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Top-Rated Roofers in Haileyville - Updated Nov 2026

Avatar for High Ground Solutions LLC
High Ground Solutions LLC
5.0(
6
)
Roof - Clean

Serving Haileyville, OK and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

"Jesse at High Ground Solutions was great! He put together some garage cabinets we purchased, he was on time, didn’t take long, his charge was very reasonable and they looked great when he was done. He’s a pro!"
6 neighbors recently requested a quote
Avatar for Outdoor Creations Roofing
Outdoor Creations Roofing
4.7(
25
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Haileyville, OK and surrounding areas

In business since 2012

Free estimates

Credit card accepted

"Outdoor Creations did a very fantastic job on our damaged and leaking roof. They just happened to be driving pass our home one day and observed that our roof needed repair. They stopped by and politely introduced themselves, and asked permission to inspect the roof. After discovering some serious damage from the weather, they facilitated and handled the insurance issues concerning the needed repairs in a professional manner. After the details were completed their crew came and finished the job in two and a half days. The crew was very polite and skilled, and they did a great job. Jake conducted himself with honesty and integrity. The information they gave was clear, and they were happy to answer all our questions. The great news is my wife and I have a brand new roof on our house because they stopped by one day. We are very pleased with their work. Thanks to Jake we no longer have a leaking roof. We highly recommend Outdoor Creations and the work they do. Desmond and Pauline Shepherd Tulsa, OK"
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+3

Recommended by95%of homeowners
Avatar for Aaron Branhan
Aaron Branhan
5.0(
12
)
Inspection - Roofing

Serving Haileyville, OK and surrounding areas

In business since 2020

Free estimates

Emergency services offered

"I woke up, on a Sunday, to a hole in a barn roof. I sent out a request through Angi and within 15 minutes, got a call from Aaron. He was there within an hour and assessed the situation. We ended up replacing the whole roof, which I knew I was going to have to do, but was putting it off for a few months (until the hole showed up). Aaron explained everything completely and offered to place tarps over the roof until the decking and roof could be replaced. Within a few days, I had a new roof that looks amazing, at a cost that was quite affordable!"
Response time12 hrs
Recommended by54%of homeowners
Avatar for Whip Roofing
Whip Roofing
5.0(
4
)
Asphalt Shingle Roofing - Install or ReplaceAsphalt Shingle Roofing - Install or Replace - For BusinessAsphalt Shingle Roofing - Repair+26 more

Serving Haileyville, OK and surrounding areas

In business since 2014

Free estimates

Emergency services offered

"They did an outstanding job. We were very happy, A very good quality shingle at a very reasonable price. The roof was absolutely beautiful. What also impressed us was the owner was on site overseeing the job most of the time. The men working for him were very courteous and competent. They cleaned up the area after the roofing was done so well it was a rare thing to find even a small bit of debris."
Recommended by100%of homeowners
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Roofing FAQs, answered by experts

Homeowners insurance typically covers roof repairs or replacement if the damage is caused by a sudden, accidental event or a covered peril, such as a storm, wind, hail, fire, or a falling tree. However, insurance will not cover repairs or replacement for issues stemming from a lack of maintenance, normal wear and tear, or a roof that is simply old and at the end of its lifespan. If a leak or damage occurs due to neglect, you will likely have to pay for repairs out of pocket.

You can put new shingles over old shingles, but most municipalities only allow for two layers of shingles before you have to rip off the old roof and start fresh. In some areas, only a single layer of shingles is allowed due to the weight a bundle of shingles adds to your structure. In most cases, it’s a good idea to remove your old shingles before you install new shingles, especially if you suspect that a roof leak may have compromised the decking underneath.

You can replace a roof in the winter, though it’s not the most popular time to do so. The biggest drawback of winter roofing work is the weather. Snow and ice make for dangerous, slippery working conditions. Plus, shingles can only be installed in temperatures above 40 to 45 degrees. 

The best time to replace a roof is in the spring or fall when the weather is mild. However, you can likely save some money by booking the job in the winter off-season, when roofers have more availability. 

Once framing is complete, you will need the following materials to roof a house:

  • Wood sheathing

  • Drip edge, a.k.a metal flashing

  • Underlayment for waterproofing

  • Roof covering, like metal or asphalt shingles

No, cool roofs are not suitable for all climates. Cool roofs are very good at reflecting solar heat, so they’re suitable for homes in warm or hot climates. However, they’re not good at retaining heat, so they’re not suitable for homes in cold climates.

The Haileyville, OK homeowners’ guide to roofing services

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