Checkered Flag Roofing . . . A Winning Decision!

Making Checkered Flag Roofing The Trusted Roofing Contractor in Burlington & South East, WI.

We Are Wisconsin’s Hail & Storm Damage Experts.


We know the ins and the outs of storm damage and insurance claims. Checkered Flag will walk you through the entire process and make sure that if your house has been damaged from a storm that you will be compensated.

Call today for a FREE Hail Inspection of your property!

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Wisconsin Hail Damaged Roof

Checkered Flag Roofing Offers Many Services

We are Burlington’s full service roofing contractor. There is no need to call more than one contractor, at Checkered Flag Roofing we handle all of your roofing and siding needs.

Storm Damage Repair

Determining if your house has storm damage or knowing how to contact your insurance company to file a claim can be a daunting and confusing undertaking. Checkered Flag is here to help you through the entire process.

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Wisconsin Roof Leak Inspection

Residential Roofing

Residential roofing is our pride and joy. This is what we do on a daily basis. We are detail oriented and make sure that your roofing job is completed properly.

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Wisconsin Siding


We believe that siding is a service that should go right along with roofing. We help you choose what styles and materials will work best for your home. A new face lift makes for great curb appeal.

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Soffit & Fascia

The installation of soffit and fascia is a detail oriented process, that requires years of experience. Make sure that on your next facia or soffit job you contact Checkered Flag Roofing first.

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With the variety of gutter options, we will walk you through the differences. Choosing between seamless gutters or picking what type of gutter guard works for your home, we will help you decide what fits your budget.

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Commercial Roofing

Whether its for your home or business, we are the contractor for you. We specialize in small to midsize commercial roofs. With our experience and knowledge, protecting your home or business is our #1 priority.

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You Can Trust Checkered Flag, Your Local Burlington Roofing Contractor

Here at Checkered Flag we do things by the book and cut no corners. When choosing a contractor to work on your roof or siding, make sure that you choose one that you can trust!

Fully Insured Burlington Roofing Contractor

Fully Insured

We are fully insured to protect you and your home from start to finish.

BBB A+ Rating

At Checkered Flag Roofing our reputation is everything. Our A+ BBB rating has been earned through hard work and dedication to our customers.

Wisconsin Licensed Roofers


We are a fully licensed roofing and siding contractor in South East Wisconsin. Checkered Flag Roofing is the contractor that you can trust.

Why choose Checkered Flag Roofing?

  • No Obligation Estimates

  • Full Service Roofing Contractor

  • Fast Turnaround

  • Premium Quality Work

  • Fully Insured

  • Fully Licensed in WI

  • A+ BBB Rating

  • 5 Year Labor Guarantee

  • Specialize in Storm Damage Repairs

  • Insurance Claim Experts

  • Owner / Operator

  • Over 20 Years Experience

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Our Guarantee

We are Wisconsin’s trusted roofing contractor, we stand behind our work! To prove how much we are dedicated to your job, we have a 5 year labor guarantee! You can rest with ease when you choose Checkered Flag Roofing for your next home improvement project.

Commercial Roofing Contractor Burlington

About Us

Established in 2010, Checkered Flag Roofing was created out of the necessity for a better way of approaching the home improvement needs of the customer, the community and the latent stigma of the contractor base. The industry had a bad reputation and Checkered Flag Roofing was going to change it !!

Checkered Flag Roofing listens to their customers and as a team develop and initiates what is best for the homeowner.  We pride ourselves in educating the homeowner in design options – from products and colors to workmanship standards and structural integrity !

Checkered Flag Roofing IS your winning decision – and the contractor of choice for your next exterior home improvement project !

Customer Reviews: We Love Our Customers, And They Love Us.

We are fully dedicated to customers. When you choose Checkered Flag Roofing, there is no need to worry about customer support. With all of our happy clients, you cannot go wrong with Checkered Flag. Check out what our customers are saying about us!

“Everything about Checkered Flag was simply awesome!”

“Vince was wonderful to work with and my roof is beautiful! I had several quotes and Checkered Flag was by far the most reasonable and affordable! I met up with Vince early in the morning and by the time I got home that evening, I not only had a new roof, but everything was cleaned up perfectly. I would never have known they were even there! I highly recommend Checkered Flag! I hear they do more than roofs, too!”Michelle T

Checkered Flag is a great roofing company! Vince and his crew put a new roof on my house about a year ago. They are very professional and easy to work with. They go above and beyond what is promised. The work quality is top notch and fairly priced. Recently I had a leak on a rental property I own. I called Vince and he immediately came by to look at the situation. After accessing the problem he told me of chimney repair company the is better suited to handle the leak. I called the recommended company and my problem is now gone. Thank you Checkered Flag. You are a class act!!
David S.
Checkered Flag Roofing was hired to roof and side our 100+ year old home.We found the owner to be very helpful,knowledgeable,reliable and listened to our concerns.The extensive work was finished in a timely manner and exceeded our expectations! The workers were professional,neat and considerate.We are very pleased with the end result.WE HAVE recommended this company to many of our friends!
Susan C.
Simply said, Vince did a great Job. He paid very close attention to detail and did extra stuff other roofing contractors wouldn’t normally do. For no extra charge Vince painted the old vent caps to match the new ones (his idea). He also cut up and removed a very old tv antenna from site. Checkered Flag Roofing deserves every referral that I can send their way.
Jack R.
I sit on the board of a condo complex in Pewaukee, WI. Checkered Flag Roofing did a very large job re-roofing our entire complex due to hail damage claim we had with our insurance company. The owner was very hands on and did an excellent job guiding us through the process and working with our insurance adjuster to make sure we the customer were taken care of properly. They were both very knowledgeable with regards to all aspects of the job. Their crews were also very professional and they did a great job with clean up and all of our residents in the complex were pleased. This large project went off without any problems at all and Vince communicated with our board on a daily basis while the work was being done. I would recommend Checkered Flag Roofing to anyone who is looking to have any work done on their roof. These guys did an excellent job.
Scott O.

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