Elite Technical Precision and Professionalism - Highly Recommended I recently hired Anchor Point Roofing for two major projects: a complete repair of a 20-year-old flat roof on our main apartment building and a full tear-off, decking boards repair, and reshingle of our detached garage. The experience was flawless from start to finish. Key Highlights: Next-Level Inspection: Our inspector, Paul Rodriguez, provided an incredibly professional initial report. Paul didn't just say the roof needed repairs; Paul actually chalked up every single defect on the roof and provided a corresponding photo with a point-by-point explanation for each. Paul also provided me an online video walkthrough, which made the issues completely transparent before any work began. Navigating the 3-Week January 2026 Cold Spell: Managing a roofing project during a Chicago winter is a major challenge, especially during the extreme three-week January cold spell. Throughout this brutal stretch, Sara was fantastic--she stayed in constant contact, monitored the weather closely, and scheduled the crew the moment it was safe and permitted for the work to proceed. On-Site Project Management: Anchor Point's on-site project manager, Ever, did an amazing job overseeing the execution. Ever was very personable and met with me to ensure I was completely satisfied with the progress and the final results. Ever was very engaged and stayed in communications while the work progressed. Professional Work Crew: The onsite crew--Jesus, Miguel, and Cristopher, who made a point of introducing themselves--did an outstanding job. There were several other team members I didn't get a chance to talk with directly, but their collective effort was evident in the high-quality results. They were all respectful of the property, and the cleanup was spotless--not a stray nail left behind. Comprehensive Post-Job Documentation: After the repairs were finished, they provided a final gallery with over 100 before-and-after pictures. Seeing the completed work--including drone shots!--matched against those initial chalked defects Paul identified provided absolute peace of mind. Anchor Point Roofing is easily the most transparent and professional roofing contractor I have ever worked with. If you value technical precision and clear communication, this is the company to call. read more

Anchor Point Roofing was great to work with and I would recommend them to anyone looking for a roofer without hesitation. I had a flat roof on a two flat that hadn't seen any maintenance in a long time and was leaking. Jim came out to look it over and presented options for both repair and replacement. I opted for replacement, and they basically handled everything from that point on. They also handled all permitting requirements with the city. My job turned out to be a little involved, lots of rotten decking that needed replacement, but it was no problem for Jim's crew, they got everything done, the new roof looks great, doesn't leak anymore, and they cleaned up well after they were done. Also very communicative through the whole process and send you tons of photos so you can see what's going on. Their pricing was fair from what I found, I probably had half a dozen roofers quote the job and Anchor Point was average. Also the pricing is transparent, they quoted tearing up to two layers of roofing off and some minor allowance for replacing decking. When it turned out I needed extensive decking replacement, Jim called and explained what costs were involved and why. It helps that they take so many pictures, so you can see clearly what the issue is and why they need to change the scope of work. At the end of the day I felt confident that Anchor Point was taking good care of my house, doing things the right way, and not cutting corners or rushing to complete the job (they originally planned on working only for a few days on my place and it ended up taking them 2 weeks). read more

In September 2024 I met Jim Copenhaver when he was quoting a roof replacement at a neighbor's home. I was working in the front yard when Jim indicated to me that a section of shingles and plywood on my roof was raised. The next day Jim returned with a drone to scan the roof so I could see the problem. Wow! A detailed proposal immediately followed. The crew that did the work was first-rate in communication and workmanship. The lead worker showed me a tablet with before and after photos of the roof and explained the work done. My neighbor also hired Anchor Point to do a full roof replacement and commented that Anchor Point was the most professional company he ever hired. In June 2025 a skylight started to leak water on stairs leading to the second floor. I called Anchor Point. The estimator indicated that a replacement skylight typically has a lead time of 5 to 7 weeks (not the best news). Two days later Sara emailed and said she found the exact skylight I needed locally. Anchor Point's team will go above and beyond to solve a problem. An Anchor Point crew was scheduled for three days later. The crew immediately assessed the job, determined materials needed, and installed the skylight in a few hours. Outstanding job! I highly recommend Anchor Point's entire team for their exceptional professionalism, excellent work, response time, attention to detail. Over the years I have worked with several roofing companies in Chicago, but the best experience was with Anchor Point. read more

Anchor Point Roofing was a great company to work with. Jim Copenhaver was a pleasure. He addressed all our needs and wants. Due to the Chicago weather in November, they got a late start. But they kept us updated throughout the process. Jesus was the foreman on the job and was outstanding. He made suggestions on repitching our flat garage roof which made the job a little less stressful for us and kept the job moving. During construction we had 8-10 workers here at one time. We contracted for 2 flat roofs & 1 shingled roof with dormers. The weather & shorten days made the job almost 30 days but Jim & office staff, Kris and Sara kept us informed. Kris even stopped by once to deliver paperwork. Jim came to make a final walkthru when they were done & to address any issues (which were small & taken care of even before job was done.) We were in need of further siding work, etc & Jim recommended a company he worked with before. They worked out great as well. In fact all was done before the end of the year. Roofing price was fair. We only had to add a couple of items which we agreed to the price at the time of installation. Highly recommend Anchor Point Roofing for all your roofing needs. read more

I live in Cincinnati and rent my house in Chicago. My tenants called and told me we had a leak. Based on their description I knew it was coming from a flat section of our roof that had two air conditioners mounted on top. I had three roofers come out. Jim and his team were very thorough. They did a complete roof inspections and provided me with a significant number of pictures pointing out the problem area plus another small problem around my furnace vents which the other roofers also identified. The other roofers wanted to rip off the roof and replace it for approximately $8k and also indicated that was a starting point as they were not sure what else they could find wrong after the tear off. When I talked with Jim he indicated if it was his house he would go with a repair. In addition the other roofers wanted nearly $3k to fix the problem around the vents when Jim simply replaced the cover and did some minor repairs for a third of the price. Living remotely, I thought there was a pretty good chance I would be taken to the cleaners. With Jim I felt like I was getting an honest assessment and honest effort to fix the problem at a reasonable price. read more

I had an undetermined aged roof that had a few leaks throughout the past year that I previously patched. I called up Anchor Point to provide a flat roof replacement quote. Estimator showed up and explained in detail all the requirements, correct ways to replace the roof, as well as detailed potential pitfalls. There were delays in scheduling due to weather, but that is reasonable as once the roof is torn off, it has to be waterproof before the next rain. The general foreman provided excellent value and answered the multitude of questions I had during my various inspections of the process. After the roof was torn off, front parapet masonry work was required and offered to pull in their own sub to perform the work and maintain schedule. This work was absolutely necessary as I was seeing moisture/water damage in the unit below, but couldn't identify any obvious penetration points previously. There were a few mixups in invoicing, but were promptly rectified by their back-office support. All-in, the process was effortless, informative, professional, and adhered to a reasonable schedule. read more

I can't say enough good things about Anchor Point Roofing. They were extremely responsive at the beginning and scheduled an initial estimate within a few days of my reaching out. The technician that came out was extremely friendly, brought his own ladder and was VERY thorough in his assessment of my problem. He showed me in both pictures as well as having me come up to the roof to point out all the work that needed to be done (rather than other vendors who only spent less than 10 minutes and didn't give even 10% of the overview of charges. After deciding to move forward, the level of PROFESSIONAL communication that was provided to give an overview of what I could expect was far beyond anything I've ever experienced. The crew showed up on time, were all very respectful, gave me an overview of what they were doing and even ended early. Post the job, they sent dozens of photo evidence chronically the initial issues and showing all the work they did to remedy them. I would highly recommend working with this company. read more

I manage a commercial property that was experiencing a leaky roof and water migration to an interior utility equipment room. I needed to get the issue resolved quickly and saw Anchor Point's work trucks in the area and decided to give them a call. Jim contacted me soon after the initial call and came onsite for an inspection. Based on what was discussed in that meeting and Jim's assessment of the situation, upon inspection, I knew I would be in good hands w/Anchor Point. The team that was sent to do the job communicated all that was planned for the work to be performed, took photos of the before and after and kept me informed as the job progressed. The entire job was completed within a week of the initial contact. I was also happy to find out the company is local and I'm always willing to support local businesses. I would recommend Anchor Point Roofing and will use them again for any future needs. Thanks Jim & Team read more

I recently hired Anchor Flat Roof Repair to fix some issues with my roof, and overall, I'm very pleased with the outcome. The team was professional, responsive, and clearly knowledgeable about flat roof systems. They arrived on time, kept me informed throughout the process, and worked diligently to ensure everything was done to a high standard. There was some scope creep during the project, as additional issues were discovered once work began. While this did increase the cost, it was warranted, and I appreciated Anchor's transparency in explaining why the extra work was necessary to avoid bigger problems down the line. In the end, the roof is in great shape, and I feel confident it will last for years to come thanks to their thorough approach. I would recommend Anchor to anyone needing roof repairs--they do quality work and take the time to get it right! read more

Anchor Point roofing was amazing! Jim stopped by for an estimate and recommended replacing the roof. He uses a drone to examine the roof and was able to show me pictures to explain his recommendation, which is just awesome. The roofers were great, removing the old shingles, examining the plywood (everything was OK there, thank goodness!) and replacing the shingles with a nicer product that looks great. They completely finished the project in a day and a half, and did a good job cleaning up. Importantly, while up on the roof they discovered some cracks in my chimney cap that I wouldn't have known about until the chimney started leaking (or collapsed). Being able to get this fixed now saved me time and money later on. In short, I can't recommend Anchor Point roofing enough! read more

Jim and his team are amazing!! From the moment we contacted his company to request a quote, through the completion of our roof repairs it was such a smooth process which I did not expect. Every person we were in contact with at the company (office & roofers) gave us the best customer service! Above and beyond is definitely an accurate statement. Jim helped me through some insurance paperwork even after the project was done! They are very honest, punctual, detailed, and have competitive and fair pricing. I contacted several other companies who came out and provided us with quotes and recommendations but our initial experience with Jim and team was so exceptional that it wasn't even a question. I will be using them for all my future projects. Highly recommend them!! read more

I hired Anchor Point to repair a couple of small leaks for me on one of our rental homes, and they did a fantastic job. I really liked the salesman, Jim, who did a great job answering all of my questions. After using this company for that repair, I decided to let them bid the roof for my new home. I did obtain three bids, but I didn't go with the cheapest bid, because there were so many unknowns. I ended up hiring Anchor Point again, because of the first experience that we had with this company. All of the workers seemed competent and courteous. And I must say, I have not been finding nails and debris in my yard weeks after the project, as with other roofs that I've had done. I couldn't be happier with the completed project and the communication. read more

Anchor Point Roofing was a great experience from the start to finish. It was really hard finding roofers who were willing to actually go on our roof and give us an idea of what was going on. (We have a very tall building). Jim was super responsive, came out within days and gave me a detailed estimate explaining what they would do and even included photos and video from when he was on the roof. We had a prior roofer come out and tell us everything on our roof needed replaced but Jim was really honest and told us that wasn't the case. Their prices were fair and work was scheduled really fast. We will definitely call Anchor Point Roofing in the future if we have any more roofing work needed. read more

They did an amazing job. Was one of three companies I contacted on yelp and Jim did an outstanding job of coming over, finding the main issue (the others didn't btw) and came up with a reasonable quote. The job was top quality and all documented with pictures. Would highly recommend them. The other companies a) didn't find the main issue before they started the work and were just saying "trust me what we'll do with catch everything or b) wanted to just put me on some standard plan they offered. High quality process and high quality work delivered if I would sum it up. Definitely would recommend you at least see what they have to say if you're having issues. read more

Our flat roof needed to be replaced and Anchor Point went above and beyond! We had several contractors come out for estimates but the team at Anchor were by far the most communicative, kind, thorough and transparent from the get-go. Plus, their pricing was in line with what the others offered. Jesus and his team worked tirelessly for days and did a beautiful job (this was also confirmed by our neighbor--a perfectionist and former contractor). Jim and Kris maintained great communication and made sure we were satisfied every step of the way. I would recommend Anchor Point to anyone in the Chicago area with any roofing woes! read more

We used Anchor Point Roofing to replace our house and garage roof. The experience with Anchor Point was unlike most business interactions - in a very positive way. From the intial contact, through inspections, quote, roof replacement and after sales follow up their service was exceptional. As noted in other reviews, the combination of technology and personal service delivered a satisfying experience. I always felt I knew what was happening. Their use of pictures and drone video allowed me to safely see what was done with my roof. I have recommended them to friends and family and would use them again. read more

One of our bedrooms had water damage. The day it was found, I started looking for roofing companies with a good reputation. I hit the jackpot with Anchor Point Roofing as they exceeded all of my expectations. The pricing was fair; the work was done as promised, and immaculately; the team that works there was a dream to work with, each conscientious, honest, and great at their jobs. The owner clearly cares about his customers, his employees and providing quality work. If all businesses operated in this excellent manner, wouldn't it be painless to spend money? read more

I highly recommend Anchor Point Roofing to anyone looking for professional and excellent roof repair. I was very impressed with their work and I'm happy to admit that Jim was able to fix problems that we have been struggling to repair. He was very responsive and thorough , explained everything that had to be done and why. The process was easy and time efficient. Jim was on time and very respectful to our property. It was a pleasure to work with him. Overall great service and excellent job! I love the fact that this is a family owned and operated business. read more

At this point in my life, I only want to deal with contractors who are reliable and I can trust. Jim is all that and more. He is a gentlemen and such a pleasure to work with. I know that if there is any problem, he will make it right. This includes even after the job is completed. It is really great to work with someone who stands behind his work, who is reliable, punctual and trustworthy. If I didn't need something, he had no problem telling me and even fixed a different issue just because he was up on the roof anyway. I am very satisfied. read more