Charter Oak Roofing is Milford's local roof replacement specialist. Free written estimates, honest recommendations, and workmanship we stand behind.
Whatever your roof needs, we start with a free inspection and an honest recommendation — even if that answer is "your roof is fine."
The most popular, cost-effective option for Connecticut homes. Architectural shingles in the color and style that fits your house.
Learn more →Premium roofing built to last 50+ years. Handles Connecticut winters and coastal salt air with ease.
Learn more →Not sure if you need a replacement? We come out, take a look, and give you an honest answer at no cost.
Learn more →After a storm hits your area, we assess wind and hail damage before it turns into leaks and rot.
Learn more →Drone-verified, every job photographed. Licensed and insured — every roof backed by our workmanship warranty.
We come to your home, assess your roof, and document everything with photos.
A detailed, itemized quote — no guessing, no surprises, no pressure.
We replace most Milford roofs in a single day, start to cleanup.
Drone photos of the finished roof and a workmanship warranty in writing.
★★★★★ 5.0 Star Rating on Google · 16 Reviews
"The crew showed up on time, finished the whole roof in one day, and left the yard cleaner than they found it. The drone photos at the end were a great touch."
"They told us honestly that half the roof just needed a repair, not a full replacement. That honesty is why we hired them for the full job two years later."
"Fair price, clear written estimate, and the standing seam metal roof looks incredible. Neighbors keep asking who did it."
Big roofing chains send salesmen. We send roofers. Charter Oak Roofing is local to Milford — we live here, we work here, and our reputation rides on every roof.
Leave your info and we call you back within the hour. No pressure, no obligation.
Based in Milford, we replace roofs across New Haven and Fairfield counties.
