★★★★★ 4.9 Stars · 388+ Reviews

Storm Damage? Free Roof Inspection in Chili — Call Now

Same-Day Appointments Available · 24/7 Emergency Service

Free storm damage inspections. Manufacturer-backed warranties. Fast estimates for Chili homeowners.

Call (877) 349-1553

📞 (877) 349-1553

Free estimates · Financing options available

Same-Day Service Licensed & Insured Free Estimates

<60 Min

Response Time

12+

Years Experience

4.9

Star Rating

388+

Happy Reviews

If your Chili home needs a new roof or a repair, Highland Roofing & Maintenance is the contractor to call. We're based in Highland and our crews are in Chili every week, inspecting roofs, replacing shingles, and handling storm damage claims.

Our Services in Chili

FREE INSPECTION

Roof Replacement

Full tear-off and replacement with GAF Timberline HDZ, Owens Corning Duration, or CertainTeed Landmark shingles. Includes ice and water shield, synthetic underlayment, new drip edge, and ridge ventilation. Most Chili roofs completed in a single day.

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SAME-DAY ESTIMATE

Roof Repair

Leak repairs, missing shingle replacement, flashing reseals, pipe boot replacement, and valley repairs. We diagnose the actual problem with a hands-on inspection — no guessing from the ground. Written estimate before any work starts.

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EMERGENCY TARPING

Storm Damage Repair

Hail damage, wind damage, and rain intrusion repair for Chili homes. Free storm damage inspections with photo documentation. We handle the insurance claim process from filing through supplement negotiation.

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FREE CONSULTATION

New Roof Installation

New construction and addition roofing with manufacturer-certified installation. We work from architectural plans, coordinate with your builder, and install to factory specs so your warranty is valid from day one.

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40-70 YEAR LIFESPAN

Metal Roofing

Standing seam and exposed fastener metal panels in steel and aluminum. 40 to 70 year lifespan with minimal maintenance. Energy-efficient cool-roof coatings available for Chili heat.

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AVAILABLE

Shingle Roofing

Shingle Roofing services for Chili — call for details.

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COMMERCIAL & RESIDENTIAL

Flat Roofing

TPO, EPDM, and modified bitumen systems for flat and low-slope roofs. Proper drainage, flashing details, and penetration sealing to prevent ponding water. Commercial and residential flat roofs in Chili.

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MAINTENANCE PLANS

Commercial Roofing

TPO, EPDM, PVC, and built-up roofing for Chili commercial properties. Office buildings, retail centers, warehouses, and multi-family. Preventive maintenance contracts available to extend roof life.

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AVAILABLE

Gutter Installation

Gutter Installation services for Chili — call for details.

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AVAILABLE

Roof Inspection

Roof Inspection services for Chili — call for details.

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AVAILABLE

Emergency Roof Repair

Emergency Roof Repair services for Chili — call for details.

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AVAILABLE

Skylight Installation

Skylight Installation services for Chili — call for details.

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What Chili Customers Say

★★★★★

"The Golden Pledge warranty was a big factor in our decision. 25 years on workmanship plus 50 on materials. Highland Roofing & Maintenance is one of the few local companies that can even offer it."

— Karen T., Chili

★★★★★

"Hail punched through half our shingles last spring. Highland Roofing & Maintenance handled the entire insurance claim — met the adjuster, filed the supplement, and we paid nothing out of pocket besides the deductible."

— Jennifer H., Chili

Join 388+ Happy Customers — Call (877) 349-1553

Why Chili Residents Choose Highland Roofing & Maintenance

12+ Years of Experience

We've been installing and repairing roofs for over 12 years. That experience shows in how we handle complex roof lines, unexpected deck damage, and insurance claim disputes. We've seen everything and know how to handle it.

Manufacturer-Certified Installation

We hold certifications from GAF, Owens Corning, and CertainTeed. That means the manufacturers have trained and vetted our crews and will back our installations with their strongest warranties. Your Chili roof gets factory-level quality control.

Free Inspections & Honest Estimates

We don't charge for inspections and we don't pad estimates. If your Chili roof needs a repair, we'll tell you. If it needs a replacement, we'll explain exactly why. No high-pressure sales, no scare tactics.

No Subcontractors

Every Chili roof is installed by our own trained crews, not subcontractors pulled from a labor pool. That means consistent quality, accountability, and a crew that knows our standards from the first nail to the last drip edge.

Chili Roofing FAQ

You get two warranties: the manufacturer's material warranty (30-50 years depending on the shingle) and our written workmanship warranty. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on materials.

Often, yes. Not every roof problem requires a full replacement. If the damage is isolated (a few missing shingles, a flashing leak, a small area of hail damage), a repair may be the right call. We'll inspect and give you an honest recommendation.

Most residential roofs are completed in a single day. We stage materials the day before and our crew arrives at 7 AM. Larger homes, steep pitches, or multi-layer tear-offs may take two days. We never leave a roof uncovered overnight.

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SAME-DAY APPOINTMENTS AVAILABLE

Storm Damage Waits for No One. Call Highland Roofing & Maintenance at (877) 349-1553.

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

Call Now — Free Estimate

📞 (877) 349-1553

★★★★★ 4.9/5 from 388+ Reviews · Licensed · Insured

About Our Chili Roofing Services

Every roof we install in Chili meets local building code requirements and manufacturer specifications. That matters because it protects your warranty. Cut corners during installation and the manufacturer can void your coverage. We don't cut corners.

Whether you're in downtown Chili or one of the surrounding neighborhoods, Highland Roofing & Maintenance has you covered. Call (877) 349-1553 for a no-obligation estimate. We'll show up when we say we will.

Distance from Highland to Chili means nothing to us. Our crews are already working there. No extra fees, no delays, no subcontractors.

Other Areas We Serve

Belgium, WI → East Troy, WI → Glenbeulah, WI → Jefferson, WI → Marathon, WI → New Franken, WI → Porterfield, WI → Sherwood, WI →