About us
Roofers first. Salesmen never.
A local Milford roofing company built on straight answers and one-day installs.
Our story
Homeowners deserve a roofer who tells them the truth.
Charter Oak Roofing was built on a simple idea. No commissioned salesmen, no scare tactics, no “sign tonight for the discount.” Just an honest assessment, a detailed written estimate, and a crew that shows up when we say we will.
We’re named after Connecticut’s Charter Oak because we’re rooted here. We live in the Milford area, and our reputation walks around town with us. That’s why every roof we install is treated like it’s on our own house.
Every job is planned and supervised from tear-off to the final magnetic nail sweep. That’s how most roofs get finished in a single day without cutting corners.
- Licensed & insured Connecticut contractor, HIC #0701539
- 2026 GAF Certified Residential Roofing Contractor
- 5.0-star Google rating across 23 reviews
- GAF System Plus warranty plus 5-year workmanship warranty
- Drone photos of your finished roof, every time
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!
Great communication, fair price, and quick, quality work.
Amazing customer service in fantastic results. Everyone I dealt with was polite and professional. Best in the area – highly recommended!
Recently had my roof redone and I couldn’t be more happier with the work that was done. Great job again fellas thank you!!!
FAQ
About Charter Oak
Who owns Charter Oak Roofing?
Charter Oak Roofing LLC is locally owned and run out of Milford, Connecticut. Mike Plaskon runs day-to-day operations and oversees jobs from start to finish.
Why is it called Charter Oak?
It's named after Connecticut's Charter Oak, because we're rooted here. We live in the Milford area and our reputation goes everywhere we do.
Do you use salesmen?
No commissioned salesmen. The people who inspect your roof are roofers, and they give you a straight answer.
Free estimate
Meet us at your free estimate
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
