Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 259+ reviews

Cortland Roof Repair & Replacement. Free Estimates

We've replaced 259+ roofs across Illinois. GAF Timberline HDZ, Owens Corning Duration, CertainTeed Landmark. Same-day estimates. Manufacturer warranties up to 50 years.

19+
Years
500+
Projects
4.9
Rating
19+
Years Experience
500+
Projects Completed
4.9
Star Rating (259+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Cortland 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

A roof replacement in Cortland typically runs $8,500 to $24,000 depending on the size and pitch. We give you an exact number upfront with a written proposal. No surprises on install day.

roof repair
SAME-DAY

Roof Repair

Step flashing at chimney walls is the number one leak source we see in Cortland. Improper step flashing causes roof leaks. It's that simple. We install new step flashing with a chimney cricket for proper water diversion, sealed with Geocel tripolymer sealant. Fix it once, fix it right.

storm damage repair
LICENSED

Storm Damage Repair

Our storm damage process: free inspection, full photo documentation, direct filing with your insurance carrier, meet the adjuster on-site, and handle the repairs once approved. We don't ask for money upfront on insurance claims.

new roof installation
TOP RATED

New Roof Installation

Building a new home in Cortland? Our crew works directly with your GC or we self-perform. We handle everything from the decking up: underlayment, ventilation design, material installation, and final inspection.

metal roofing
GUARANTEED

Metal Roofing

Standing seam metal lasts 40-60 years with practically zero maintenance. Higher upfront cost than shingles, but you'll never replace it again. Our Cortland metal crews do residential and commercial.

shingle roofing
INSURED

Shingle Roofing

Asphalt shingle roofing is the most common and cost-effective roofing system in Cortland. Our crews install 15-20 shingle roofs a month. We know the product inside and out. Nailing patterns, exposure measurements, hip and ridge details.

flat roofing
FREE ESTIMATE

Flat Roofing

We repair and install flat roofs on Cortland homes, garages, commercial buildings, and additions. TPO for reflectivity, EPDM for budget, PVC for chemical resistance near restaurants and kitchens.

commercial roofing
SAME-DAY

Commercial Roofing

Modified bitumen (mod-bit) is still the best choice for high-traffic commercial roofs in Cortland. We torch-apply SBS-modified base and cap sheets over properly primed concrete or approved decking. Two-ply mod-bit systems carry 20-year NDL (No Dollar Limit) warranties through GAF, Firestone, or Johns Manville. NRCA member. We follow the manual.

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

Free roof inspections for Cortland homeowners. No catch, no obligation. We inspect your roof, hand you the report, and let you decide what to do next. If you need work, we'll quote it. If you don't, we'll say so.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Storm damage, fallen trees, sudden leaks. We handle all roofing emergencies in Cortland. First we stop the water, then we fix the cause. Emergency response available 7 days a week.

skylight installation
INSURED

Skylight Installation

Skylight installation costs $1,200-$3,500 in Cortland depending on size, type, and roof pitch. That includes the unit, flashing kit, interior trim, and roof patch-in. We handle everything from the outside in.

Why Choose Cortland Roofing & Maintenance?

Trusted by homeowners and businesses across Cortland.

4.9-Star Google Rating

259+ 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.

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.

Written Warranty

Manufacturer warranty plus our workmanship warranty in writing. If something fails because of our installation, we come back and fix it at no charge. Period.

Clean Job Sites

We run magnetic nail sweeps three times. Once during tear-off, once after install, once before we leave. Tarps on the ground, dump trailer in the driveway. Your yard looks the same when we're done.

Our Work

Recent Projects

roof replacement project

Roof Replacement

Cortland, IL

roof repair project

Roof Repair

Cortland, IL

storm damage repair project

Storm Damage Repair

Cortland, IL

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

Your Custom Proposal

Multiple material options at different price points so you can compare. GAF, Owens Corning, CertainTeed. We install all three and let you pick what fits your budget.

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

Quality Check

Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 4.9/5 from 259+ reviews
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"Our insurance company tried to lowball us on the storm claim. Cortland Roofing & Maintenance supplemented the estimate and got it approved for $7,000 more. They know the Xactimate system better than the adjuster did."

D
Dave W.
Cortland
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"The crew showed up at 7:30 and was done by 4. Old roof off, new one on, yard cleaned up. I watched from the window. These guys don't mess around."

S
Stephanie O.
Cortland
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"Went with the Owens Corning Duration shingles in Estate Gray. The SureNail strip is legit. You can see each shingle is locked down tight. Happy with the choice."

P
Paul A.
Cortland

Service Areas

Areas We Serve

Roofing Cortland and Hartsburg, La Prairie, Mclean, Northbrook, Rantoul for 19+ years. Every roof we install gets the same attention whether it's across town or across the county.

Hartsburg La Prairie Mclean Northbrook Rantoul Sims Villa Grove Alsip Bristol Colfax
J

Meet the Owner

Jake Thomas

Owner & Lead Contractor

Jake has been serving Cortland 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 259+ five-star reviews."

License #155277 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

The shingles carry the manufacturer's warranty. Typically 30-50 years for architectural shingles. Our installation warranty covers any defects in our workmanship. If something goes wrong because of how we installed it, we fix it at no cost. Both warranties are in writing and we provide them at the final walkthrough.

We recommend GAF, Owens Corning, or CertainTeed. And we're certified by all three, so the choice is yours. In Cortland, 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.

Age is the biggest factor. If your shingles are 20+ years old and you're seeing curling, cracking, or granule buildup in the gutters, it's time. Other red flags: leaks, missing shingles, daylight in the attic, and your neighbors all getting new roofs (same-age homes in a subdivision often need replacement around the same time).

Yes. One day is standard for most residential jobs. We start early, work efficiently, and finish before dark. If your roof is larger than 40 squares or has a complex layout, it might push to day two. Either way, we seal everything watertight before we leave each night.

Absolutely. A new roof shouldn't mean emptying your bank account. We have 0% intro options, low fixed-rate plans, and extended terms up to 12 years. Quick credit check, fast approval, and you can get your roof done this month instead of waiting until you've saved enough.

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 259+ Reviews  ยท  Licensed  ยท  Insured