Take a look at our past work!

Charleswood Roofing & Exteriors

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

Our Work

83 Kinlock Ln , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Driftwood
51 Forestgate Ave , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Driftwood
23 Huntsman Cir , Winnipeg, MB, US
  • CertainTeed Landmark
  • CertainTeed Landmark: Georgetown Gray
35 Huntingdale Road , Winnipeg, MB, CA

Customer Review


We had Charleswood Roofing (CWR) do a complete re-shingling of our roof in May 2020, and we were very happy with the entire process.

Within a few days of initially contacting CWR, the company owner (Jonathan) came out to examine our roof and to take measurements. A couple of days later we received a detailed roofing estimate via email. This estimate included options and costs for various grades of shingles, as well as links to websites that provided additional information on these types of shingles.


A few days later we met with Jonathan at the CWR office, and he patiently answered all of our questions which helped us in picking out our desired shingle type and colour.


Once installation day arrived, Josh and his roofing team arrived at 7:30 AM to start preparing the work area around our house - laying down drop cloths to protect our back deck, and front yard from any debris. By 8:00 AM the team was on the roof and ripping off the old shingles. Despite the very warm weather, these guys were consistently pleasant and professional as they went about their roofing work. This roofing project took two days to complete, and the final result was a beautiful new roof that we are very happy with. On completion of the roofing work on day # 2, and before leaving our property, the roofing team did a thorough clean up of the yard, picking up any debris that could be found.


On the day after the roof was complete (Day 3), two additional CWR supervisors came by to do a final inspection of the roof work. They got up on the roof to examine the new shingles, and cleaned up any missed debris and roofing nails that may have fallen into the eaves trough. After coming down from the roof, they also walked around the entire yard with a special tool (large magnet on wheels) that picked up any roofing nails that were hiding in the grass. They also answered any final questions that we had concerning the roofing work that was done.

We found this entire process to be very thorough, and the CWR staff were very friendly and professional. We are quite satisfied with the entire experience of working with Charleswood Roofing, and we would certainly recommend them to anyone looking to re-shingle their roof.

  • CertainTeed NorthGate
  • CertainTeed NorthGate: Driftwood
19 Waterbury Dr , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Driftwood

Customer Testimonials

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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.
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David Yarycky - 631 Waterloo Street , Winnipeg, MB, CA
Charleswood Roofing did an amazing job to get my project finished. It wasn’t a big job but they were professional right from the start to finish. They came when the said, finished the job from start to finish and left my property how they found it. I would recommend Charleswood Roofing and will use them on my next project.
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Mitchell Rygiel - 15 Prominence Point , Winnipeg, MB, CA
We hired Charleswood Roofing & Exteriors to install HardieBoard siding on our home, and we are pleased with the results. Throughout the installation process, the team demonstrated a high level of professionalism, skill, and attention to detail. The installation was completed using industry best practices and finished within the expected timeline. The craftsmen on-site were not only knowledgeable, but also proactive in problem solving when they encountered a unique challenge during the install. T... Read more
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Luda Fain
The Charleswood Roofing made all in the best quality, gave extend explanation about the work. We very appreciate their service. The price is fair , worth every dollar invested. Thank the company and all their workers.
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Gerald Medel
Charleswood Roofing responded to my request for eavestrough service promptly and professionally. Their crew contacted me the day before the project began, communicated with me throughout, and sent me photos of the final product once they were finished. My yard was clean and tidy when I got home and the eavestroughs looked great. 10/10, would recommend!