Charleswood Roofing & Exteriors

All 8 of the one and two-star reviews we hold for Charleswood Roofing & Exteriors, most recent first.

• 1 out of 5Katelynne SEdited a month ago

  Hired them to complete eaves and downspouts. They installed only 4 downspouts for the entire house (causing pooling of water in sections) I hired them based on their reviews, especially as a first time home owner leaving this review so …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Hi Katelynne, We are sorry to hear this is your opinion, especially after all of the detailed conversations we have had with you about the ice damming causing the eaves trough to overflow. We understand too that there are some details on your older home which cause an eyesore when we install the trough level. Unfortunately, should we install it to follow the eaves, it would not properly shed water. We have certainly not cut off communication on this issue and hope that you are open to discussing our suggestions and options for solutions to these problems, however we do maintain that the installation itself was done well and you have some other unfortunate contributing factors such as weather/climate and shifting foundation issues to contend with. Please feel free to contact us again. You have our number!

• 1 out of 5Justin Kace2 months ago

  Yesterday on Apex Street, I observed a Charleswood Roofing crew working during a rainstorm with thunder and lightning in the area. Several workers appeared to be wearing runners rather than footwear typically …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Good Morning Mr. Kace! Thank you for outwardly and publicly expressing your “concern”, even though you weren’t able to tear yourself away from Google reviews to make a call to emergency services yourself while you thought that someone might be hurt! I hope the serotonin and dopamine rush from you writing this post was epic! There are a few minor corrections that need to be made for this, your second Google review, (both one star interestingly)... No one fell off a roof. This is perhaps an important detail to you. I’m assuming you didn’t have a great vantage point, which may also be why you missed harnesses on the roof. A ladder did slip from a solid footing which became instantly slick with the sudden and unexpected rain! Thankfully, no one was hurt, and those of us who have true care for our crews and weren’t worried about concern-trolling did ensure that the person was double-checked for injuries by medical professionals! They are happily back at work now, enjoying our positive-attitude work environment and the love they receive as part of our crew. Running shoes with a grippy sole are some of the best footwear for roofing! They provide excellent traction on slopes - which is what they are designed for!!! The rain, which came suddenly, did catch the crew by surprise and they immediately took appropriate action to: Leave the job site safe before departure (securing any hanging items like gutters so they wouldn’t be blowing dangerously in the wind). Withdraw from the roof for safety It strikes me that if only your cousin, Justin Time was there, we could have avoided this foible! Thankfully, we have taken appropriate measures to ensure that we have a better perception of weather conditions moving in on us to avoid any other minor incidents. Safety is an ongoing learning and improving endeavour! My name is James. I am a manager at Charleswood Roofing. You are welcome to contact me at (204) 505-3051 and they can give you my direct number if you have an

• 1 out of 5Travis Black4 months ago

  April 15,2026 Seen an individual this morning driving one of their pickup trucks, they were speeding, not using signals while changing lanes right in front of my (illegally too just past Higgins underpass on main st) then went through a crosswalk that was activated and had someone crossing. This was all on main st from Higgins to Redwood north bound. Pretty sad to see this.

  Reply from the business

  Thanks for you review Travis. We will look into this with our team.

• 1 out of 5Rania Eskandara year ago

  Refused to repair my roof (still under warranty)and they already received the insurance report which clearly indicate that no hail damage was observed on my roof .they are not committed to help with that issue . I don’t recommend using this business at all try to find a better one.

  Reply from the business

  Thank you for your review Rania. We're sorry you feel this way, however, we have been committed to assisting with this issue. We are currently waiting to hear from your insurance company as hail damage was observed on your roof.

• 1 out of 5James2 years ago

  This company over books and relies on sub contractors . Poor quality , workmanship , poor communication. Andrew and Ben , you should be ashamed of yourselves .

  Reply from the business

  Thank you for your feedback. We are sorry that you are disappointed in our services. It is our policy to come behind our technicians and provide a final inspection, which gives us an opportunity to do any adjustments to the work as needed. Although you have denied us that option, we have offered to and would love the opportunity to come down, and perform that task.

• 1 out of 5Test Ing4 years ago

  I didn't have a roofing experience with Jon's company, only an unpleasant customer service experience. …

  Google cut this review short. The full text is on their Google profile.

• 1 out of 5Myke Lewis5 years ago

  Oh, how I long for the days when roofers working next door would blast AC/DC or Zep from their radios all day long. Today, I listened to a one-man noise-parade blasting eurotrash rave music as loudly as possible from his pickup. Seriously, hire some people with actual taste.

• 1 out of 5Adam Carroll7 years ago

  We did not end up going with Charleswood Roofing so I cannot speak to their workmanship, but the quoting process was not the kind of service I was expecting. Someone came out to assess for a quote and told me I would receive a quote the following day. 3 days later I followed up because I had not heard anything. When the sales person called me back, he asked if I was getting a quote from another company that is popular in my area. I said yes, and he seemed dejected and implied that he would not be able to beat their price. He then went on to say that the type of shingles that company uses “have had issues” (those were not the brand of shingles that company quoted me on). I thought it was very unprofessional to subtly try to badmouth another company. He then said he would see what he could do to compete on price and have my quote for me “first thing in the morning”. I received the quote after 5pm the following day. It was the highest quote I received by more than $3000. He did not follow up.

  Reply from the business

  Mr. Carroll, We are sorry to hear of your experience with one of our associates. We have discussed this issue with our sales associate and it is obvious there were differences in your quotes and in no way did we badmouth your other company's quote, nor would we. We strive for providing professional and honest service in every job we estimate and our reputation speaks for itself. It is important that we are comparing the exact products,services and workmanship warranties provided in each quote. We are pleased that you have found a contractor to complete your roofing project. Have a good summer.

• professional crew19
• polite staff15
• shingle replacement11
• eavestrough installation8
• eavestrough replacement8
• impeccable siding6
• ease of dealing5
• downspout repair3
• facia installation2
• friendly installers2

14 more of the 139 reviews we hold text for, most recent first. We do not hold every review Google has.

• 5 out of 5Kevin Armstronga week ago

  very quick to respond and great workmanship, would highly recommend!

• 5 out of 5randolph dhanoosingh2 weeks ago

  I certinly will recommend this company,the workers were very polite professionall and polite.The job site was cleaned after the job was done.

• 5 out of 5Can Kavaklıoğlu3 weeks ago

  Very professional and fast service, many thanks!

  Reply from the business

  Thanks for the review, Can!

• 5 out of 5Markus Notorius3 weeks ago

  they did a great job, very professional and friendly crew.

  Reply from the business

  Thanks for trusting us with your home Markus!

• 5 out of 5SHARON PAULHUS3 weeks ago

  Charleswood Roofing are a pleasure to deal with. We are vey happy with our new exterior siding!

  Reply from the business

  Thanks for the review Sharon!

• 5 out of 5Barbara Lamba month ago

  Charleswood Roofing is an exceptional company. There was no pressure from the fellow that came out to do the estimate and he took the time to hear my story. I was in a bind to have my father’s roof replaced so I could put it on the market. …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you for your thoughtful review! We're glad we were able to help make this process just a little bit easier for you, given the tight timeline.

• 5 out of 5Carla Nepona month ago

  I dealt with Charleswood roofing for my roof in 2021.I now found that my gazebo roof got ruined by the Winnipeg rain storm that had flooding, hail and wind . Knowing that my house is up for sale they came to re do my roof quickly and …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you so much for your continued trust and for taking the time to leave such a thoughtful review! We truly appreciate that you chose Charleswood Roofing again when your gazebo roof was damaged by the recent storm. We understand how important it was to get everything taken care of quickly with your home on the market, and we're glad our team could respond promptly and complete the work efficiently. Your kind words about our workmanship, pricing, and service mean a great deal to us. We wish you all the best with the sale of your home, and thank you again for your recommendation!

• 5 out of 5Calais Cowiesona month ago

  I could not be happier with my choice to work with this company. The customer service was stellar, the initial inspection of my home was thorough and insightful and the crew that came to work on my home was friendly, professional and hard-working. My highest recommendation!

  Reply from the business

  Thanks for your review Calais! We're thrilled to hear that you had such a positive experience from start to finish.

• 5 out of 5Rob ArmstrongEdited a month ago

  The crew that came out to replace the shingles did an excellent job! Very professional very well mannered. Very respectful. Highly recommended!

  Reply from the business

  Thank you for your kind words and recommendation! We're thrilled to hear that you were happy with our service team. Professionalism, respect, and quality workmanship are values we take great pride in, and it's wonderful to know our team delivered on all three. We truly appreciate your trust in us and look forward to helping you with any future roofing needs.

• 5 out of 5Chris Barretta month ago

  Great service as per usual. This time I had cover put on my eavestroughs for the garage.

  Reply from the business

  Thank you for your continued support! We're so glad to hear you had another great experience with us.

• 5 out of 5esther ruiz2 months ago

  Fantastic job from start to finish! The crew was professional, efficient, and the quality of the work was excellent. Kris and Andrew were both incredibly friendly, helpful, and professional throughout the entire project. They made the whole …

  Google cut this review short. The full text is on their Google profile.

  Reply from the business

  Thank you so much for your review! We're delighted to hear that you had a great experience from start to finish and that you were pleased with both the quality of our work and the professionalism of our crew. We will be sure to pass along your kind words to Kris and Andrew. Providing friendly, helpful service and making the roofing process as smooth and stress-free as possible is exactly what we strive for with every project.

• 5 out of 5Ronald Klassen2 months ago

  Nathaniel and crew did a great job. Were quick, cleaned up and confirmed that I was happy.

  Reply from the business

  Thanks for your review Ronald - happy to hear you had a great experience with our exterior team!

• 5 out of 5Benita Lynn2 months ago

  We had someone come by today to follow up on the work they did for us. The care and attention they showed is remarkable. I highly recommend them.

  Reply from the business

  Thanks for the kind words Benita!

• 5 out of 5Cliff King2 months ago

  They did a great job! Very efficient and professional

  Reply from the business

  Thanks for the review Cliff!

• States years in business

  “…Choice Protecting Winnipeg homes for over 15 years with complete roofing systems…”

• Free estimates

  “…Snow Removal Projects FAQs Contact Free Estimate Services Complete Roofing Systems…”

• Family owned

  “…Quality Materials Expert Craftsmanship Family-Owned Business Winnipeg Weather Experts…”