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 Replacement Across Maitland
Roof replacement in Maitland typically runs $8,500 to $22,000 depending on size, pitch, and whether your home needs decking replaced. Most full replacements take 3 to 7 days once materials land. If you’re calling from Dommerich Hills, English Estates, or anywhere else in Maitland, we’re the crew that shows up with a written price already in your hand, not a number that changes after tear-off. Call (448) 218-0800 and we’ll walk the roof, document what we find, and send a line-by-line estimate you can actually read.
Maitland is different from Orlando, Winter Park, and the rest of the county. The housing stock skews older. The architectural review process is stricter. The roofs we replace here were built in a different era, with different materials and different failure points. We know what to expect before we pull the first shingle because we’ve opened enough Maitland roofs to recognize each neighborhood’s fingerprint.
Why Crestview Roofing Co Orlando Is Maitland’s Preferred Roof Replacement Company
Dylan Pace and our crews work in Maitland weekly. We know the Dommerich Hills homes with their 1963 clay tiles and the English Estates houses where the original low-slope sections were never flashed correctly. That local knowledge changes how we quote, because we’re not charging you to learn on your roof.
We operate under The Relay Standard, which is the system Dylan built the company on. You get a written price before any work starts, photo updates before and after every phase, and a live arrival time you can track from your phone. When we say a crew will be on site Tuesday at 7:15 a.m., that’s the moment they pull into your driveway. No four-hour windows.
Every replacement we install in Maitland is covered by the 365-Day Done Right Promise. If a repair fails within a full year, we come back and correct it at no charge. That includes a free second visit, no negotiation. The guarantee is written into every job, included at no extra cost. We also answer the phone 24/7 with a live person, so when a summer storm rips flashing loose at 9 p.m., you’re not leaving a voicemail and hoping for Monday.
Styles & brands we work with
New Roof Installation in Maitland
New Roof Installation in Maitland usually means a full tear-off down to the decking, replacing damaged deck boards, laying new synthetic underlayment, and installing the shingle or tile system you’ve chosen. For older Maitland homes, especially those in the 32751 zip around Lake Lily or along Horatio Avenue, the decking often has rot from decades of slow underlayment failure. Expect $9,000 to $18,000 for a typical single-family home, with roof size and decking replacement being the two biggest cost drivers.
Synthetic Underlayment Over the Old Hot-Mopped Layer
The 1960s homes in Maitland were originally built with hot-mopped asphalt underlayment, which turns brittle and disintegrates after 40 to 50 years. When we install a new roof, we strip everything to bare decking and put down a synthetic underlayment rated for high UV and wind-driven rain. It’s the single most important upgrade for Maitland’s summer thunderstorm pattern.
Architectural Shingles That Fit Maitland’s Review Standards
Maitland’s architectural review process can restrict shingle color and profile in certain neighborhoods. Before we order materials, we confirm what’s permitted for your specific street. We install dimensional shingles from GAF, CertainTeed, and Tamko, and we’ll match the profile that clears review the first time.
Reroofing in Maitland
Reroofing in Maitland can mean two very different jobs. For homes with asphalt shingles, it usually means a full replacement because shingles can’t be installed over a failing system. For tile homes, reroofing often means lifting the original clay or concrete tiles, replacing the underlayment, and re-bedding the same tile. That second scenario is the one Maitland homeowners miss all the time, and it’s the difference between a $7,000 job and a $20,000 tear-off. Expect $7,500 to $16,000 for shingle reroofs and $12,000 to $22,000 for tile re-bed and underlayment work, depending on access and how much decking is compromised.
Tile Re-Bed and Underlayment Replacement
We opened up a Dommerich Hills roof where the 1963 clay tiles looked fine from the street. But the original hot-mopped underlayment beneath had turned to dust, and wind-driven rain was getting through the valleys. We lifted the tile, replaced rotted decking, installed new synthetic underlayment, ice and water shield, drip edge, and fresh flashing, then re-bedded the original tile. The homeowner kept their original roof profile, skipped the architectural review delays of a full replacement, and saved around $9,000 compared to a new tile roof.
When the Decking Fails Before the Shingles Do
On Maitland homes with older dimensional shingles, the visible failure is often granule loss and curling, but the real rot is underneath. Summer thunderstorms with 50 mph gusts drive water under the first course of shingles if the starter strip and underlayment weren’t installed correctly. We replace decking where the wood has softened, then build the system up correctly from the drip edge out.
Trusted Brands We Service in Maitland
We install and repair roofs using materials from GAF, CertainTeed, and Tamko, among others. The brand choice matters less than the installation details, so we stock our local Orlando warehouse with the profiles Maitland homes actually use: dimensional shingles in the colors you see on Dommerich Hills and English Estates, plus underlayment, flashing, and starter strip matched to the climate. That means we order less per job and can start faster when your permit clears. Manufacturer warranties transfer with the home, so if you sell in five years, the next owner inherits the coverage.
See the difference
Before
After
Before
After
Before
AfterCommon Roof Replacement Problems We See in Maitland Homes
- Flashing failure around penetrations, not shingle failure. A homeowner sees worn shingles and approves a full replacement, but the actual leak source is failed flashing around a chimney or vent stack. Wind-driven rain punches through those gaps in summer storms. If we replace the roof without repairing the flashing, the leak comes back.
- Original clay tile still intact, underlayment completely gone. In Dommerich Hills and English Estates, the 1960s hot-mopped underlayment disintegrates while the tile above it still looks fine. We diagnose this before recommending replacement, and often a re-bed job saves the tile and passes review.
- Low-slope sections leaking into soffit and fascia. Many 1960s Maitland homes have low-slope roof sections that weren’t properly underlaid or started. Water backs up under the first course of shingles during heavy rain, dribbles into the soffit, and rots fascia boards. Our replacement includes ice and water shield and correct starter strip on every slope.
- Decking rot that only shows up after tear-off. We can’t see decking condition from above. When the old roof comes off, we photograph what’s underneath and send you the images before any replacement boards go down. If rot is found, you approve the added cost in writing before we touch it. No change order shows up on the final invoice without your signature.
Pricing for Roof Replacement in Maitland, FL
Here’s what you can expect in Maitland’s market right now. A standard full replacement with architectural shingles on a 2,000-square-foot home runs $9,000 to $14,000. Add $2,500 to $5,000 if decking needs extensive replacement. Tile re-bed and underlayment work runs $12,000 to $22,000. A new tile roof starts around $18,000. What moves these numbers: roof pitch, number of valleys, whether you’re in an HOA with review requirements, and how much decking has to come out. We deliver a written line-item quote before any work starts, and the number on that page is the number on the invoice.
Call (448) 218-0800 to schedule a free estimate. We’ll inspect, photograph, and price the work in writing, then you decide.
We Also Serve Cities Near Maitland
Our Roof Replacement crews work throughout the area, including Winter Park, Orlando, Longwood, and Winter Springs. If you live in Maitland or one of the surrounding communities, we’ll schedule the same written estimate and same written guarantee. The process doesn’t change at the city line.
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 Replacement in Maitland
No, not necessarily. If your clay tiles are still solid and the leak is coming through the valleys or around penetrations, the underlayment beneath the tile is likely the failure point, not the tile itself. We can lift the tile, replace the underlayment, repair any rotted decking, and re-bed the original tile. That job typically costs $12,000 to $22,000 versus $18,000 or more for a full tile replacement, and it avoids triggering Maitland’s architectural review for a roof profile change. Call (448) 218-0800 and we’ll inspect the roof before you commit to a tear-off.
Maitland’s review process means certain neighborhoods have restrictions on shingle color, material type, and roof profile. Before we order anything, we confirm what your specific street allows. That extra step prevents you from buying materials that get rejected, which costs time and money. We handle the permit paperwork and make sure your chosen shingle or tile matches the approved profile so the job passes on the first submission.
Summer thunderstorms in Maitland produce wind-driven rain that hits your roof at an angle, unlike the vertical fall of ordinary rain. That angled rain finds gaps in flashing around chimneys, vents, and valley intersections, or pushes under the first course of shingles on low-slope sections. Regular rain doesn’t create the same wind pressure, so the leak stays hidden. We can trace and correct the flashing and underlayment issues before replacing anything cosmetic. Call (448) 218-0800 for an inspection that photographs exactly where water is getting in.
Yes, in most cases. The original clay tile colors used in Dommerich Hills and English Estates are still manufactured, and we can source exact matches from the same Florida suppliers we’ve used for years. If the exact color is discontinued, we can blend reclaimed tile with new to keep the roof visually consistent. Matching tile helps you pass architectural review and preserve the home’s original character.
We use synthetic underlayment rated for high wind and high UV, not felt paper. Synthetic underlayment holds up to Maitland’s summer thunderstorms, resists tearing during installation, and gives us a dry-in layer that lasts through any delays before shingles or tile go on. On low-slope sections and valleys, we add ice and water shield for extra protection against wind-driven rain backing up under the first course.
Written by Dylan Pace, Owner at Crestview Roofing Co Orlando, serving Maitland and the surrounding area.