Serving Naylor and the surrounding Ripley County area — Bootheel Roofing brings premium metal & shingle roof systems, hands-on craftsmanship, and honest, locally owned service to every roof across the Missouri Bootheel.
A friendly small town along US-160 in Ripley County, Naylor sits in the rolling country between the Bootheel lowlands and the Ozark foothills. Bootheel Roofing proudly serves Naylor and the surrounding Ripley County area with premium metal and shingle roofing, bringing hands-on craftsmanship and honest, locally owned service to homes and businesses across Naylor, Doniphan, Neelyville and the surrounding Ripley County area.
When you hire Bootheel Roofing, you get a team that lives and works right here in the Missouri Bootheel. Owner Jayden Woolverton has led the company since 2011, and he's on the job personally — not handing your roof off to a subcontractor. Based in nearby Poplar Bluff, we respond quickly to Naylor and treat every roof like it's on our own home.
We specialize in durable metal and shingle roofing, and we're licensed, insured, and locally owned — the kind of roofer who protects your home like a fortress. Whether it's a full roof replacement, a stubborn leak, storm damage, or gutters and siding, you get quality materials, real craftsmanship, and straight answers instead of a sales pitch.
The Bootheel's weather — wind, hail, heavy rain, summer heat, and winter ice — takes a toll on Naylor roofs year after year. Catching problems early and building with quality materials is how you stay ahead of it. Bootheel Roofing provides free estimates and free storm-damage inspections, and we'll help you through an insurance claim if you need it. Call or text 573-238-9666 to get on the schedule.
From new roofs to storm repairs, gutters, and commercial systems — here's the full range we bring to Naylor homes and businesses.
Metal, asphalt shingle, EPDM & flat roof installation built to protect your home for decades.
Fast, reliable repairs for every type of roof — we find the real source and fix it right.
Replacement, tear-off, decking, inspections, maintenance, ventilation & waterproofing.
Storm & hail damage, leak detection, chimney flashing & insurance claim help.
Gutters, siding, skylights, soffit & fascia, and gable vents for the whole exterior.
Durable metal & low-slope commercial roofing for local businesses.
Bootheel-area homeowners consistently point to the same things — fair pricing, prompt service, and workmanship they can trust. Here's what a few of them have to say about Bootheel Roofing.
"Jayden and his crew put a new metal roof on our house and it looks incredible. They were fast, professional, and cleaned up everything when they finished. Fair price and honest from start to finish — exactly what you want in a roofer. Highly recommend Bootheel Roofing!"
— Satisfied Customer • Google Review
"We had a bad leak after a storm and Bootheel Roofing came out quickly, found the problem, and had it fixed right. No high-pressure sales pitch, just straight answers and quality work. You can tell they take pride in what they do."
— Satisfied Customer • Google Review
"Best roofing experience we've had. From the free estimate to the finished roof, everything was handled professionally and on time. The craftsmanship is top-notch and the price was fair. We'll be using Bootheel Roofing for anything roof-related from now on."
— Satisfied Customer • Google Review
Locally owned and operated from Poplar Bluff, Bootheel Roofing proudly serves Naylor and communities throughout the Missouri Bootheel — licensed & insured, with fast local response.
Answers to the questions Naylor-area homeowners ask us most before scheduling roofing work.
Absolutely. Bootheel Roofing is based in Poplar Bluff and proudly serves Naylor and the surrounding Ripley County area. We're a short drive away, which means fast, dependable, genuinely local service.
Because we're based nearby in Poplar Bluff, we respond quickly to Naylor — and after severe weather we prioritize emergencies to get your home protected fast. Give us a call at 573-238-9666 and we'll get you on the schedule.
Yes. The Bootheel gets wind and hail regularly, and we provide free storm-damage inspections, photo documentation, and professional assessments, plus help through the insurance process. Your carrier determines coverage, but we make it easier.
Everything from new roof installation (metal, asphalt shingle, EPDM, and flat) to repairs, full replacement, storm and specialty repairs, gutters, siding, soffit and fascia, and commercial roofing — all built on premium metal and shingle systems.
Yes — Bootheel Roofing is a locally owned, licensed and insured roofing contractor. That's real peace of mind along with your new roof.
The fastest way is to call or text us at 573-238-9666, or fill out the form on our contact page. We'll inspect your roof, answer your questions, and provide a detailed estimate — free, with no obligation.
Locally owned and based in Poplar Bluff, serving communities across the Missouri Bootheel. Click any town to learn more about Bootheel Roofing there.
Locally Owned • Licensed & Insured • Metal & Shingle Roofing • Free Estimates • Serving the Bootheel Since 2011