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 Oconomowoc, 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 Oconomowoc.
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:
Oconomowoc is a scenic city located in Waukesha County, Wisconsin, with a population of approximately 17,000. Nestled between several lakes, including Lac La Belle, Fowler Lake, and Oconomowoc Lake, the city has long been a popular resort destination. Its natural beauty, combined with its proximity to Milwaukee, makes it an attractive location for both residents and visitors. Founded in the 1830s, Oconomowoc's historic downtown district features a variety of shops, restaurants, and cultural venues, many housed in buildings dating back to the late 19th and early 20th centuries. The city's history as a resort town is evident in the grand homes and historic hotels that still line the lakeshores. The city's parks, trails, and lakes offer ample opportunities for outdoor recreation, including boating, fishing, swimming, hiking, and picnicking. Oconomowoc’s public parks are well-maintained, with popular spots like Roosevelt Park and Fowler Lake Park providing scenic views and recreational facilities. Oconomowoc has experienced rapid growth in recent years, with a thriving local economy that includes businesses in healthcare, retail, manufacturing, and real estate development. The city is also home to several excellent public and private schools, making it a popular place for families. With its lakeside charm, rich history, and strong community spirit, Oconomowoc offers residents a peaceful yet vibrant lifestyle, while still providing easy access to the amenities of larger cities like Milwaukee.
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