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Typical Greater Boston range for this kind of work, from regional averages — not a quote from O'LYN Roofing. 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
O'Lyn Roofing is a Norwood-based roofing contractor with 533 Google ratings averaging 4.8, a BBB A+ grade, and similarly strong marks on Best Pick Reports and Angi — the kind of volume that comes from years of steady work across the Boston suburbs. The through-line in the reviews is candor before the sale. Multiple homeowners describe O'Lyn as the only roofer who visited in person rather than quoting off a satellite image, or who talked them out of a bigger job than they needed — one reviewer spent two years chasing a chimney leak before an O'Lyn technician diagnosed it by listening and inspecting rather than pushing a quick fix or a full replacement. On the job itself, crews are repeatedly credited for finishing fast (a full roof from Thursday morning to Friday afternoon is typical), texting photo updates during the workday, and handling complicated work — a 150-year-old leaky slate roof on a two-unit house was rebuilt into a modern, properly ventilated asphalt system. The company has also donated and replaced both dugout roofs for Norwood Little League. The front end of the process is where complaints cluster. In 2025 reviews, one customer waited a month for an estimate that never arrived, another was ghosted entirely after a quote visit, and a third described an automated scheduling call showing up unannounced on a holiday during a rainstorm. A 2024 review describes a signed contract the company later said it couldn't honor because of a measurement error, and a 2022 review describes tar stains left on a new deck and metal debris near a front door with young children in the house. A separate 2025 review describes a leak-diagnosis visit that never found the source, later solved easily by a different company. None of that shows up in the last six months — the 41 most recent reviews are all positive. For a straightforward roof job, the execution track record is deep; if your project starts with an estimate or a smaller repair, it's worth confirming a callback timeline upfront.
O'Lyn Roofing exceeded my expectations from start to finish. Jake Becker was fantastic—professional, knowledgeable, and responsive. He took the time to explain my options, brought multiple samples to my home, and made the entire process so easy. The installation crew was also impressive, they arrived on time, worked through a very hot day, and completed my new roof in just 12 hours. The quality of workmanship is outstanding, and the whole experience was seamless. If you're looking for a roofing company you can trust, stands behind their work and lives up to their commitments, I highly recommend O'Lyn Roofing
O'Lyn roofing was great to work with. Danny the project manager answered every question I had professionally and with kindness. There were a lot of folks on the team, so the work was completed quickly. The new roof looks great, and we're looking forward to having one less thing to worry about when winter snows come.
It was a pleasure working with O’Lyn Roofing company From Shawn in sales to Dan E and his team They were on time and work area was cleaned up each day Dan also took time to answer all my questions in a professional manner
O’Lyn did a great job. They were professional and worked straight through until they were finished. Danny ran the job and the quality of the work was top notch. He was easy to work with and knowledgeable about the work they were doing.
Very positive experience. Great communication. Hard working crews. Quality work. Guy always kept us informed of next steps and was great to deal with. Job was full roof replacement.
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Certified attributes are verified against the public registry. Others are the business's own statement.
Established 4.2 rating
Takes small jobs others refuse5.0
Ice dam calls answered next day5.0
Completed a $444,500 window/siding projectNot yet rated
Water intrusion stopped4.5
$228,000 Brookline renovation3.4