Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 149+ reviews

Old Saybrook, CT Roof Repair & Replacement. Licensed & Insured

5/5 stars from 149+ homeowners in Old Saybrook. Manufacturer-certified roofing contractor. Free inspections. Financing available.

19+
Years
500+
Projects
5
Rating
19+
Years Experience
500+
Projects Completed
5
Star Rating (149+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Old Saybrook 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

Our Old Saybrook crews tear off and replace 15-20 roofs a month. That kind of volume means tight installs, clean job sites, and no wasted time. Most homes are done in a day. Two-story steep-pitch jobs take two.

roof repair
SAME-DAY

Roof Repair

Not every problem needs a full replacement. Sometimes it's a blown-off shingle, a cracked pipe boot, or deteriorated valley flashing. We diagnose the actual issue and fix that. We don't upsell you into a new roof you don't need.

storm damage repair
LICENSED

Storm Damage Repair

After a storm in Old Saybrook, half the roofers in town show up knocking on doors. Most of them aren't from here. We are. We've been handling storm claims in Old Saybrook for 19 years. We know the adjusters, we know the process.

new roof installation
TOP RATED

New Roof Installation

We install new roofs on new construction, room additions, detached garages, and covered patios. Our Old Saybrook crews handle residential and light commercial. Standard install time is 1-3 days depending on size.

metal roofing
GUARANTEED

Metal Roofing

Standing seam metal roofing with Kynar 500/Hylar 5000 PVDF finish. The coating that keeps color for 40+ years without fading or chalking. We install Sheffield Metals and McElroy Metal panels in 24-gauge Galvalume steel with concealed Z-clips. UL 2218 Class 4 impact resistance. UL 790 Class A fire rating. Wind uplift tested to ASTM E1592. The only roof you'll ever need in Old Saybrook.

shingle roofing
INSURED

Shingle Roofing

Architectural shingles are what 80% of Old Saybrook homeowners choose. They look better than 3-tab, last longer, and handle wind better. We install GAF Timberline, Owens Corning Duration, and CertainTeed Landmark.

flat roofing
FREE ESTIMATE

Flat Roofing

TPO single-ply membrane in 60-mil or 80-mil thickness, hot-air welded seams, fully adhered or mechanically attached over polyiso insulation board. We install per NRCA and manufacturer specifications. Ponding water is the number one cause of flat roof failure. We use tapered ISO insulation to create minimum 1/4" per foot slope to drains. FM 4473 rated systems available for hail-prone Old Saybrook areas.

commercial roofing
SAME-DAY

Commercial Roofing

Our Old Saybrook commercial crews handle everything from small retail strip centers to 50,000 sq ft warehouses. TPO, EPDM, modified bitumen, metal. We're certified installers for all major commercial membrane systems.

gutter installation
LICENSED

Gutter Installation

Gutters aren't glamorous, but they're protecting your foundation, your fascia, and your landscaping. We install seamless aluminum gutters custom-formed on-site from a roll of coil stock. No seams means no leaks.

roof inspection
TOP RATED

Roof Inspection

Roof inspections after a storm are free. Always. We document hail hits, wind damage, and any pre-existing issues so your insurance claim is accurate and complete.

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

VELUX FS fixed skylights and VS vented skylights installed with EDL flashing kits for profile roofing. The flashing integrates with your shingle courses per IRC R903.2 weather protection requirements. We cut the opening, frame the curb with doubled 2x lumber, install the skylight with factory sealant, and weave the flashing into the existing shingle field. Leak-proof when done right. And we do it right in Old Saybrook.

Why Choose Old Saybrook Roofing & Maintenance?

Trusted by homeowners and businesses across Old Saybrook.

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.

Insurance Claims Handled

Storm damage? We work with your insurance company directly. Free inspection, Xactimate documentation, adjuster meeting on-site. We fight for full replacement when your roof qualifies.

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.

5-Star Google Rating

149+ homeowners reviewed us. We don't pay for reviews or offer discounts for them. Those are real people who hired us and took the time to say we did a good job.

Our Work

Recent Projects

View All Projects โ†’

Simple Process

How It Works

1

Complimentary Assessment

Before we quote anything, we inspect everything. Shingles, flashing, pipe boots, ridge vent, soffit, gutters. You get a full written report with photos.

2

No-Surprise Quote

You get a written proposal with material specs, labor breakdown, timeline, and total cost. The number on the quote is the number you pay. No change orders, no hidden fees.

3

Professional Crew

Our crews average 8 years of experience each. They tear off the old roof, inspect the decking, replace any damaged boards, and install your new system from the deck up.

4

Your Approval

We walk the property with you, show you the finished roof, answer any questions. Then we run the magnetic nail sweep and clean up every scrap of debris.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 149+ reviews
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"Needed emergency tarping after a tree hit our roof. They were there in about 3 hours. On a Saturday. Tarped the whole section, removed the branch, and had a crew out Monday morning for the repair."

S
Stephanie W.
Old Saybrook
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"Used Old Saybrook Roofing & Maintenance for a leak repair over our bathroom. Turned out to be a cracked pipe boot โ€” $425 fix. Honest guys, could have told me I needed a new roof but they didn't."

B
Brian E.
Old Saybrook
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"I'm a contractor and I use Old Saybrook Roofing & Maintenance for all my roofing subs. Their installs pass inspection every time. Their crew lead has been doing this 20+ years and it shows."

M
Maria G.
Old Saybrook

Service Areas

Areas We Serve

Old Saybrook Roofing & Maintenance provides roofing services throughout Old Saybrook and the greater CT area. Free estimates everywhere we serve.

South Windham Washington Depot Woodstock Canaan East Berlin Guilford Middlebury North Granby Prospect South Windsor
T

Meet the Owner

Todd Stewart

Owner & Lead Contractor

Todd has been serving Old Saybrook for over 19 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 149+ five-star reviews."

License #776441 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

There's no single "best" shingle. It depends on what you need. For warranty coverage, GAF Timberline HDZ with Golden Pledge is the best in the industry. For wind resistance, Owens Corning Duration with SureNail locks down tight. For value, CertainTeed Landmark or IKO Cambridge give you solid performance at a lower price point. We carry all of them.

Absolutely. Our team includes HAAG Certified Inspectors who document storm damage the way insurance adjusters expect. We file the claim, meet the adjuster, handle supplements if the initial estimate is low, and complete the repairs. We work with every major carrier in Connecticut.

Manufacturer warranties range from 30 years to lifetime depending on the shingle line. Our workmanship warranty covers our labor and installation for the term stated in your contract. The best combo is the GAF Golden Pledge: 50-year material plus 25-year workmanship. That's what being a Master Elite contractor gets you.

A typical Old Saybrook home with a 25-35 square roof runs $10,000-$18,000 for a full tear-off and install with architectural shingles. Steep-pitch homes and multi-story homes cost more because of safety requirements and access difficulty. Metal roofing is $12-$22 per sq ft. We quote exact numbers, not ranges.

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˜… 5/5 from 149+ Reviews  ยท  Licensed  ยท  Insured