Skilled Roofing Companies Oregon WI (Top 6 Contractors)

If you are searching for roofing companies Oregon WI homeowners can trust, you want contractors with a verifiable track record, proper credentials, and real experience handling Wisconsin’s seasonal demands. Oregon sits in southern Dane County, and the best roofing contractors in the region serve it as a regular part of their market. If you already know you need a new roof, explore our residential roofing services to see what Badgerland Exteriors brings to Oregon homeowners.

Here is what this guide covers:

• The top 5 skilled roofing contractors serving Oregon, WI
• What makes each one worth calling
• What to look for before signing anything

We’re proud to serve homeowners in Oregon, WI, and nearby communities with roof replacement, storm damage inspections, siding, and gutters.

6 Skilled Roofing Companies Serving Oregon, WI

Oregon homeowners have strong options in the local market. The six companies below have verifiable reviews, documented service in Dane County, and the credentials worth checking before any work begins.

1. Badgerland Exteriors

Badgerland Exteriors has been replacing roofs and handling exterior work for homeowners in Oregon and across south-central Wisconsin since 2009. Founded by AJ Stoffels, Badgerland has built a strong reputation on an honest, education-first approach that puts homeowner understanding ahead of closing a sale. Free estimates and free storm damage inspections are available, with a response window of 24 to 48 hours.

• In business since 2009: Long enough in the Wisconsin market to know what holds up and what doesn’t.
• 10-year workmanship warranty: On full roof replacements, one of the stronger labor warranties available from a local contractor.
• Free storm damage inspections: With written documentation to support insurance claims at no charge.
• Financing available: Through Acculynx for qualified homeowners, so cost doesn’t force a delay.
• Education-first approach: Honest assessments, no pressure, and straight answers about what your roof actually needs.

2. Oliwill Construction

Oliwill Construction is a McFarland-based exterior contractor run by brothers Oliver and William. Known for owner involvement from estimate through completion, Oliwill handles residential roofing, siding, gutters, and windows with a reputation for clean job sites, efficient timelines, and final invoices that match the original quote. A major manufacturer preferred contractor designation reflects their installation standards.

• Owner-run from start to finish: The people you talk to are the people doing the work.
• Well reviewed across verified platforms: Communication, punctuality, and cleanup are consistently called out by reviewers.
• Manufacturer certified: Preferred contractor status with higher installation standards and better warranty options for homeowners.
• Estimates that hold: Reviewers regularly note no financial surprises from estimate to final invoice.
• Locally rooted: A family-run operation built one project at a time in this part of Wisconsin.

3. Ridge Top Exteriors

Ridge Top Exteriors is a Madison-area family-owned exterior contractor in business since 2002. They carry an A+ BBB rating and have earned GAF Master Elite status, a designation held by fewer than 3 percent of contractors nationally, reflecting ongoing training and elevated installation standards. A large share of their business comes from referrals, and 24-hour emergency service is available year-round.

• GAF Master Elite Contractor: A designation fewer than 3 percent of roofing contractors nationally earn.
• Since 2002: Over two decades of exterior work across Madison and Dane County.
• A+ BBB rating: A strong complaint-free record across verified platforms.
• 24-hour emergency service: Available every day of the year for urgent roofing situations.
• Referral-driven business: A significant share of new clients come from past customers recommending them.

4. Infinity Exteriors

Infinity Exteriors has been serving Wisconsin homeowners since 1997 and operates a Madison location that covers the Oregon area. With a strong Google rating across thousands of verified reviews and an A+ BBB rating, Infinity is one of the largest and most established exterior contractors in the state. They handle residential and commercial roofing, siding, windows, and gutters, and offer financing options for qualifying homeowners.

• In business since 1997: One of the most established roofing contractors in south-central Wisconsin with decades of completed projects.
• A+ BBB rating: Accredited since 2005 with a well-documented track record.
• Full exterior capability: Roofing, siding, windows, and gutters all under one contractor, from repair to full replacement.
• Financing available: Flexible options for homeowners who need to spread the project cost.
• No-pressure inspections: Honest evaluations with no obligation, and clear communication throughout the project.

5. Heins Contracting

Heins Contracting is a Madison-based family-owned contractor founded by Bryan Heins that has been serving Dane County homeowners for over 20 years. The company specializes in residential and commercial roofing, including asphalt, metal, and flat roofing, along with siding, windows, gutters, and ice dam removal. They hold an A+ BBB rating and a strong Google rating from hundreds of verified reviews.

• 20+ years in the market: A long track record of exterior work across Dane County and the Madison metro.
• Family-owned and operated: Hands-on ownership with a reputation for clear communication and care on every project.
• A+ BBB rating: Accredited and well-regarded across multiple verified review platforms.
• Storm damage and insurance experience: Documented history helping homeowners through the claims process.
• Full exterior services: Roofing, siding, windows, gutters, gutter protection, and ice dam removal.

6. Craftsman Exteriors

Craftsman Exteriors is a Madison-based roofing and siding contractor serving south-central Wisconsin. Owner Scott Philipps leads a family-owned operation known for competitive pricing, no-pressure consultations, and personal involvement in every project. Most full roof replacements are completed in a single day. Craftsman handles roofing, siding, windows, and gutters, and is fully licensed, bonded, and insured.

• Scott handles consultations himself: You’re talking to the decision-maker from the first conversation, not a salesperson passing notes.
• Well reviewed by a large volume of verified customers: Reviewers consistently note price, communication, and quality in the same breath.
• Most full replacements wrap in a single day: Efficient timelines that reviewers appreciate, especially with Wisconsin weather being unpredictable.
• No high-pressure sales: A core part of how they operate, consistently reflected across customer feedback.
• Fully licensed, bonded, and insured: They handle permits on your behalf, which removes one more thing to manage on your end.

What to Look for When Comparing Roofing Contractors in Oregon

Finding the right contractor is as important as finding the right material. According to the National Roofing Contractors Association, even the best roofing materials can result in a leaky roof if installed improperly, and good workmanship and attention to detail are just as important as material selection. Here is what to evaluate before committing.

• Wisconsin Dwelling Contractor license: Required for work that needs permits. Ask for the number and verify it through the state before anyone starts.
• General liability and workers’ compensation: Ask for current certificates from both before work begins.
• A detailed written proposal: Get at least three written estimates for any roofing project before deciding. Each should spell out scope, materials, labor, warranty, and payment terms so you can compare accurately.
• Workmanship warranty: Manufacturer warranties cover materials; workmanship warranties cover the installation. Look for a minimum of five years on labor, and favor contractors offering ten or more.
• Storm damage experience: Storm damage can cause leaks and structural issues that aren’t visible from the ground. Tarping a damaged roof can prevent further water damage while waiting for a full repair, and a contractor with real insurance experience is worth having in your corner.

Frequently Asked Questions About Roofing Companies in Oregon, WI

Oregon homeowners tend to ask the same questions before calling a contractor. Here are direct answers.

How do I choose a roofing contractor in Oregon, WI?

Start with Google reviews and the BBB, then ask neighbors who have recently had roofing work done. Prioritize contractors with verifiable local experience in Dane County, proper licensing and insurance, and a workmanship warranty on their labor. Any of the six companies in this guide are worth contacting for a free estimate.

Do roofing contractors in Oregon offer free estimates?

Yes. Badgerland Exteriors, Oliwill Construction, Ridge Top Exteriors, Infinity Exteriors, Heins Contracting, and Craftsman Exteriors all offer free estimates and can typically schedule an on-site assessment within a few days of first contact.

What does a roof replacement cost in Oregon, WI?

For most Oregon homes using architectural asphalt shingles, a full replacement runs between $10,000 and $18,000 depending on roof size, pitch, and whether decking repairs are needed. Roof longevity typically ranges from 20 to 50 years depending on materials, so the cost per year of service life is often a more useful number than the upfront price. The only accurate figure is one based on an in-person assessment of your specific home.

Is there a best time of year to replace a roof near Oregon, WI?

The cheapest time to replace a roof is typically late winter through early spring, when contractor demand is lower and scheduling is more flexible. If your roof is actively damaged or leaking, timing should be driven by urgency rather than price.

Do Oregon roofing contractors handle storm damage claims?

Several do. Badgerland Exteriors and Heins Contracting both have documented experience helping homeowners through the storm damage and insurance claim process, from inspection and documentation through communication with adjusters.

Reach Out to a Contractor You Can Trust

Any of the six companies in this guide are worth a call if you are starting your search in Oregon. If you want to begin with a locally founded, education-first contractor that has been serving Dane County since 2009, request your free roofing estimate from Badgerland Exteriors today.