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 Chestertown roofers to your door, usually the same day you call.
Big Toms Roofing isn't a national call center that dispatches whoever's cheapest that week. We're a licensed roofing operation built around Chestertown and the surrounding Chestertown, MD 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 Chestertown job.
High winds, hail, and fallen limbs don't schedule appointments, and neither should your repair. Our Chestertown 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 Chestertown commercial division services TPO, EPDM, modified bitumen, and built-up roofing systems on retail, industrial, and multi-family properties.
After a wind or hail event, insurance companies want documented proof of damage. Our inspection team photographs and reports storm damage in a format adjusters recognize, which speeds up claim approval.
Ice damming is a real problem in Chestertown, MD 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.
Every one of these commitments exists because a Chestertown homeowner asked for it, complained about a competitor's lack of it, or we learned it the hard way.
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.
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.
We document damage the way adjusters expect to see it, which shortens the back-and-forth on storm claims.
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 Gutter Installation jobs in Chestertown.}
"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."
"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 Chestertown 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 Chestertown and the neighborhoods around it, from established residential streets to newer developments and commercial corridors.
We regularly work in the following Chestertown-area zip codes: 21620 21690
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 Chestertown, MD
