Dennis Roofing Contractor | Serving Dennis From Chilmark

"Their crew showed up at 7 AM, tore off the old roof, replaced eight sheets of plywood, and had new shingles down before dinner. Jobsite was cleaner when they left than when they arrived."

"Hail punched through half our shingles last spring. Chilmark Roofing & Maintenance handled the entire insurance claim — met the adjuster, filed the supplement, and we paid nothing out of pocket besides the deductible."

"We got three quotes for a full tear-off and Chilmark Roofing & Maintenance was the most thorough. They showed us the rotted decking in the photos before replacing it. New Timberline HDZ shingles look great."

Free Inspections & Honest Estimates

We don't charge for inspections and we don't pad estimates. If your Dennis 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.

Storm Damage Specialists

Hail, wind, and monsoon damage are common in MA. Our team includes HAAG Certified inspectors who document damage the way adjusters expect it. We handle the entire insurance claim process so you don't have to.

Manufacturer-Certified Installation

We hold certifications from GAF, Owens Corning, and CertainTeed. That means the manufacturers have trained and vetted our crews and will back our installations with their strongest warranties. Your Dennis roof gets factory-level quality control.

Licensed, Bonded & Insured

Chilmark Roofing & Maintenance carries full liability insurance and workers' compensation for every crew member. We're licensed across MA and pull local permits for all Dennis projects. Your property and your investment are protected.