Take a look at our past work!

Charleswood Roofing & Exteriors

The company performs work related to Weathered Wood, Kaycan Wolf White, Moire Black, CertainTeed Landmark PRO, CertainTeed Landmark

Our Work

69 Deloraine Dr. , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Driftwood
55 Colebrook Dr. , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Weathered Wood
59 Hillberry Bay , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Moire Black
619 Elmhurst Rd , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Burnt Sienna
6 Marston Drive , Headingley, MB, CA

Customer Review


Charleswood Roofing installed new shingles on our house & shed this week in Headingley. I'm very satisfied with the complete experience. Jerry gave me samples to take home to show my wife, and he also gave us locations where we could view various shingle colours on houses they had done so we could see them installed. Jonathan & Jerry were great to deal with and Josh's crew were obviously very experienced, and competent. They did a very careful job and did complete cleanup after. Jonathan came later to do an inspection and also performed some extra detailed work in a known problem area with poor drainage. I highly recommend Charleswood Roofing.

  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Burnt Sienna

Customer Testimonials

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Michelle Bell - 1280 Liberty Street , Winnipeg, MB, CA
The entire experience was great. From prompt replies for the quote, detailed breakdown of costs and options, ease of payment and communication about the job. Really appreciated the attention to detail and how well the crew cleaned up every night. Our new roof looks great and I would recommend them to anyone looking for quality work done professionally.
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the pegger
Our home was in the narrow path of one of the recent hail storms. After the neighbours started making claims, I contacted our insurance provider. Their agent arrived, stated that we needed the shingles and eaves trough replaced and then emailed me a quote. I emailed them back, thanked them for their quote and asked a couple of questions. No reply, I emailed again, no reply. I called them and left a voice mail, no reply. I then called the company (name I recognized) that was doing the roof ... Read more
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christine.hanna1
Called early morning 03Nov2025. 2 nice gentleman fixed the shingle within hour and finished same day 4:00pm. Thanks so much we appreciate as winter is just around the corner..
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Ron Statham - 22 Inverness Boulevard , Winnipeg, MB, CA
A pleasurable experience, professional,respectful,honorable and fair. Totally recommend. Ron Statham
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Stuart Irvine - 18 Woodfield Bay , Winnipeg, MB, CA
This is our second roof by Charleswood Roofing. Communication, price, quality of work and speed of completion was all first class. They are very organized (probably because they have been reroofing homes in Charleswood, especially, for many years). I always recommend them to anyone I know who is needing a new roof.