Dempsey Roofing LLC

Dempsey Roofing has built a genuinely deep track record around owner Radek — 95 reviews since 2021 across four platforms, and the name that comes up review after review is his: personally answering calls, showing up to inspect a roof the same day or the next, and walking homeowners through pricing and material choices before a crew ever arrives. Its Massachusetts home improvement contractor registration is active, and it's held an A+ BBB rating and accreditation since late 2024. The written record backs up the reputation. Google alone carries 129 ratings at 5★, and the last six months brought 11 reviews with no complaints — a roof finished start to finish in a single day is the recurring story, whether it's a straightforward asphalt shingle job, a rubber roof on a low-slope garage, or, in one case, a 150-year-old house with an out-of-square roofline that needed custom drip edge and full resheathing. Several reviewers specifically describe Radek telling them a roof could wait, or that only part of it needed replacing — restraint that shows up often enough to be a real pattern, not a one-off. That said, the record isn't spotless: in an October 2025 review, one customer described a re-roof that developed multiple leaks Dempsey couldn't resolve, backed by a forensic report from other roofers documenting installation mistakes, and ultimately had another company redo the entire roof. It's an outlier against dozens of otherwise clean accounts, but worth asking about directly — specifically what warranty or callback process covers a leak after the fact. For a straightforward re-roof, repair, or a straight answer about whether a roof actually needs replacing, Dempsey is a strong, well-documented call in the Billerica area — just get the leak-callback policy in writing before signing.