Free Estimate 📞 (877) 586-1316 24/7
Professional Roofing hero
โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 296+ reviews

Professional Oldsmar Roofing Contractor

We've replaced 296+ roofs across Florida. GAF Timberline HDZ, Owens Corning Duration, CertainTeed Landmark. Serving Oldsmar and Brandon, Cypress, Fort Myers Beach, Homestead, Lake Worth Beach.

19+
Years
500+
Projects
5
Rating
19+
Years Experience
500+
Projects Completed
5
Star Rating (296+ Reviews)
โœ“
Licensed & Insured

Our Services

Our Roofing Services

Full-service roofing contractor in Oldsmar โ€” from asphalt shingle roof replacement and emergency hail damage repair to metal roofing, flat roof systems, and gutter installation. Every project is installed by manufacturer-certified crews with workmanship warranties.

roof replacement
FREE ESTIMATE

Roof Replacement

We handle the whole replacement from permits to final inspection. Our Oldsmar office pulls the permit, coordinates the dumpster, runs the crew, and schedules the building inspector. You sign the contract and we handle the rest.

roof repair
SAME-DAY

Roof Repair

Step flashing at chimney walls is the number one leak source we see in Oldsmar. Improper step flashing causes roof leaks. It's that simple. We install new step flashing with a chimney cricket for proper water diversion, sealed with Geocel tripolymer sealant. Fix it once, fix it right.

storm damage repair
LICENSED

Storm Damage Repair

Hail, wind, fallen branches. Florida storms do real damage to roofs. We respond within 24 hours, tarp exposed areas to prevent further damage, and start your insurance claim with a detailed inspection report.

new roof installation
TOP RATED

New Roof Installation

Atlas Pinnacle Pristine shingles with Scotchgard algae protection. Ideal for Florida humidity. We also install Tamko Heritage laminated shingles for budget-conscious builds and Malarkey Vista AR with Flexor SBS polymer-modified asphalt for high-wind zones. Your installer should match your material choice to your climate, not just your budget.

metal roofing
GUARANTEED

Metal Roofing

Corrugated metal and R-panel are cost-effective options for barns, detached shops, and covered patios in Oldsmar. We install 29-gauge and 26-gauge corrugated with exposed fasteners using neoprene washer screws. For homes, we recommend 24-gauge standing seam with concealed fasteners. Cleaner look, no exposed fastener maintenance. DaVinci composite shake and slate profiles give you the metal longevity with a traditional Florida aesthetic.

shingle roofing
INSURED

Shingle Roofing

GAF Timberline HDZ architectural shingles with StrikeZone nailing area. The highest-selling shingle in North America. Impact-rated to UL 2218 Class 4 when installed with the full GAF Roof System. Our Oldsmar crews install Timberline in the full system configuration to qualify for Golden Pledge warranty. ASTM D3462 and D7158 Class H certified.

flat roofing
FREE ESTIMATE

Flat Roofing

Flat roof leaks usually happen at penetrations, seams, or flashing details. We locate the source, repair it properly, and coat the surrounding area. If the membrane is shot, we'll recommend replacement. Not a band-aid.

commercial roofing
SAME-DAY

Commercial Roofing

TPO is our most-requested commercial membrane in Florida. Reflective, energy-efficient, and it welds together at the seams for a watertight bond. We install 60-mil and 80-mil systems with 15-20 year manufacturer warranties.

gutter installation
LICENSED

Gutter Installation

Gutters aren't glamorous, but they're protecting your foundation, your fascia, and your landscaping. We install seamless aluminum gutters custom-formed on-site from a roll of coil stock. No seams means no leaks.

roof inspection
TOP RATED

Roof Inspection

Roof inspections after a storm are free. Always. We document hail hits, wind damage, and any pre-existing issues so your insurance claim is accurate and complete.

emergency roof repair
GUARANTEED

Emergency Roof Repair

Fallen tree limb damage requires structural assessment before repair. We check rafter integrity, decking condition, and whether the ceiling joists below were impacted. If structural members are cracked or displaced, you need a framing carpenter before we re-roof. We coordinate with trusted Oldsmar contractors for structural work. Insurance carriers require separate line items for structural vs. roofing repairs. We document both.

skylight installation
INSURED

Skylight Installation

Skylight installation costs $1,200-$3,500 in Oldsmar depending on size, type, and roof pitch. That includes the unit, flashing kit, interior trim, and roof patch-in. We handle everything from the outside in.

Why Choose Oldsmar Roofing & Maintenance?

Trusted by homeowners and businesses across Oldsmar.

Insurance Claims Handled

Storm damage? We work with your insurance company directly. Free inspection, Xactimate documentation, adjuster meeting on-site. We fight for full replacement when your roof qualifies.

GAF Master Elite Contractor

Only 3% of roofers earn this certification. It means we can offer the Golden Pledge warranty: 25-year workmanship plus 50-year materials. Best warranty in roofing, full stop.

5-Star Google Rating

296+ homeowners reviewed us. We don't pay for reviews or offer discounts for them. Those are real people who hired us and took the time to say we did a good job.

Clean Job Sites

We run magnetic nail sweeps three times. Once during tear-off, once after install, once before we leave. Tarps on the ground, dump trailer in the driveway. Your yard looks the same when we're done.

Our Work

Recent Projects

roof replacement project
roof repair project
storm damage repair project
View All Projects โ†’

Simple Process

How It Works

1

Schedule Your Inspection

Our inspector walks the roof looking at shingle condition, flashing integrity, vent function, and signs of moisture underneath. 30-45 minutes for most Oldsmar homes.

2

Transparent Pricing

We price by the roofing square with all materials itemized. You'll see exactly what you're getting. Shingle brand, underlayment type, ventilation specs, flashing details.

3

Roof Goes On

Crew shows up on time with all materials pre-staged. Tarps go down, old roof comes off, new roof goes on. Most Oldsmar homes are done in a single day.

4

Inspection & Cleanup

Before we leave: magnetic nail sweep across the entire yard, driveway, and walkways. Dump trailer hauled off. Gutters cleaned out. Your property looks better than when we arrived.

Verified Reviews

What Our Customers Say

โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 296+ reviews
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"They replaced our gutters along with the roof. Seamless aluminum, everything matches. No more overflow when it rains hard. Wish I'd done this years ago."

M
Mark J.
Oldsmar
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"We were quoted $18,500 for a 32-square replacement with Timberline HDZ. They hit the number exactly. No change orders, no surprise fees. That's rare in this business."

A
Amber O.
Oldsmar
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"Storm chasers were going door to door after the hailstorm. Called Oldsmar Roofing & Maintenance instead because they're actually from Oldsmar. Got a fair deal and a warranty that means something."

S
Stephanie B.
Oldsmar

Service Areas

Areas We Serve

Local roofing coverage across Oldsmar and Brandon, Cypress, Fort Myers Beach, Homestead, Lake Worth Beach. One phone call to (877) 586-1316 and we schedule your free inspection.

Brandon Cypress Fort Myers Beach Homestead Lake Worth Beach Miami Beach Orange City Port Richey Steinhatchee Winter Haven
C

Meet the Owner

Chris Carter

Owner & Lead Contractor

Chris has been serving Oldsmar for over 19 years, building a reputation on honest work, fair pricing, and crews that treat every home like their own. What started as a one-truck operation has grown into a full-service Roofing company โ€” but the values haven't changed.

"We don't cut corners. Every job gets the same attention to detail whether it's a small repair or a complete replacement. That's how you earn 296+ five-star reviews."

License #CCC1358523 19+ Years Experience Locally Owned & Operated

FAQ

Frequently Asked Questions

Most residential roofs in Oldsmar are done in one day. We show up at 7 AM, tear off the old roof, install the new system, and clean up by end of day. Two-story homes, steep pitches, or large roofs might take two days. We never leave a house uncovered overnight.

Absolutely. Our team includes HAAG Certified Inspectors who document storm damage the way insurance adjusters expect. We file the claim, meet the adjuster, handle supplements if the initial estimate is low, and complete the repairs. We work with every major carrier in Florida.

You get two warranties: one from the manufacturer on the materials and one from us on the workmanship. As a GAF Master Elite contractor, we can offer the Golden Pledge. That's 25 years on workmanship plus 50 years on the shingle. Owens Corning and CertainTeed have similar programs. Our own workmanship warranty is in writing and covers installation defects.

Yes. We offer 12-month same-as-cash, low-interest plans up to 144 months, and no-money-down options through GreenSky and Hearth. Credit approval takes about 5 minutes. A new roof is a major expense. Financing lets you get it done now without draining your savings.

Common signs: curling or cracking shingles, missing shingles after wind events, granule loss (look in your gutters), daylight visible through the attic, sagging roof deck, and age. Most asphalt roofs last 20-30 years in Florida. If you see any of these, call (877) 586-1316 for a free inspection. We'll be honest about whether you need a replacement or just a repair.

Have more questions? Call (877) 586-1316

SAME-DAY APPOINTMENTS AVAILABLE

Get Your Free Roof Inspection Today

24/7 emergency service. Most appointments available within 48 hours.

📞 Call (877) 586-1316

โ˜…โ˜…โ˜…โ˜…โ˜… 5/5 from 296+ Reviews  ยท  Licensed  ยท  Insured