Verified record
Typical Greater Boston range for this kind of work, from regional averages — not a quote from Flynn Roofing Company. Use it to sanity-check bids, then get the real number in writing.
A square is 100 sq ft of roof surface — bigger than the floor plan because of pitch and overhangs.
Estimated range
$9,000 – $18,600
Typical roofing project around $13,800
Flynn Roofing is a Weymouth-based roofing company run by Stephen Flynn, with Robyn Flynn handling office communication, and the through-line across 47 reviews since 2021 is precision: full roof replacements finished in a single day, yards and driveways swept clean of every nail, and an owner who shows up personally to inspect the job before quoting it. That personal attention shows up again and again. Reviewers describe Stephen climbing onto the roof himself to take measurements, walking through materials and process before anyone commits, and — in an April 2026 review — telling a homeowner their roof was actually fine rather than selling them a replacement they didn't need. A 2026 review describes him responding to a fallen tree and storm damage quickly and completing emergency repairs that held up through the rest of the recovery. Reddit users describe getting a list of 300+ past customers to call as references when requesting a quote. Real repeat business shows up throughout: one family, in a 2025 review, describes using Flynn for their main roof, their garage roof, and more recently a rubber roof over their sunroom, across several years. Skylights, gutters, and chimney flashing repairs come up alongside full roof replacements, and reviewers who priced out several roofers consistently say Flynn's estimate was detailed and fairly priced rather than the cheapest or most expensive. The company's Massachusetts home improvement contractor registration is active, and the Better Business Bureau lists it as an A+ accredited business. Across dozens of reviews there's essentially nothing to flag — for a roof replacement or repair in the Weymouth area, this is about as well-documented a roofer as they come.
“When getting quotes they also sent along a spreadsheet of 300+ names and told me to call any one of them as a reference. It was impressive and I found out why. Very good”
Very communicative, professional and prompt. Price was competitive with other companies. They showed up on time, got the job done quickly but efficiently, and made an effort to make sure the yard was cleaned and put back exactly as they had found it after the job. Would definitely recommend.
Flynn Roofing Company did a fantastic job replacing my old 3-tab asphalt roof. I had gotten several estimates from roofers. Flynn was by far the clearest, most detailed and most transparent contract and statement of work I received. Stephen Flynn (owner) met me at my home for the initial inspection to describe exactly what would be done. I had a detailed estimate and contract within a couple of days. All materials were exactly what was stated and work was completed exactly as described by Stephen and in the contract. His crew was professional and hard-working. They completed the job, which included roof sheathing repair and gutter work, in a single day. My wife was worried that the process would destroy the landscaping (flower gardens, shrubs, etc) but all was well after completion. Landscaping was unharmed and my yard was left cleaner than when they arrived!! It's been a couple of weeks now and we haven't found a single stray nail or shingle fragment. The property really was left spotless. I like that they used top-tier materials (Certainteed Landmark Pro shingles) and installed to meet or exceed recommendations of the manufacturer. They are installing a system of materials that are designed to work well together. They provide a written transferable warranty for materials and installation. I found them on Certainteed website on a list of certified installers and read dozens of positive reviews from people in my area. They've been in business for decades. Bottom line is I knew it was going to be a lot of money to do a roof properly regardless of who did it, so: -I wanted it done right -I didn't want to over-pay -I wanted to feel good about my choice It all went really well. It looks great. The price was fair. They exceeded expectations. I feel like I made the right choice. Highly recommend!
Highly recommend! I'm so glad, I hired Flynn Roofing. They were courteous, professional, easy to work with and helpful with answering questions. They arrived on time, finished on time, cleaned up like they were never there and the roof is beautiful.
If you are in need of a new roof or roof repair, call Flynn Roofing for your estimate. What you'll get is a prompt reply and a presentation of what services they offer, what materials they use and recommend, how the process will work, time frame, etc as well as a very reasonable estimate. Most importantly, no high pressure sales tactics which is what cemented the deal for us! Steve (owner) is a very personable and professional guy! Others we received estimates from were just pure salesmen who brought lots of props, some spent way too much time talking about themselves and some offered gift cards or money! if we chose them. Of all the estimates we got, only Steve Flynn went up on our roof to assess it up close. The estimate we received was completely reasonable and fair and included stripping the entire roof. The day of install, the crew arrived exactly when stated at 7 AM and immediately went to work. They were so polite and respectful of our property. The roof was completed shortly after 2 PM and clean up began immediately! Our yard was left cleaner than when they arrived. Communication during the entire process was excellent! Any questions we had were answered. We are very happy with our new roof. My wife loves the color we selected! Overall, an all around awesome experience with Flynn Roofing!
Great roofing company to work with. I did lots of research and I chose well. The owner and his wife are delightful. The estimate was fair and in the middle of the three I got. The crew was great. Nice, efficient and left the property immaculate. Great Certainteed warranty too.
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Certified attributes are verified against the public registry. Others are the business's own statement.
Established 5.0 rating
Slate & copper roofing4.8
Kitchen and bath renovation that also waterproofed a basement3.9
Emergency response3.3
Fixes what others turn down4.1