only in need of minor repairs, but again, his crew got it done so it looked like it had never happened. I attached some before and after photos so you can see their work.
Roof Repair in Kissimmee, FL
A small roof leak can worsen when repeated rain reaches underlayment, decking, insulation, or interior finishes. Common warning signs include ceiling stains, missing shingles, curling or cracked shingles, displaced tiles, damaged flashing, loose trim, debris in valleys, and moisture around penetrations.
Our roof repair process begins with a comprehensive inspection of the affected area and surrounding roofing system. We identify visible roof damage, explain the likely source, and provide a detailed estimate for the recommended repairs. Repair work may include replacing damaged shingles, correcting flashing, addressing a penetration, or repairing another localized condition.
What appears to be a simple roof repair may involve a broader issue beneath the surface. We do not recommend covering a symptom without evaluating how water entered the roof.
New Roof and Roof Replacement in Kissimmee
A new roof or re-roofing project begins with an assessment of the existing covering, visible deck condition, roof pitch, drainage, ventilation, flashing, penetrations, and access.
A complete written estimate should identify:
- Roofing materials and product line
- Tear-off or preparation
- Underlayment and flashing
- Deck-repair allowances
- Ventilation work
- Labor, cleanup, and disposal
- Permit responsibility
- Manufacturer and workmanship warranties
- Project exclusions, schedule, and payment terms
Roof replacement cost depends on measured area, material waste, roof complexity, selected system, deck repairs, and other project conditions. Generic square-foot pricing cannot replace a property-specific estimate.
Metal Roofing for Kissimmee Homes
Metal roofing is a strong option for Kissimmee residents who want durable roofing materials and a distinct architectural appearance.
QueenTile Stone-Coated Steel
QueenTile combines formed steel panels with a stone-coated surface. Verona creates a tile aesthetic, while Shake and Slate-inspired profiles offer additional design options, subject to current availability.
Metal Alliance Standing Seam
Standing seam metal uses long steel panels and concealed fasteners. Fiddler’s offers 24- and 26-gauge options based on the selected panel profile, finish, roof geometry, project requirements, and material availability.
Compare both options on our residential metal roofing page.
Shingle Roofs and Tile Roof Repair
Asphalt shingles remain a familiar roofing choice for many Central Florida homeowners because they offer broad curb appeal and a lower upfront cost than many premium metal systems. Fiddler’s installs qualifying GAF shingle roofing systems and holds GAF Master Elite® certification.
Manufacturer material warranties and the contractor’s workmanship warranty are separate. The proposal should identify the selected shingles, accessories, registration requirements, and available warranty coverage.
For existing tile roofs, Fiddler’s provides tile roof repair after evaluating damaged tiles, flashing, underlayment concerns, penetrations, and the surrounding roof area.
Commercial Roofing in Kissimmee
Fiddler’s provides commercial roofing services for commercial buildings and businesses in Kissimmee, subject to project fit.
Commercial roofing services may include:
- Roof inspections
- Leak investigation and repairs
- Roof maintenance
- Full roof replacement
- Standing seam or another appropriate metal system
- TPO roofing
- Modified bitumen
- Commercial roof coatings
- Storm damage assessments
Commercial roofing projects vary in size, access, drainage, occupied-building requirements, and operational constraints. The proposed roofing system should fit the commercial property rather than relying on one standard material for every business.
Free Roof Inspections in Kissimmee
A free roof inspection can identify visible issues before a repair or replacement scope is finalized. Depending on access and conditions, roof inspections may review:
- Roof covering condition
- Flashing and penetrations
- Missing shingles or displaced materials
- Valleys and drainage patterns
- Visible signs of moisture
- Ventilation components
- Storm-related damage
- Accessible deck or interior indicators
Fiddler’s provides photos of identified problem areas and discusses repair, maintenance, or replacement options.
Roofing Systems for Kissimmee Weather
Kissimmee roofs face intense sun, humid conditions, heavy downpours, and strong storm winds. UV exposure can age asphalt shingles and sealants, high wind can lift loose or damaged materials, and poor drainage can cause ponding water on low-slope areas. Repeated temperature changes can also stress flashing, fasteners, and transitions.
Humidity and shade may support algae or organic growth on roof surfaces. Organic staining does not by itself establish the condition beneath the roof, but it is one more reason to keep drainage paths clear and schedule periodic roof inspections.
High-quality materials are only one part of the solution. Product approvals, deck attachment, underlayment, flashing, edge details, and quality workmanship all affect how the roof protects the property.
Kissimmee Permits and Local Building Requirements
A property with a Kissimmee mailing address may be inside the City of Kissimmee or in unincorporated Osceola County. The correct permitting authority and requirements must be confirmed before work begins.
The written proposal should state whether a permit is required for the roofing job, who is responsible for submitting it, and which product documentation or inspections are included. Roofing materials and installation details must follow the applicable Florida Building Code, product approvals, and local requirements.
Our Professional Roofing Process
Inspection and consultation
Roofing-system and material selection
Detailed written estimate
Permit and scheduling coordination
Roof preparation and professional installation
Cleanup and final quality check
Required jurisdictional inspection and final walkthrough, where applicable
Clear communication matters throughout roofing projects. Customers should know the selected materials, repair or replacement scope, schedule, payment terms, and warranty documents before work starts.
Why Choose Fiddler’s Roofing?
Fiddler’s Roofing has served Central Florida since 2003. We are a Florida Certified Roofing Contractor, license CCC1333004, and a GAF Master Elite® contractor for qualifying shingle systems.
Our goal is to provide quality roofing services without pushing every customer toward the same roof. We compare roofing types, explain the scope, and recommend repair or replacement based on the property.
Review customer testimonials and learn more about Fiddler’s Roofing.
Kissimmee Roofing FAQs
Should I Repair or Replace My Roof?
The answer depends on roof age, material condition, location and extent of damage, deck condition, previous repairs, and the expected value of additional repair work. An inspection is the starting point.
What Roofing Systems Do You Offer in Kissimmee?
Our roofing solutions include QueenTile stone-coated steel, standing seam metal, GAF shingles, tile repair, eligible low-slope systems, TPO, modified bitumen, and roof coatings, depending on whether the property is residential or commercial.
Do You Provide Storm Damage Assessments?
Yes. Fiddler’s provides residential storm damage assessments and commercial storm damage assessments. Coverage decisions remain with the insurance carrier.
Is Financing Available?
Roof financing options may be available for qualified applicants. Rates, terms, payments, and approval are determined by the financing provider.
5.0
180+ reviews
Request a Free Estimate in Kissimmee, FL
Need roof repair, a new roof, commercial roofing, or help choosing between metal and shingles?
Schedule a free inspection with Fiddler’s Roofing. We will evaluate the property, explain the available roofing solutions, and provide a written estimate for your Kissimmee roofing project.