Roof replacement · Milford, CT
Charter Oak Roofing is Milford’s local, GAF Certified roofing company. Free written estimates, honest recommendations and two warranties on every new roof.
In short
Charter Oak Roofing is a licensed and insured residential roofing contractor in Milford, Connecticut. We replace and repair asphalt shingle and standing seam metal roofs, install gutters, and do free roof inspections across New Haven and Fairfield counties.
What we do
GAF Timberline shingles in Good, Better and Best packages. Most roofs done in one day.
Learn more ›MetalFull metal roofs and metal accents on porches and bump-outs. Built for wind and salt air.
Learn more ›RepairPipe boots, skylights, chimney flashing and missing shingles. Fixed fast, explained clearly.
Learn more ›GuttersAluminum K-style gutters sized and pitched to move water off your roof and away from the house.
Learn more ›InspectionA photo-documented look at your roof and an honest answer, even if it’s ‘your roof is fine.’
Learn more ›StormAfter wind or hail we check for lifted, creased and missing shingles before they turn into leaks.
Learn more ›Best · Better · Good
Every estimate shows all three side by side so you can choose. We don’t list a price here because no two roofs are the same. Size, slope, layers, decking and the materials you pick all change the number.
Thickest shingle and premium components
Priced on your roof’s size, slope and materials.
Our most popular package
Priced on your roof’s size, slope and materials.
Solid protection at the lowest cost
Priced on your roof’s size, slope and materials.
Backed in writing
As a 2026 GAF Certified Residential Roofing Contractor, we can register your roof for GAF’s System Plus Limited Warranty. Our own workmanship warranty sits on top of it.
Covers the GAF roof system on qualifying installs when GAF shingles are paired with GAF accessories like starter strip, leak barrier and ridge cap. Only certified contractors can offer it.
If something we installed fails because of how we installed it, we come back and fix it. In writing, with your contract.
How it works
We walk the roof, check decking, flashing and ventilation, and photograph everything we find.
An itemized quote with Best, Better and Good options. No guessing, no pressure, no sign-tonight deals.
Most roofs are torn off, replaced and cleaned up in a single day, supervised start to finish.
Drone photos of your finished roof, a magnetic nail sweep, and your warranties in writing.
Recent projects
Reviews
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!!!
Where we work
FAQ
Every roof is priced on its own size, slope, condition and the materials you pick, so we don't publish one number. We measure your roof, check the decking and ventilation, and give you a free written estimate with Best, Better and Good options side by side.
Most homes are done in one day, from tear-off to cleanup. Larger or more complex roofs can take two days. A crew lead supervises the job the whole time.
If your roof is under about 15 years old and the problem is in one spot, a repair usually makes sense. If shingles are curling, cracking or missing in several areas, or the roof is 20 years or older, replacement is usually the better investment. We'll tell you which one you actually need.
Yes. Charter Oak Roofing LLC is a licensed Connecticut home improvement contractor, HIC #0701539, with general liability and workers' compensation insurance on every job.
Yes. We are a 2026 GAF Certified Residential Roofing Contractor, which lets us offer the GAF System Plus Limited Warranty on qualifying GAF roofs.
Every full replacement includes the GAF System Plus Limited Warranty on qualifying GAF roof systems plus our own 5-year written workmanship warranty.
Yes. Ask about financing options when we give you your estimate and we'll walk you through what's available.
We're based in Milford and work across New Haven and Fairfield counties, including Stratford, Orange, West Haven, New Haven, Shelton, Trumbull, Fairfield, Westport, Seymour, Naugatuck and Bethany, and we take jobs elsewhere in Connecticut.
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.
