Roof Repair & Replacement in Cheshire, MA
Same-Day Appointments Available · 24/7 Emergency Service
Free storm damage inspections. Manufacturer-backed warranties. Fast estimates for Cheshire homeowners.
Call (877) 586-1316Emergency tarping available · Call 24/7
Holliston Roofing & Maintenance is a licensed and insured roofing contractor serving Cheshire and all surrounding communities. Our Holliston-based crews handle residential and commercial roofing with the same attention to detail on every job.
Our Services in Cheshire
What Cheshire Customers Say
"Emergency tarping after a windstorm ripped our ridge cap off. Holliston Roofing & Maintenance had a crew out within three hours and tarped the exposed section before rain moved in. Saved us from interior water damage."
"Had a bad leak around the chimney flashing after a storm. Holliston Roofing & Maintenance came out next day, found the failed step flashing, replaced it, and sealed everything properly. No more dripping. Solid work."
"The Golden Pledge warranty was a big factor in our decision. 25 years on workmanship plus 50 on materials. Holliston Roofing & Maintenance is one of the few local companies that can even offer it."
Why Cheshire Residents Choose Holliston Roofing & Maintenance
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 Cheshire roof gets factory-level quality control.
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.
Free Inspections & Honest Estimates
We don't charge for inspections and we don't pad estimates. If your Cheshire 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.
Licensed, Bonded & Insured
Holliston Roofing & Maintenance carries full liability insurance and workers' compensation for every crew member. We're licensed across MA and pull local permits for all Cheshire projects. Your property and your investment are protected.
About Our Cheshire Roofing Services
We've completed hundreds of roofing projects across Cheshire, from single-story ranch homes to multi-story commercial buildings. Every project gets a dedicated project manager, a written estimate before work starts, and a final walkthrough when we're done.
Cheshire homeowners can reach us at (877) 586-1316 or through the form on this page. No voicemail, no phone tree. A real person answers during business hours. We return after-hours messages first thing in the morning.
We serve Cheshire from our Holliston headquarters. Most Cheshire inspections are scheduled within 48 hours of the initial call.