Roofing Company in Madison, Wisconsin

Dependable & Trusted Roofing, Siding, Gutter & Window Experts

Residential Roofing Built for Wisconsin Weather

At Oliwill Construction, we know that a roof isn’t just part of your home. It’s the first line of defense against everything Mother Nature throws our way. From harsh winter snow and ice to summer storms and unpredictable Midwest weather, Madison’s climate demands a roof built to last. That’s why we offer top-quality roof installations with craftsmanship, materials, and service you can count on.

      EXCELLENT  
   Based on 219 reviews 
    
 
 
 
   
 
 
       Posted on Google  
   
   Amy Ramesh 
 
 
 
 Trustindex verifies that the original source of the review is Google. Fantastic, helpful, easy to contact, answered all questions, great completed work. By far the best experience I've had with fixing my 98 year old home in the 23 years I've owned it
  
 
      Posted on Google  
   
   Duane Hansen 
 
 
 
 Trustindex verifies that the original source of the review is Google. I chose Oliwill to replace my roof (storm damage) as their cost matched my insurance payment. They did a nice job. Quality material and did adequate clean up after. A couple shingles didn’t appear adequately flat and once alerted, they came back and took care of that final detail.
  
 
      Posted on Google  
   
   Brian 
 
 
 
 Trustindex verifies that the original source of the review is Google. I'm not good at writing reviews so I will keep it simple... All I can say is I'm very glad I chose OliWill Construction to replace my roof. The reason I chose OliWill is the level of professionalism and knowledge during and after his inspection outperformed the other contractors. On the day of replacement they were on-time and worked all day until it was finished.  The crew were also very respectful of my property and cleaned up extremely well after they completed the work. I highly recommend OliWill Construction and will use their services again for future home projects.
  
 
      Posted on Google  
   
   Heidi Olsen 
 
 
 
 Trustindex verifies that the original source of the review is Google. I’m extremely pleased with my gutter installation. The team communicated clearly from start to finish, which made the whole process feel smooth and stress‑free. They took the time to listen to my concerns and made sure every detail was handled the way I wanted. The workmanship is excellent — the gutters look clean, well‑fitted, and built to last. They were respectful of my property and didn’t try to upsell anything unnecessary. Overall, the combination of great communication, quality work, and genuine attentiveness made this a standout experience. I’d confidently recommend them.
  
 
      Posted on Google  
   
   Lisa 
 
 
 
 Trustindex verifies that the original source of the review is Google. I had hail damage on my house and garage roof, gutter guards and some siding.  Oliver was quick with an estimate for replacement  and scheduling time was reasonable as well. He had great communication along the way and is quick to text. The crew was wonderful and not a single plant was trampled. They were all friendly, efficient and clean up was amazing. I’m very happy with the whole experience and would highly recommend.
  
 
      Posted on Google  
   
   Mike Grupe 
 
 
 
 Trustindex verifies that the original source of the review is Google. I was very pleased with every aspect of the job. Oliver, who originally gave us an estimate, was friendly and professional. William, who came to the house before the work was done, was also helpful and a pleasure to talk to. I had a good experience with the people who did the work. They were efficient and cleaned up well after the work was done. I also had a good experience working with Karina, who works in the office. She promptly answered my questions and sent documents and information. I would definitely work with Oliwill Construction again.
  
 
      Posted on Google  
   
   Devin Martin 
 
 
 
 Trustindex verifies that the original source of the review is Google. Storm damage can be hectic and stressful. Oliwill came through with a quote for a new roof and gutters that was better than the out-of-town storm chasers, keeping our money in our community.
  
 
      Posted on Google  
   
   Kathleen Sloniker 
 
 
 
 Trustindex verifies that the original source of the review is Google. After recent storms had left 3 holes in our roof, Oliwill patched the holes that same day, so we did not sustain any more damage to the house with the predicted rain. Within a couple of weeks they replaced the roof, soffits, and gutter guards. Everything looks great and was done so quickly! I would highly recommend Oliwill for your roofing needs!
  
 
  
  
 
 
     Verified by Trustindex  Trustindex verified badge is the Universal Symbol of Trust. Only the greatest companies can get the verified badge who has a review score above 4.5, based on customer reviews over the past 12 months. Read more

Why Choose Oliwill Construction for Your Next Roofing Project

Local Expertise & Understanding: As a company rooted in south central Wisconsin, we understand exactly what it takes to build roofs that stand up to Madison’s seasonal extremes.
Licensed, Insured & Professional: We’re fully licensed and insured, so you’ve got peace of mind that your property is in qualified hands.
Quality Materials & Durable Construction: Whether you choose classic asphalt shingles or more durable metal roofing, we select materials suited to withstand heavy snow loads, wind, rain and ice; common factors in Dane County weather.
Projects Big or Small: From single-family homes and garages to duplexes and townhouses, no project is too simple or too complex.
Comprehensive Exterior Services: We don’t stop at roofing. Gutters, siding, windows – we’ve got you covered, simplifying exterior renovations or full-home upgrades.
Customer Satisfaction & Reputation: With numerous positive reviews from satisfied clients across Madison and surrounding communities, homeowners and businesses trust Oliwill for reliable, timely and professional work.

Roof Installation Services We Offer in Madison

At Oliwill, we provide a full suite of services to meet your roofing needs:

New Roof Installation

For newly constructed homes or buildings, we install complete roofing systems from the ground up, built to meet local building codes and weather requirements.

Full Roof Replacement

If your existing roof shows signs of wear, shingle curling or cracking, leaks, storm damage, or sagging, we can remove the old roof, repair decking if needed, and install a fresh, durable system.

Material Options for Every Need & Budget

Metal Roofing

For homeowners seeking maximum durability, energy-efficiency, and long-term protection against Wisconsin weather (hail, wind, snow).

Asphalt Shingles

A popular, cost-effective option, offering reliable protection for decades.

Custom & Specialty Roofs

For steep roofs, unique rooflines, or commercial-grade installations, we tailor the roofing system to fit your needs.

Our Roof Installation Process

Free Consultation & Estimate: We begin with a detailed inspection of your property, evaluate your needs, and recommend the roofing solution that best fits your budget, goals, and local weather demands.
Proposal & Planning: You receive a transparent, written proposal outlining scope of work, materials, timeline, and costs.
Professional Installation: We install your chosen roofing system with precision, following local building codes and best practices to ensure the roof withstands snow load, wind, and precipitation common to Madison.
Clean-Up & Final Inspection: We leave your property clean and perform a final inspection to ensure quality, safety, and durability.
Customer Satisfaction Guarantee: Our work is backed by our commitment to quality and customer satisfaction.

Is It Time for a New Roof?

Signs You Should Consider Replacement. Your roof may need replacement if you notice:

Curling, cracked, or missing shingles
Granule loss or worn-out asphalt shingles
Leaks or water stains inside your home
Damaged, rotting, or soft roof decking
Visible daylight in the attic or sagging rooflines
Evidence of frequent repairs or weather-related damage (wind, hail, ice)

If any of these apply or if your roof is simply aging it’s worth contacting Oliwill for a no-obligation inspection and free estimate.

Ready to Discuss Your Roof Replacement Project?

To explore your project further or to acquaint yourself with our diverse roof replacement offerings, please don’t hesitate to contact us at today!

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