Consistent 5-star reviews — near-perfect averages across five platforms since 2023
Named crew praise — reviewers repeatedly credit specific technicians by name
Fast leak response — a same-visit roof leak diagnosis and repair reported
Community goodwill
What does a roof replacement cost in Greater Boston?
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.
— donated dugout roofs and a free roof to a family in need
Half-century track record — family-run since 1974 with an A+ BBB grade
Project communication — a 2026 review wanted more updates during a gutter job
O'LYN Roofing has been patching, replacing, and reinstalling roofs around Norwood and the rest of Greater Boston since 1974, when Michael Olen started the company as a young cabinet maker turned roofer. More than fifty years later it's still a family operation — his wife Linda now serves as President — and roofing, not any one add-on service, is clearly what people call them for.
The volume behind that is hard to miss. Best Pick Reports puts them at 4.9 stars across 229 ratings, Google shows a perfect 5 from 27 reviews, and Angi and HomeAdvisor both show 5.0 from a handful more; the Better Business Bureau accredits them at an A+. Across the reviews and mentions on file since 2023, the same names keep coming up — Steven, John, Jake, Shawn — homeowners crediting a specific technician by name rather than a generic "the crew." One Google reviewer described Steven finding and patching a roof leak in a single visit; another said Jake spent an hour on-site walking through ice-dam concerns before ever quoting a price. In the six months leading up to this, every new review held five stars, the same pattern the older reviews show going back to 2023.
The reputation runs deeper than review sites. In 2015 the Boston Globe reported O'Lyn fielding more than 4,000 calls in a single month during a brutal New England winter, and in 2013 the company replaced a roof for free for a single mother during a Norwood community event — the kind of local footprint that shows up again in a recent donation of two dugout roofs to Norwood Little League.
Not everything is frictionless. A 2026 Best Pick Reports review of a gutter and downspout job — otherwise called "fantastic" — flagged wanting more communication from the project team along the way, worth asking about on anything that stretches over multiple days.
O'Lyn is the call for a full roof replacement, a stubborn leak, or slate and historic roofing — the company leans into being the area's self-described "Victorian Specialist" for older homes — with gutters, skylights and flat roofing as real but secondary parts of the business. Before booking, get the project timeline and a communication plan in writing, particularly for gutter or drainage work tacked onto a bigger job.
Heard around town
News & the web
Working at O'LYN Roofing: 10 ReviewsAug 28, 2025
“Working at O'LYN Roofing: Employee Reviews | Indeed.com ... # Working at O'LYN Roofing: 10 Reviews ... ## 10 reviews ... ### Ok- but negotiate higher pay ... They’ll pay you very little & take advantage during pay negotiations if you let them.Project manager constantly blew off customers who expected calls back and reps took heat/yelling for it.Family owned, wife is a bit snarky and “I’m better than you” - can be off putting at times but ignore it and...Show more ... ### Think twice before working ... When I first started working at this company, I was excited. But after working there for the”
Contractors overwhelmed as winter repairs fuel demand - The Boston GlobeMar 21, 2015
“Workers with O'Lyn Roofing made repairs to a West Roxbury home.Pat Greenhouse/Globe Staff/Globe Staff ... O’Lyn Roofing in Norwood estimated that it received more than 4,000 calls over a month of wintry weather, its phones ringing more than 100 times an hour after the biggest storm. As of this week, the company’s workers had whittled down a backlog of ice-related repairs to 60. Those will be done by April - hopefully. Then it is on to the roof replacements that were scheduled for February but postponed. By the time O’LYN takes on new contracts, it could be T-shirt weather. ... Mark Negron, a d”
Medfield Mom Has New Roof After Winning ContestNov 13, 2013
“## O'Lyn Roofing of Norwood installed the free roof on Saturday, Nov. 9, during a community celebration featuring free lunch and raffles. ... Eva Pantelides O’Brien now has one less thing to worry about. ... The single mother of two was worried about losing her house insurance because of a faulty roof, but on Nov. 1[O’Brien learned she was the winner of a free roof](https://medfield.patch.com/groups/goodnews/p/medfield-mom-wins-free-roof)as part of the No Roof Left Behind program. ... On Saturday, Nov. 9, local sponsor O’Lyn Roofing of Norwood showed up with a crew of more than 20 people and t”
We had O'Lyn replace our gutters and gutter guards and reposition some of the down spouts. They did a fantastic job and came up with some very helpful solutions for our drainage issues. Our only complaint is a minor one. We would have appreciated more communication with the project manager after the job started. Overall, we are pleased and would use O'Lyn again.
I contacted O'Lyn to replace my aging roof. They got right back to me to set up an appointment. Jake spent an hour explaining everything about the replacement, and addressed my concerns about the ice dams I had noted from last winter. He was also clear about any extra costs if they found they needed to replace any of the decking. The work was started about a week later. The crew arrived and started work immediately. The project manager was on sight to answer any questions and to address any of my concerns. They put down protection for my A/C, patio, plants and windows. They worked all day and were able to finish my small house in one day. They cleaned up everything, and there was no damage. They did a great job, and the roof looks great! The only extra costs were to replace a couple of boards. I found O'Lyn Roofing to be very professional and would recommend them.
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 has been an incredible partner to Norwood Little League for many years, and this season they truly went above and beyond for our community. Their team generously donated and replaced both dugout roofs at Kelley Field, ensuring our players have a safe and secure space as they take the field this season. From start to finish, the O’LYN team was responsive, professional, and efficient—completing the work quickly so everything was ready well before Opening Day. The dugouts look fantastic, and the impact of their support goes far beyond the roofs themselves. Their continued commitment to giving back to the community and supporting local youth sports does not go unnoticed. We are incredibly grateful to O’LYN Roofing for their generosity and partnership—thank you for helping make Norwood Little League a better place for our players and families!
