- New Berlin, Milwaukee, Waukesha & Brookfield
Veteran-Owned Roofing & Exteriors in Southeastern Wisconsin
160+ five-star reviews across New Berlin, Milwaukee, Waukesha & Brookfield. Veteran-owned. ShingleMaster™ PRO. Free estimates.
Four Leaf Roofing & Windows is a veteran-owned roofing and exterior company serving New Berlin, Milwaukee, Waukesha, Brookfield, and the wider Milwaukee metro. With 160+ five-star reviews and CertainTeed ShingleMaster™ PRO certification, we handle roof replacement, roof repair, storm damage, windows, siding, and gutters across southeastern Wisconsin. Licensed, insured, and built on craftsmanship since 1994. Call (414) 455-2345 for a free estimate.
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160+
Google Reviews
4.9 Star
Google Rating
Licensed & Insured
WI CCB# 85-3470994
ShingleMaster™
PRO
Veteran-Owned
Since 1994
Free Estimates
With No Obligation
The Roofing Problems Southeastern Wisconsin Homeowners Face
Southeastern Wisconsin homes face three recurring roof threats: hail and wind damage, freeze-thaw deterioration, and water intrusion from failed flashing. Each worsens when left unaddressed and hiring an uninsured or out-of-town contractor adds financial risk most homeowners discover only after a claim is denied.
What happens if storm damage to a roof goes unrepaired?
Unrepaired storm damage spreads fast. A single hail-cracked shingle or compromised flashing seal admits water within one rain event, and granule loss from 1-inch hail shortens an asphalt roof’s lifespan by 5 to 10 years. Early inspection turns a $300 repair into avoided five-figure interior damage.
Four Leaf documents hail and wind damage, provides information homeowners can share with their insurance carrier, and coordinates directly with adjusters when appropriate. Our Storm Damage Restoration team conducts thorough hail and wind damage inspections, produces
How do you choose a roofing contractor in Wisconsin you can trust?
A trustworthy Wisconsin roofing contractor holds a state license, carries liability and workers’ compensation insurance, and issues a written estimate that matches the final invoice. Uninsured and storm-chasing crews leave homeowners personally exposed to property-damage and injury liability that licensed, insured contractors absorb.
Four Leaf Roofing & Windows holds WI CCB# 85-3470994, carries full liability and workers’ compensation coverage, and completes every project with one in-house, CertainTeed Master Craftsman certified crew, the same crew from the first inspection through the 50-point final check.
Roofing & Exterior Services We Provide
Four Leaf Roofing & Windows delivers complete roofing and exterior solutions, from full roof replacements to window installations, siding, and gutters. Every service is performed by our in-house crew with no subcontractors, available across our entire Milwaukee-metro service area, and backed by manufacturer warranties and a lifetime workmanship guarantee.
Roof Replacement
A complete Roof Replacement from Four Leaf Roofing & Windows is backed by ShingleMaster™ PRO 3-Star and 4-Star SureStart™ PLUS warranties. Our CertainTeed Master Craftsman certified installers use materials rated for Wisconsin’s freeze-thaw cycles and temperature swings from -20°F to 100°F. Every replacement concludes with a 50-point workmanship inspection before our crew leaves the site.
Roof Repair
A compromised flashing seal or cracked shingle can allow water infiltration within a single rain event, turning a $300 repair into a $10,000 interior damage claim. Our Roof Repair services address leaks, failed flashing, damaged shingles, and ice-dam vulnerabilities. We offer emergency response across the Milwaukee metro, with same-day inspections available for active storm damage.
Storm Damage Restoration
Southeastern Wisconsin sees several damaging hail events each year, and hailstones 1 inch or larger cause immediate granule loss on asphalt shingles, reducing a roof’s remaining lifespan by 5 to 10 years. Our Storm Damage Restoration team conducts thorough hail and wind damage inspections, produces documentation homeowners can share with their insurance carriers, and coordinates directly with adjusters when appropriate.
Window Replacement
Single-pane windows in a Milwaukee-metro home can lose up to 10 times more heat per square foot than an insulated wall, directly increasing heating costs. Our Window Replacement service installs energy-efficient, weather-sealed windows engineered specifically for Wisconsin winters. All installations carry both manufacturer warranties and our workmanship guarantee.
Siding Installation
LP SmartSide and fiber-cement siding are durable options designed to resist moisture, severe weather, and impact damage, making them well-suited to Milwaukee-metro hail and wind seasons. Our Siding Installation team has handled siding insurance claims for over a decade, from storm damage documentation through final installation.
Seamless Gutters
Sectional gutters develop leaks at every joint; seamless gutters eliminate that failure point entirely. Our custom-fabricated Seamless Gutters are built on-site in heavy-gauge aluminum, sized to handle Wisconsin’s peak rainfall events, and available with GutterRx gutter guards that block debris and reduce annual maintenance requirements.
Why 160+ Milwaukee-Area Homeowners Gave Us 5 Stars
Four Leaf Roofing & Windows has earned 160+ five-star reviews and a 4.9-star Google rating by combining CertainTeed ShingleMaster™ PRO installation standards with the accountability of a veteran-owned operation. Our no-subcontractor policy keeps one crew responsible for every project from start to finish. Our WI CCB# 85-3470994 is on file, and every team member is covered by full liability and workers’ compensation insurance.
Where Does Four Leaf Roofing & Windows Work?
Four Leaf Roofing & Windows serves the greater Milwaukee metro across both Milwaukee County and Waukesha County, and extends throughout southeastern Wisconsin. Each city below has its own dedicated service page with local project galleries, pricing context, and city-specific service details.
New Berlin
Roofing Contractor in New Berlin, WI — Our home base and headquarters, located at 2875 S Moorland Rd, New Berlin, WI 53151. Located on S Moorland Road, Four Leaf Roofing & Windows serves homeowners throughout New Berlin and nearby Waukesha County communities, including Muskego. Local homeowners rely on us for hail inspections after Wisconsin storms, roof replacements for aging homes, and exterior upgrades that improve curb appeal and energy efficiency.
Milwaukee
Milwaukee Roofing Services — Milwaukee homes range from older brick properties near the city center to newer developments on the outskirts. Our team regularly handles challenges common in these homes, including aging flashing, steep roof sections, ventilation issues, and storm-related repairs.
Waukesha
Waukesha Roofing Company — Full-service roofing and exteriors for Waukesha County properties. Four Leaf Roofing & Windows provides roof replacement, storm damage restoration, siding, windows, and seamless gutters throughout Waukesha, completed by the same crew and backed by the same manufacturer warranties available on every project we complete.
Brookfield
Brookfield Roofing Services — Premium exterior work for Brookfield residences. From ShingleMaster™ PRO roof replacements to LP SmartSide siding and energy-efficient window installations, our team delivers the same craftsmanship standards and warranty protection to every Brookfield property we serve.
Joseph T. O’Brien
Founder, United States Navy Veteran
Our Craftsmanship, Our Crew, Our Community
Joseph T. O’Brien founded Four Leaf Roofing & Windows in 1994 after completing service in the United States Navy, bringing military precision and accountability to the Milwaukee metro’s exterior contracting industry. With more than 30 years of hands-on experience across southeastern Wisconsin, Joseph T. O’Brien built Four Leaf on a clear principle: deliver a roof that lasts, stand behind the work unconditionally, and treat every homeowner the way you’d want your own family treated.
Every project at Four Leaf Roofing & Windows is completed by our in-house crew. No subcontractors. No handoffs to unfamiliar teams.
Our roofers are CertainTeed Master Craftsman trained, operate exclusively across New Berlin, Milwaukee, Waukesha, Brookfield, and the surrounding Milwaukee metro, and take ownership of every job from the initial inspection through the 50-point post-installation check. The same crew that installs your roof also returns for your free annual inspection.
Veteran-owned means more than a designation on a website. It means every job site operates with the discipline, follow-through, and accountability that military service demands. Since 1994, Four Leaf Roofing & Windows has protected Milwaukee-metro homes through Wisconsin’s harshest winters, hail seasons, and wind events, and our lifetime workmanship warranty is the clearest signal that we expect our work to outlast the competition.
Frequently Asked Questions about Roofing in Wisconsin
What areas in Wisconsin does Four Leaf Roofing & Windows serve?
Four Leaf Roofing & Windows serves 15+ cities across southeastern Wisconsin, including New Berlin, Milwaukee, Waukesha, Brookfield, Mequon, Franklin, Muskego, Germantown, Menomonee Falls, Pewaukee, Oak Creek, Racine, and Kenosha. Our headquarters is at 2875 S Moorland Rd, New Berlin, WI 53151, and our in-house crews dispatch across the full Milwaukee metro and Waukesha County. Each primary city has a dedicated service page with local project galleries, city-specific service details, and direct contact options.
Why does Four Leaf have 160+ five-star reviews?
Homeowners across New Berlin, Milwaukee, Waukesha, and Brookfield consistently cite our clear written estimates, transparent pricing, dependable scheduling, and thorough job-site cleanup. Located on S Moorland Road, Four Leaf Roofing & Windows has completed roofing projects throughout New Berlin neighborhoods including Muskego, Moorland, and the surrounding Waukesha County area.
Four Leaf Roofing & Windows holds 160+ five-star reviews and a 4.9-star Google rating because every project is completed by our in-house, CertainTeed Master Craftsman–certified crew and backed by a lifetime workmanship warranty and a 50-point post-installation inspection.
Are you licensed and insured in Wisconsin?
Yes. Four Leaf Roofing & Windows holds WI CCB# 85-3470994 and carries full liability and workers’ compensation insurance on every project across our service area. Wisconsin contractor licensing requires adherence to all state building codes and permit standards on every job. Our liability and workers’ compensation coverage provides added protection for homeowners throughout the project—protection that unlicensed or underinsured contractors may not provide.
Do you offer free estimates across the Milwaukee metro?
Yes. Four Leaf Roofing & Windows provides free, written estimates for all six services: roof replacement, roof repair, storm damage restoration, window replacement, siding installation, and seamless gutters. Standard estimates are delivered within 24 hours of the on-site inspection. Storm damage inspections include a complimentary insurance claim review at no charge. Call (414) 455-2345 or submit the form above to schedule yours.
What services do you provide beyond roofing?
Beyond roofing, Four Leaf Roofing & Windows provides window replacement, siding installation, and seamless gutter systems with optional GutterRx gutter guards, all available across our entire Milwaukee-metro footprint. Every service is backed by manufacturer warranties and our lifetime workmanship guarantee. Homeowners who bundle two or more services receive a single combined estimate that maximizes warranty coverage and reduces total project cost. Ask about current bundle pricing when you schedule your free estimate.
Ready to Start Your Roofing or Exterior Project?
Whether your home is in New Berlin, Milwaukee, Waukesha, or Brookfield, Four Leaf Roofing & Windows is ready to inspect your property and provide a clear written estimate at no cost and with no obligation. Our team responds to standard estimate requests within 24 hours and dispatches for same-day storm inspections when active damage requires it. Call (414) 455-2345 or submit the form to get started.
- Hours: Monday–Sunday, 24/7 storm response available
- Office: 2875 S Moorland Rd, New Berlin, WI 53151
- Email: fourleafcontracting@gmail.com
BBB Accredited — A+ Rating · Featured in Milwaukee Magazine — Face of Roofing 2024 & 2025 · NARI Member · CertainTeed ShingleMaster™ PRO
