The Best Roofing Contractor in Pine Island, FL

Trusted Fort Myers Roofing has offered award-winning residential and commercial roof installation, replacement and emergency repair in Pine Island, FL for more than 20 years. Our crews have worked on homes in Matlacha, Bokeelia and St. James City, where salt air off Pine Island Sound and tropical storms take a toll, and each roof we complete is protected by our 5-year written workmanship warranty. We also serve nearby Cape Coral, Sanibel, North Fort Myers, and Punta Gorda.

Why Choose Trusted Fort Myers Roofing for Expert Roofing Services?


20+ Years of Roofing Experience

Serving Southwest Florida since 2001, Trusted Fort Myers Roofing brings decades of experience to residential roofing projects, including roof installation, repair, and replacement.

BBB Accredited, Licensed, and Insured

Trusted Fort Myers Roofing is BBB-accredited, licensed, and insured. We use quality roofing materials and follow proper installation practices.

Free Roofing Estimates

We provide free roofing estimates so you can review the expected costs, material options, and work involved before replacing your roof.

5-Year Workmanship Warranty

We offer a 5-year written workmanship warranty on qualifying roof replacement work, with coverage subject to the warranty's terms and conditions.

Get a Free Roof Estimate

GAF President's Club Award (2019)

Licensed and Insured

Latest Roof Installations in Pine Island, Florida

White TPO Low-Slope Roof Installed at Trotwood Ave, Pine Island, FL

This raised bayfront home is surrounded by tall cabbage palms, and its low-slope roof with a small center gable had been holding water in several spots, leaving stains on the ceiling above the wraparound windows.

Our crew removed the old roofing, added tapered insulation to improve drainage toward the edges and installed a white TPO membrane with heat-welded seams for a single, watertight surface that reflects the strong Gulf sun.

The center gable was reflashed where it rises from the flat section, and we trimmed back the palm fronds brushing the roof edge so they stop scraping the new membrane during windy days.

Turnaround time: 4 days

Final price: $18,700

Light Gray Asphalt Shingle Roof Installed at Rainbow Dr, Pine Island, FL

This raised waterfront home has two connected hip roofs at different heights, with the taller section rising over the main living space and a lower roof covering the side wing and elevated entry deck.

Our crew stripped both roofs to the deck, installed new synthetic underlayment with ice and water shield along every eave and added step flashing where the lower roof meets the taller wall, a common leak point on homes this close to the water.

Light gray architectural shingles rated for high winds finished both levels, and we used corrosion-resistant drip edge and fasteners throughout so the roof stands up to the humid, salty breezes coming off the Gulf.

Turnaround time: 4 days

Final price: $19,400

Silver Ribbed Metal Roof Installed at Thomas St, Pine Island, FL

This stilt home sits high above ground level with a screened gable porch on one end and a long side-gable roof over the main living area, which meant every panel had to be lifted well above the usual working height.

Trusted Fort Myers Roofing used a material lift to safely raise the panels, then installed a synthetic underlayment over the full deck before fastening the new silver ribbed metal panels with neoprene-sealed screws along each purlin line.

The screened porch roof was tied into the main gable with matching ridge and rake trim, and our crew sealed every fastener and edge with coastal-grade materials so the roof stays tight against the salt air and summer storms rolling in off the Gulf.

Turnaround time: 5 days

Final price: $23,500

Trusted Roofing Experts for Pine Island, Florida Homes

Coastal-Rated Metal for Matlacha Cottages

Matlacha’s brightly painted fishing cottages sit just feet from Matlacha Pass, and many were rebuilt after Hurricane Ian’s surge swept through in 2022. Metal roofs are a popular choice here, yet many standard panels carry finish warranties that don’t cover homes this close to salt water.

Our crews install panels with marine-grade coatings backed by coastal exposure warranties, so the paint and metal stay protected right up to the shoreline. Owners also get the color options that suit Matlacha’s classic, colorful look.

High-Temp Underlayment for St. James City Homes

Canal homes across St. James City deal with intense sun and heavy humidity, and the space beneath metal or tile roofing can get extremely hot in summer. Ordinary underlayment softens and breaks down under that heat, which shortens the life of the whole system.

Trusted Fort Myers Roofing uses high-temperature self-adhered underlayment rated up to 250°F beneath metal and tile installs. It stays bonded to the deck through the hottest months and keeps the home sealed if the top layer is ever damaged.

Blocking Wind-Driven Rain in Bokeelia

Homes on the northern end of Bokeelia face open water across Charlotte Harbor, where storms push rain sideways with real force. That wind-driven rain often sneaks under ridge caps and the open ends of metal panels.

We seal panel ends with closed-cell foam closures and Z-flashing at the ridge and eaves, then fasten high-wind ridge caps along every hip. These small details make a big difference when a summer squall rolls in off the harbor.

Replacing Temporary Storm Patches

Plenty of island roofs still carry quick fixes from past storms, like roof cement smeared over cracks or shingles nailed back down without proper sealing. Those patches tend to fail within a season or two and leave hidden damage behind.

During inspections, we remove old patchwork, check the decking underneath and complete permanent repairs with matching materials. When a patched roof has too much underlying damage, owners get an honest recommendation on whether a full replacement makes more sense.

Trusted Fort Myers Roofing

The Best Roofing Contractors in Southwest Florida!

Need a roof repair, replacement, or new installation? We're here to help. Get honest advice, clear pricing, and a free roofing estimate for your home.