Veteran Owned · GAF Certified Plus
Trust The Best
Roofing Company
In Chatham County
Roof replacement, repair, storm claims, gutters, and siding from a veteran-owned Pittsboro crew.
Chatham Magazine
Named to Best of Chatham 2026
Chatham County readers vote every year for the businesses they trust. In our first year open, they put Skyline Exterior Group on the list.
Read the Best of Chatham post
Free · No pressure · On site within 48 hours
A free estimate from the crew that shows up
Tell us your name, phone, and address. We call you back to set a time, walk the roof with CompanyCam photos, and hand you a firm quote the same day. No storm-chaser sales script, and 0% and low-APR financing is there if you need it.
Recent roofs we installed
Every photo below is a Skyline job in North Carolina. No stock. No storm-chaser templates. Every job documented.
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PITTSBORO, NC -
CHAPEL HILL, NC -
APEX, NC -
SILER CITY, NC -
SANFORD, NC -
CARRBORO, NC
Every job photographed and documented with CompanyCam.
What homeowners say on Google
5.0 RATING
- Melissa Lautieri
We recently had our roof replaced and the process was seamless! These days it feels like companies try to hustle you left and right but this company rises above and works with you with integrity every step of the way. Erica was top-notch. An absolute angel. She deserves a raise!!
- Oliver George
Skyline Exterior Group did a roof inspection for me and exceeded my expectations on every level. They showed up right on time, which I really appreciated, and their knowledge of roofing was evident throughout the entire process. They took the time to explain what they were looking at and gave me honest, straightforward feedback. This is the kind of company you can trust. Five stars, no question.
- Mason B
We just had our roof replaced by Skyline Exterior Group and honestly I can’t say enough good things. My wife is a Chatham County Chamber Ambassador and trust me, she does not hand out compliments easily. Skyline more than passed her test. Honest, transparent, and built on a story that genuinely warms your heart. Really glad to have a company like this serving Pittsboro. If they passed her bar, they’ll pass yours.
Why homeowners pick Skyline
- 01
We do the job right. Every single time
No upsells you don’t need. No shortcuts. Photo documentation on every roof. If something isn’t right, we come back and fix it.
FULL REPLACEMENT, BEAR CREEK · PHOTOGRAPHED AFTER THE MAGNETIC SWEEP - 02
We give back to those who served
For every 100 roofs we install, we donate one complete roof, at no cost, to a veteran, first responder, or family in need.
THE 100 ROOF PROMISE · GRADY BENDEL AND BRIAN RICE, MARCH 2026 - 03
Industry-leading materials. Industry-leading warranties
GAF Certified Plus contractor. We install GAF Timberline HDZ shingles with manufacturer-backed warranties most local roofers can’t register.
GAF TIMBERLINE HDZ WITH LAYERLOCK · CHARCOAL
One free roof for every 100 we install
For every 100 roofs Skyline installs, we donate one complete roof, at no cost, to a veteran, first responder, or family in need. Nominated by neighbors. Verified by our team.
29of 100
What we handle
Five services, one licensed crew. Every one is a job our own crew does, start to finish.
Roof Replacement
Full tear-off, never an overlay. GAF Timberline HDZ shingles with LayerLock, most jobs finished in 1 to 2 days, and a 50-year workmanship warranty registered before we call it done.
- Full tear-off to the deck, dried in the same day
- GAF Timberline HDZ, the most installed shingle in North America
- Lifetime limited manufacturer warranty plus our 50-year workmanship warranty
Roof Repair
Leaks, flashing, pipe boots, and wind damage, fixed by the crew that would rather repair a good roof than sell you a new one. Photo evidence with every recommendation.
- In-person inspection within 48 hours with CompanyCam photos
- Honest repair-or-replace call: under 15 years and localized means repair
- Emergency tarping available 24/7
Storm Damage Repair and Insurance Claims
After hail or wind, we document the damage, meet your adjuster on the roof, and handle the claim paperwork. On approved claims you typically pay only your deductible.
- 24/7 emergency tarping to stop the water
- Timestamped CompanyCam documentation insurers cannot wave away
- Adjuster meetings and claim paperwork handled start to finish
Gutter Installation and Repair
Seamless gutters cut on site to your roofline, plus guards, downspouts, cleaning, and repair. Bundle them with a roof replacement and they go on in the same visit.
- Seamless runs, no mid-span joints to leak
- Guards, downspouts, and fascia repair
- Sized to your roof, not a one-size sectional kit
Siding Installation and Repair
Siding installation, repair, and replacement matched to your roof, with the same photo documentation and workmanship warranty as every Skyline job.
- Premium architectural materials
- Repair where the roof meets the wall, replace where the siding has failed
- Scheduled alongside a roof or gutter job when it makes sense
How the process works
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1. Request your free estimate
Send your name, phone, and address, or call. We get back to you to set a time. No sales visit to get started.
2 MIN -
2. On-site inspection
On site within 48 hours if you want us. CompanyCam photo documentation of everything we find, and a firm same-day quote.
48 HRS -
3. Install day
Tear-off, dry-in, new shingles, clean site, magnetic sweep, registered warranty. Most jobs done in 1 to 2 days.
1-2 DAYS
Roofing in Pittsboro, Chatham County, and the towns around it
- Pittsboro NC 27312
- Apex NC 27502
- Chapel Hill NC 27514
- Siler City NC 27344
- Sanford NC 27330
- Carrboro NC 27510
- Moncure, Goldston, and more
Same crew, same pricing, and the same 48-hour inspections in every one of these towns. A little farther out? Call us anyway. We do not turn down a roof over a mile or two.
See every town we serveRoofing questions, answered
Short answers here. The long ones, with sources, are in our roofing guides for homeowners.
Most full replacements run $8,500 to $18,000. A typical 2,000 square foot home lands between $11,000 and $14,500. A free on-site estimate narrows that range to your actual roof, with a firm quote the same day.
Most jobs are done in 1 to 2 days: tear-off, dry-in, new shingles, clean site, magnetic sweep, registered warranty. You’ll know your install date before we start.
Request it online in about two minutes, or call. We get back to you to set a time, and in-person inspections happen within 48 hours with a firm quote the same day.
Yes. Skyline Exterior Group holds NC General Contractor License #108831 and is fully insured. A certificate of insurance is available on request, before any work starts.
Yes. We document the damage with CompanyCam, meet your adjuster on site, and handle the claims paperwork. On approved claims, you pay only your deductible.
Our default is GAF Timberline HDZ with LayerLock technology, covered by a lifetime limited manufacturer warranty plus our own 50-year workmanship warranty. As a GAF Certified Plus contractor we can also register System Plus and Silver Pledge upgrades most local roofers can’t.
Yes. 0% and low APR options with terms from 12 to 120 months. The decision uses a soft credit pull, so checking your options won’t affect your score.
Rule of thumb: a roof under 15 years old with localized damage is usually a repair. Over 18 years old, or with widespread wear, replacement usually wins on cost per year. We’ll tell you which one honestly.
We do. Permits are pulled under Skyline’s NC General Contractor license, and we provide any paperwork your HOA needs before work begins.
Pittsboro, Apex, Chapel Hill, Siler City, Sanford, Carrboro, and Moncure, plus Bear Creek, Bonlee, Goldston, and Bennett. In short: all of Chatham County and the towns around it, and a little farther when you call.
Free Estimate
Get your free roofing estimate
Tell us your name, phone, and address. We call you back to set a time, and we are on site within 48 hours when you want eyes on the roof. No pressure, no storm-chaser sales script.