Take a look at our past work!

Charleswood Roofing & Exteriors

The company performs work related to Pewter, Moire Black, CertainTeed Landmark PRO, Weathered Wood, CertainTeed Landmark

Our Work

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
7 Haddington Bay , Winnipeg, MB, US
  • CertainTeed Landmark PRO
  • CertainTeed Landmark PRO: Driftwood

Customer Testimonials

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Justen Forge
Excellent! Professional, prompt, personable and precise! Highly recommended! We needed a new roof, long overdue in fact. Andrew from Charleswood Roofing responded quickly, attended promptly onsite with an estimate and quote. Aaron showed up to install the new shingles, which had already been delivered onto the roof earlier. I am truly impressed with the careful attention to detail, efficiency and organization that the installer employed. The finished job looks amazing. You couldn't tell anyo... Read more
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bruce nahorny
Charleswood roofing delivered as promised ; called every day to explain the progress on my roof and was very professional in all respects They took extra care in ensuring no nails were left on the site; did my roof in 2 days with 5 staff on hand..I have used them in the past for roof repairs and I CERTAINLY RECOMMEND THEM.Their staff is prompt and pay attention to detail.Also ; never a problem to reach them by phone.
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Alison Miller
We were thrilled with the service! The crew showed up on time and worked so hard putting in an almost 12 hour day to get the job done in one day! They left the site absolutely spotless, you would never have known they had been there if it weren't for the new roof! They let me know when they arrived on site and when they were leaving. Checked to see if I had any questions and answered any questions I had about the condition of the roof under the old shingles. Would definitely recommend Charles... Read more
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Tara Zevena
The crew that replaced our shingles was professional and personable. We paid what we were quoted and the job site was clean when the crew departed. Thank you!
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Mark Melsness
We recently had our roof and eavestroughs replaced due to damage from last year's hailstorm. There were many emails back and forth with our insurance company. Charleswood Roofing really went to bat for us to get a fair replacement. They also did the work earlier than expected to avoid the anticipated additional tariff costs.