Verified record
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 roofing and gutter contractor, and a 2026 customer said Jake brought multiple samples to their home and the installation crew completed their new roof in 12 hours on a very hot day. The company says on its website that it is family-owned with 51 years in business, and names Michael Olen as owner and Linda Olen as president. Its Massachusetts home improvement contractor registration, number 101297, held by O'LYN CONTRACTORS, INC., is active on the state registry. On Google it holds 4.8 stars from 533 ratings, and its BBB grade is A+. A 2026 customer said Jake quoted a wait of 4-5 weeks for a new roof, but the team was ready in one week and finished the roof between a Thursday morning and Friday night. A 2026 customer said the company replaced a 150-year-old leaky slate roof on a two-unit house with an asphalt shingle roof, and that no one tried to upsell them. A 2026 customer said two skylights were replaced by two installers. A 2026 customer wrote, "Great work but overprice." A 2025 customer said owner Michael O'Lyn had a fascia piece replaced without an added cost after the narrower aluminum gutters did not cover it. A 2024 customer said O'Lyn sent a technician within a day or so after the warranty on their membrane roof had expired, and the technician's tentative conclusion was that the leak came from one of the windows. A 2023 customer said the work crew completed a roof, gutter and downspout project in two days, working 12 hours per day, and said O'Lyn pricing was not the lowest. A 2025 customer said the company called on a holiday, came by to look at the gutters while they were out of town, and then canceled their scheduled consultation by voicemail. A 2025 customer said the company came out to give a quote and never sent one despite multiple attempts at contact. A 2025 customer said they were still waiting for an estimate after a month. A 2025 customer said the company was hired to find a leak and never got to the bottom of the problem, and the next company found it. A 2024 customer said they spent about $12,000 on reflashing and repointing a chimney to stop a leak, the same leak returned the next time it rained, and a customer service rep said there was no warranty for the work. In that same 2024 review, the customer added that the company later sent someone to apply a water sealer product, which seemed to have helped. A 2024 customer said the company called after a signed contract to say they measured wrong and could not honor it. A 2022 customer said the roofers left a mess in the yard and tar marks from falling debris stained their new deck.
“In MA, O'Lyn roofing. They are fair, honest and reasonable.”
“O'Lyn Roofing?”
“**Case Status: CLOSED**”
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.
6 changes recorded — last scanned Sep 9, 2026.
Copper roof replacements4.6
Diagnoses before replacing4.3
Addition finished under time and on budget4.3
Additions and whole-house remodels3.8
25 permitted projects since 2004Not yet rated