Your roof is your home’s first line of defense against the elements. When it's damaged—whether by storms, age, or structural issues—you need more than a patch job. You need a team that understands roofing and structure. That’s where Old School Contracting comes in.
We offer high-quality, honest roof repair services in Waukesha, backed by over 30 years of hands-on construction and framing experience. From minor leaks to structural roof reinforcement, we deliver long-term solutions, not temporary fixes.
Call us Anytime!
(262) 442-8040
If you’ve noticed dark spots on your ceilings, shingles in your yard, or areas of your roof that appear to sag, don’t wait—these problems only get worse (and more expensive) with time.
Roof Leak Repair
We locate the source of water intrusion and fix it fast—whether it’s a flashing failure, valley leak, or punctured shingle. Our repairs stop leaks and prevent mold, rot, and further interior damage.
Structural Roof Repair
When the issue goes deeper than the shingles, we’re ready. Our team repairs sagging roof lines, bowed rafters, and broken trusses with structural solutions that restore your roof’s strength.
Storm Damage Repairs
Has your roof been damaged by a recent storm? We offer quick assessments, emergency tarping, and full repair services to get your roof back to pre-storm condition—often assisting with insurance documentation.
Roof Decking Replacement
Rotten or soft roof sheathing can’t support new roofing. We replace damaged decking with solid materials that ensure long-lasting performance for your entire roofing system.
We combine traditional craftsmanship with modern repair techniques to deliver roofing solutions built to last—no shortcuts, no surprises.
Even a small leak can lead to thousands in damage. If you suspect roof issues, trust the professionals at Old School Contracting. We’ll inspect, repair, and protect your roof with skill and integrity. Call (262) 442-8040 or go to our contact form to schedule your free roof repair estimate in Waukesha.
A: That depends on the extent of the damage. We offer honest evaluations and always prioritize cost-effective repairs when possible. If a new roof is needed, we’ll walk you through your options.
A: Common culprits include aging shingles, failed flashing, clogged gutters, or damage from wind and hail. We inspect your roof thoroughly to find the exact cause.
A: Repair costs vary depending on the problem. Minor fixes may cost a few hundred dollars, while major structural repairs may be more. We offer free estimates so you know upfront.
A: Yes! We can document storm damage and provide detailed repair estimates to help streamline the claims process.
A: We respond quickly—especially for leaks or storm damage. Many repairs can be completed in a single day depending on severity.
A: We proudly serve Mukwonago, WI, as well as Rock, Walworth, and Waukesha counties. Other areas we proudly serve include:
Waukesha is a vibrant city located in southeastern Wisconsin, about 20 miles west of Milwaukee, with a population of around 72,000. Founded in 1834, Waukesha is known for its rich history, natural springs, and thriving arts scene. The city’s natural beauty is highlighted by its historic spring water, which became famous in the 19th century for its purported health benefits, attracting visitors and residents alike. Today, Waukesha's downtown area reflects a blend of modern development and historic architecture, with various shops, restaurants, and cultural venues. Waukesha is home to numerous parks, including the large Minooka Park, where residents enjoy outdoor activities such as hiking, fishing, and picnicking. The Fox River also winds through the city, providing opportunities for canoeing and kayaking. The city’s economy is diverse, with key sectors in manufacturing, retail, and healthcare. Waukesha has also become a hub for technology and business development, attracting entrepreneurs and professionals. Waukesha is well known for its commitment to education, with a number of public and private schools as well as nearby universities, including Carroll University, Wisconsin's oldest institution of higher learning. The city hosts a variety of cultural events, including the Waukesha Freeman Friday Night Live music series and the annual Waukesha County Fair, which draws large crowds. With its thriving economy, growing community, and dedication to preserving its historic charm, Waukesha is a key city in the Milwaukee metropolitan area, offering residents a balance of suburban tranquility and urban conveniences.
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