Top 5 shingle roofing contractors in Chestnut Hill, MA

"We recently had our roof installed by Trinity Roofing, and I could not be more impressed with the entire experience. From the very first meeting, Julian was outstanding—professional, knowledgeable, and incredibly patient in walking us through our options. He gave us a clear perspective on how we should be thinking about our roof, even explaining details like ridge vents versus other venting systems—things we had no clue about before. What really stood out was that there was no pressure or upselling, just honest advice that gave us confidence we were making the right decisions. Both Julian and Jason were fantastic to work with—attentive, responsive, and committed to doing the job right. The final installation looks fantastic, and the peace of mind knowing it was done with such care and expertise is priceless. If you’re looking for a roofing company that is professional, trustworthy, and truly puts the customer first, I highly recommend Trinity Roofing."

"Jayson was very professional and easy to work with. I never felt pressured on picking out the shingles or scheduling the roofing job. The roofers were respectful and thorough. I was happy that it only took 1 day and they did great job cleaning up. The best part is how beautiful my roof came out. I posted a picture but it doesn't do the roof justice how nice it is in person."

"Jayson and his team were very professional and timely. Our roof needed some replacing and they showed up on time and completed the replacement on time. I was esthetic about the final product and they also did a stellar job with the clean up. I would highly recommend Trinity Roofing and thank you to Jayson and his team."

"The professionalism, the knowledge and expertise that was shared throughout the entire process of my new roof was beyond words. I cannot thank Trinity roofing, Jayson (owner), his son Julian, for the outstanding service and expertise we received in our roofing experience. Thank you Jayson, thank you Julian for all you did for us!!! Sterling B."

"Jayson and his team did an excellent job. Jayson and his son went over all the details step by step for us to make an informed decision on the roofing project. Jayson's team showed up on time and finished installing our new roof and updated skylights by the end of the day, including clean up. The new shingles and skylights look fantastic and clean up was awesome. Bottom line, we would recommend Trinity Roofing to anyone as they perform high quality work at a reasonable and competitive price."

"Shane was extremely fair, and very knowledgeable. His team was able to not only replace the roof, but hang gutters as well in less than 2 days of work. Came out great. Would recommend to anyone that needs a new roof."

"Shane was very knowledgeable, never once pushy in our conversations. He quoted a reasonable estimate, and got our roof redone within a day, mind you, we never even set a timetable or deadline. Roof looks nice and complements the house."

"At ROI CHAMPS, We've Been working with Shane for few years now setting up his roofing appointments. The guy actually answers his phone, handles the work load, and keeps it real on what's working and what's not. He got that rare combo of being funny as hell but also dead serious about doing quality work. No bs just straight talk and a real win-win attitude."

"Shane was great, and his employees are hard workers! Roof came out beautifully. He also gave us a free upgrade on shingles because the distributors was out of the color I wanted, so I got a very close match for same price! Thanks again."

"Shane was great to work with the work was done in one day the crew protected my property and cleaned up thoroughly after!"

"I hired Stella Roofing Services to replace my 23 year-old roof. I chose them after reviewing several bids because Steven took the time to come to my home and evaluate our needs properly. He was honest and never tried selling me on something that I didn’t need. Just that his team would do a great job at a fair price. And he delivered. Everything happened as he had scheduled from supplies being delivered to the dumpster being delivered. His team arrived early and worked late. Jeff, the PM touched base with me often all the way. When the job was finished, the team cleaned up so you wouldn’t even know they were there. I’m happy to recommend Stella Roofing Services for any home improvement projects."

"It was time for a new roof after hearing drips on a bedroom celling when it was raining out. I called Stella Roofing and that same day Steve came by and was up on the roof checking things out. (in the rain) He explained to me what he found and showed me pictures of the conditions the roof was in. He put together an estimate for a new roof and to replace two existing skylights for us. To our Surprise, the estimate was lower than what we thought it would be. A week and a half later Steve's roofing crew was on our roof, removing the old and installing new shingles and two new skylights. All in one Day!! They did a "Great Job" for us, they cleaned up the job site (even came back to check our driveway a day later) We are Very Very Satisfied with Sella Roofing Services. If you are looking to Replace (or New) roof give the a call also and get an Estimate. Thank You Steve, and to your Roofing Crew also !!! Jim"

"Stella did a great job replacing my roof. Steve and everyone on the crew was professional and courteous. The work proposal described the process completely so there were no surprises. The roof looks great and matches the garage better than expected! Highly recommended!"

"We had a great experience working with Steve and his team to replace our roof and skylights. They were a referral from a neighbor, and we will in turn refer others to Stella. The work seems to have been done well (though I don't really know exactly how to evaluate that), but there are a few other things I do know: (1) Communication was efficient and easy, and everything was directly with Steve—the owner—who was always responsive by email, by text, by phone, or in person as needed. (2) Pricing was good, comparing across quotes from several roofers. (3) There was no pushy sales tactics; Steve gave us lots of information we asked for about shingle options and skylight options, but never pushed us either to make more expensive choices or to make decisions quickly. Work was done on schedule as expected, at the promised cost, and things were cleaned up as expected. Thanks to Steve and his colleagues!"

"I had a issue with my roof, which is about 14 years old, the person that installed it was no longer to be found, I had shingles missing from the ridge and from the side of the roof and just wanted to repair my roof. I met Steve from Stella Construction a few years ago, through family members who used Stella Construction to replace and repair there roofs. Steve came out and looked at my roof and picked out all the faults on my roof made by the previous roofer. Steve knows the roofing business, I hired Stella Construction to repair my roof, did a great job."

"We recently worked with CAN Construction to replace the roof and fascia trim on our detached garage. Everything from scheduling to installing to to collecting payment was done with professionalism and attention to detail. The quote we received included a document with comprehensive information about the roofing technology we were signing up to have installed. It linked out to a website where we reviewed the quote and electronically signed. Super easy! Nate and Rocky were a pleasure to work with. They left no questions unanswered, so we were completely comfortable with and trusting of the work they did on installation day. CAN Construction are the best roofers in the area."

"We were having problems with rain coming through the top of the window for ages. Nate came right away, assessed the situation and recommended a solution. I was impressed with Nate as he suggested we could use a less expensive handyman for the job. It was a small job but we wanted the experts to fix our problem. It was completed and we have had no problems since. We highly recommend Can Roof Construction."

"Nate and his crew were excellent - hard working, courteous and communicative. We had no issues whatsoever with our full roof replacement. I cannot say enough about their professional level of service and I would recommend them without hesitation. They also were able to complete our roof quickly as we were working toward a home closing. Thank you CAN team!"

"I recently had the pleasure of working with CAN Roof Construction for a much-needed roof replacement for my house in Holliston, and I couldn't be more pleased with the outcome. From start to finish, their team demonstrated professionalism, expertise, and a commitment to excellence that surpassed my expectations. (and I have high expectations) Scheduling the project with Nate was seamless and stress-free. He was responsive, accommodating, and made sure to address all my concerns and preferences. His communication throughout the process was exemplary, keeping me informed every step of the way. During the actual replacement, Rocky, was hands-on and meticulous in overseeing the project. His attention to detail and dedication to ensuring everything was done correctly was truly commendable. I was particularly impressed by their commitment to replacing all water-damaged wood, leaving no “shingle” unturned in guaranteeing the longevity and integrity of my new roof. What truly sets CAN Roof Construction apart is their embodiment of the values of hard work and honesty. Their dedication to delivering exceptional results and their unwavering integrity are a testament to their values. In an industry where trust is paramount, they have undoubtedly earned mine. I wholeheartedly recommend CAN Roof Construction to anyone in need of roofing services. With their expertise, professionalism, and commitment to excellence, you can trust that your project and house will be in good hands. Thank you, Nate, Rocky, and the entire team, for a job well done!"

"Great experience working with Nate and CAN Roof. Had our roof replaced and exterior of the house cleaned. The guys worked so hard and did an amazing job. Our driveway looks so clean! We will use them again and would absolutely feel comfortable recommending CAN Roof Construction!"

"Above Brothers Construction was amazing from the first conversation to the completion of the project. The entire team was all professional, hard working, great communication and the job happened exactly as described. Best experience I’ve had with a contractor, would recommend 10/10. Thank you to Alex and the team at ABC for my beautiful siding and gutters."

"Alex is honestly the most responsive contractor I’ve ever worked with. He replies super quickly (even on weekends sometimes!) and he and his team always show up right on time. They are respectful, professional, and take pride in their work. When I had an emergency roof repair — a hole in the soffit and fascia that could let animals into my attic — Alex’s team came out the very next morning to patch it. I really appreciated how quickly they helped in that situation. They also repaired some siding trims and installed a chimney cap for me, and all the work was done with high quality and care. Their pricing is also fair and transparent. I’d definitely recommend Alex and his team to friends or neighbors looking for a reliable roofing contractor."

"I was very pleased with my roof replacement by Above Brothers Construction. I dealt with Alex from the beginning, he stayed in touch throughout the process, he was there on the day the crew came out to start the work, and he even stopped by afterwards. He was always helpful in answering questions and helping me understand the process."

"I had a Fed Ex truck back into the overhang above my garage door and damage my vinyl siding and metal corner bead, I called Above Brothers construction and Alex responded promptly and came out within a day and gave me a very reasonable estimate compared to other ones I had received so I scheduled an appointment to have it fixed and within a day or two Danny I think his name was came out and did the great repair in a couple of hours and even went over my driveway with a magnet to make sure he didn't miss any nails he may have dropped, all in all a job well done, and after reading all these fantastic roofing reviews and my vinyl siding repair experience I asked Alex to give me a new roof estimate which I received back within a day so stay tuned for that review."

"The job by this company was excellent. They were prompt and on time. Even though there were unforseen problems with the roof everything came out fine. Punctuality, organization, and clean up was excellent. The representative that I dealt with, Alex, made sure all the problems were solved. Through all problems they were more than willing to work with me and they became no problems. I would heavily recommend that you check them out."