Roofing Company in Cottage Grove, Wisconsin

Your Local Roofing, Siding, Gutter & Window Specialists

Residential Roofing Made for Midwest Weather

Cottage Grove homes see their fair share of wear and tear, from long and brutal winters to sudden summer storms and very harsh humidity. The Oliwill Construction team helps homeowners stay ahead of it with roofing work that’s done right the first time. We use the best materials for the job, take the time to install them properly, and are always clear with homeowners about what’s being done and why.

Why Choose Oliwill Construction as Your Roofing Partner

  • Familiar with Local Conditions: Working in Cottage Grove and across south central Wisconsin provides familiarity with what roofs here experience, from heavy snow to wind-driven rain, and building with that in mind.
  • More Than Just Roofing: In addition to roof work, we handle siding, gutters, and windows; our team can take care of your exterior projects as well.
  • Experience With All Types of Homes: We work on everything from single-family houses and garages to duplexes and multi-unit properties, adapting our approach based on the structure.
  • Properly Licensed and Insured: Oliwill Construction is fully licensed and insured, so homeowners are certain the work is being handled responsibly and professionally.
  • Material Choices That Make Sense: Materials are chosen based on how they perform and last in Wisconsin weather, with options such as asphalt shingles or metal roofing.
  • A Reputation Earned Locally: Much of our work comes from referrals and repeat customers throughout Dane County, built on jobs finished on time and with quality craftsmanship.
House From Birds Eye View

Roof Installation Services We Offer in Cottage Grove

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

New Roof Installation

When a home or building is starting from scratch, we handle the entire roofing process, coordinating installation so the finished roof meets local code and is ready for Wisconsin weather from day one.

Full Roof Replacement

Older roofs eventually reach a point where repairs stop making sense. When shingles fail, leaks appear, or storms take their toll, we tear off the existing roof, address any underlying issues, and install a new system made to perform in the long-term.

Material Options for Every Need & Budget

Metal Roofing

A strong option for homeowners who want something for the long haul. It performs well against hail, high winds, and heavy snow, and assists with temperature control inside the home.

Asphalt Shingles

Often used on residential homes, asphalt shingles provide consistent protection and keep installation and replacement costs lower than many alternatives.

Custom & Specialty Roofs

For roofs with steeper pitches, uncommon designs, or specific structural needs, we design and install roofing systems that match the structure and the way the building is used.

Our Roof Installation Process

  1. Initial Visit and Estimate: The process starts with an on-site look at your roof, where we check existing conditions, talk through concerns, and give an estimate based on the work that actually needs to be done.
  2. Clear Scope Before Work Begins: Before anything moves forward, you will receive a written outline covering materials, labor, schedule, and cost.
  3. Installation: Once scheduled, the roof is installed according to local code and manufacturer requirements, with attention paid to how it will handle wind, snow, and rain.
  4. Site Cleanup and Walkthrough: After the work is finished, the area will be cleaned and the roof inspected to make sure everything was completed correctly.
  5. Standing Behind the Work: We don’t consider a job finished until the work meets our standards and the homeowner is satisfied with the result.
birds eye view of roofing on a house
Roof up close from on top of roof

Is Your Roof Due for Replacement?

It may be time to think about a replacement if you’re seeing issues like:

  • Shingles that are lifting, breaking down, or missing altogether
  • Excessive grit collecting in gutters or bare spots on shingle surfaces
  • Water marks, damp areas, or leaks inside the house
  • Roof decking that feels soft, looks deteriorated, or shows signs of rot
  • Sagging sections of the roof or daylight visible from the attic
  • Ongoing repairs or damage caused by repeated storms, hail, wind, or ice

If your roof is showing any of these signs, or if it’s simply reaching the end of its lifespan, Oliwill Construction can take a look and provide a free inspection and estimate with no obligation.

Start Your Roofing Project Today

Have any questions or want to receive a free estimate for your roofing project? Reach out today to learn more about our replacement and installation options.