From Our Family to Yours — Thank You for Voting Us Best Roofing Contractor
November 12, 2025
November always brings a sense of reflection and gratitude. It’s a time to slow down, appreciate the people who make life meaningful, and acknowledge the moments worth celebrating. This year, our family at Dick’s Roof Repair Service has something especially heart-filling to give thanks for:
We’ve been voted Best Roofing Contractor in the Best of Kenosha 2025 — for the 8th year in a row.
Eight consecutive wins. Eight years of trust from homeowners and businesses across Kenosha and the surrounding communities. We don’t take this lightly — it means the world to our family.
A Legacy Built on Family, Community, and Craftsmanship
Dick’s Roof Repair was founded in 1957, right here in Kenosha. For 68 years, we’ve served Southeast Wisconsin and Northeast Illinois with a simple philosophy: do the job right, treat people well, and the rest will follow.
We’re proud to share that our third generation reached another milestone this year as Josh Milkie joined the company as Sales Rep and Marketing Coordinator after a successful career in media. Josh now works alongside his sister, Laura, and his brother, Steve, while their father, Jeff, continues to guide daily operations.
Being a family business isn’t a tagline; it’s how we show up every day. When you choose Dick’s, you’re not hiring a giant corporation. You’re working with a team that cares about your home, your neighborhood, and your investment.
More Than Roofing — We Protect Your Home from the Outside In
If you’re thinking about home projects for 2025, now is the perfect time to schedule a consultation — especially before winter weather takes a toll. Roofing may be in our name, but homeowners trust us for much more. We provide complete exterior home protection, including:
Rooted in Gratitude
As a family, we talk about how lucky we are to live and work in a community that values local business. This award isn’t just about being the best roofing contractor — it’s about being a trusted partner to the families we serve.
To every homeowner who has referred us…
To every customer who left a review…
To every person who voted for us…
Thank you. Your trust fuels our business and keeps this Kenosha legacy thriving.
Spring projects sneak up fast, and it’s never too early to start planning. If you’re considering a new roof, fresh siding, upgraded windows, or any exterior improvements, now is the perfect time to request a free estimate and reserve your spot on our spring schedule.
Call our team at (262) 654 6644 or Request a free estimate »
