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 Pewaukee, 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 Pewaukee.
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:
Pewaukee is a city located in Waukesha County, Wisconsin, just northwest of Milwaukee, with a population of around 14,000. Known for its beautiful Pewaukee Lake, the city offers residents and visitors an array of outdoor recreational activities, including boating, fishing, and swimming. Pewaukee Lake is one of the city’s main attractions, drawing those who enjoy the peaceful waters and scenic beauty. The city is a blend of suburban and rural living, with quiet neighborhoods, parks, and green spaces, all while being close to the conveniences of Milwaukee. Pewaukee’s economy is supported by small businesses, retail establishments, and a growing number of professionals who commute to Milwaukee. Pewaukee has several parks, including the Pewaukee Lakefront Park, which provides access to the lake, as well as walking trails, picnic areas, and sports fields. The city's parks and trails offer excellent opportunities for outdoor activities, such as hiking and biking. Education is an important focus in Pewaukee, with the Pewaukee School District known for its high-quality schools and community involvement. The city also hosts several annual events like the Pewaukee Lake Water Ski Show and the Pewaukee Farmers Market, which bring together the local community. Pewaukee offers a balanced lifestyle, with small-town charm, outdoor recreation, and easy access to nearby cities, making it a desirable place for families and young professionals alike.
Service Area Map
© Old School Contracting. All Rights Reserved.
