Your Trusted Southwest Florida Roofing Experts

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When it comes to protecting your home or business, you need a roofing company you can rely on. At Black Flag Roofing, we bring local expertise, personalized service, and unmatched reliability to every project. Serving Southwest Florida—including Lee and Collier Counties—and beyond, we’re your neighbors, committed to keeping your roof strong against hurricanes, wind, and the ultimate test of time.

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Roofing Done Right—By Locals, For Locals

Founded by Chris Little and Spenser Pollard, Black Flag Roofing is built on a promise: to deliver white-glove service with a personal touch. We’re not a faceless corporation—we’re a locally owned team, directly involved in every job, ensuring your peace of mind. From residential shingles to commercial waterproofing, we’ve got Southwest Florida covered.

Why Choose
Black Flag Roofing?

Local roots

Local Roots

Proudly serving Southwest Florida with knowledge of our unique weather challenges.

Trusted Quality

Trusted Quality

High standards for every roof, every time—residential, commercial, or multi-family.

Reliable Response

Reliable Response

Fast, reachable, and ready to tackle hurricane damage or urgent repairs.

Our Services

At Black Flag Roofing, we offer a full range of roofing services tailored to the unique needs of our community. From storm-ready residential roofs to durable commercial systems, our local expertise ensures your property stays protected. Owners Chris Little and Spenser Pollard oversee every project, delivering the white-glove service Southwest Florida trusts.

What Our
Customers Say

When it comes to roofing, there is no one I trust to take care of my clients more than Spenser at Black Flag Roofing. His professionalism, integrity, and commitment to quality are second to none. In an industry where trust and reliability are everything, Spenser stands out as someone who truly delivers on his word. He approaches every project with transparency and clear communication. We never feel like we are getting ripped off or taken advantage of and his pricing is always competitive. Living in South Florida, a dependable roof is crucial — with Black Flag, we have complete confidence that our clients are in the best hands. If you’re looking for a roofing company you can truly trust, Spenser and his team should be your first and only call. 

-Anthony Caraballo

Broker Associate at The McCumber Group

Working with Spenser and Chris at Black Flag Roofing was a breath of fresh air. From the beginning, it was clear that this wasn’t just about selling a roof—it was about building trust and doing right by their clients. These two genuinely care more about the people they serve than the paycheck, and that kind of integrity is rare in this industry. I had the pleasure of seeing firsthand how committed they are to quality, transparency, and true professionalism. There’s no doubt in my mind that Black Flag Roofing is going to thrive—because when you put the customer first, success always follows. 

-Tyler Yehl

I had a new roof put on my house in 2023. My experience with Spencer Pollard from first meeting him and throughout the entire process was nothing but professional. His character is a reflection of his success in the roofing business. He is genuine, polite, kind, trustworthy, thorough, knowledgeable and an all around great person. To this day he continues to be available to me if anything should arise. I would hands down highly recommend Spencer if you are looking for a new roof. You will not regret the decision. 

-Kathy Polk

I worked with Chris Little and Black Flag on several projects already. I was very impressed with both their ability to work out claims with insurance companies, as well as roofing skills. The entire process was very detail oriented, from the initial staging of the equipment needed to replace the roofs,  to keeping the owners informed with the progress with weekly updates to us as management. I also use Black Flag for our yearly maintenance needed on many associations. Its nice to finally work with a company that has someone that answers the phones and gets leaks, maintenance and replacements done in a timely manner. We really appreciate what they did for our company in making replacement of roofs as simple as it can possibly be. Thanks Chris!!  

-Paul Farese
President of Cambridge Management

I had the pleasure of working with Chris, and I can confidently say that he's incredibly professional and efficient. He went above and beyond to help one of my clients resolve an issue with their roof, showing a level of care and commitment that truly sets him apart. Chris is not only highly skilled in his field but also down-to-earth and genuine in his approach. He’s the kind of person who is always willing to go the extra mile to help others, no matter the situation. His honesty and work ethic speak for themselves, and I trust him completely. I highly recommend his services to anyone, as I know the quality of work his company delivers is top-notch and dependable. 

-Corey Small
The Local Insurance Finders