Roof Replacement Services in Southeast Wisconsin
Asphalt shingle roofs built to handle 40+ inches of annual snowfall, installed by CertainTeed ShingleMaster™ PRO roofers with 30+ years of local experience.
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An aging roof doesn’t fail all at once. It sends warning signs. Granules collecting in your gutters. A ceiling stain that comes back after every rain. Shingles curling at the edges. Energy bills climbing because your attic is exposed to moisture. If your roof is 20 or more years old, or has sustained storm damage that compromises more than a third of its surface, a patch won’t solve the underlying problem. You need a full replacement before the damage spreads to your decking, insulation, and interior.
Four Leaf Roofing & Windows provides complete roof replacement services across Southeast Wisconsin. As a ShingleMaster™ PRO contractor, our veteran-owned team replaces asphalt shingle, cedar shake, slate, metal, and Euroshield rubber roofing systems, all backed by our lifetime workmanship warranty and ShingleMaster™ PRO 3-Star and 4-Star SureStart™ PLUS warranties.
Every replacement begins with our free 50-point inspection, followed by expert material guidance, professional tear-off, and precision installation by our own trained crew. Call (414) 455-2345 for your free 50-point roof inspection.
When Does a Roof Need Full Replacement vs Repair?
Replace your roof when it is 20 or more years old, has three or more active leaks, shows widespread granule loss, or has storm damage covering more than one-third of the surface. Isolated damage on a newer roof usually calls for roof repair instead.
The line between repair and replacement comes down to how widespread the damage is and how much life the roof has left.
Repair makes sense when:
- The damage is localized (a few missing shingles, one small leak, flashing that pulled loose in a single spot)
- The roof is under 15 years old
- The underlying decking is dry and solid.
In these cases, a targeted fix restores protection at a fraction of replacement cost.
Replacement makes sense when:
- The roof is 20+ years old. Asphalt shingles are engineered for a defined lifespan, and once they pass it, granules shed and the mat underneath breaks down.
- There are three or more active leaks, signaling system-wide failure, not a single weak point.
- Storm damage is widespread. When hail or wind damage affects multiple roof sections, full replacement may be more practical than targeted repairs.
- Energy bills are rising. A failing roof lets moisture into your attic and conditioned air escape, driving heating and cooling costs up.
When you are not sure which path is right, our free inspection gives you a documented answer (not a sales pitch). If a repair will genuinely serve you better, we will tell you.
What Roofing Materials Does Four Leaf Install?
Four Leaf installs five roofing systems: asphalt shingle, cedar shake, natural slate, metal, and Euroshield recycled rubber. Each is matched to your home’s structure, budget, and the demands of the Wisconsin climate.
Asphalt Shingle Roof Replacement
The most popular choice for Wisconsin homes. We install CertainTeed Landmark-series shingles with wind-resistance and warranty coverage that varies by product line. Impact-resistant options are also available.
Cedar Shake Roof Replacement
Natural cedar shake and shingle roofing for homes seeking a classic Wisconsin aesthetic. Cedar is naturally insulating and weather-resistant when properly installed and maintained, and it ages into a distinctive silver-gray.
Slate Roof Replacement
Premium natural slate roofing with a 75-100 year lifespan, often outlasting the home itself. Slate is heavy and requires a structural assessment before installation. Our team has 30 years of slate installation experience.
Metal Roof Replacement
Standing seam and metal shingle options engineered for Wisconsin snow loads. Metal offers a 40-70 year lifespan with virtually zero maintenance and optional energy-efficient reflective coatings.
Euroshield Rubber Roofing
Recycled rubber roofing tiles that mimic slate or shake at a fraction of the weight and cost. Euroshield carries a Class 4 impact rating (the highest available), making it ideal for Wisconsin hail zones. Made from approximately 95% recycled materials, including recycled tire rubber, with a 50-year warranty.
How Much Does a Roof Replacement Cost in Wisconsin?
A new asphalt shingle roof costs $8,000–$17,000 for most Wisconsin homes. Cedar runs $15,000–$30,000, metal ranges $12,000–$25,000, and slate or Euroshield vary by structure. Final price depends on roof size, pitch, and material. See our full Wisconsin roofing cost guide.
Three factors drive your final number more than anything else:
- Size: Roofing is priced per square (100 square feet). A 1,750 sq ft roof needs fewer materials and labor hours than a 3,000 sq ft home.
- Pitch and complexity: Steep roofs, multiple valleys, dormers, and skylights add labor time and safety requirements.
- Material: Asphalt sits at the affordable end while slate and metal command a premium for their lifespan.
Insurance and financing. When storm, hail, wind, or another covered event causes the damage, homeowners insurance may cover the affected portion of the roof, subject to the policy terms, approved scope, and deductible. We document everything during the inspection to support your claim. For out-of-pocket projects, we offer 0% financing for up to 21 months so you can protect your home now and pay over time.
What Happens During a Four Leaf Roof Replacement?
A Four Leaf roof replacement follows nine steps: free 50-point inspection, material selection, full tear-off, deck repair, ice & water shield, underlayment, shingle installation, ridge cap and ventilation, then cleanup and a final walkthrough. Most projects finish in 1–3 days.
Here is exactly what to expect:
01
Free 50-point inspection
We assess every component and give you a written report.
02
Material selection
You choose the system that fits your home and budget with our guidance.
03
Full tear-off
We remove the old roof down to the deck, so nothing failing is left behind.
04
Deck repair
We inspect the wood decking and replace any rotted or soft sections.
05
Ice & water shield
A waterproof membrane goes along eaves and valleys to stop ice dams.
06
Underlayment
A protective layer covers the entire deck beneath the shingles.
07
Shingle (or panel) installation
Your chosen material is installed to manufacturer spec.
08
Ridge cap & ventilation
Ridge vents and drip edge complete the system and let your attic breathe.
09
Cleanup & final walkthrough
We run magnetic sweeps for nails, haul away debris, and walk the finished roof with you.
Because every component (shingles, underlayment, flashing, and ventilation) is installed as one integrated system rather than piecemeal, your roof performs and lasts as the manufacturer intended. Roof replacement is one of the many residential roofing services our team provides across Southeast Wisconsin.
Why Choose Four Leaf for Your Roof Replacement?
Four Leaf Roofing & Windows is a CertainTeed ShingleMaster™ PRO contractor, with 160 five-star Google reviews and 30 years serving Southeast Wisconsin. Every roof carries a lifetime workmanship warranty and is installed by our own crew.
- ShingleMaster™ PRO: We carry advanced CertainTeed Master Craftsman installer certifications and employ an on-staff Shingle Quality Specialist. Our crew has proven, comprehensive expertise across the entire CertainTeed Integrity Roof System. As a ShingleMaster™ PRO contractor, we are authorized to offer homeowners upgraded, extended 3-Star and 4-Star SureStart™ PLUS warranties.
- 160 five-star reviews: Our reputation is built on completed projects, not promises.
- Veteran-owned, 30 years: A locally rooted team led by U.S. Navy veteran Joseph T. O’Brien who understands Wisconsin’s freeze-thaw cycles, hail, and snow loads.
- Lifetime workmanship warranty: We stand behind every installation for as long as you own the home.
- No subcontractors: Our own trained crew is on your roof from start to finish.
- BBB Accredited — A+ Rating: Verified A+ rating, accredited since 2024.
- Featured in Milwaukee Magazine: Named a Face of Roofing in 2024 and 2025.
Where Does Four Leaf Replace Roofs in Southeast Wisconsin?
Four Leaf replaces roofs across Southeast Wisconsin from our New Berlin headquarters at 2875 S Moorland Rd, New Berlin, WI 53151, serving 15+ surrounding communities. Free 50-point inspections and written estimates are available throughout the region.
Explore roof replacement in your area:
Why 160 Milwaukee-Area Homeowners Gave Us 5 Stars
Frequently Asked Questions About Roof Replacement
How Long Does a Roof Replacement Take?
Most residential roof replacements in Wisconsin take 1-3 days depending on roof size, complexity, and weather. A standard 1,500-2,000 sq ft asphalt shingle roof typically takes 1-2 days from tear-off to final cleanup.
How Much Does a New Roof Cost in Wisconsin?
A new asphalt shingle roof costs $8,000-$17,000 for most Wisconsin homes. Cedar runs $15,000–$30,000. Metal ranges $12,000-$25,000. Final price depends on size, pitch, and material.
Does Homeowner Insurance Cover Roof Replacement?
Wisconsin homeowner insurance typically covers roof replacement when damage is caused by storms, hail, wind, or fallen trees. Coverage does not apply to normal wear and age-related deterioration.
Can a Roof Be Replaced in Winter in Wisconsin?
Yes. Professional roof replacement is possible in Wisconsin winters. When conditions allow, our crew follows manufacturer requirements and appropriate cold-weather installation methods to help the roofing system seal properly.
How Do I Know If I Need a New Roof or Just Repairs?
Consider replacement when your roof is 20+ years old, has three or more active leaks, shows widespread granule loss, or has storm damage covering more than 30% of the surface. Otherwise, roof repair may be enough.
Do You Install Gutters During a Roof Replacement?
Yes. Gutters are often replaced alongside a new roof for a fully sealed, water-managed system. Ask about pairing our gutter services with your roof replacement for coordinated protection.
Schedule Your Free Roof Inspection
Schedule your free 50-point roof inspection today. Call (414) 455-2345 to speak with our veteran-owned team and get a written estimate with no obligation.
Four Leaf Roofing & Windows | (414) 455-2345 | fourleafcontracting@gmail.com | New Berlin, WI Hours:Monday–Sunday, 24/7 storm response available Credentials: BBB Accredited — A+ Rating · Featured in Milwaukee Magazine — Face of Roofing 2024 & 2025 · NARI Member · CertainTeed ShingleMaster™ PRO
Financing Available!
Financing as low as 0% for up to 21 Months
Call us at (414) 455-2345 for details.
