Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 310+ reviews

Local Chaplin Roofing Contractor | 15+ Years

Full tear-off and replacement down to the roof deck. Ice and water shield, synthetic underlayment, new flashing. No shortcuts. Free estimates, no pressure. Ever.

15+
Years
500+
Projects
4.9
Rating
15+
Years Experience
500+
Projects Completed
4.9
Star Rating (310+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Chaplin โ€” from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.

roof replacement
FREE ESTIMATE

Roof Replacement

We handle the whole replacement from permits to final inspection. Our Chaplin office pulls the permit, coordinates the dumpster, runs the crew, and schedules the building inspector. You sign the contract and we handle the rest.

roof repair
SAME-DAY

Roof Repair

Leak repairs in Chaplin start at $350 for a simple fix. We find the source with a water test or thermal scan, repair the damage, and warranty the work. If the repair costs more than 30% of a replacement, we'll tell you.

storm damage repair
LICENSED

Storm Damage Repair

We work with every major insurance carrier. State Farm, Allstate, USAA, Liberty Mutual, Farmers, Nationwide. Our supplement team knows Xactimate line items and fights for full replacement when your roof qualifies.

new roof installation
TOP RATED

New Roof Installation

A new roof installation starts with getting the specs right. Roof pitch determines your material options. Attic space determines ventilation needs. Local code determines underlayment requirements. We handle all of that before the first shingle goes on.

metal roofing
GUARANTEED

Metal Roofing

Metal roofing costs more upfront at $12-$22 per sq ft installed in Chaplin compared to $4-$8 for shingles. But it lasts 2-3x longer and your energy bills drop 15-25%. Math works out over time.

shingle roofing
INSURED

Shingle Roofing

Your shingle choice determines your warranty, your curb appeal, and how your roof handles Connecticut weather. We'll show you samples, explain the differences, and let you pick what fits your budget. No pressure.

flat roofing
FREE ESTIMATE

Flat Roofing

Commercial flat roof replacement in Chaplin starts with a core sample to check the existing insulation. If it's waterlogged, everything comes off. If it's dry, we can sometimes overlay. Saves you $2-$4 per square foot.

commercial roofing
SAME-DAY

Commercial Roofing

Roof coatings can extend the life of your commercial roof by 10-15 years for a fraction of replacement cost. We apply silicone and acrylic coatings over existing TPO, EPDM, and metal substrates. Not every roof qualifies. We'll be straight with you.

gutter installation
LICENSED

Gutter Installation

If your gutters overflow during rain, they're either clogged, undersized, or pitched wrong. Sometimes all three. We'll assess the issue and fix it. Might be a cleaning, might be a replacement.

roof inspection
TOP RATED

Roof Inspection

Buying a home in Chaplin? Get an independent roof inspection before you close. Home inspectors look at the roof from the ground with binoculars. We get on it. Big difference.

emergency roof repair
GUARANTEED

Emergency Roof Repair

We keep tarps, plywood, and common repair materials on every truck. When you call (877) 586-1316 for an emergency, our crew shows up ready to work. Not ready to give you a sales pitch.

skylight installation
INSURED

Skylight Installation

Tubular skylights bring light into tight spaces. Closets, laundry rooms, interior bathrooms. They use a reflective tube through the attic space, so they work even when the roof is far from the ceiling. Installed in a few hours.

Why Choose Chaplin Roofing & Maintenance?

Trusted by homeowners and businesses across Chaplin.

GAF Master Elite Contractor

Only 3% of roofers earn this certification. It means we can offer the Golden Pledge warranty: 25-year workmanship plus 50-year materials. Best warranty in roofing, full stop.

Manufacturer Certified

GAF Master Elite, Owens Corning Preferred, CertainTeed SELECT ShingleMaster. We carry certifications from the big three. That means factory-trained crews and the best available warranties.

Financing Available

A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.

Licensed & Insured

Fully licensed, bonded, and insured in Connecticut. We carry $2M in general liability. Workers' comp on every crew member. Your property is protected if anything goes sideways.

Our Work

Recent Projects

roof replacement project

Roof Replacement

Chaplin, CT

roof repair project

Roof Repair

Chaplin, CT

storm damage repair project

Storm Damage Repair

Chaplin, CT

View All Projects โ†’

Simple Process

How It Works

1

We Inspect First

We climb up, walk the entire roof, and document what we find with photos and measurements. Takes about 30 minutes. You'll see exactly what we see.

2

Written Estimate

Our Chaplin estimator builds your proposal same-day in most cases. Includes material options, warranty comparison, and a realistic timeline for your specific roof.

3

Build Day

Dumpster arrives at 7 AM. Tarps on the landscaping. Tear-off starts immediately. New ice and water shield, underlayment, drip edge, shingles, ridge vent. All in sequence.

4

Your Approval

Our project manager does a final inspection against the manufacturer's installation checklist. We register your warranty the same day. You get the paperwork within a week.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 310+ reviews
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"We were quoted $18,500 for a 32-square replacement with Timberline HDZ. They hit the number exactly. No change orders, no surprise fees. That's rare in this business."

J
Jeff H.
Chaplin
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"Asked for a second opinion because another company said I needed a full replacement. Chaplin Roofing & Maintenance said I only needed valley flashing repair and some shingle replacement. Saved me about $14,000. I trust these guys."

J
Jeff K.
Chaplin
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"We had hail damage from the March storm. They met with our adjuster, got the roof approved for full replacement, and finished the job in one day. Five stars doesn't feel like enough."

M
Mike P.
Chaplin

Service Areas

Areas We Serve

We're based in Chaplin and cover all of Cornwall, Fairfield, Lebanon, New Haven, Oxford. Same crew, same quality, no travel charges.

Cornwall Fairfield Lebanon New Haven Oxford Seymour Thompson Willimantic Bolton Cos Cob
T

Meet the Owner

Timothy Thomas

Owner & Lead Contractor

Timothy has been serving Chaplin for over 15 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company โ€” but the values haven't changed.

"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 310+ five-star reviews."

License #860327 15+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

We recommend GAF, Owens Corning, or CertainTeed. And we're certified by all three, so the choice is yours. In Chaplin, the most popular pick is GAF Timberline HDZ in Weathered Wood or Charcoal. For hail-prone areas, look at the impact-resistant versions rated UL 2218 Class 4. We walk you through the options during the estimate.

Most residential roofs in Chaplin are done in one day. We show up at 7 AM, tear off the old roof, install the new system, and clean up by end of day. Two-story homes, steep pitches, or large roofs might take two days. We never leave a house uncovered overnight.

Yes. We handle insurance claims regularly. It's a big part of what we do in Chaplin. Free inspection, photo documentation, claim filing assistance, and we meet the adjuster on-site. If the claim is approved, we do the work at the insurance-approved price. You pay your deductible and we handle the rest.

Catch the water with a bucket, move valuables out of the drip zone, and call us at (877) 586-1316. Don't get on the roof yourself. It's dangerous and you probably can't fix it permanently anyway. We respond to emergency leaks within 24 hours in Chaplin and tarp the area to stop further damage.

We partner with GreenSky and Hearth for roofing financing. Options include 12-month same-as-cash (0% if paid in full within 12 months), 5-year fixed rate, and 7-10 year extended plans. Monthly payments on a $15,000 roof run about $150-$250/month depending on the term. Apply during the estimate.

Have more questions? Call (877) 586-1316

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

📞 Call (877) 586-1316

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 310+ Reviews  ยท  Licensed  ยท  Insured