
Roof repair · Milford, CT
Leaks fixed fast. Explained clearly.
Pipe boots, skylights, chimney flashing, missing shingles and storm damage. We find the actual cause and fix it right.
What we repair
Most leaks come from a handful of places.
- Pipe boots. Rubber collars around vent pipes crack in the sun and let water in.
- Skylights. Reflashing or full skylight replacement.
- Chimney flashing. Step and counter flashing that has pulled away from the brick.
- Missing or lifted shingles after wind storms.
- Ice dam leaks at the eaves in winter.
We show you photos of what we found, explain your options and give you a written price before we start.

Reviews
What homeowners say
Mike was quick to respond and came out promptly for a roof inspection, which I was incredibly grateful for, especially since I had an active leak. He was also able to complete the repair quickly and efficiently. Throughout the process, Mike provided helpful updates and oversaw the work from start to finish. He was honest, fair, and extremely knowledgeable, and he clearly explained my options—which was especially helpful as a new homeowner. I would absolutely call Charter Oak Roofing again for any future roofing needs and highly recommend Mike and his team!
We purchased our home 2 1/2 years ago. We were mislead about the age of the roof which was irreparable after February's wind storm. We checked out several roofing companies who were overpriced. We chose Mike Plaskon and his Charter Oak Roofing. They offered us quick, professional, courteous service and installation. We would only recommend this company to do business with!
Super impressed with the roof replacement! Great communication, hardworking crew, and they finished sooner than expected. Would definitely recommend!
FAQ
Roof repair questions
What should I do if my roof is leaking right now?
Move valuables, put a bucket under the drip and call us at (203) 736-7739. We respond quickly to active leaks and can often get a temporary fix in place fast.
What are the most common causes of roof leaks?
Cracked rubber pipe boots, failed flashing around chimneys and skylights, missing or wind-lifted shingles, and ice dams along the eaves.
Can you replace a skylight?
Yes. We can reflash an existing skylight or replace it entirely, either on its own or during a roof replacement.
Is a repair worth it on an older roof?
Sometimes. If the roof is under about 15 years old and the problem is in one spot, a repair usually makes sense. If it's 20+ years old with wear everywhere, we'll tell you honestly that replacement is the better spend.
Do you charge to look at a leak?
Roof inspections are free. If you need a repair, you get a written price before any work starts.
Free estimate
Get your leak looked at
Tell us a little about your roof and we’ll call you back, usually within the hour during business hours. No pressure and no obligation. Ask about financing options.
- Call or text
- (203) 736-7739
- [email protected]
- License
- CT HIC #0701539