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★★★★★ 4.8/5 from 453+ reviews

Local Osceola Roof Repair & Replacement | 23+ Years

23+ years protecting Osceola homes and businesses. 4.8-star rated. Insurance claims handled.

📞 (877) 349-1553
23+
Years
500+
Projects
4.8
Rating
23+
Years Experience
500+
Projects Completed
4.8
Star Rating (453+ Reviews)
Licensed & Insured

Our Services

Our Roofing Services

Professional Roofing solutions for residential and commercial properties in Osceola.

roof replacement
FREE ESTIMATE

Roof Replacement

Full tear-off down to the decking, inspect every board, replace what's rotten, and install a complete roofing system from ice and water shield up. Most residential jobs finished in 1-2 days.

roof repair
SAME-DAY

Roof Repair

Step flashing at chimney walls is the number one leak source we see in Osceola. 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

Wind speeds over 60 mph cause shingle tab lift and seal failure. Hail over 1" diameter causes fractures through the shingle mat to the fiberglass reinforcement. Our HAAG-trained inspectors know the difference between cosmetic damage and functional damage. That distinction determines your insurance payout.

new roof installation
TOP RATED

New Roof Installation

Building a new home in Osceola? 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 Osceola metal crews do residential and commercial.

shingle roofing
INSURED

Shingle Roofing

Designer shingles like GAF Camelot and Owens Corning Berkshire mimic slate and cedar shake. Higher cost than standard architectural, but the look is incredible. We install all designer profiles in Osceola.

flat roofing
FREE ESTIMATE

Flat Roofing

Flat roofs need special attention. Water doesn't run off, it sits. We install TPO, PVC, EPDM, and modified bitumen systems designed to handle ponding water in Wisconsin's climate.

commercial roofing
SAME-DAY

Commercial Roofing

Flat roofs on commercial buildings are a different animal. We install and repair TPO, EPDM, modified bitumen, and built-up systems. Our Osceola commercial crew handles retail, warehouse, office, and multi-family buildings.

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

Our Osceola roof inspections cover shingles, flashing, pipe boots, ridge vent, soffit, gutters, and decking condition. You get a written report with photos. If nothing's wrong, we tell you that.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Emergency roof repairs for active water intrusion follow a strict protocol: tarping with reinforced polyethylene sheeting secured to the roof deck, interior water extraction guidance, and temporary flashing at penetrations. Our Osceola emergency crews carry 20x30 tarps, 2x4 nailer boards, and masonry anchors for various deck types. Permanent repairs are scheduled within 48-72 hours once materials are sourced.

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.

Ready to Get Started?

(877) 349-1553

Free Estimates • Available 24/7 • Licensed & Insured

Why Choose Osceola Roofing & Maintenance?

Trusted by homeowners and businesses across Osceola.

Licensed & Insured

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

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.

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.

23 Years in Osceola

We've been roofing Osceola homes since before half these companies had a website. 23 years means we know the local codes, the weather patterns, and the materials that hold up here.

Our Work

Recent Projects

View All Projects →

Simple Process

How It Works

1

Complimentary Assessment

Our inspector walks the roof looking at shingle condition, flashing integrity, vent function, and signs of moisture underneath. 30-45 minutes for most Osceola homes.

2

Your Custom Proposal

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

3

Professional Crew

No subcontractors. Our crews, our equipment, our supervision. A project manager checks in throughout the day and does a final quality inspection before cleanup.

4

Quality Check

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

★★★★★ 4.8/5 from 453+ reviews
★★★★★

"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."

K
Kevin O.
Osceola
★★★★★

"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."

T
Tim E.
Osceola
★★★★★

"Had a flat roof leak on our commercial building downtown. Osceola Roofing & Maintenance patched it temporarily, then came back and did a full TPO replacement the next week. Solved a problem we'd been chasing for two years."

A
Amber F.
Osceola

Service Areas

Areas We Serve

Serving Osceola and neighboring areas for 23+ years. We know the building codes and weather patterns here. It matters when you're choosing a roofer.

Eastman Glenwood City Jim Falls Marengo New Glarus Potosi Shiocton Verona Allenton Bonduel

FAQ

Frequently Asked Questions

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.

Depends on size, pitch, and materials. Average in Osceola is $12,000-$16,000 for a standard residential replacement with architectural shingles. We price by the square and itemize everything so you can compare to other quotes. Free estimates. Call (877) 349-1553.

First: put a bucket or container under the drip. If there's a visible bulge in the ceiling, carefully poke a small hole to let water drain into a bucket. This prevents the ceiling from collapsing. Then call (877) 349-1553. We do emergency tarping and temporary leak stops within 24 hours. The permanent repair follows once conditions allow.

Common signs: curling or cracking shingles, missing shingles after wind events, granule loss (look in your gutters), daylight visible through the attic, sagging roof deck, and age. Most asphalt roofs last 20-30 years in Wisconsin. If you see any of these, call (877) 349-1553 for a free inspection. We'll be honest about whether you need a replacement or just a repair.

Here's the process: we inspect your roof for free, document any storm damage with photos, and help you file the claim. Your insurance company sends an adjuster. We meet them on-site and walk the roof together. If approved, we do the work at the agreed price. If the estimate seems low, we supplement it with additional documentation.

Have more questions? Call (877) 349-1553

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

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

Call Now — Free Estimate
📞 (877) 349-1553

★★★★★ 4.8/5 from 453+ Reviews  ·  Licensed  ·  Insured

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