Take a look at our past work!

Charleswood Roofing & Exteriors

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

Our Work

319 Belvidere St , Winnipeg, MB, US
  • CertainTeed Landmark
  • CertainTeed Landmark: Georgetown Gray
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

Customer Testimonials

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Great Nate Eavestrough Cleaning
We recently worked with Charleswood Roofing and were thoroughly impressed with their professionalism, communication, and quality of work. As a service-based company ourselves, we truly value punctuality and safety on-site—and they deliver on all fronts. — Great Nate Eavestrough Cleaning Inc.
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Ryan Harras - 478 Saint Charles Street , Winnipeg, MB, CA
Very professional and courteous company to deal with. Employees were respectful, on-time, knowledgeable, and did a great job. Could tell that they take pride in their work. Highly recommend!
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Sylvia Lagasse - 5677 Rannock Avenue , Winnipeg, MB, CA
Jonathan and Aaron, owners of Charleswood Roofing, are the most professional, friendly and dedicated people I have ever had the pleasure of hiring. Thank you for all the great services and and most especially your kindness. Thx a bunch!
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Marc Landry - 3602 Vialoux Drive , Winnipeg, MB, CA
I had my roof, soffits, fascia and eavestroughs replaced by Charleswood Roofing. Out of all quotes i received Charleswood was by far the most thorough, and their pricing was as competitive as the others. They brought up possible issues, and suggestions that none of the other companies even mentioned. They were also the only company that brought up safety. Work was completed as per schedule, and I was very happy with the final product. I would recommend to friends and family.
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Jon Pilkey - 51 Atkinson Road , Winnipeg, MB, CA
I was very impressed with Aaron Scott who helped me out with the repair on my roof. He was very professional and was able to repair it in a timely manner.