Free in-home measure and quote - PGT, CGI and CWS impact lines compared on your actual openings, style by style
Before
After
Before
After
Before
AfterTrusted Roof Replacement & Installation for Naples Homeowners
A full Roof Replacement & Installation in Naples typically costs between $15,000 and $45,000 depending on square footage, roofing material, and whether you’re removing one layer or two. Most homes in Collier County fall in the $18,000 to $28,000 range for architectural shingle replacement. Asphalt shingle roofs in Southwest Florida last 15 to 22 years before the salt air and afternoon thunderstorms catch up with them, and once you’re seeing granule loss in your gutters or curling at the eaves, you’re on borrowed time. Ed Winslow has been replacing roofs across Naples since 2011, and we answer the phone live, 24/7, at (239) 899-6411 when you’re ready to talk numbers.
What our neighbors in home service areas appreciate most is that we treat a roof the same way we treat a window or a door: as a long-term investment that has to survive hurricane season, not just the next rain. We’re locally owned and owner-operated with a published address and license number, and every roof we install carries the 36500-Day Done Right Promise. If it’s not done right, we make it right. Period.
What Our Roof Replacement & Installation Service Includes
Complete Tear-Off and Decking Inspection
Before any new roof goes on, the old one comes off, every layer of it. Florida building code allows for a second layer in some cases, but we don’t recommend it in Naples; the extra weight shortens the life of the new shingles and hides decking damage that’s already started. Once we’re down to bare plywood or OSB, we inspect every sheet for rot, delamination, and water staining. If decking needs replacement, we show you the damage before we charge you for the repair – no photos from a phone screen, no “trust us” line items. We stand on the roof with you or your representative and point at the problem.
Underlayment and Waterproofing System
Naples roofs fail from the inside out far more often than from the top down. The underlayment is what keeps water out of your attic during a driving rain that gets under the shingles, and we install synthetic underlayment as standard on every replacement. Synthetic underlayment costs more than felt, but it grips better underfoot during installation, lays flatter in Florida heat, and doesn’t wrinkle or absorb moisture the way 15-pound felt does. In valleys and around penetrations we add ice and water shield, which in our market acts as a secondary barrier against wind-driven rain, not just ice dams.
Shingle, Tile, and Metal Roof Installation
Most Naples homeowners choose architectural asphalt shingles for cost and longevity, but plenty of homes in Port Royal, Pelican Bay, and Grey Oaks call for tile, and a growing number of new builds in Estero and Ave Maria are going standing seam metal. We also offer Bonita Springs Roof Replacement & Installation for homes in that area. We install all three. For shingle roofs we use manufacturer-certified nailing patterns and starter strips at every eave and rake, which is where wind uplift starts. Tile roofs get new underlayment and battens, not just re-set tile, because tile work is only as good as what’s under it. Metal roofing is fastened with concealed clips where possible, which gives the roof a clean look and eliminates thousands of exposed fasteners that back out over time.
Flashing and Ventilation
Flashing failures are the number one source of roof leaks we find in Naples, especially around chimneys, skylights, and where a roof meets a wall. We replace all flashing on every roof job, not just the pieces that look bad. Step flashing, counter flashing, pipe boots, and vent collars all get replaced or re-sealed. Ventilation gets the same attention: a roof in Southwest Florida needs balanced intake and exhaust to keep attic temperatures down, which extends shingle life and lowers cooling bills. If your current roof doesn’t have enough intake venting, we’ll tell you before we start, not after the roof is on.
Cleanup and Final Inspection
We run a magnetic sweeper over the property twice, once after tear-off and once after installation, and we don’t leave until the nails are out of the driveway and the flower beds. The crew does a full walkthrough with you at the end of the job, shows you the finished roof from the ground, and hands you the manufacturer warranty paperwork plus our 36500-Day Done Right Promise in writing. If there’s a problem with any part of the installation, you call us and a live person at (239) 899-6411 answers. We come back.
What happens when you call
- 1
A real person answersNo phone trees - you reach a local pro.
- 2
You get an upfront price rangeHonest numbers before anyone is dispatched.
- 3
A background-checked tech heads outLicensed & insured, dispatched right away.
- 4
You approve before work beginsNothing starts until you say go.
Brands We Service for Roof Replacement & Installation
We’re an authorized installer for eight premium product lines, and on the roofing side that includes Mr-Glass skylights and sun tunnels. We’ve specified and installed Mr-Glass glass in dozens of Naples homes, and their low-profile aluminum frames and integrated flashing systems handle Florida’s wind-driven rain better than older designs. When we replace a roof that has existing skylights, we service those units at the same time, re-flashing them to match the new underlayment and shingle profile, not just leaving the old flashing in place and hoping it holds.
We also carry and install Therma-Tru entry doors as part of exterior packages where a roofline change or new porch addition requires a new front door, and PGT impact windows and doors commonly go hand-in-hand with roof work in Naples. If you’re re-roofing because of storm damage, odds are good we’re also quoting you impact windows the same week. Whether you have Mr-Glass, PGT, or any other make on the roof or around the house, we can help. We service what we sell, and we install what we sell.
Signs You Need Roof Replacement & Installation Right Now
- Granule loss in the gutters or downspout splash blocks. Asphalt shingles shed granules as they age, and once you see a measurable buildup, the shingles are losing UV protection and burning through their service life. Granule loss accelerates in Naples because the summer sun sits directly overhead for months at a time, cooking the asphalt binder underneath.
- Curling, cupping, or lifting shingle edges. When shingles start to curl at the corners, they’re no longer shedding water efficiently, and the exposed edges become wind lift points during a tropical storm. Curling shingles usually mean the roof has 1 to 3 years left at best, and a windstorm may take that to zero in one afternoon.
- Water stains on ceilings or walls after a heavy rain. Interior water staining is a symptom of a breached roofing system, not just a single torn shingle. By the time you see it on the drywall, the leak has already traveled through insulation and started to rot the decking, and the visible stain is only half the story.
- Daylight visible through the attic roof decking. If you can see daylight from inside your attic, water can get in through the same gaps. This is one of the easiest signs to check yourself from the attic access, and it’s one of the most urgent; the gaps are direct entry points for wind-driven rain during a Naples summer storm.
- Roof age over 15 years on an asphalt shingle system. Architectural shingle roofs in Southwest Florida typically last 15 to 22 years, and tile underlayment often needs replacement around year 20 even if the tile itself looks fine. If your roof is nearing or past that age and you’re planning to stay in the home for another decade, replacing the roof now is cheaper than replacing it after a failure.
Our Roof Replacement & Installation Process - Step by Step
- 1
Free estimate and roof assessment. We come to your home in Naples, walk the roof, measure the square footage, and write you a line-item estimate the same day. The estimate includes tear-off, decking replacement contingency, underlayment, material, flashing, ventilation, permits, and cleanup, so there are no change orders on the back end unless we find decking damage we couldn’t see from the surface, and we’ll show you before we add the line.
- 2
Material selection and scheduling. We’ll bring shingle, tile, and metal samples to your home and talk through price, lifespan, and warranty differences in plain language, not brochurespeak. Once you choose, we pull the permit and get your job on the calendar with a start date and a daily work window, not a vague “sometime next month.”
- 3
Tear-off and decking inspection. The crew strips the old roof to the decking, including all felt and underlayment, and we inspect every sheet before anything new goes down. If we find rot or delamination, we stop, bring you up to look at it, and get your signoff before we replace the decking and continue.
- 4
Installation with manufacturer-specified methods. We install the underlayment, flashing, and roofing material exactly to manufacturer spec, because that’s what keeps the material warranty valid and what keeps the roof on in a storm. The crew is uniformed, background-checked, and works the same job from start to finish, so you know who’s on your roof and who’s accountable.
- 5
Final walkthrough and cleanup. We walk the property with you, confirm the roof is installed to spec, hand you the warranty packet and the 36500-Day Done Right Promise, and run the magnet sweep twice. If you find anything after we leave that isn’t right, you call (239) 899-6411 and Ed Winslow makes it right. That’s the promise.
How Much Does Roof Replacement & Installation Cost in Naples?
A typical architectural shingle roof replacement in Naples runs $18,000 to $28,000 for a single-story home up to about 2,200 square feet of roof area. We also provide our Roof Replacement & Installation in Marco Island with similar pricing structures. A tile roof replacement, which includes all new underlayment, usually lands between $30,000 and $45,000 and up depending on tile profile and roof pitch. Metal standing seam roofing in Naples typically runs $28,000 to $55,000 depending on panel gauge, seam profile, and complexity. Smaller homes in East Naples or Golden Gate with simple rooflines fall toward the bottom of those ranges; two-story homes in Port Royal or Pelican Bay with steep pitches, multiple valleys, and tile-to-shingle transitions fall at the top.
What moves the price most is roof size, material choice, number of valleys and penetrations, decking condition, and the pitch of the roof. Steeper roofs cost more because the installers work on harnesses and the material waste factor goes up. Decking replacement, when needed, typically adds $65 to $90 per sheet in Naples, and the number of sheets depends on what we find after tear-off. The best way to avoid overpaying is to get a line-item estimate that names every component, has no hidden allowances, and includes the permit. Our free estimate from (239) 899-6411 gives you exactly that, with no trip charge inside Collier County and no obligation to say yes.
Roof Replacement & Installation Near Naples - Our Service Area
We install roofs across all of Naples, including North Naples, East Naples, Naples Park, Golden Gate, Lely Resort, and the Vineyards, and we also serve the surrounding communities of Marco Island, Bonita Springs, Estero, Immokalee, and Ave Maria. For full-scope roof replacement work, we typically have a crew on-site within two to four weeks of the permit being issued, and our Roof Replacement & Installation in Naples team handles projects across the metro. We’re the one down the road.
Serving Naples, FL - Our Local Coverage Area
We’re based in the Naples area and know this community well. Use the map below to see our service coverage - if you’re nearby, we can almost certainly help.
Frequently Asked Questions - Roof Replacement & Installation in Naples
Roof replacement is the complete removal of your existing roofing material and underlayment down to the decking, followed by installation of a new roof system, including new underlayment, flashing, and shingles, tile, or metal. It’s different from a re-roof, which layers new shingles over old ones and is not something we recommend in Naples because it hides decking damage and shortens the life of the new roof. Call (239) 899-6411 for a free estimate and we’ll tell you which approach makes sense for your home.
Most asphalt shingle roof replacements in Naples take 1 to 3 days on site, depending on roof size, pitch, and how much decking needs to be replaced. Tile roofs take longer, typically 5 to 10 days, because each tile is set individually. Metal roofs usually take 3 to 7 days. Then the permit inspection lands within a few business days, and we’re done. Call (239) 899-6411 and we’ll give you a realistic timeline for your specific roof.
A roof replacement in Naples typically runs $18,000 to $28,000 for architectural shingles, $30,000 to $45,000 for tile, and $28,000 to $55,000 for metal, depending on roof size, pitch, and decking condition. Our estimates are line-item and fixed: you see the exact price for tear-off, decking contingency, underlayment, material, flashing, ventilation, permit, and cleanup before you sign. Call (239) 899-6411 for a free, no-obligation estimate with no trip charge in Collier County.
Yes. We’re an authorized installer for PGT impact windows and doors and Mr-Glass skylights among eight premium brands, and we service what we install. When we re-roof a house that has Mr-Glass skylights, we re-flash them to the new underlayment at the same time. If your project needs PGT impact windows alongside the roof, we can quote both in the same visit. Call (239) 899-6411 to schedule a combined estimate.
Yes, we answer the phone live 24/7 at (239) 899-6411, and we respond to roof leaks and storm damage in Naples with tarp service and emergency repair when needed. A live person answers, not a voicemail loop and not a call center. If your ceiling is actively leaking, call us now and we will get someone to you.
Every roof we install includes the manufacturer’s material warranty plus our 36500-Day Done Right Promise, which means if it’s not done right, Ed Winslow makes it right. Period. The material warranty depends on the product you choose, and we’ll give you the paperwork at the final walkthrough. Call (239) 899-6411 and we’ll walk through warranty terms for each option before you decide.
Move vehicles out of the driveway and away from the roof line, take down anything hanging on interior walls near the roof, and secure loose items in the attic, because the house will vibrate during tear-off and installation. Clear the area around downspouts so material can be removed safely. We’ll go over the rest with you at scheduling. Call (239) 899-6411 and we’ll send you a prep checklist with your estimate.
Schedule Your Roof Replacement & Installation Service in Naples Today
We’re published locally, we answer the phone at 2 a.m., and Ed’s name is on the door and on every roof we install. Call (239) 899-6411 for a free, no-obligation estimate on your Naples roof replacement, and we’ll give you a line-item price that won’t change once work starts. Upfront pricing. No surprises on the invoice. Free second opinions on any written estimate. We’re the one down the road.
Written by Ed Winslow, Owner at Winslow Windows & Doors, serving Naples since 2011.
Six Reasons Homeowners Choose Winslow Windows & Doors
Impact systems engineered to design pressures up to +/-100, matched to your wind zone - your openings hold when the storm arrives.
Low-E insulated impact glass from our manufacturer lines commonly cuts monthly cooling bills 20-30%.
Laminated impact glass shuts out up to 40% of outside noise - traffic, neighbors, weather.
Monitoring services run $30-90 a month. Laminated impact glass resists forced entry around the clock, with no subscription.
Florida homeowners average around 25% savings on the windstorm portion of their policy after protecting every opening - some homes qualify for more.
A full impact package upgrades curb appeal, buyer confidence and appraised value in one project.