Highfill Painting Named in Style Weekly’s Best of Richmond 2026

We’re still a little stunned typing this out. Highfill Painting is the only painting company named in Style Weekly’s Best of Richmond 2026, placing Top 3 in Home Renovation/Contractor in Style Weekly’s annual Best of Richmond awards… and because this award is decided entirely by community votes, it means more to us than we can easily put into words. So before anything else: thank you. If you nominated us, voted for us, or told a neighbor about us, you’re the reason we’re writing this post.

What This Award Actually Means

Style Weekly’s Best of Richmond program has been a fixture in our region for years. It spotlights businesses, organizations, and professionals across all kinds of industries, and the winners aren’t chosen by a panel or an editor — they’re chosen by readers. Nominations and votes come straight from the community. That’s what makes this recognition special to us. It isn’t a trophy we bought or a list we paid to be on. It’s a reflection of the people we’ve worked with and worked for.

When you hire a painter, you’re letting someone into your home or your business. You’re trusting them with your walls, your time, and your space. We’ve never taken that lightly, and to know that the Richmond community trusts us enough to put our name at the top of the list — that’s the kind of thing that keeps us going.

How We Got Here

Our founder, Matt Highfill, didn’t start this company in a vacuum. He got into painting after spending time around homeowners who’d been burned by previous contractors — people who’d been left frustrated, ignored, or treated like an afterthought once the deposit cleared. Those conversations stuck with him. They showed him exactly what so many clients were missing during renovation and improvement projects, and they shaped the kind of company he wanted to build.

From day one, the goal was simple: be the painter people actually want to call back. That meant professionalism, clear communication, and a consistent experience from the first estimate to the final walkthrough. It sounds basic, but in our industry it’s surprisingly rare — and it’s exactly that approach that helped us grow across the Richmond area. Over the years we’ve completed projects for homeowners, businesses, and property managers, in everything from cozy interiors to large commercial spaces.

A Milestone Built on Relationships

We’ve hit some meaningful moments as a company, but this one is different. Because Best of Richmond comes down to public voting, it’s a direct reflection of the relationships we’ve built — one project, one conversation, one satisfied client at a time. Every person who took a minute to vote was, in a sense, vouching for us. We don’t forget that.

It also lands at a time when so many homeowners and businesses across Richmond are investing in their properties. Painting remains one of the most reliable ways to refresh an interior, protect exterior surfaces from our Virginia weather, and prepare a building for years of use. As more people take on these projects, programs like Best of Richmond give the community a way to point to the businesses that have earned their trust. We’re honored to be one of them.

What’s Next

Honestly? Not much is going to change — and we mean that as a good thing. We’re going to keep showing up for homeowners and businesses throughout the Richmond area the same way we always have: with respect, honesty, and genuine care. This award isn’t a finish line. It’s a reminder of why we do this and who we do it for.

At Highfill Painting, clients come first. We believe great results start with treating people well, which is why we’ve never wanted anyone to feel like “just another job.” That belief is what’s set us apart — in the quality of our work, the materials we use, the experience we provide, and our commitment to helping prolong the life of your home. Being named Richmond’s best is a milestone we’ll carry proudly into 2026 and beyond.

So once more, from all of us here: thank you, Richmond. We couldn’t have done it without you. If you’ve got a project in mind — interior, exterior, residential, or commercial — we’d love to hear from you.

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Customer Reviews

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Holly Price profile picture
Holly Price
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Highfill Painting were wonderful to work with. The painters were here on time, they were respectful, and worked hard everyday. I was super impressed at how well they cleaned up everyday after they finished working. Our Project Manager Heather, came by everyday to ensure everything was going as planned and that we were happy with the progress and results. She wanted to make sure (even though it did cost us more than the original estimate) that things were done right and we avoided issues down the road. Examples are she called out additional rotted boards. Our house is Cedar siding so just painting over it would have just caused more issues later. While it cost more, you pay for the quality you get and we are very satisfied with the quality of work and the strong work ethic from all of their employees. I would 10/10 recommend them to anyone looking to paint their exterior or interior of their home! I’ve included a before and after of the front of our home. It looks like a completely different home now, and we love the color!!!
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Casey Hutcherson profile picture
Casey Hutcherson
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From start to finish I was continuously impressed with Highfill and their professionalism. We had three quotes from three different companies and John from Highfill is the only one that sat down and explained to me exactly how they work and why, although they might come in as the highest quote, I was getting more with Highfill because of their warranty (if the paint chips, they will make it right). Next, we worked with Heather and Jay as our project managers. In a man-dominated construction world, it's rare that you get to work with women. Although this isn't always the case, usually women tend to be better communicators, have exceptional attention to detail, and often approach such projects with the goal of making a house a home rather than just getting the job done. This was definitely the case with Heather and Jay who were both professional, clearly knew their industry well, and were never condescending. I always felt like they had our best interests at heart and wanted to make us happy. We had three outer buildings that were getting painted and I made it clear that I didn't just want them painted/stained over but wanted the rotting wood to be replaced. The cost did rise quite a bit more but Heather/Jay had keen eyes and made sure that if there was an area that was compromised, they would fix it before staining. It feels like our buildings will last so much longer now with the care they've been given. The crew was also great although I never communicated directly with them because Heather and/or Jay made sure they were present and overseeing the job. Samantha in the office was also a joy. From beginning to end I felt like the individuals at Highfill were more like friends- they were respectful, courteous and made me feel like we were in great hands. We will be repeat customers. I never leave reviews but felt this time is was worth it!
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Jenny Purvis profile picture
Jenny Purvis
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We had a great experience with this company. Heather was a wonderful project manager and very friendly and communicative. The workers worked very hard every day. We are very pleased with the results. We recommend them highly.
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S. T. profile picture
S. T.
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Writing I had several companies to choose from and took the time to read all the reviews before deciding to call Highfill Painting. Based on the positive feedback, I felt confident in my choice. Aaron came out from Highfill and was very professional, courteous, and pleasant to work with. I really appreciated his professionalism and friendly demeanor which deserves 10 stars. I’m glad I chose Hightower and will definitely recommend Aaron to other people I know!
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Heidi Grimsley profile picture
Heidi Grimsley
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My husband and I are extremely impressed by the work the Highfill team did. We had them paint almost our entire downstairs plus the stair well. We also had all our kitchen cabinets painted. Evan and Heather were a pleasure to work with. Our project manager , Heather, was here every day to check on progress and she definitely has an eagle eye for anything that needs to be fixed. The painters arrived on time everyday and were professional and respectful of our property. We will be using them again to do our bathroom. Highfill will be our go to paint company from now on.
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Rob Thompson profile picture
Rob Thompson
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Zach was a good job foreman and the painters were good to work with. Good experience 👍
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William Carter profile picture
William Carter
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Sheri came out and gave me an estimate to replace the siding on my shed. She was very professional and knowledgeable. She’s an excellent representative for Highfill Painting.
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Cathy Sawyer profile picture
Cathy Sawyer
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Very professional and efficient painters. Everyone was knowledgeable and helpful. Process was flawless!