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 Longwood
A full roof replacement in Longwood typically runs $11,500 to $19,800 for a standard asphalt shingle roof on a 1,800 to 2,400 square foot home, with architectural shingles adding $2,000 to $4,500 over three-tab. Most Longwood replacements take two to four days once materials are staged and the permit is posted. If you’re searching Longwood for a roofer who gives you a written price before any work starts and sends photo proof when the job is done, you’re in the right place. Call (448) 218-0800 and we’ll schedule a free inspection at your Longwood home.
Longwood homeowners inherit something most Central Florida roofers don’t talk about until the tear-off begins: original wood plank decking that no longer meets current nail-holding code. We’ll get into that below, because it’s the single biggest reason a Longwood replacement quote moves. But first, understand this: our written price covers what the inspector will require, not just what you can see from the street. That’s the difference between a roofer who quotes low and bills high, and Crestview, where the number on the page is the number on the invoice.
Key Takeaways for Longwood Homeowners
- Full roof replacement in Longwood: $11,500 to $19,800 for asphalt shingles on a typical home.
- Pre-1980 Longwood homes often have plank decking that fails current code and must be redecked. We catch this at inspection, before the permit is pulled.
- Every Crestview job includes a written price before work starts, before-and-after photos, and a live trackable arrival time.
- Our 365-Day Done Right Promise covers every repair for a full year, in writing, included at no extra cost.
- Call (448) 218-0800 for a free inspection and line-item quote in Longwood.
Styles & brands we work with






Why Crestview Roofing Co Orlando Is Longwood’s Preferred Roof Replacement Company
Longwood is not a one-size-fits-all roofing market. Drive through the historic district and you’ll see 1920s Craftsman bungalows with original cedar shakes. Ten minutes north, you’re in mid-century ranch neighborhoods like Sanlando Springs, where 1960s three-tab shingles sit on plank decking that predates modern wind codes. Then there are the newer subdivisions west of I-4, built to post-Andrew standards. A roofer who treats all three the same is going to miss something. We don’t.
Crestview Roofing Co Orlando, led by Dylan Pace, has been replacing roofs in Longwood long enough to know what the building department flags, what the inspector measures, and what older framing is actually capable of holding. We work with GAF, CertainTeed, and Owens Corning materials, but more importantly, we write the real scope into the contract before the permit is ever pulled. Our Longwood customers get a written price, a live arrival time they can track like a rideshare, and photo documentation before and after. That’s The Relay Standard, and it’s how we run every job.
Scheduling for Longwood is coordinated from our South Florida dispatch office, but the crews who show up at your door are local, background-checked, and uniformed. You’ll know exactly who is arriving before they pull into your driveway. And when you call with a question at 9 p.m., a live person answers. No voicemail loops, no Monday callbacks.
Flat Roof Replacement in Longwood
Flat Roof Replacement in Longwood is a different animal from pitched roof work, and it shows up more often than you’d think: carports, patio covers, the low-slope sections on split-levels, and entire mid-century modern builds where the roof line runs nearly flat. A flat roof replacement in Longwood usually runs $8,500 to $14,000 for a modest single-story section, with the final number driven by the membrane system you choose and whether the existing substrate has water damage. Longwood’s daily summer thunderstorms are brutal on flat roofs. Water pools in the low spots, finds its way through worn seams, and by the time you see a stain on the ceiling, the decking underneath is already spongy.
Membrane Systems We Install
We install TPO, modified bitumen, and PVC membrane systems, each suited to different Longwood conditions. TPO reflects heat well, which matters on a flat roof that bakes in the Florida sun from noon to six. Modified bitumen handles foot traffic better, which is practical if your flat section doubles as a balcony or service area. If you have a patio cover attached to a 1950s home, the original built-up roof is probably at the end of its life. We’ll tell you honestly what replacement makes sense, and what it will cost before any tear-off happens.
When to Replace vs. Patch
If your flat roof in Longwood is under 10 years old and leaking at a single seam, a repair may buy you a few more years. We’ll say so. But if the membrane has multiple patches, the seams are lifting, or the decking has softened from repeated ponding after storms, you’re at the point where patching is just paying for the same leak twice. We’ll show you photos of what we find, because you deserve to see the same evidence we do.
Roof Replacement Contractor in Longwood
Hiring a Roof Replacement Contractor in Longwood means choosing someone who will open up your roof and not flinch at what’s underneath. Longwood homes built before 1980 frequently have original 1×6 wood plank decking. Current Florida building code sets minimum nail-holding standards that dried, split plank decking simply can’t meet. So when the tear-off happens, the inspector often requires complete redecking with OSB or plywood. A contractor who doesn’t flag this until after the roof is open will hand you a change order for $4,000 to $7,000. We write it into the contract before the permit is pulled. That’s the visibility we sell, and it’s the reason Longwood homeowners call us first.
Dylan Pace and the Longwood Team
Dylan Pace runs our Longwood operations with a simple rule: every surprise should be discovered before the work starts, not after. Our inspection process is methodical. We look at the decking from the attic, we check the nailing pattern on the existing shingles, we test the nail-holding on exposed plank sections, and we photograph everything. Then we write your quote line by line. If redecking is required, you’ll see it as a specific dollar line item, not a vague “contingency” buried in fine print.
How We Handle Code-Triggered Redecking
Here’s what happens in practice. Our crew opened up a 1962 ranch in the Sanlando Springs neighborhood and found the original 1×6 plank decking had dried and split around the nails. We wrote a redecking allowance into the contract before the permit was pulled, then replaced the entire deck with 7/16 OSB, new drip edge, and a GAF Tiger Paw underlayment so the architectural shingles could meet their 130 mph wind rating. The inspector signed off without a single change order. That’s the standard on every Longwood replacement we do.
Trusted Brands We Service in Longwood
We install and repair roofs using shingles and systems from GAF, CertainTeed, and Tamko. For Longwood homeowners, this matters in a few specific ways. GAF’s architectural shingle line is our go-to for older ranches where homeowners want the look of a dimensional shingle with a 130 mph wind rating. CertainTeed’s Landmark Pro is popular in Longwood’s newer subdivisions for its algae resistance, which matters in a climate where humidity and tree canopy feed streaking on north-facing slopes. Tamko’s Heritage shingles are a solid mid-range choice when budget is the first consideration and the home is a standard gable. Whatever brand fits your Longwood home and budget, we’ll price it before you sign, and we’ll warranty it through our 365-Day Done Right Promise.
See the difference
Before
After
Before
After
Before
AfterCommon Roof Replacement Problems We See in Longwood Homes
- Code-triggered redecking: Pre-1980 plank decking in Longwood often can’t meet current nail-holding requirements, so the inspector requires full redecking. We catch this during inspection and price it in the contract, not as a surprise change order.
- Hail and wind claim denials: Insurance adjusters have gotten smarter about checking decking condition. If the old planks couldn’t hold nails, the shingles were never properly attached, and the claim gets denied. We document decking condition before any claim is filed.
- Missing ice and water shield at valleys and penetrations: Longwood’s summer storms exploit any gap around chimneys, vents, and valley intersections. Older homes where original flashing was reused are the most vulnerable. We replace flashing and install ice and water shield as standard on every replacement.
- Algae and granule loss on north-facing slopes: Longwood’s humidity keeps north slopes damp long after the south side dries. Organic shingle mats break down faster, and granules wash away years before the shingle’s rated life. We recommend algae-resistant shingles for any Longwood roof with heavy tree cover.
Pricing for Roof Replacement in Longwood, FL
Let’s talk real numbers for Longwood. A standard three-tab shingle replacement on a 1,800 square foot ranch runs $11,500 to $14,000. Architectural shingles on the same home run $14,500 to $17,800, and that’s the upgrade most Longwood homeowners choose for the better wind rating and the dimensional look. Add full redecking, which is likely on pre-1980 homes, and you’re at $18,000 to $19,800. Flat roof sections run $8,500 to $14,000 depending on the membrane. Tile and metal are present in Longwood but less common; if that’s your roof, call us for a specific quote because those numbers vary too widely to give a useful range. Every quote we write is line-item, fixed, and delivered before any work starts. Call (448) 218-0800 to schedule your free estimate in Longwood.
We Also Serve Cities Near Longwood
Crestview Roofing Co Orlando handles full Roof Replacement across the I-4 corridor. Our Roof Replacement in Longwood clients often ask if we cover neighboring cities, and the answer is yes. We regularly work in Winter Springs, Maitland, Winter Park, and Apopka, with the same written pricing, photo documentation, and 365-Day Done Right Promise on every job.
Serving Longwood, FL - Our Local Coverage Area
We’re based in the Longwood 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 Longwood
Yes, most likely, if your home still has its original 1×6 plank decking. Current Florida code sets minimum nail-holding standards, and dried, split planks from the 1950s and 60s rarely meet them. The inspector will flag it during the tear-off inspection. That’s why we check your decking from the attic during our initial visit, so you see the redecking line item in your contract before the permit is ever pulled. Call (448) 218-0800 and we’ll inspect yours at no charge.
You need it, and here’s why. Longwood’s afternoon thunderstorms dump water fast, and the wind drives it sideways into valleys, chimneys, and vent pipes. Ice and water shield is a self-sealing membrane that prevents water from working its way under shingles at those vulnerable intersections. Northern climates use it for ice dams; Longwood uses it for monsoon-style rain and wind-driven water. We install it as standard on every replacement, not as an add-on.
A “square” is 100 square feet. Roofers quote by the square because shingles are packaged and priced that way. A 2,000 square foot home in Longwood might have a 2,400 square foot roof surface, or 24 squares, because of pitch and overhangs. When you see a quote that says “24 squares at $550,” that’s $13,200. We quote line items in plain English and include the square count so you can verify the math yourself.
Because the wind rating is only valid if the shingle is fastened exactly as the manufacturer tested it. The GAF and CertainTeed warranties we install require six nails per shingle in a specific placement, not the four nails that many crews use to save time and material. If the nailing pattern is wrong, the 130 mph rating means nothing, and your insurance company can deny a future wind claim on that basis. We nail per manufacturer spec on every Longwood roof, and we photograph the installation as proof.
Yes, within reasonable limits. We can’t source original 1920s cedar shake, but we can match the profile and color with modern architectural shingles or synthetic shake products that pass current wind code. The bigger issue is structural: original Craftsman framing often needs supplemental fastening to meet modern uplift requirements. We’ll show you what’s possible, what it costs, and what the historic district review board, if applicable, will need to see. Call (448) 218-0800 and we’ll bring samples to your bungalow.
Get Your Free Longwood Roof Replacement Estimate
You’ve just read more about Longwood roof replacement than most contractors will tell you in a year of callbacks. That’s intentional. The more you know about your decking, your nailing pattern, and what the inspector will flag, the better the decision you’ll make. And the more likely you’ll compare our written quote to everyone else’s vague proposal and notice the difference. Call (448) 218-0800 to schedule your free inspection. We’ll show up on time, walk your roof, photograph what we find, and hand you a line-item price before we leave. No four-hour windows, no quotes that balloon at the door. That’s The Relay Standard, and it’s how we do every roof in Longwood.
Written by Dylan Pace, Owner at Crestview Roofing Co Orlando, serving Longwood, FL.