How Tilehurst Roofing Orlando Was Born in Orlando
We didn’t create Tilehurst Roofing. The name and the Kingswell Guarantee behind it already existed, built by a family that believed roofs should be done once and done right. What we did, starting in 2000, was bring that standard to Orlando. And we did it because this market was crying out for it.
Greg Holloway remembers the exact pattern: homeowners across Orlando kept telling the same story. A roofer quoted one price over the phone, then found “unexpected damage” the moment the crew climbed up. The final bill came in thousands higher. No written estimate, no accountability, and a roof that leaked again six months later. In neighborhoods from Conway to College Park, people stopped trusting the trade entirely. Greg saw families patching the same spot three times because nobody would actually fix it right. He knew the Kingswell model, the written price before work starts, the comeback guarantee, belonged here. So he opened this branch in Orlando in 2000 with one simple commitment: bring the Kingswell Way to a city that had every reason to be skeptical.
Greg Holloway’s Personal Connection to the Roofing Trade
Greg didn’t grow up dreaming about shingles. He grew up helping on job sites, the kind of teenager who got handed the jobs nobody else wanted. Hauling bundles up ladders. Picking up nails at the end of a long Florida afternoon. He learned the trade the old way, not from a manual but from watching experienced roofers read a roof like a doctor reads symptoms. He can still remember the first time he watched a crew tear off a failed roof in Orlando and saw what was underneath: rotted decking, improper flashing, shortcuts hidden under layers that looked fine from the street. That image never left him.
What kept him in roofing wasn’t the paycheck. It was the moment after. When a homeowner walked outside, looked up, and finally felt safe. That quiet relief. In a city where afternoon thunderstorms roll in without warning, a good roof isn’t a luxury. It’s the difference between sleeping through a storm and racing for buckets. Greg would tell you that if he weren’t roofing, he’d probably be building something else with his hands. He’s not the type to sit behind a desk. The work matters to him in a way that’s hard to put into words, but it’s the reason he’s still climbing ladders after more than a decade in the trade. The heat on an Orlando roof in August doesn’t bother him nearly as much as a homeowner who’s been lied to does.
Meet Greg Holloway – The Person Behind Every Job
Greg Holloway is the Owner & Founder of Tilehurst Roofing Orlando. He’s spent his entire adult life in roofing, working his way through every role from carrying materials to running jobs. He’s a state-licensed professional who takes continuing education seriously, because roofing materials and codes change and so should the people installing them.
What makes Greg different from a corporate franchise technician is that his name is on the work. When a roof fails in Orlando, it’s his phone that rings. When a homeowner has a question, they get an answer from someone who’s actually stood on their roof. On weekends, you might find Greg fishing somewhere quiet or taking apart an engine just to put it back together. He’s the kind of person who fixes things properly because he can’t stand doing it any other way. And he brings that same stubbornness to every roof he touches. If you hire his team, you’re getting someone who takes your roof personally.
Our Promise to Orlando Homeowners
Every job we take follows the Kingswell Way, five promises we don’t bend on. We say the price before the work starts, in writing, so there are no surprises at the end. We show up in the window we gave you, because a no-show roofer is the reason so many Orlando homeowners are skeptical. We leave the place cleaner than we found it, every nail, every scrap of old shingle, every wrapper. We put the guarantee in writing, so you know exactly what’s covered. And if something fails inside that guarantee period, we come back and fix it at no charge. Those aren’t slogans. They’re how Greg runs this branch, and they’re why people in Orlando stay with us when the roof finally needs attention again.
Our Credentials
When you hire a roofer, you’re letting strangers into your home. You should know what you’re getting:
- State-licensed. Every professional working under the Tilehurst Roofing name in Orlando is required to hold the license the state of Florida requires for roofing work. We don’t cut corners on credentials.
- Insured & bonded. Every pro working under our name is required to carry the insurance and bonding their state requires. That protects you and your property while work is underway.
- Local experience. Greg and his team have been roofing Orlando homes since 2000. They’ve seen what Florida weather does to roofs over time, and they know what holds up here.
- Strong local reputation. Homeowners across Orlando and the surrounding communities continue to recommend our team. We earn that by doing the work right and standing behind it.
Why does this matter to you? Because a license proves the person on your roof is accountable to someone other than themselves. Insurance protects your home if something goes wrong during the job. And a local reputation means the people who’ve hired us already are the best reference we could ask for. That’s the kind of certainty Orlando homeowners deserve.
Rooted in Orlando
We work across Orlando and the communities around it: Deltona, Kissimmee, Altamonte Springs, Winter Garden, University, Casselberry, Meadow Woods, DeBary, Lake Butler, Forest City, and Conway. After Orlando storms, we’re the ones checking roofs while neighbors are still picking up branches. Greg has been part of this area long enough that running into past customers at a local restaurant isn’t unusual. It’s a good feeling, and it keeps us honest.
Written by Greg Holloway, Owner & Founder at Tilehurst Roofing Orlando, serving Orlando since 2000.