190+ reviews

Roofing Contractor in Windermere, FL

A leaking roof, storm damage, or an upcoming replacement can leave you with a lot of questions. Fiddler’s Roofing helps Windermere homeowners and businesses understand their roofing options and move forward with a clear plan.

We provide roof repairs, complete roof replacements, and new roof installation, with a specialty in architectural metal roofing. Choose from standing seam and QueenTile stone-coated steel systems, or explore shingle roofing and other solutions suited to your property. Our recommendations start with the roof you have and the results you need—not a single material we recommend to everyone.

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Residential Roofing for Windermere Homeowners

Your roof should complement your home while addressing its practical needs. We help homeowners compare repairs, replacement materials, and installation options based on roof condition, design, budget, and long-term plans.

Our residential services include roof inspections, leak repairs, storm damage repairs, roof replacement, new roof installation, metal roofing, GAF shingles, and tile roof repair. Low-slope roofing and coatings are also available for suitable roof sections.

      EXCELLENT  
   Based on 188 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Jonathan Rares 
 
 
 
 Trustindex verifies that the original source of the review is Google. Kevin was very knowledgeable, communicated well, and got the job done quickly. Would highly recommend Fiddlers roofing!
  
 
      Posted on Google  
   
   Creative Auto Style 
 
 
 
 Trustindex verifies that the original source of the review is Google. Fiddlers Roofing did an excellent job with my tile roof replacement in West Palm Beach, Florida. From start to finish, the team was professional, reliable, and thorough. Kevin was especially great to work with—he is extremely honest, straightforward, and genuinely cares about his customers. He clearly explained the tile roof replacement process, answered all my questions, and made sure the work was completed properly. If you’re looking for a dependable roofing contractor in West Palm Beach, Florida, I highly recommend Fiddlers Roofing for quality roofing work and trustworthy service!
  
 
      Posted on Google  
   
   Springfield MB Church 
 
 
 
 Trustindex verifies that the original source of the review is Google. Working with Kevin and his team was great.  They kept us informed with important updates and did a wonderful job with roof.
  
 
      Posted on Google  
   
   Brent Winters 
 
 
 
 Trustindex 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 Gonzalez 
 
 
 
 Trustindex 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 Downard 
 
 
 
 Trustindex 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 fraser 
 
 
 
 Trustindex 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 Castellano 
 
 
 
 Trustindex 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 Mills 
 
 
 
 Trustindex 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 Hause 
 
 
 
 Trustindex 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 Hause

Roof Repair & Roof Leak Detection

A ceiling stain tells you there is a problem, but it does not necessarily identify where the water entered. Our repair assessment looks beyond the visible symptom to inspect the surrounding roofing materials, flashing, valleys, and penetrations.

We evaluate damaged shingles, displaced materials, deteriorated details, and previous repairs before recommending the work. When a targeted repair is appropriate, we explain what it will address. When the damage is widespread or the roof is approaching the end of its useful life, we discuss whether replacement offers a more practical solution.

Roof Repair for Storm & Wind Damage

High winds and falling debris can damage a roof even when the full extent is difficult to see from the ground. Following severe weather, a professional assessment can help you understand which areas need attention.

Fiddler’s Roofing evaluates storm-related damage and can provide photographs and a repair or replacement estimate for your records. We explain the roofing work recommended for the property; any insurance coverage decision remains with your carrier.

For a roof affected by a storm or an active leak, call (689) 407-4077 to discuss the situation and inspection availability.

Roof Replacement & New Roof Installation in Windermere

Replacing a roof is an opportunity to address the complete roofing system—not just change the surface material.

We assess the existing covering, visible decking, ventilation, drainage, and roof details before preparing a proposal. Your written estimate should explain the selected materials, preparation work, underlayment, flashing, deck-repair allowances, cleanup, permit responsibilities, and warranty terms.

The price depends on the roof’s measured area, complexity, material selection, and required repairs. A property-specific estimate gives you a more useful basis for planning than a general price per square foot.

Metal Roofing That Fits Your Home’s Architecture

Metal roofing offers more than one look. We help you compare systems that suit your home’s exterior, roof shape, and maintenance expectations, from traditional profiles to clean vertical panels.

QueenTile Stone-Coated Steel Roofing

Prefer the appearance of tile, shake, or slate? QueenTile combines formed steel panels with a textured stone-coated finish.

Its architectural profiles offer alternatives to the vertical-panel appearance commonly associated with metal roofing. We review the available profiles, colors, and installation requirements so you can compare the proposed system with your home’s design. Product choices are subject to availability.

Standing Seam Metal Roofing

Standing seam creates a streamlined appearance with raised seams and concealed attachment points. Fiddler’s Roofing installs systems using steel supplied through Metal Alliance.

Available 24- and 26-gauge options depend on the selected panel, finish, roof design, and project requirements. The proposal identifies the complete system, including the details needed at edges, transitions, and roof penetrations.

GAF Shingle Roofing & Tile Roof Repair

Asphalt Shingle Roofing

For homeowners considering a shingle roof, we install qualifying GAF roofing systems and help explain the available product and warranty options.

Fiddler’s Roofing holds GAF Master Elite® certification. Enhanced warranty eligibility depends on the system installed and the applicable written terms; coverage should be confirmed for your specific proposal.

Tile Roof Repair

A tile roof problem may involve more than a broken tile. We evaluate the affected area for displaced materials, flashing defects, penetration issues, and possible underlayment concerns before defining the repair scope.

Commercial Roofing in Windermere

A commercial roofing project needs to account for the building’s operations as well as its roof.

Fiddler’s Roofing works with business owners, property managers, and facility teams on inspections, leak investigation, repairs, maintenance, and replacement. Available systems include commercial metal roofing, TPO, modified bitumen, and coatings for eligible roofs.

We review drainage, rooftop equipment, access, existing materials, and building-use requirements before recommending a solution. Where restoration is being considered, the existing roof must be evaluated to determine whether it is a suitable candidate.

Free Roof Inspections: Know What Needs Attention

Not sure whether your roof needs a repair or a replacement? Start with an inspection.

Depending on access and conditions, we examine visible roofing materials, flashing, penetrations, drainage, previous repairs, and signs of moisture or storm damage. We explain identified concerns, provide photographs of problem areas, and discuss the next steps.

A standard inspection is primarily visual and non-destructive. Suspected damage beneath the roof covering may require further investigation before the full scope can be confirmed.

Roofing Planned for Central Florida Conditions

Sun exposure, humidity, heavy rain, and storm winds all belong in the conversation when planning a Windermere roofing project. Material selection matters, but so do the roof’s drainage, ventilation, and installation details.

We consider the complete assembly, including underlayment, flashing, attachment methods, and transitions. A material name alone does not establish how the finished roof will perform; the selected products and installation must work together as a system.

Windermere Roofing Permits & Community Requirements

Confirm the Permitting Process for Your Property

Before setting the installation schedule, confirm the permitting authority and requirements for the project address. For projects under the Town of Windermere’s jurisdiction, building department services are provided through PDCS.

The roofing proposal should identify responsibility for permit submissions, supporting documentation, and required inspections, so these items are addressed before work begins.

Review HOA Requirements Before Selecting Materials

For a home subject to homeowners association requirements, confirm any necessary architectural approval before finalizing the roofing material, profile, or color.

Bring applicable community requirements to the consultation. Permit documentation and HOA approval should be addressed as distinct project requirements, with responsibilities identified in the written scope.

What to Expect From Your Roofing Project

Assessment and recommendations. We inspect the accessible roof areas, discuss your concerns, and compare appropriate repair or replacement options.

A written proposal. You receive the proposed scope, material selections, pricing, allowances, and project terms before authorizing the work.

Preparation and installation. The project proceeds through the agreed preparation, approved deck repairs, and installation of the specified roofing system.

Cleanup and completion. We review the completed work, remove project debris, and coordinate the required closeout steps and inspections applicable to the project.

Why Work With Fiddler’s Roofing?

Central Florida Experience

Fiddler’s Roofing has served Central Florida since 2003. Our approach emphasizes attention to the customer, respect for the property, and clear communication throughout the work.

Roofing Credentials You Can Check

Our Florida roofing contractor license is CCC1333004, listed by the state under Kevin Daus and Fiddler’s Quality Roofing, LLC. Fiddler’s Roofing is also listed by GAF as a Master Elite® contractor.

Options Beyond One Roofing Material

Metal roofing is a specialty, but it is not the only option we offer. We help you compare the proposed system with alternatives and explain the work needed for your property.

Serving Windermere & Nearby Communities

Contact our Windermere location on Conroy Windermere Road for help with your roofing project.

Alongside Windermere, Fiddler’s Roofing lists service in Bay Hill, Gotha, Dr. Phillips, Ocoee, and Winter Garden, with Horizon West also covered on the company’s website.

Call (689) 407-4077 with your property address to discuss the work you need and confirm scheduling.

Financing for Eligible Roofing Projects

A roof repair or replacement can be an unexpected expense. Fiddler’s Roofing offers access to financing through Service Finance Company, LLC for qualified homeowners and eligible projects.

Ask about available programs when requesting your estimate. Approval, interest rates, repayment terms, and promotional conditions are determined by the financing provider. Review the financing agreement before accepting an offer.

Windermere Roofing FAQs

How Do I Know Whether to Repair or Replace My Roof?

The decision depends on the extent of damage, the condition of the remaining roof, previous repairs, and the value of further repair work. An inspection helps establish which approach is appropriate for your property.

Can I Choose a Metal Roof Without the Vertical-Panel Look?

Yes. QueenTile stone-coated steel offers tile-, shake-, and slate-inspired profiles. These provide a different architectural appearance from standing seam panels. Available options depend on the product line and your project’s requirements.

What Will My Roofing Estimate Include?

Ask for a scope that identifies the roofing system, preparation, installation work, repair allowances, project price, schedule, and exclusions. Permit responsibility and warranty terms should also be clear before work starts.

Do You Inspect Roofs After Wind or Storm Damage?

Yes. We assess visible storm-related conditions and can provide photographs and an estimate for recommended repairs or replacement. Contact your insurance provider directly for questions about coverage.

Do You Work on Commercial Properties?

Yes. Our commercial services include inspections, repairs, maintenance, restoration, and replacement, with the roofing system selected according to the building and project requirements.

How Do I Schedule a Roof Inspection in Windermere?

Call (689) 407-4077 or submit the inspection request form with your contact information, property address, and a brief description of the issue.

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