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Top-Rated Wood shake or composite roofing installers and replacers in Middlesboro - Updated Nov 2026

Avatar for Stefaniak Construction
Stefaniak Construction
4.7(
13
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

In business since 2017

Free estimates

Credit card accepted

"I’ve had Stefaniak Construction replace my decking and railings, install exterior french doors as well as windows, and several smaller tasks and am extremely pleased with how they all turned out. Will be hiring them for more projects in the future."
Custom fireplace
Installed new door where window was built stairs and finishing up stain
We started to tear the chimney down
Custom fireplace
Outside after we stained everything

+55

Recommended by100%of homeowners
Four Seasons
4.6(
15
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

"We had a great experience with Four Seasons. Joe finished two projects for us in one day and he did an excellent job with both of them. He replaced rotted wood around one window and the bottom of an exterior door frame and repainted the wood. It was not an easy job because our house is older and there was more wood to be replaced in the door frame than we thought but Joe figured out a creative solution. I would definitely hire him again!"
Handymen Project
We installed this new door frame
Fire alarm
Framed in a door
Fire alarm

+33

Recommended by93%of homeowners
Avatar for In Town Plumbing Service
In Town Plumbing Service
5.0(
5
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

Free estimates

Emergency services offered

Credit card accepted

"Jordan and his coworker were able to come on short notice and arrived on time. They did a great job and did it to my specifications. I’ve already hired them to install a new bathroom faucet and flooring in both bathrooms."
Here we are putting down flooring for an elderly couple we are putting down sheets of paneling down to cover the older floor and laying floating floor down it turned out really nice
Water leak
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+2

Recommended by100%of homeowners
Affordable Roofing Services
4.0(
4
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

In business since 2005

Free estimates

Emergency services offered

"I was complaining about the existing roof leaking.  Roger came out and gave me an estimate that I liked so I had him replace the roof .
He replaced the roof and it looked good.  The first rain came and the roof still leaked.  Roger came out the same day and redid the roof.  I am still now waiting for it to rain again so we can check it out.  I really think that Roger did a good job, he was always right out when I called about a problem and so far everything is well.  More after the next rain,"
Recommended by75%of homeowners
H.I.T Construction LLC - Facebook
4.8(
3
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

In business since 2016

Emergency services offered

Welcome to HIT Construction! We take pride in the quality of work and customer satisfaction that we give each and every customer! We are known to pay exquisite attention to detail while making customer satisfaction our top priority. Call us today to learn more about how we can help you!

Response time2 days
Response rate100%
Recommended by100%of homeowners
Ramos Upgrades
5.0(
2
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

In business since 2021

Free estimates

Credit card accepted

"My roof had developed a leak. I called Ramos Upgrades and an inspection was performed immediately upon request. The entire roof was replaced within one week from the inspection. The roof looks great! They cleaned up very well with no trace of any nails or other debris left behind. Price was well below quotes I had gotten a few months prior. I highly recommend if you need any roof work, call Ramos Upgrades!"
Roofing Project
Recommended by100%of homeowners
Avatar for American Home Shield – Home Warranty
American Home Shield – Home Warranty
3.5(
5,689
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

In business since 1971

Credit card accepted

"AHS is ok. They cover repairs of most everything under the roof of your house. The companies that contract with them are not always the best. You call AHS with the issue, they send a fax to the repair company and give you the contact info. If they don't contact you within 24 hours, you call them. Sometimes they answer, sometimes they don't. When they arrive (usually three days or so later), they service the item. if it has issues within the 90 days, you call AHS again, they are sent out with no charge. If the serviceman decides the unit is unrepairable, AHS will allow you to choose a replacement from their listing (usually not as good as what you have) they will install and remove your old item, or give you wholesale amount to buy and install your own. Prices vary on what you want covered and what you want the copay to be, plus where you live. For me it is 49.99 per month with a 75.00 time of service order. You can have more than one item serviced at the same time under the same fee. If you have a SEAR product the repair guys are great. Not that wild about the other ones they send out. But it is a big savings compared to calling someone on your own. The cost of service is only the 75.00 copay."
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+2

Recommended by65%of homeowners
Avatar for S&K Construction
S&K Construction
3.7(
3
)
Wood Shake or Composite Roofing - Install or Replace

Serving Middlesboro, KY and surrounding areas

With over 10 years of experience, I take pride in my quality work. We are owner operated, and believe in building long-term relationships with our clients through honesty along with exceptional work. We pride our company on reliability, great communication, integrity, and personalized customer service. We are experts in our trade and will do our best to keep you as educated as we can on your particular project. We will get the job done right the first time and ensure customer satisfaction. We look forward to working with you!

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+3

Recommended by100%of homeowners
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FAQs for wood shake or composite roofing installation and replacement projects in Middlesboro, KY

Cedar shakes and wood shingles might seem similar, but they have some important differences. Cedar shakes are hand-split, giving them a unique, textured appearance that adds rustic charm to your roof. They're great for homeowners who want a distinctive look. Wood shingles, conversely, are machine-made, providing a smooth, uniform appearance for a more modern look. Shakes tend to be more expensive due to the craftsmanship involved but offer exceptional beauty and resilience.

A well-maintained cedar shake roof can last up to 60 years. However, factors like severe weather and improper ventilation can reduce its lifespan. You should consider replacing your roof if you notice persistent leaks, visible water damage, curling or splitting shakes, moss growth, rot, or missing shakes. Regular inspections can help you determine when it's time for a replacement.

When hiring a roofing contractor for your cedar shake roof, asking the right questions is important. Make sure they are fully certified and have extensive experience with cedar installations. Verify that their team is licensed, bonded, and insured. Ask for details about the materials they use, such as the type of underlayment and fasteners, and how they ensure proper ventilation. Getting multiple written estimates can help you compare options and choose a contractor who offers quality workmanship at a fair price.

The Middlesboro, KY homeowners’ guide to wood shake or composite roofing installations and replacements

From average costs to expert advice, get all the answers you need to get your job done.