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 Gutter Installation job with a written warranty.
Big Toms Roofing has spent years building a reputation in Winchester for doing Gutter Installation 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.
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.
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.
Downtime costs money, so commercial Gutter Installation jobs get scheduled around your operating hours whenever possible, with clear communication to property managers and tenants throughout the project.
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.
A roof is only as good as the parts that direct water off it. We repair and replace step flashing, valley flashing, chimney flashing, and gutters that have pulled away from the fascia — small jobs that prevent big leaks down the road.
We're not trying to be the biggest Gutter Installation 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.
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.
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.
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 Gutter Installation 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."
"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."
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.
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
