We received a quote from CWR in fall of 2018, and we also consulted two other roofing companies that had done work in the area recently. Between the three quotes were values of approximately 50 dollars on the taxed in completed amount. The fellow that came out to do the quote was very personable, Stu, and careful not to cause any damage to the roof or eaves troughs. The quote was very detailed in that they assessed the venting, and also provided that information of the assessment without contract, should we have chosen another company. The last time the roof was done was in 2003, and I did it myself as well as the neighbors roof on a very wet and hot weekend in July. We used IKO shingles Citadel three tab that were supposed to have a 25 year expectancy. Reality is that truly never is the case as life of the shingle, manufacturing technique and quality control are always varied and batches can be mixed and much like Monday and Friday manufacturing line product. Needless to say they were in real rough shape. Both roofs. There are definitely differences in shingle quality and manufacturing QA/QC. At the time CWR was updating the way that they processed their accounts and quotations, so there were a few growing pains, but the on-line system that they are using is pretty upscale, and as a middle-aged person the system was easy to use. I think its a great way to do business moving forward with technology today and client service, given that society is so impatient to wait for anything and answers. Having said all the above, May 21st/ 19, I had to take my hounds for grooming early the morning that they were to come. When I returned from the groom shop they were here and had about half the roof stripped off. The trailer was on the front lawn, and they used sheeting to not damage the lawn or cause rutting. CWR did ask if we were good with that, and they would only do it if the lawn was firm. We were definitely good with that to make their day a little easier. I was home when the gents were doing the work and when they allowed I went up to have a look at the work. One employee told me that he was excited to use the colour of shingle that we chose because he had never installed it before. Josh and his crew, short one staff, were very courteous, clean, professional, and efficient. They had a bit of fun getting the sewer vents modified for the new stack, but with some of my tools and their strong will they made it happen. We had a few good chuckles. Initially our plan was to do it ourselves, but the price was reasonable with the given market we are in. We opted for the under-lay as it provided the extended/ transferable warranty to the next homeowner. The few hundred dollars extra was in our opinion worth it. Factored in the value outweighs the initial cost. Learned experience has taught me that you get what you pay for. We weren't sure if they would be able to finish in one day, however they were here for just over 7 hours start to finish. If I wouldn't have been here we would never have known that anyone was even here that day. The real clincher is that they even picked up the cigarette butts that other smokers, that walk by the property on the city sidewalk, threw into the boulevard in front of the house. IMPRESSIVE! If we were to have to do it all again..... CWR gets the job! Keep up that level of professionalism and way of handling yourselves, and those that comprehend real conditions ( weather, time and personal life) will always recommend CWR to others that may need service from your company. We were VERY pleased with the guys and their work ethic as well as the way they cleaned up and were so very respectful in asking for water and washroom when they needed it. I like the on-line thing, I think it bodes well with the societal structure that we are progressing toward. We love the look of the roof and especially the colour! Sorry it took so long to give feedback! Just had to test it with rain! Thanks again for the great work, and well..... should we ever need...you'll hear from us again. Kind Regards, Jeremy

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.

Very happy customer. We contacted Charleswood in the fall of 2019 to replace our shingles, skylight and eavestrough, as well as do spray foam for all vaulted portions of our home. We contacted a number of different companies within Winnipeg. Of the three that gave us quotes, Charleswood was the most affordable. They were also to only ones that recognizes that our roof was having serious issues that couldn't wait, so they did a patch job to tide us over until the spring when the job could be performed. Thank goodness they did that because due to the pandemic, supplies cease to produce shingles and skylights and our job was delayed until August 2020. As for the job itself, we couldn't be happier. The work is excellent. They took their time to ensure everything was done properly and looked good. Any issues they found were explained to us. All the workers were super friendly and always took the time to answer questions or explain issues they found/work needed. During the replacement, a huge electrical issue was discovered. They recommended an excellent electrician who was able to be onsite the next day. In addition to the actual job, all dealings we've had with the company have been fantastic. Everyone has answered all our questions as promptly as possible. The work itself is a quality above and beyond what I have experienced in the past. Because of our skylight, we actually have a close-up of large sections of the roof and we are very very impressed. Those sections that we cant see, they took pictures of so we could inspect the work. We couldn't be happier. When our shingles need replacing in 25 years, we'll use them again. I highly recommend this company for any of your roofing needs.

I had the pleasure of hiring Charleswood Roofing to address a pressing roofing issue that arose in May. During a rainstorm, I noticed water cascading down the wall of my sunroom due to a hole in the roof. To my surprise, a raccoon had managed to find its way into the roof, causing the damage. After contacting several roofing companies, Charleswood Roofing stood out by promptly responding to my call, providing a detailed quotation, and offering invaluable advice. What truly impressed me was their commitment to resolving my situation promptly. Recognizing the urgency of my roof's condition, Charleswood Roofing managed to expedite the entire project. The following week, a proficient team of six professionals arrived with the necessary materials in tow. They wasted no time in tackling the hole in my roof while simultaneously installing new shingles throughout the rest of the house. The efficiency and professionalism displayed by the Charleswood Roofing team were truly commendable. Their clear communication throughout the project ensured I was kept in the loop at every step. The project was completed within the agreed-upon budget, without any unexpected surprises along the way. Though the raccoon responsible for the damage didn't pitch in to cover the bill, Charleswood Roofing's exceptional service and skillful team more than made up for it. If you're in need of roofing services, I wholeheartedly recommend Charleswood Roofing for their expertise, reliability, and outstanding customer care. My experience with them was nothing short of impressive, and I am grateful for their dedication to resolving my roofing woes promptly and professionally.

I am pleased to share my positive experience with Charleswood Roofing. After receiving three estimates for my roofing project, all within a similar price range, I ultimately chose Charleswood Roofing, and I believe it was the right decision. While their estimate wasn't the lowest, it was comprehensive. Their proposal stood out because of its detailed breakdown and various options. One aspect I found particularly helpful was the inclusion of photographs illustrating the current condition of my roof. This visual aid helped me understand the issues they addressed and added a level of transparency that I appreciated. What truly convinced me was their attention to detail. Charleswood Roofing was the only company that identified a damaged vent pipe during their assessment and included the cost of repair in the estimate. This thoroughness demonstrated their commitment to a complete and well-executed project. Throughout the process, from initial consultation to final installation, the team at Charleswood Roofing was professional and knowledgeable. The crew arrived as scheduled, worked efficiently, and left the area clean. This level of professionalism contributed to a positive overall experience. While Charleswood Roofing's estimate wasn't the lowest, I believe the additional cost was justified by the comprehensive approach, the inclusion of repair details, and the overall quality of service. I am confident in recommending Charleswood Roofing to others based on my satisfactory experience with their services

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.

I noticed my roof leaking during the storm this weekend, and I saw a man looking at a neighbours house and figured maybe he was a handy man of some sort, so I went over and told him about the leak. He introduced himself as Cary Hebert who works for Charleswood roofing. He said he would gladly come and check out the leak after he was done giving a quote on my neighbours home. When he was done over there he came straight over and asked if he could set up his ladder and go on the roof to see what was going on. He went up, identified the issue and came back down to explain to me what the problem was. He made sure I understood exactly what he was saying, and afterwards told me that because the leak was quite bad he could take some time out of his day to go up and fix it. He said it was a straightforward repair and it wouldn’t take too much time. When he was done he told me that there was no cost for the repair! Thank you Cary! I would definitely recommend this man to all of my friends.

It was time to have our twenty year shingles replaced and on the recommendation of a neighbor we contacted Charleswood Roofing. After receiving a few other quotes they came in very competitive, however, it was not only the quote that helped in our decision to go with them it was the initial contact and the reassurance they offer. From the initial quote to the end of the project every single employee offered professionalism and attention to detail. Any concerns or issues we had they would address immediately and correct the problem with no hesitation. I would highly recommend them to anyone looking at having their shingles replaced. I want to thank all the J's starting at Jon and Jerry (assessor and sales), Josh (install foreman) and his incredible crew, Jeff (supervisor) and Geoff (manager). These individuals are very knowledgeable good at what they do, be reassured you cannot go wrong with them. Thank you! Charleswood Roofing.

Received excellent service from Charleswood Roofing. I approached them late in the season for a quotation, and was promised that my garage roof would be completed this year. With the onset of rainy weather and early winter I was very pleased that they were able to complete my project as promised. I received a phone call about noon to say a crew would be at my house within an hour. Arriving about 1.00 pm, the job was completed by 4.00pm, The work crew were very efficient and courteous, and their presence was non intrusive. Upon completion they did a full cleanup, and even returned the following day to do a final roof check and cleanup. Dealing with Jeff for my quotation, and later with the office staff to settle my account, was a pleasurable experience. I am very pleased with the quality of work, the crew, administration, warranty, and price, and would highly recommend this company.

The people I dealt with at Charleswood Roofing, from the office staff to the estimator to the roofer's kept me informed on what to expect and a timeline. They exceeded my expectations by being able to re-shingle my roof several weeks early and the foreman on site, Tyson, kept me up to date during the day with any issues/concerns he came across. He was able to explain to me why some of my issues that I was having with the roof prior would now be fixed and why. He went over and above to fix a downspout that wasn't long enough by attaching a spare one I had, which will prevent water wearing on the shingles on an overhang. The staff on site seemed to love what they do, even with extreme heat. They cleaned up the yard and left it as they found it. This company is very professional and easy to deal with. I would highly recommend them!

Need a roof - This is who you get to do the job. My shingles arrived Thursday as promised and complete roof installed Friday, May 6th.. Tellus the Foreman ( I believe) was very very personable as well as his 4 Ukrainian employees, who were so friendly despite the language barrier. We had some good laughs while having lunch outside at our picnic table. One could tell they were all very professional in carrying out their work. Following completion of the job, Tellus did an inspection of all the work done. Clean up followed and again well done. Later in the day, Jonathon Scott (Owner) did the FINAL INSPECTION, and again the job was noted to have been competed to a high and professional standard. And my wife and I could not agree more. And the PRICE - Very Fair. So, THANK YOU - CHARLESWOOD ROOFING for a professional job well done.

My wife and I had recently had the privilege of working with Jeff Joyal and his team from Charleswood Roofing. Our project was a very complex one, requiring immediate attention. Jeff and his team was very honest and forth coming regarding the details of our project. We are both thrilled and extremely satisfied that our project is now completed. The workmanship and the level professionalism was also outstanding including everyone that we interacted with through out the process. Charleswood Roofing went above and beyond the details that was required for this project once again a heartfelt Thank You to Jeff and his amazing team for providing such great customer service. .... The CHESTERS

I would highly recommend Charleswood Roofing. Their team was very professional starting with the estimating process, picking out the shingle type and colour, and finally invoicing where Ashley was very helpful. Tyson and his crew were first class and they really seemed to enjoy their job and working with each other. They did my roof in early spring when the weather was still a little erratic. They spread the job out over a few days only doing a section of the roof that they could complete each day. It worked out well as we had a couple of rain days. They did an amazing job cleaning up after themselves each day. You would never know they were there. Thanks again!

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.

We had Charleswood Roofing replaced our shingles last year. From the day i requested for a quote, Jeffrey came to check and measure our roof. He is nice, kind and knowledgeable of their product. I liked their quoting system via email. The crew that installed our roof were polite and on time, they finished the job within the day and cleaned up after themselves. The process was smooth and everything goes well. Now, im still pleased looking at our beautiful atlantic blue shingles chosen by my son who was 4 years old then. Thank you Charleswood Roofing, HAPPY with the service! Maria R.

I didn't have a roofing experience with Jon's company, only an unpleasant customer service experience. After speak to him twice on the same day, Jon didn't return my voicemail and text (in which I requested that he patch my roof and provide quote). I was overwhelmed with process of finding a roofer as my roof was leaking with more rain was in the forecast. He seemed frustrated when I asked him to explain how a temporary patch would hold as he had no time to install a new roof. He said he had too many jobs to choose from and his afternoon was already booking up.

We recently had our 30 yr old roof replaced by Charleswood Roofing and are thoroughly impressed! From beginning to completion, they were friendly, professional, informative and produced high quality workmanship in a timely fashion. The crew assigned were hard working and professional, with periodic inspections of their work done throughout the day. Once done, a final inspection was made with impressive scrutiny. Our roof was completed in a single day without a shred of debris to be found anywhere! I would highly recommend them. You won't be disappointed!

I’ve used Charleswood roofing 3 times now, they’ve replaced our shingles, siding and soffits/fascia. I cant say enough good things about the company, when we were in the market for a new roof we called 3 different companies, Charleswood was the only one to actually climb up there and stomp around a bit. The other two gave us a quote judging by what they saw on the ground. Charleswood took the time to answer all of our questions without making us feel rushed, or like we were wasting there time. Hire them for your next project you won’t be sorry.

Charleswood Roofing was a pleasure to deal with. Jonathan was easy to work with and very efficient. He went above and beyond what we expected. The entire process from the initial estimate, to the finished roof, was seamless, efficient and exactly what we hoped for. The crew that shingled our roof left our yard and driveway in immaculate condition. Charleswood Roofing provided excellent service and we are very happy with the Roofing job done on our home. I would highly recommend Charleswood Roofing to anyone looking to reshingle their roof.

First time I've had a roof reshingled. Was a little apprehensive about what company to choose and so after extensive research, chose Charleswood roofing. Best decision I ever made! Responded quickly to my inquiry regarding an estimate and answered any and all my questions. Started project on time and because of their expertise and skilled workmanship, completed my beautiful new roof in two days way beyond my expectations! Jon and his crew were professional from start to finish.Would unequivocally recommend this company in the future.

I had some shingles lifted up from one of the recent windy days. Charleswood Roofing was able to fix the issue properly on the same day that I called them, for a very reasonable price. The two workers that showed up were polite, knowledgeable, and answered all of my questions. The work was completed quickly (they wanted to have it fixed up and waterproof before the rain that we were forecasted to get later that day). They took before and after pictures, and explained why they did the work that they did. Highly recommended!

We had used Charleswood Roofing for getting our shingles replaced and new soffit and fascia and some siding. They did a wonderful job from start to finish. Jonathon actually came in and sat down and went over everything with us very thoroughly which you don’t see a lot anymore with all companies. He also made sure to come back after all the work was done to check over everything once again to make sure it was all done right and we were happy. We would recommend Charleswood Roofing to any of our friends or family!

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.

Exterior upgrades: From start to finish top marks! old exterior of house and garage removed. New shingles, insulation added to outside of house new siding,and stone work .New soffits fascia eavestrough and down spouts.Their staff did a great job all very professional and hard working during the hottest part of the summer.They also did a great cleanup after they finished the work! The pricing for the job was also very reasonable.

After experiencing a severe thunderstorm, we noticed water leaking into our kitchen. We called Charleswood roofing and they sent to men out that day. They did an inspection of the entire roof and then repaired the problem area. The two men were professional, knowledgeable and explained in detail what they found and repaired. We were so pleased that they addressed the problem so quickly and dealt with it effectively.

Charleswood Roofing was recommended to us as the best roofing contractor. My neighbor said just call them up for a quote and don't bother getting one from anyone else. That's what we did and we got a good price and the installation was excellent. The clean up was thorough and you couldn't even tell it had been a construction site. You can go wrong on choosing CW for a contractor.

I can’t recommend a company more highly. The team was great, and when we ran into an issue with our (lack of) insulation Jon found us someone who could come the next day to do the job. Every step in the process from quote to completion has been so quick and easy. I can’t express my gratitude enough for the teams amazing service, skill, and professionalism.

I've called 4 roofing companies, only 2 of them called back. Charleswood is one of them. Aaron called me during the day before heading over to my rental property, suggested to patch the roof before it rains. The communication was great, the way how Aaron structure the conversation was the key point for the job, not the roofing skills.

If it were possible to give 6 star rating we would. They were prompt, efficient, cleaned up the yard flawlessly and had a crew who had marvellous work ethics. I was given samples of shingles to take home and was encouraged to look at all options for roofing materials. This is superior company and I recommend it without reservation.

Needed a repair for a water leak coming in around a gas fireplace chimney. Received prompt service. Cary, one of the service personnel called ahead, and was promptly able to fix the problem. I also asked for an inspection of the roof to identify any other problems which he also fixed. Very happy with the service.

We were extremely impressed with the job Charleswood Roofing recently did re-shingling our garage roof. It was a relatively small project and yet every step of the process was done with the utmost professionalism, care and attention to detail. Many thanks to John V, Ernest, Kyle and their awesome team! :)

Charleswood Roofing recently did my roof in South Winnipeg. They quoted me a very competitive price and were fast and efficient in getting the job done. Jeff was great to work with, kept me informed every step of the way and went above and beyond to resolve any issues. I would definitely recommend them.

When our roof needed to be replaced, they were the first company to provide us an estimate. They were also the quickest company to fit us in with the most accurate and detailed quote. Great family business and quality workmanship and workforce. Highly recommended; turn key roofing solution!

They did a great job. The crew were courteous , ensured they cleaned up every day, and I liked that they made sure rain could not cause damage by completing sections at a time. when shingles were delivered , they stayed off the interlocking bricks, worried about potential damage.

Thanks to the whole group at Charleswood Roofing. Excellent work on our soffit, fascia, and eavestrough. Also did some metal cladding on some wood that will never need painting again! There was a slight delay because of some supply chain issues, but it was well worth the wait.

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.

I recently had Charleswood Roofing replace the eavestrough on my house and garage and add metal soffits and fascia to the garage. They installed the water diverters that I supplied. Great job. Everything looks so good now, and no more drips from worn out eaves.

Outstanding work by Charleswood Roofing. Had shingles and some roof decking replaced along with soffit and facia and from the quote to the work being done they were consummate professionals. Would highly recommend them and would absolutely use them again.

Very professional, and not just the owner. The roofers themselves were also very professional. A hard working Ukrainian crew. They were also on time and cleaned up thoroughly after they finished the job. We are very happy we went with Charleswood roofing.

We had a relatively small project requiring new eavestrough installation in one area and repairing a downspout coming out of an old scupper drain in another area. We were very pleased with the response, advice on alternatives, pricing and work done.

Great company to work with. Understanding and helpful in picking the right shingles to make the house look it's best. Fast and efficient work crew. Great clean up afterwards, it's like they weren't there, except for the new roof. Highly recommend.

Great and dependable Company, quick response time and very professional installation of my evestroughs. Charleswood Roofing previously did a fantastic job on my roof a few years back. I will definitely use the services of this company again.

We got eavestroughs installed on our garage and we are very happy with the work! It looks great, no mess made, quick and the crew were all friendly. We will definitely be calling them back for when we want our house eavestroughs repalced.

Johnathan and his team were fantastic. They came to the rescue the same day that I called, did a great job resolving the issue and at a very fair price !! I completely recommend Charleswood Roofing to anyone with roofing needs .

We're happy with Charleswood Roofing. Very professional, very quick, and very thorough. Both crews (roof and eavestroughs) worked quickly - including the cleanup - and both jobs were inspected separately the next day.

My roof was done by Charleswood Roofing recently in Westwood. The quote was very comparable with other companies if not better. Workmanship was outstanding. I would highly recommend Charleswood Roofing.

When I called for an estimate on adding a roof vent to exhaust my range hood, I received the same prompt response as when I had Charleswood replace our shingles 4 years ago. Great people to work with.

A big thank you to John V. And Jerad H. and crew, professional, personable, and quality job. They protected my yard and flower beds and the clean up was excellent. Neat and tidy! Thanks again!

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!

Justin and Matthew visited our home today to fix a few shingles around our chimney and did an excellent job. Very impressed with their workmanship and attention to detail. Well done.

Job well done from start to finish. Fairly priced and complete estimate, came when they said they would and did a great job completing the roof in one day. Impressed.

New roof looks great and the guys were basically done in a day. I had an issue with a leaky roof vent, and Aaron put in the extra time to make it right. Thanks guys.

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

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.

The job was relatively small. Good workmanship, friendly service and priced competitively. I would not hesitate to go back to them for future work.

I had Charleswood Roofing replace my roof in July 2018. This IS the company that all roofing companies in Winnipeg strive to be!

This company is very helpful and answers all your questions and makes you feel at ease. Very polite and reasonable prices.

The quality of the workmanship, the product used and above all the service were second to none. Highly recommended.

Did a great job fixing a roof leak I had in a very tricky spot. Treated the project like it was their own house.

Thank you guys for your great and professional job! It was great pleasure to work with you!

Incredibly pleased. Great work. Courteous, clean, attentive. Definitely recommend.

Fast courteous and a stickler for detail. Explained the whole roofing process.

Great, trustworthy company to work with for all things exterior.

Straight forward and honest, you can't go wrong with these guys!

Great company, trustworthy, workers responsible.

Awesome work. great hrs, people friendly

A great company you can trust.

Great work