Storm Damage? Free Roof Inspection in Winter Haven — Call Now
Same-Day Appointments Available · 24/7 Emergency Service
Owens Corning Preferred Contractor. 19+ years experience. Free roof inspections in Winter Haven.
Call (877) 586-1316Emergency tarping available · Call 24/7
Oldsmar Roofing & Maintenance is a licensed and insured roofing contractor serving Winter Haven and all surrounding communities. Our Oldsmar-based crews handle residential and commercial roofing with the same attention to detail on every job.
Our Services in Winter Haven
What Winter Haven Customers Say
"They replaced all our gutters along with the roof. Seamless aluminum, properly pitched. Water actually drains into the downspouts now instead of overflowing at every seam. Night and day difference."
"What sold me was the inspection report. Detailed photos of every damaged area, measurements, written explanation of what needed repair versus replacement. No other company gave us anything close to that level of documentation."
"Hail punched through half our shingles last spring. Oldsmar Roofing & Maintenance handled the entire insurance claim — met the adjuster, filed the supplement, and we paid nothing out of pocket besides the deductible."
Why Winter Haven Residents Choose Oldsmar Roofing & Maintenance
Free Inspections & Honest Estimates
We don't charge for inspections and we don't pad estimates. If your Winter Haven roof needs a repair, we'll tell you. If it needs a replacement, we'll explain exactly why. No high-pressure sales, no scare tactics.
5/5 Stars | 296+ Reviews
Our reputation is built one roof at a time. 296+ homeowners across Oldsmar, Winter Haven, and surrounding areas have rated us 5/5 stars. We earn every review. No incentives, no discounts for feedback.
Manufacturer-Certified Installation
We hold certifications from GAF, Owens Corning, and CertainTeed. That means the manufacturers have trained and vetted our crews and will back our installations with their strongest warranties. Your Winter Haven roof gets factory-level quality control.
GAF Master Elite Certified
Only 2% of roofing contractors in the country hold GAF Master Elite certification. That gives Winter Haven homeowners access to the Golden Pledge warranty: 25 years on workmanship, 50 years on materials. It's the strongest warranty in the industry.
About Our Winter Haven Roofing Services
Our Winter Haven customers get the same crew quality, warranty coverage, and pricing as our Oldsmar clients. No travel surcharges, no subcontracted labor, no shortcuts. We use our own trained crews on every job.
We serve Winter Haven and all nearby communities without charging travel fees. Call (877) 586-1316 to set up your free inspection. Most Winter Haven inspections happen within 24 to 48 hours of the call.
We treat Winter Haven the same as our home market in Oldsmar. Your Winter Haven project gets the same crew, the same materials, and the same warranties as any Oldsmar job.