Roofing Services in Milford, CT

Roof replacement, metal roofing, free inspections, and storm damage assessments โ€” all from one local, licensed company.

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Asphalt Shingle Roof Replacement

The workhorse of Connecticut roofing. Architectural shingles deliver 25โ€“30 years of protection at the best price point, with dozens of colors to match your home. Every install includes ice-and-water shield, synthetic underlayment, proper ventilation, and new flashing.

Asphalt Shingle Roofing โ†’
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Standing Seam Metal Roofing

The premium, buy-it-once option. Standing seam metal lasts 50+ years, sheds snow, resists coastal wind and salt air, and gives your home a sharp modern profile. Popular on shoreline homes and porch roofs across Milford.

Metal Roofing โ†’
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Free Roof Inspections

Not sure what your roof needs? We inspect it for free, document everything with photos, and tell you the truth โ€” repair, replace, or leave it alone. No pressure, no obligation, no invented problems.

Free Inspections โ†’
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Storm Damage Assessments

After wind, hail, or a nor'easter, small damage becomes big leaks fast. We assess storm damage before it gets worse and document what you may need for an insurance claim.

Storm Damage โ†’
Close-up aerial of new architectural asphalt shingles installed by Charter Oak Roofing in Connecticut
Every Job, Every Time

What's Included in Every Charter Oak Roof

  • Complete tear-off โ€” we never roof over old shingles
  • Ice & water shield at eaves and valleys (critical for CT winters)
  • Synthetic underlayment across the entire deck
  • New drip edge, pipe boots, and flashing
  • Ridge vent for proper attic ventilation
  • Magnetic nail sweep of your lawn and driveway
  • Final drone photos so you see exactly what you paid for
Get Your Free Estimate
Free Estimate

Ready for a Roof You Never Have to Think About Again?

Free written estimate. Honest answers. Most roofs done in one day.

Call (203) 736-7739 Request a Callback
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