Metal roofing
Architectural shingles
Tile 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 Installation Across Maitland
A new roof over your Maitland home should run somewhere between $9,800 and $18,500 for a standard single-family house, depending on material choice and the condition of what’s underneath. That’s the honest range we quote across Maitland, and it holds whether you’re in Dommerich Hills or a newer stretch off Lake Lucien. We’re Crestview Roofing Co Orlando, and we handle roof installation in Maitland with a written price before any work starts, a live trackable arrival time, and photo documentation at every step. If you’re weighing a full replacement or a new installation and want straight numbers, call (448) 218-0800 and we’ll walk you through what applies to your specific roof.
Why Crestview Roofing Co Orlando Is Maitland’s Preferred Roof Installation Company
Dylan Pace runs our crews with one rule: the number on the written estimate is the number on the invoice. That matters in Maitland, where architectural review boards and aging housing stock make roof work more complicated than what a drive-by quote can capture. We’ve worked the neighborhoods around Dommerich Hills, English Estates, and the streets off Maitland Boulevard long enough to know what a 1968 roof hides before we lift the first tile.
Every job is bound by The Relay Visibility Guarantee, part of the Relay Home Co. family. That means a written price before work begins, before-and-after photos, a live arrival time you can track, and a digital invoice sent by text. There’s no phone tag and no mystery truck in your driveway. A live person answers our line 24/7, even during the afternoon thunderstorms that roll through the Maitland area from June through September.
Styles & brands we work with
Roof Flashing Installation in Maitland
Roof flashing installation in Maitland is one of the most underspecified parts of any roofing bid, and it’s where older homes around Lakeside and Druid Park fail most often. Flashing is the metal strips that seal the joints where your roof meets a chimney, skylight, vent pipe, or wall. When it’s old, corroded, or installed without a proper cricket, wind-driven rain gets pushed up and under the shingles during our summer storms, and water ends up in the ceiling before anyone sees a missing shingle.
Why Older Maitland Flashing Fails
Much of Maitland’s mid-century housing stock was flashed with galvanized steel that has long since rusted through at the seams. Homes along Eaton Street and in the neighborhoods off 17-92 were built when builders often caulked flashing into place rather than overlapping it correctly. Once that caulk dries and cracks, the flashing becomes decorative. We replace it with code-compliant step and counter flashing, sealed and fastened to outlast the roof surface itself.
What Flashing Installation Costs Here
A complete flashing replacement on a typical Maitland chimney runs $400 to $900 including materials and labor. Skylight flashing runs $350 to $800 depending on the skylight brand and roof slope. Re-flashing an entire roof perimeter, which we do on most full installations, adds roughly $1,200 to $2,800 to the job. These are written, fixed numbers we give before any work begins, not estimates that shift once the old metal comes off.
TPO Roofing Installation in Maitland
TPO roofing installation in Maitland is a flat-roof solution that’s becoming more common on the mid-century modern homes and garage roofs scattered through the city’s older sections. TPO stands for thermoplastic polyolefin, a single-ply membrane that’s heat-welded at the seams to form a watertight barrier. For Maitland’s low-slope designs, particularly the flat carport and lanai roofs on 1970s homes near the Maitland Community Park area, TPO gives you a roof that reflects heat, holds up to ponding water, and resists the UV exposure that eats asphalt roll roofing fast in this climate.
Where TPO Makes Sense in Maitland
If your home has a low-slope or flat section that’s been repeatedly patched with tar or silicone coating, TPO is almost always the smarter fix. The membrane goes down over a clean substrate, seams are welded by a crew who actually knows the material, and the result is a 20-plus-year surface that doesn’t need re-coating every two years. We also install TPO on new additions and detached structures.
TPO Installation Pricing
A standalone TPO installation on a two-car garage or lanai roof in Maitland typically runs $2,800 to $5,200. If we’re tying TPO into a larger shingle roof replacement on the main structure, the marginal cost drops and we’ll show you both numbers side by side before you sign. The price includes tear-off of the old surface, any seam welding, and new edge metal installed to code.
Common Roof Installation Problems We See in Maitland Homes
- Original underlayment turning to powder. In Dommerich Hills and English Estates, we regularly open up 1960s clay tile roofs where the tile itself is still perfectly sound but the hot-mopped underlayment beneath has disintegrated. The homeowner sees stains on the ceiling and assumes the roof needs a full replacement; the actual fix is a re-bed and underlayment job at a fraction of the cost.
- Flashing that never got upgraded. When a previous owner re-covered a roof, the old galvanized flashing around chimneys and skylights often stayed in place. Maitland’s wind-driven thunderstorms push water under that old metal and into the house. We see this on mid-century homes all around Lake Sybelia.
- Hidden decking rot. Intact shingles can hide rotted plywood or plank decking underneath, especially on low-slope 1970s designs where water sat under the surface after a slow leak. A permit-triggered inspection opens the roof and exposes framing that no longer meets current code.
- Undersized framing that won’t pass inspection. Many Maitland homes built between 1960 and 1985 have rafter sizing that was fine under the old code but fails today’s wind-load requirements once the roof comes off. We see this most often in the neighborhoods east of Maitland Avenue, and it’s exactly why our quotes include written allowances instead of silent surprises.
See the difference
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We Also Serve Cities Near Maitland
Along with Maitland, our crews cover Winter Park, Orlando, Longwood, and Winter Springs. If you’re near the Maitland-Winter Park line or off 434 in Longwood, the same written pricing and the same 365-Day Done Right Promise apply. One call to (448) 218-0800 gets you scheduled anywhere in the service area.
Serving Maitland, FL - Our Local Coverage Area
We’re based in the Maitland 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 Installation in Maitland
The original clay tiles on 1960s-era Maitland homes are often in perfectly usable condition, but the hot-mopped asphalt underlayment beneath them has a lifespan of about 40 years. In Dommerich Hills and English Estates, the underlayment has usually turned to dust by now, which lets water through even though the tiles above look fine. A re-bed involves removing the tile, installing new synthetic underlayment and code-compliant flashing, and resetting the original tile. It typically runs $4,200 to $7,500 versus $22,000 to $38,000 for full tile replacement, so it’s worth confirming which one you actually need before budgeting. Call (448) 218-0800 and we’ll send someone to assess your roof honestly.
The three most common are undersized rafters, missing hurricane strapping, and inadequate roof-to-wall connections. Older Maitland homes were built under codes that didn’t require the same wind-load resistance as current Florida building code, so once the roof is open, the inspector often requires additional metal connectors and in some cases engineered framing fixes. We build a fixed allowance for these into every contract, and we show you photos of anything we find before we touch it. That’s the Crestview way: no surprise charges, no “we had to upgrade and here’s the bill.”
In several of Maitland’s established neighborhoods, particularly around Dommerich Hills and English Estates, the city’s architectural review board requires replacement roofs to match the original material profile when visible from the street. That often means if you have clay tile, you’re expected to stay with clay tile or an approved lookalike. We can walk you through which materials are approvable on your street before you spend money on samples, and we’ll include the review and permit process in the written quote. Call (448) 218-0800 to get started.
The inspector checks underlayment coverage, nailing pattern, flashing installation, and the structural connections that were visible while the deck was exposed. In Maitland, as in the rest of Orange County, the inspection happens in two phases: one when the old roof is off and the deck is bare, and a final inspection once the roof surface is complete. We handle scheduling, meet the inspector on site, and correct anything flagged within the same visit whenever possible. The final paperwork goes to you and the city, and it’s covered in your written estimate.
We write the known scope at a fixed price and add a transparent allowance for what we might find. Most Maitland homes built before 1990 have at least some decking that looks questionable once the shingles come off, and some have framing that will fail modern wind-load requirements. The allowance is a specific dollar figure, not a percentage, and we only draw down on it if we actually do the work. You approve anything in writing via text before we proceed. Call (448) 218-0800 for an exact quote – estimates are free and the numbers don’t change unless something hidden is found, and even then, only with your sign-off.
Schedule Your Maitland Roof Installation Estimate
Getting a roof installed in Maitland shouldn’t feel like rolling dice. We’ll send a named, uniformed technician you can track on a live arrival map, with a written price in your hand before the first shingle comes off. Whether you’re facing a full replacement in Dommerich Hills or a new TPO roof over a garage near Lake Sybelia, call (448) 218-0800 to schedule your free estimate. If it’s not done right, our 365-Day Done Right Promise means we make it right, in writing, on every job.
Written by Dylan Pace, Owner at Crestview Roofing Co Orlando, providing Roof Installation in Maitland.