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.
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 Inspection 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.
A Roof Inspection replacement is one of the biggest investments a Winchester homeowner makes in their property, and we treat it that way — daily site cleanup, magnetic nail sweeps, and a final walkthrough with the crew lead before we consider the job done.
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.
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 Inspection 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.
Certification isn't a marketing badge here — it's required training that affects how your warranty is honored.
Every completed job comes with a written workmanship warranty separate from the manufacturer's material warranty.
Our team has sat through enough adjuster meetings in Winchester, MA to know what documentation actually moves a claim forward.
Magnetic nail sweeps and tarp-protected landscaping are standard on every job, not an upsell.
{We don't cherry-pick these — they're representative of the calls, texts, and reviews we get after most Roof Inspection 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."
"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."
"Bought a house in Winchester last year and had them do the pre-purchase inspection. Found flashing issues the seller ended up covering. Saved us thousands before we even closed."
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
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
