Homeowners across Winchester call Big Toms Roofing because we do what we say — show up on time, explain what we find in plain language, and stand behind every Roof Replacement job with a written warranty.
We built Big Toms Roofing to fix a problem every homeowner in Winchester has run into: contractors who don't return calls, no-show for appointments, or pad the invoice once the tarp's already on the roof. Our Roof Replacement crews are local, licensed, and accountable — every estimate is in writing before a single shingle gets pulled.
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.
High winds, hail, and fallen limbs don't schedule appointments, and neither should your repair. Our Winchester emergency crews arrive with tarps, decking material, and fasteners to stop active leaks the same day you call, then follow up with a full repair plan once the storm passes.
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.
Commercial roofs fail differently than residential ones — ponding water, seam separation, and membrane wear don't always show up until there's a leak on the sales floor below. Our Winchester commercial division services TPO, EPDM, modified bitumen, and built-up roofing systems on retail, industrial, and multi-family properties.
A lot of roof failures are preventable with a twice-a-year inspection catching lifted flashing or worn pipe boots before they turn into interior water damage. Our Winchester inspection service checks the field, flashing, penetrations, gutters, and attic ventilation, then hands you a written report with photos.
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 Roof Replacement company in Winchester, MA — we're trying to be the one you'd actually recommend to your neighbor.
You'll know the exact scope and cost in writing before work starts, and that number doesn't move unless you approve a change.
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.
If something about the finished work doesn't sit right with you, call us back and we'll make it right — that's the deal.
Our team has sat through enough adjuster meetings in Winchester, MA to know what documentation actually moves a claim forward.
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 Roof Replacement jobs in Winchester.}
"We had a leak show up during a storm at night and I honestly didn't expect anyone to answer the phone. Big Toms Roofing had a crew tarping our roof within a couple hours and came back two days later to do the real repair. Can't recommend them enough."
"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."
"We manage a small retail plaza and Big Toms Roofing has handled our flat roof maintenance for two years now. Scheduled work, no drama, invoices that match the estimate. Exactly what we need as a property manager."
"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."
Big Toms Roofing crews are staged to cover all of Winchester and the neighborhoods around it, from established residential streets to newer developments and commercial corridors.
Zip codes we serve in and around Winchester, MA include: 1890
One call gets a licensed Winchester roofer looking at your problem, usually the same day, with a written estimate before anything starts.
📞 Call +1-855-469-0306 — Serving Winchester, MA
