Best Roofers in Winter Park FL: How to Choose the Right Contractor

Written by the licensed roofing professionals at 3MG Roofing & Solar, headquartered in Winter Park, FL. Updated February 2026.

How Do You Find the Best Roofing Company in Winter Park?

The best roofers in Winter Park FL are Florida-licensed, carry both general liability and workers compensation insurance, hold manufacturer certifications from brands like GAF and Owens Corning, maintain a local physical presence, and have verifiable track records with real customer reviews. Winter Park’s mix of historic homes near Park Avenue, HOA-governed communities in Baldwin Park and Windsong, and modern developments in surrounding areas requires a roofing contractor with versatile experience across all residential roofing systems. Here is how to evaluate contractors and choose the right one for your project, from a company headquartered right here in Winter Park.

What Should You Check Before Hiring a Winter Park Roofer?

Hiring the wrong roofing contractor is one of the most expensive mistakes a homeowner can make. A botched installation can void manufacturer warranties, create hidden leaks that cause thousands in interior damage, and leave you with no recourse if the contractor disappears. These criteria separate legitimate Winter Park roofing professionals from the contractors you should avoid.

Is the Contractor Licensed in Florida?

Every roofing contractor in Florida must hold an active state roofing license issued by the Department of Business and Professional Regulation [1]. There are two types: a Certified Roofing Contractor license (CCC) that allows work statewide, and a Registered Roofing Contractor license that is limited to specific counties. Verify any contractor’s license status, disciplinary history, and workers compensation compliance at myfloridalicense.com before signing anything. Unlicensed contracting is a felony in Florida, yet it remains common after storms when demand surges and homeowners are eager to get repairs started quickly.

Does the Contractor Carry Proper Insurance?

Beyond licensing, confirm the contractor carries both general liability insurance with a minimum of $1 million in coverage and active workers compensation coverage for all employees. Without workers comp, you as the homeowner could be held liable for medical costs if a worker is injured on your property during the roofing project [2]. Ask for current certificates of insurance and call the insurance carrier directly to verify the policy is active and has not lapsed. A legitimate contractor will provide these documents without hesitation.

Does the Roofer Have Manufacturer Certifications?

Top roofing companies earn certifications from major manufacturers like GAF Master Elite, Owens Corning Platinum Preferred, and CertainTeed SELECT ShingleMaster. These certifications require demonstrated installation expertise, ongoing training, and meeting strict business requirements including proper licensing and insurance. The practical benefit for you as a homeowner is enhanced warranty coverage. A certified installer can offer manufacturer warranties that cover both materials and workmanship for up to 50 years [3], while non-certified installers can only offer limited material-only warranties that leave you paying for labor if something fails.

Is the Contractor Local to Winter Park or Orlando?

Choose a contractor with a physical office in Winter Park or the greater Orlando area. Local companies have reputations to protect within the community, relationships with local building inspectors and suppliers, and are accessible for warranty service years after your project is complete. Storm chasers who follow weather events from out of state are often gone by the time warranty issues arise, leaving you with no recourse on a workmanship failure. Check Google Maps to confirm the contractor’s listed address is a real office location, not a virtual address or P.O. box.

What Should a Roofing Estimate Include?

A professional roofing contractor provides detailed written estimates that itemize materials by brand and product name, labor costs, permit fees, tear-off and disposal, underlayment specifications, flashing and accessory details, and any structural repairs needed. Vague one-line quotes, verbal estimates, or bids that simply state a lump sum with no breakdown are red flags that often lead to surprise change orders and corners cut during installation. You should be able to compare estimates from multiple contractors line by line to understand exactly what each one includes in their scope of work and where the differences lie.

What Red Flags Should Winter Park Homeowners Watch For?

The Central Florida roofing market includes many excellent contractors, but it also attracts bad actors, especially after major storms. Knowing what to avoid is just as important as knowing what to look for. Be immediately cautious of any contractor who demands a large deposit or full payment upfront before work begins — reputable contractors typically require no more than 10 to 30 percent to schedule the project, with the balance due upon satisfactory completion.

Other warning signs include contractors who offer to waive your insurance deductible, which is insurance fraud under Florida law. Door-to-door solicitors who arrive uninvited after a storm and pressure you to sign a contract on the spot should be declined regardless of what they promise. Contractors who want to handle your insurance claim for you through an Assignment of Benefits agreement are another risk — Florida’s 2022 insurance reforms restricted AOB abuse, but pressure tactics persist. Always take time to verify credentials, compare options, and make an informed decision on your schedule, not theirs.

What Roofing Challenges Are Unique to Winter Park Homes?

Winter Park has a distinctive housing stock that creates specific roofing considerations most generic contractors overlook. The historic homes in neighborhoods like Virginia Heights, Brewer Estates, and along Interlachen Avenue often feature older roof structures with non-standard framing, original wood decking that may need partial replacement, and architectural details like dormers, turrets, and steep pitches that require specialized flashing and installation techniques. Working on these homes without understanding their construction can lead to damage that is expensive to repair.

Winter Park’s newer HOA communities including Baldwin Park, Windsong, and Ravaudage have strict architectural review committees that regulate roofing materials, colors, and profiles. Before selecting a material, check your HOA’s guidelines and submit your proposed materials for approval. Many Winter Park HOAs require tile roofing or specific shingle color palettes, and installing non-compliant materials can result in fines and forced replacement at your own cost. An experienced local contractor like 3MG Roofing & Solar knows these community requirements and can guide you through the approval process before ordering materials.

How Much Does a Roof Replacement Cost in Winter Park?

Roof replacement costs in Winter Park generally align with Orlando area pricing, ranging from $11,000 to $30,000 for a standard residential home depending on roof size, material choice, and project complexity. However, Winter Park projects sometimes run higher due to the prevalence of tile roofs in HOA communities, the additional care required on historic homes, and the higher-end material selections that complement the neighborhood aesthetics. Homes in Windsong or along Palmer Avenue with tile roofs on 3,000-plus square foot homes can see projects in the $35,000 to $50,000 range. Get a detailed breakdown of pricing by material in our Orlando roof replacement cost guide.

How Do You Verify a Roofing Contractor’s Reviews and Reputation?

Online reviews are one of the most reliable indicators of contractor quality, but you need to know where to look and what to look for. Start with Google Business Profile reviews since these are the hardest to fake and show the most recent customer experiences. Check the BBB at bbb.org for accreditation status, complaint history, and resolution patterns. Angi and HomeAdvisor reviews provide additional data points but are less reliable as standalone indicators since contractors pay for placement on those platforms.

When reading reviews, look for specifics rather than generic praise. Reviews that mention the crew’s punctuality, cleanup quality, communication during the project, and how the company handled any issues that arose tell you far more than five-star ratings with no detail. Also pay attention to how the company responds to negative reviews — a professional, constructive response to criticism indicates a business that takes accountability seriously. Ask the contractor for references from recent Winter Park projects and actually call them to ask about their experience from start to finish.

Why Winter Park Homeowners Choose 3MG Roofing & Solar

3MG Roofing & Solar is headquartered at 1127 Solana Avenue in Winter Park, making us true neighbors in the community we serve. We hold a BBB A+ rating, serve as the official roofing and solar partner of UCF Athletics, and have completed hundreds of residential roofing projects across Winter Park, Orlando, and Central Florida since our founding. Our team understands Winter Park’s unique architectural styles, HOA requirements, and the specific challenges of working on both historic homes and modern developments in the area.

We install asphalt shingles, metal roofing, and tile systems, with expertise in all three materials and the ability to match virtually any HOA specification. Every project includes a free comprehensive inspection, detailed written estimate with no hidden fees, permit management, and a workmanship warranty backed by our local presence. We also offer flexible financing options so Winter Park homeowners can invest in the right roofing system for their home without compromising on quality due to budget constraints.

Frequently Asked Questions

How many quotes should I get for a roof replacement in Winter Park?

Getting two to three detailed estimates from licensed contractors gives you a fair basis for comparison. Be wary of both the highest and lowest quotes and focus on the scope of work, material quality, warranty terms, and the contractor’s local reputation rather than price alone. The cheapest bid often excludes items that will appear as change orders once work begins.

What should a roofing contract include in Florida?

A proper Florida roofing contract should include the full scope of work with material specifications and brands, start and estimated completion dates, total cost with a payment schedule, warranty information for both materials and workmanship, confirmation that the contractor will pull all required permits, cleanup and disposal responsibilities, and a provision for how change orders are handled if unexpected issues arise during tear-off.

How long has 3MG been serving Winter Park?

3MG Roofing & Solar has been headquartered in Winter Park since founding and has grown into one of Central Florida’s most trusted residential and commercial roofing companies. Our Solana Avenue office is staffed with project managers, estimators, and customer service representatives who are available throughout your project from initial consultation through final walkthrough.

Do Winter Park HOAs require specific roofing materials?

Many Winter Park HOAs have architectural guidelines that specify approved roofing materials, colors, and profiles. Communities like Baldwin Park and Windsong commonly require tile or specific architectural shingle options. Always submit your proposed materials to your HOA’s architectural review committee for approval before ordering. 3MG handles HOA coordination as part of our standard project management process to prevent delays and compliance issues.

What is the best roofing material for historic Winter Park homes?

For historic Winter Park homes, the best material depends on the home’s architectural style and any local historic preservation guidelines. Architectural shingles in period-appropriate colors work well for many Craftsman and Colonial-era homes. Metal standing seam in dark bronze or matte black complements mid-century and contemporary historic homes. Tile remains the standard for Mediterranean and Spanish Colonial styles found throughout older Winter Park neighborhoods. A qualified contractor will assess your home’s structure, style, and any preservation requirements before recommending a material.

References

  1. Florida Department of Business and Professional Regulation. “Contractor Licensing Requirements.” myfloridalicense.com
  2. Florida Statutes §440. “Workers’ Compensation Law.” flsenate.gov
  3. GAF. “Master Elite Contractor Program.” gaf.com

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