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 Hartland, 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 Hartland.
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:
Hartland is a picturesque village in Waukesha County, Wisconsin, with a population of around 10,000. Located just 20 miles west of Milwaukee, it offers a blend of suburban living and small-town charm. Hartland has a rich history, originally settled in the 1830s, and retains much of its historical character, particularly in its charming downtown area. The village is known for its natural beauty, with several parks and green spaces offering a variety of outdoor activities. Nixon Park, with its walking trails, picnic areas, and sports facilities, is one of the community’s favorite spots. Additionally, the Bark River flows through the village, providing scenic views and recreational opportunities. Hartland’s downtown area features a mix of quaint shops, restaurants, and local businesses, creating a vibrant atmosphere. The village is also home to excellent schools, which are part of the Arrowhead Union High School District, making it a popular choice for families. Hartland’s economy is diverse, with industries ranging from retail and manufacturing to professional services. The village has experienced steady growth in recent years, with new housing developments and businesses opening up in the area. The village also hosts several events throughout the year, including the Hartland Jazz Festival and the Fourth of July parade. With its excellent schools, vibrant community, and proximity to Milwaukee, Hartland offers a balanced lifestyle with both small-town charm and suburban convenience.
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