Homeowners across Chestnut Hill 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 Chestnut Hill 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.
From a single missing shingle to a full tear-off, our Chestnut Hill crews handle every stage of roofing work with the same attention to detail — licensed, permitted, and cleaned up when we leave.
When a tree limb punches through decking or shingles peel back in a wind event, water gets in fast. We prioritize emergency calls in Chestnut Hill above scheduled work, get a tarp on within hours, and document everything with photos for your insurance file.
A Gutter Installation replacement is one of the biggest investments a Chestnut Hill 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 Chestnut Hill 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 Chestnut Hill? 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 Chestnut Hill, 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 Chestnut Hill, 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 Chestnut Hill, 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 Gutter Installation jobs in Chestnut Hill.}
"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."
"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 Chestnut Hill and the neighborhoods around it, from established residential streets to newer developments and commercial corridors.
We regularly work in the following Chestnut Hill-area zip codes: 2467
One call gets a licensed Chestnut Hill roofer looking at your problem, usually the same day, with a written estimate before anything starts.
📞 Call +1-855-469-0306 — Serving Chestnut Hill, MA
