Our Services
Full-service roofing contractor in Winter — from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.
Trusted by homeowners and businesses across Winter.
GAF Master Elite, Owens Corning Preferred, CertainTeed SELECT ShingleMaster. We carry certifications from the big three. That means factory-trained crews and the best available warranties.
We get on the roof, take photos, and give you an honest assessment. If you don't need work, we'll tell you. No charge, no obligation, no high-pressure sales pitch.
Fully licensed, bonded, and insured in Wisconsin. We carry $2M in general liability. Workers' comp on every crew member. Your property is protected if anything goes sideways.
A new roof is a big expense. We offer 12-month same-as-cash and low-interest financing through GreenSky and Hearth. Get your roof done now, pay over time.
Simple Process
Before we quote anything, we inspect everything. Shingles, flashing, pipe boots, ridge vent, soffit, gutters. You get a full written report with photos.
Our Winter estimator builds your proposal same-day in most cases. Includes material options, warranty comparison, and a realistic timeline for your specific roof.
Our crews average 8 years of experience each. They tear off the old roof, inspect the decking, replace any damaged boards, and install your new system from the deck up.
Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.
Verified Reviews
"Had a huge oak branch go through the roof during a storm. Winter Roofing & Maintenance tarped it the same night and had the repair done two days later. Insurance covered everything and they handled the whole claim."
"I'm a contractor and I use Winter Roofing & Maintenance for all my roofing subs. Their installs pass inspection every time. Their crew lead has been doing this 20+ years and it shows."
"Storm chasers were going door to door after the hailstorm. Called Winter Roofing & Maintenance instead because they're actually from Winter. Got a fair deal and a warranty that means something."
Service Areas
Our service area includes Winter and all surrounding communities within Pound, Silver Lake, Viola, Alma, Boulder Junction. We don't charge extra for travel.
Meet the Owner
Owner & Lead Contractor
Cody has been serving Winter for over 23 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company — but the values haven't changed.
"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 182+ five-star reviews."
