Cromwell Roofing Contractor | Serving Cromwell From Cheshire

"Second roof Cheshire Roofing & Maintenance has done for us. First one on our primary home, now our rental property. Same crew both times, same attention to detail. Drip edge, ice shield, everything by the book."

"Our flat roof on the garage had been patched five times by other companies. Cheshire Roofing & Maintenance stripped it and put on a proper TPO membrane. No leaks in two years. Should have called them first."

"I called about a small leak and expected a hard sell on a full replacement. The inspector showed me it was just a cracked pipe boot — $300 repair instead of a $12,000 roof. Honest company."

Licensed, Bonded & Insured

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

Storm Damage Specialists

Hail, wind, and monsoon damage are common in CT. 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 Cromwell 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.

GAF Master Elite Certified

Only 2% of roofing contractors in the country hold GAF Master Elite certification. That gives Cromwell homeowners access to the Golden Pledge warranty: 25 years on workmanship, 50 years on materials. It's the strongest warranty in the industry.