When a shingle blows off in a storm or a slow leak finally shows up on your ceiling, you need a crew that answers the phone and shows up — not a call center that puts you on hold. Big Toms Roofing sends licensed, local Winchester roofers to your door, usually the same day you call.
Big Toms Roofing has spent years building a reputation in Winchester for doing Roofing the right way — proper permits, manufacturer-approved materials, and a crew lead on-site for every job, not just a subcontractor nobody vetted.
Whether it's an emergency leak at 2am or a planned replacement you've been putting off, Big Toms Roofing brings the same certified crew and the same upfront pricing to every Winchester job.
When a tree limb punches through decking or shingles peel back in a wind event, water gets in fast. We prioritize emergency calls in Winchester above scheduled work, get a tarp on within hours, and document everything with photos for your insurance file.
When patching stops making financial sense, a full tear-off and reroof resets the clock on your home. We strip old material down to the deck, replace any rotten sheathing, install proper underlayment and ice-and-water protection, and finish with a manufacturer-certified shingle or metal system backed by a real warranty.
We work directly with property management companies and HOAs across Winchester to keep flat and low-slope roofs maintained on a predictable schedule, instead of waiting for emergency calls that disrupt business.
Buying or selling a home in Winchester? A pre-purchase roof inspection gives you real leverage in negotiations and peace of mind about what you're actually buying — no guessing about remaining roof life.
Ice damming is a real problem in Winchester, MA winters when it happens. We install proper ice-and-water shield and improve attic insulation and ventilation to stop the freeze-thaw cycle that damages eaves.
We're not trying to be the biggest Roofing company in Winchester, MA — we're trying to be the one you'd actually recommend to your neighbor.
Every estimate is itemized and handed to you before we touch the roof — no verbal quotes that change once the ladder comes down.
Because our trucks stay staged around Winchester, we're rarely more than an hour from your address for emergency calls.
Our installers hold current manufacturer certifications, which means your warranty stays intact and the work meets code.
Every completed job comes with a written workmanship warranty separate from the manufacturer's material warranty.
We document damage the way adjusters expect to see it, which shortens the back-and-forth on storm claims.
We treat your yard and driveway like we'd want ours treated — swept, protected, and cleared before we leave each day.
We don't cherry-pick these — they're representative of the calls, texts, and reviews we get after most Roofing jobs in Winchester.
"Called around 9pm after a branch came through part of our roof and Big Toms Roofing actually picked up. They had someone out that night to stop the water and scheduled the repair for that week. That kind of response is rare."
"I got three quotes for a full reroof and Big Toms Roofing wasn't the cheapest, but they were the only ones who explained exactly what was included and stuck to it. Zero surprises on the final bill."
"They handled the entire insurance claim conversation with our adjuster, sent over photo documentation, and honestly made a stressful situation way less stressful. Roof looks great too."
"As a property manager I've worked with a lot of roofing companies and Big Toms Roofing is one of the few that actually communicates before showing up and after the job's done."
"Their inspection before we bought our house flagged ventilation and flashing problems that weren't obvious on a walkthrough. Glad we called them before closing, not after."
Our dispatch radius from Winchester reaches the surrounding Winchester, MA communities as well — if you're unsure whether your address is covered, one call confirms it in seconds.
We regularly work in the following Winchester-area zip codes: 1890
Whether it's an emergency or a project you've been planning, +1-855-469-0306 connects you to a real local roofer — not a call center.
📞 Call +1-855-469-0306 — Serving Winchester, MA
