O'LYN Roofing

O'LYN Roofing is a Norwood, Massachusetts roofing and gutter contractor that says it has served Greater Boston and MetroWest since 1974, when Michael Olen — in construction since 1972 — started the company with his wife Linda. The business describes itself as still family run, with Michael as owner and Linda as president, and puts its tenure at 51 years. That checks out in what customers have written: 65 reviews run from 2023 to 2026 across seven sources, Google shows 4.8 stars from 68 ratings, Best Pick Reports shows 4.9 stars from 229, and the Better Business Bureau lists the company as accredited with an A+ grade. The same names keep coming up across years of reviews — Shawn and Dan on roof replacements, Steve and Rick on moss and debris cleanups, Jake walking homeowners through options and samples — describing crews that show up when promised, protect A/C units and plantings during the work, and clean up after. One homeowner's north-facing roof, covered in mold, was the only job the company would take on when other contractors passed; another's storm-torn shingles were color-matched and repaired within days. Older news coverage adds some texture: a 2015 Boston Globe piece described the company fielding more than 4,000 calls in a single winter storm season, and a 2013 Patch article covered it donating a free roof to a Medfield family through a community giveaway. Not every account is positive. An April 2024 review describes a subcontracted job that left siding, a window and shutters damaged and debris scattered, with a flashing leak surfacing about a year later that the reviewer says wasn't honored under the stated 10-year workmanship warranty. A more recent complaint, from October 2025, describes a gutter-assessment visit where the technician arrived unannounced and rushed the homeowner instead of waiting as promised for a second unit owner to join. Both are outliers against a mostly 5-star record, but worth asking about directly — particularly how subcontracted labor is supervised and what the warranty actually covers. For a full roof replacement, storm repair, or gutter overhaul in the Greater Boston area, O'LYN is worth a call, especially given how often the same crew members turn up in positive accounts years apart. Before signing, ask who is doing the labor — in-house crew or a sub — and get the warranty terms in writing.