The Best Roofing Contractor in Cypress Lake, FL

Trusted Fort Myers Roofing has offered award-winning residential and commercial roof installation, replacement, and emergency repair in Cypress Lake, FL for more than 20 years. Our crews have worked on established homes near Cypress Lake Country Club and along Summerlin Road, where aging roofs and summer storms take a toll, and each roof we complete is protected by our 5-year written workmanship warranty. We also serve nearby Iona, Villas, Fort Myers Beach, and Sanibel.



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 Cypress Lake, Florida

Light Gray Asphalt Shingle Roof Installed at Marigold Ct, Cypress Lake, FL

This duplex villa shares one continuous roofline between two units, and the aging shingles had started lifting along the front gable after several rainy seasons.

Trusted Fort Myers Roofing coordinated with both owners, tore off the old roof down to the deck and replaced damaged plywood above the screened Florida room before installing new synthetic underlayment.

Light gray architectural shingles went on next to reflect more of the afternoon heat, with new drip edge and matching ridge caps tying both sides together into one seamless, uniform roof.

Turnaround time: 3 days

Final price: $16,400

Charcoal Asphalt Shingle Roof Installed at Medinah Dr, Cypress Lake, FL

This single-story ranch home still had its original shingles, which had curled along the edges and were shedding granules into the gutters after years of Florida sun.

Our crews stripped the low-pitch hip roof down to the deck, replaced a few soft plywood sections near the garage and installed a self-adhered underlayment before laying new charcoal architectural shingles.

Fresh drip edge and ridge venting finished the job, giving the home a clean, sharp look that pairs well with its white trim and peach exterior.

Turnaround time: 2 days

Final price: $11,800

Wood Asphalt Shingle Roof Installed at Bunker Way, Cypress Lake, FL

Large oak and pine trees shade this single-story stucco home, and years of falling debris had worn down the old shingles and clogged the valleys above the front entry.

Our crews removed the roof down to the deck, replaced rotted fascia boards along the gable end and installed a self-adhered underlayment across the full roof surface.

New weathered wood architectural shingles were finished with dark bronze drip edge and an open metal valley, so leaves and needles now wash off instead of piling up where the roof planes meet.

Turnaround time: 2 days

Final Price: $12,600

Trusted Roofing Experts for Cypress Lake, Florida Homes

Re-Decking Older Ranch Homes

Many Cypress Lake homes date back to the 1960s and 1970s, when roofs were often built over 1x6 board decking instead of plywood sheathing. Those gaps between boards no longer give modern shingles the solid nailing base that current codes expect.

During replacement, our crews install new 5/8-inch plywood over the existing boards or replace damaged sections outright. The fresh deck holds fasteners tighter and gives the new roof a much stronger shot at lasting its full rated life.

Insurance-Ready Roof Replacements

Older shingle roofs in established neighborhoods are often flagged during 4-point and wind mitigation inspections, which can make coverage harder to renew. Owners nearing the 15-year mark tend to feel that pressure first.

Trusted Fort Myers Roofing provides detailed documentation on every finished roof, including permit records, product approval numbers and photos of the nailing pattern and secondary water barrier. That paperwork makes the next insurance inspection far less stressful.

Flat Roofs Over Lanais and Florida Rooms

Florida room additions and enclosed lanais are common on homes around Cypress Lake Drive, and most sit under low-slope roofs that drain slowly. Ponding water on old rolled roofing eventually works its way through seams and into the ceiling below.

We replace these sections with modified bitumen or TPO membrane systems, adding tapered insulation where needed to push water toward the gutters. Clean tie-ins where the flat roof meets the main roof keep that transition from becoming the next leak.

Working Around Pool Cages and Screen Enclosures

Many backyards in Cypress Lake have aluminum pool enclosures fastened directly to the home’s fascia. Those attachment points can loosen over time and let water into the roof edge, especially after strong storms.

Before installing a new roof, we check every cage connection and reseal or reinforce it as needed. Drip edge and gutters are then fitted carefully around the enclosure so the screen frame and the new roof work together instead of against each other.

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.