A damaged roof doesn't wait for a convenient time, and neither do we. Big Toms Roofing keeps trucks staged around Winchester so a certified roofer can be looking at your roof within hours, not days, with a straight-talk estimate before any work starts.
Big Toms Roofing isn't a national call center that dispatches whoever's cheapest that week. We're a licensed roofing operation built around Winchester and the surrounding Winchester, MA communities, with crews who know the local building codes, the weather patterns, and the housing stock inside and out.
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.
A leak that starts as a small stain can rot decking and framing within weeks. Our emergency response teams treat every active-leak call in Winchester as urgent — temporary stabilization first, permanent fix scheduled right behind it.
Whether your roof is past its expected lifespan or storm damage made repair impractical, our replacement crews handle permitting, disposal, and installation start to finish, with a written timeline you can plan around.
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.
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 Skylight Repair 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.
Local dispatch means less time waiting and more time getting your roof actually fixed.
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.
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 Skylight Repair 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."
"The estimate they gave us matched the final invoice exactly, which after two other quotes from companies that kept adding line items, was a relief. Crew was professional and cleaned up better than I expected."
"After the hail storm last year, Big Toms Roofing documented everything for our claim and dealt directly with our adjuster. We barely had to do anything except sign off on the estimate."
"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."
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
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
