Roof Repair & Replacement in Gloucester, MA
Same-Day Appointments Available · 24/7 Emergency Service
Owens Corning Preferred Contractor. 14+ years experience. Free roof inspections in Gloucester.
Call (877) 349-1553Free estimates · Financing options available
Chester Roofing & Maintenance is a licensed and insured roofing contractor serving Gloucester and all surrounding communities. Our Chester-based crews handle residential and commercial roofing with the same attention to detail on every job.
Our Services in Gloucester
What Gloucester Customers Say
"We got three quotes for a full tear-off and Chester Roofing & Maintenance was the most thorough. They showed us the rotted decking in the photos before replacing it. New Timberline HDZ shingles look great."
"The Golden Pledge warranty was a big factor in our decision. 25 years on workmanship plus 50 on materials. Chester Roofing & Maintenance is one of the few local companies that can even offer it."
Why Gloucester Residents Choose Chester Roofing & Maintenance
Free Inspections & Honest Estimates
We don't charge for inspections and we don't pad estimates. If your Gloucester roof needs a repair, we'll tell you. If it needs a replacement, we'll explain exactly why. No high-pressure sales, no scare tactics.
5/5 Stars | 322+ Reviews
Our reputation is built one roof at a time. 322+ homeowners across Chester, Gloucester, and surrounding areas have rated us 5/5 stars. We earn every review. No incentives, no discounts for feedback.
GAF Master Elite Certified
Only 2% of roofing contractors in the country hold GAF Master Elite certification. That gives Gloucester homeowners access to the Golden Pledge warranty: 25 years on workmanship, 50 years on materials. It's the strongest warranty in the industry.
No Subcontractors
Every Gloucester roof is installed by our own trained crews, not subcontractors pulled from a labor pool. That means consistent quality, accountability, and a crew that knows our standards from the first nail to the last drip edge.
About Our Gloucester Roofing Services
Storms hit Gloucester hard. Hail, high winds, and monsoon rains take a toll on roofing materials, especially asphalt shingles over 15 years old. Chester Roofing & Maintenance provides free storm damage inspections and handles the insurance claim process from start to finish.
We serve Gloucester and all nearby communities without charging travel fees. Call (877) 349-1553 to set up your free inspection. Most Gloucester inspections happen within 24 to 48 hours of the call.
Gloucester is one of our most active service areas. We have jobs running in Gloucester constantly, which means quick response times and crews that know the area.