Tile roofing
Architectural shingles
Metal roofing
GAF
Owens Corning
Flat & low-slopeFree roof inspection with deck photos before we talk money - GAF and Owens Corning certified installation
Fast, Reliable Roof Replacement Across Pine Castle
If your roof in Pine Castle is nearing the end of its life, you want a straight answer: what it costs, what it takes, and what gets uncovered once the old shingles come off. Most asphalt shingle roof replacements in Pine Castle run $8,500 to $16,000 for a typical single-story ranch, and you should expect that number to move if your home still has 1950s-era skip sheathing underneath. We work in Pine Castle regularly, and we know exactly what central Florida’s storm-driven rains do to older roofing systems. Call (850) 303-7235 and we’ll put a written price in your hands before any work starts.
Why Tilehurst Roofing Orlando Is Pine Castle’s Preferred Roof Replacement Company
Tilehurst Roofing is part of the Kingswell family of roofing companies, founded in 2000, and our Pine Castle customers have stuck with us for one reason: we show up, we say the price, and we stand behind the work in writing. Greg Holloway leads our Orlando team. When a homeowner near Lake Conway or off Hansel Avenue calls us, they’re not getting a call center. A live person answers 24 hours a day, seven days a week, including evenings and weekends.
Our Roof Replacement crew knows this corner of Orange County well. We understand what happens to roofs near the wet, wind-prone edge of Orlando, and we plan every replacement around what a Pine Castle tear-off actually reveals. Every job starts with a written price before any work begins, and every roof we replace carries a written guarantee delivered before the crew leaves your driveway.
Styles & brands we work with






Reroofing in Pine Castle
Reroofing in Pine Castle is rarely a simple shingle swap. Homes here are predominantly modest, mid-20th-century single-family houses, and many still sit on the original asphalt shingles and aging decking installed when the neighborhood went up. We tell every Pine Castle homeowner the same thing before we quote: the real cost is in what’s underneath. You’ll get an inspection first, a line-item allowance for decking replacement written into the contract, and any surprise priced and approved in writing before we touch it.
Inspection Before Any Numbers
We don’t give a final reroofing price over the phone, and we don’t want to. The roof has to be walked, the attic checked, and the decking condition assessed. On Pine Castle homes built in the 1950s and early 1960s, what we find up there determines whether reroofing is a two-day job or a four-day job.
Code-Triggered Decking Upgrades
Once walls and ceilings are open, building code has opinions. If we pull off old shingles and find skip sheathing with gaps wider than the code allows, the new underlayment and shingles can’t go on until the decking is brought up to standard. We plan for this. Your contract includes a decking allowance so a code upgrade doesn’t become a fight mid-project.
Flat Roof Replacement in Pine Castle
Flat Roof Replacement in Pine Castle has its own set of rules, because low-slope sections on older Florida homes fail differently than pitched roofs. Pine Castle’s intense afternoon thunderstorms dump water fast, and a flat roof with worn flashing or a clogged scupper will find a way to let that water inside. Expect a flat roof replacement on a typical Pine Castle home to run $6,500 to $12,000 depending on square footage, membrane type, and whether the decking underneath needs work. We give you a fixed written quote before any material is ordered.
Low-Slope Membrane Choices
We install TPO, modified bitumen, and PVC systems depending on the roof’s slope, the home’s orientation, and how much ponding water the existing design allows. CertainTeed and Owens Corning both manufacture flat-roof membrane systems we stock for fast turnaround in Pine Castle. We’ll explain the tradeoff between membrane thickness and warranty length in plain terms before you decide.
Drip Edge and Underlayment on Low Slope
On a low-slope Pine Castle roof, underlayment and drip edge are not extras. Skipping proper underlayment lets afternoon thunderstorms drive water under the shingle or membrane edges, and that’s how you get moisture intrusion inside a brand-new roof. We include code-required underlayment and drip edge in every flat roof quote, never as a change order surprise.
Trusted Brands We Service in Pine Castle
You shouldn’t be stuck with whatever shingle happens to be on the truck. Tilehurst Roofing Orlando offers material options from seven leading manufacturers, including GAF, CertainTeed, Owens Corning, IKO, Atlas, Tamko, and Boral. For Pine Castle homes exposed to hurricane-force wind and heavy rain, we often recommend CertainTeed or Owens Corning architectural shingles for the wind ratings and warranty transferability. If you want a specific brand and color, we’ll order it and schedule your replacement around delivery. The product fits the home, not our inventory.
See the difference
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After
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AfterCommon Roof Replacement Problems We See in Pine Castle Homes
- Original 1950s skip sheathing. Many Pine Castle homes still have the spaced, plank-style sheathing that was code when Eisenhower was president. Once we tear off old shingles, the gaps between those planks mean a decking replacement is often unavoidable and code-triggered.
- Reused flashing at chimneys and valleys. Decades-old flashing has been leaking slowly for years. Reusing it under a new roof guarantees moisture intrusion eventually, so we replace flashing as standard on every Pine Castle replacement, not just when it looks damaged.
- Missing or damaged drip edge on low-slope sections. Every afternoon thunderstorm is a test of the roof’s edge. Without proper drip edge, water wicks under the shingle edge and into the decking.
- Granule loss and shingle blow-off from wind exposure. Pine Castle sits on the wet, wind-prone edge of Orlando, and original three-tab shingles rarely survive a serious storm season intact. We see granule loss, lifted tabs, and blown-off ridge caps on most older Pine Castle roofs.
Pricing for Roof Replacement in Pine Castle, FL
Here are real dollar ranges for Pine Castle’s market. A standard architectural shingle roof replacement on a 1,200 to 1,800 square foot ranch runs $8,500 to $16,000. If hidden decking replacement is needed, add $1.50 to $3.00 per square foot of decking. Flat roof replacement runs $6,500 to $12,000. The three factors that move your number: the condition of the decking once shingles come off, the roof’s slope and height, and whether original flashing can be saved (we replace it regardless, so that’s already in the quote). Every price is written and fixed before work starts. Call (850) 303-7235 for a free estimate.
We Also Serve Cities Near Pine Castle
Tilehurst Roofing Orlando works throughout the greater Pine Castle area, including Roof Replacement in Pine Castle and the surrounding communities of Orlando, Deltona, Kissimmee, and Altamonte Springs. If you’re just outside Pine Castle and wondering whether we cover your street, call us. The answer is probably yes.
Serving Pine Castle, FL - Our Local Coverage Area
We’re based in the Pine Castle area and know this community well. Use the map below to see our service coverage - if you’re nearby, we can almost certainly help.
FAQs About Roof Replacement in Pine Castle
The most common hidden problem is original skip sheathing, spaced plank decking that was standard on 1950s and 1960s Pine Castle ranch homes. Once old shingles come off, gaps up to six inches between planks are common, and current code requires solid decking before underlayment and shingles can go on. We budget a decking allowance into every Pine Castle replacement quote so this doesn’t stall your project. Call (850) 303-7235 for a quote that anticipates what your roof will actually reveal.
Yes. When a reroofing permit is pulled for a home in Orange County, the replacement underlayment and decking must meet current Florida building code, even if the original roof predates those standards. We pull permits on every Pine Castle roof replacement and schedule the required inspections. The Kingswell Way means any code-driven upgrade is in your written contract before we begin, not discovered later. Call (850) 303-7235 to talk through what your permit will require.
Pine Castle’s subtropical climate brings intense afternoon thunderstorms, high humidity, and occasional hurricane-force winds, especially between June and September. We schedule tear-off in the early morning so the new underlayment and shingles are down before storms roll in, and we monitor weather daily during your job. Wet decks and sudden downpours are why we keep crews in Pine Castle local and don’t stretch scheduling across counties. Call (850) 303-7235 to schedule around the storm cycle.
Yes, and most Pine Castle homeowners we replace for choose architectural shingles. They’re thicker, carry higher wind ratings, and hold up better against the storm-driven rains and hurricane threats common on this side of Orlando. CertainTeed and Owens Corning architectural lines both offer wind warranties rated for central Florida conditions. The upgrade typically adds $1,200 to $2,800 to a Pine Castle roof replacement. Greg Holloway can walk you through the numbers for your specific roof.
We replace flashing as standard on every Pine Castle roof replacement, not just when it looks damaged. Original flashing around chimneys and valleys on a 1960s home has been leaking slowly for decades, and reusing it under new shingles is how moisture gets into a brand-new roof. The cost of new flashing is in your written quote before we begin. Call (850) 303-7235 for an exact price on your roof.
On a 1962 ranch near Lake Conway, our crew pulled off two layers of original asphalt shingles and found skip sheathing with gaps up to six inches, plus early signs of rot at the chimney flashing. We wrote a change order for full decking replacement and ice and water shield before laying architectural shingles, and the new roof passed inspection the first time. That’s how we work in Pine Castle: open it up, tell you what’s there, price it in writing, and fix it right.
Written by Greg Holloway, Owner at Tilehurst Roofing Orlando, serving Pine Castle and greater Orlando.