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Oldcastle Roofing: The Orlando Owner’s Guide
Oldcastle roofing replacement in Orlando typically runs $8,000 – $20,000 installed, and roof repairs on Oldcastle systems generally land between $400 and $1,800 depending on the extent of the failure. We stock common Oldcastle-compatible flashing, ridge caps, and underlayment on our trucks, and we can source full panels or tiles within days if your roof needs more than a patch. Most Orlando homeowners discover an Oldcastle roof problem the same way: a damp spot on the ceiling after an afternoon thunderstorm, granules piling up in the gutters, or a shingle flapping loose after the wind picks up off Lake Eola. The failure rarely announces itself. It shows up as a slow leak, and by the time you see the stain, the water has already been working its way through the decking for weeks.
If you have an Oldcastle roof and something looks wrong, call us at (850) 920-7745. We’ll tell you what we’re seeing, what it costs, and whether you need us this week or can wait a season. Tell me what the problem is. We’ll figure out the rest from there.
Which Oldcastle Models This Applies To

Oldcastle’s roofing line includes several product families, and the parts are not interchangeable across all of them. The big split is between their architectural asphalt shingle lines (common on Orlando homes built in the 1990s and early 2000s) and their concrete and clay tile profiles, which show up on higher-end Spanish-style and Mediterranean builds in neighborhoods like College Park and Winter Park.
The compatibility gotcha we see most often in Orlando: Oldcastle’s tile profiles have changed over the years, and a tile that looks visually identical to your existing roof may be from a different production run with a slightly different curvature. Installers mix tiles between runs and the rows don’t seat flush, which leaves gaps where wind-driven rain gets under the tile. Getting the right match matters. If you can get into the attic, look for the original bundle wrapper stapled to a rafter, or check the back of a loose tile for a molded-in date code. If you can’t find a label, take a photo of the tile’s edge profile and a close-up of the surface texture and send it to us before you buy anything.
On the asphalt shingle side, most Oldcastle architectural shingles accept standard industry accessories: compatible ridge caps, hip and ridge shingles, starter strips, and flashing. Aftermarket underlayments (such as synthetic underlayments from GAF or CertainTeed) are generally acceptable and in some cases outperform the original material. On the tile side, we push OEM parts harder because the profile matching is more exacting. Quality aftermarket concrete tiles exist, but they’re not always a true match at the overlap point, and that’s where leaks start.
Mason Remodeling Co Orlando is an independent service provider and not affiliated with Oldcastle. We work on Oldcastle roofs because homeowners here have them, and because we stock the parts to fix them correctly.
Styles & brands we work with







Signs Your Oldcastle Roofing Is Failing
- Granules collecting in gutters or at downspout elbows. Asphalt shingle surfaces shed granules as the asphalt binding weathers under Orlando’s UV and humidity. A consistent heavy accumulation means the shingle’s protective layer is thinning, and the underlying mat is next.
- Cracked, chipped, or slid concrete tiles. Concrete tiles are brittle. A fallen branch or a foot in the wrong place cracks them, and a cracked tile channels water to the underlayment below. One or two missing tiles might be a simple swap; a wide field of spalled or cracked tiles usually signals age and a full reroof conversation.
- Stains on ceilings or at wall-to-ceiling corners after rain. Water marks inside your home mean the roof has already been compromised, often at a flashing point: chimney, skylight, plumbing vent, or a wall where two roof planes meet. The leak may not drip every storm, but the water is still entering and collecting.
- Curling or lifting shingle edges near roof eaves. Orlando’s afternoon storms push wind in every direction, and shingle edge seals fail first. Once the seal breaks, the shingle flaps, rain gets driven underneath, and the decking starts wicking moisture.
- Daylight visible through the roof deck from inside the attic. If you can see pinpricks of light through the plywood, you’re also seeing paths for water. This is a structural decking issue, not a shingle issue, and it means the roof has likely outlived its full service life.
See the difference
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AfterReplacement Cost & What’s Included

For a full Oldcastle-compatible roof replacement in Orlando, expect $8,000 to $20,000 installed. The spread comes down to roof size, pitch, tear-off layers, and whether we’re matching asphalt shingles or concrete tile. A smaller ranch in Conway might land near the bottom of that range; a two-story tile roof in Windermere with a steep pitch and multiple valleys will push toward the top.
Roof repairs sit lower: $400 to $1,800, with smaller flashing repairs and single-tile replacements at the bottom and larger decking repairs or valley rebuilds at the top. Every estimate is written and line-itemed before work begins, including disposal, underlayment, fasteners, and labor. No verbal ballparks that grow into a bigger invoice. The 365-Day Done Right Promise applies: if our roofing work isn’t right within a year of completion, we fix it at no cost to you.
We also install or repair roofs using GAF, CertainTeed, and Owens Corning materials, so if you’re not tied to the Oldcastle brand and want to compare, we can price both paths honestly.
DIY or Call Us?
You can safely check a few things from the ground or from inside the attic: look for missing tiles or shingles from the yard, check the attic for dark stains on the decking, and clear debris from your gutters. Those checks cost you nothing and give us useful information before we arrive.
What I’d tell you not to do is climb onto a single-story roof, and never a two-story, to inspect or patch this yourself. Roof work in Orlando means working on surfaces that are hot, often slick with mildew, and pitched. A fall from eave height changes your year in a way no roof repair is worth. If you suspect an Oldcastle tile or shingle failure, call (850) 920-7745 and let us put eyes on it. The estimate is free. The peace of mind of keeping both feet on the ground is also free, and you can take that one to the bank.
FAQs

Concrete tile roofs in Orlando commonly leak through worn underlayment rather than visible tile damage. The underlayment has a shorter service life than the tile, and the leak shows up as stains while the tiles still look intact. We inspect the underlayment condition before recommending tile replacement, because a full tile swap is often unnecessary if the tile itself is sound.
Expect $8,000 to $20,000 for a full roof replacement and $400 to $1,800 for repairs, including materials and labor. A written quote with specific dimensions, material counts, and labor hours is provided before you commit, so you know the exact number before work begins.
Yes. If the tiles are from a current production run and the underlayment below is intact, we can swap individual cracked pieces and the repair usually falls on the lower end of the $400 to $1,800 range. If the tiles are from a discontinued profile or the underlayment shows deterioration, we’ll need to discuss a broader scope.
A standard repair takes one visit, usually half a day. A full roof replacement on an average Orlando home runs three to five working days depending on the tear-off and weather. We’ll give you a written schedule with the estimate so there aren’t any surprises about trucks in the driveway.
We stock flashing, ridge caps, and underlayment for Oldcastle-compatible roofs on our trucks, and we order tile or shingle matches from our supplier network as needed, typically within a few business days. You don’t need to source parts yourself; we handle the part identification, ordering, and installation.
Written by Isaac Pruett, Owner, Mason Remodeling Co Orlando at Mason Remodeling Co Orlando, serving Orlando and nearby areas.


