New Skylights Installed Right — Guaranteed Leak-Free
Bring Natural Light In — Without the Leaks
A skylight transforms a dark room. It cuts daytime lighting costs, improves ventilation, and makes any space feel bigger and more inviting. But in Florida, a skylight is also a roof penetration — and if it's not installed with proper flashing, waterproofing, and drainage integration, it becomes a leak waiting to happen. Wilson Roofing installs skylights the right way: fully flashed into your existing roofing system, sealed for Florida's storm-driven rain, and backed by our workmanship guarantee.
Whether you're adding a skylight to an existing roof or including one in a new roof installation, our crew ensures the opening is properly framed, flashed with step and counter-flashing, and sealed to handle everything Florida's climate throws at it. We also handle skylight additions during full roof replacements — the most cost-effective time to add one.
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A Roof Cut Done Right Stays Dry for Decades
Adding a skylight to an existing roof means cutting an opening in a system that was designed to keep water out. It's not a DIY job and it's not a job for a general handyman. Wilson Roofing handles the full process: locating the optimal position based on rafter spacing and interior layout, cutting and framing the curb, installing ice-and-water shield membrane, integrating step flashing with the existing shingles or metal panels, mounting and sealing the skylight unit, and verifying drainage paths. We also handle any interior framing and drywall finishing needed to complete the light shaft from roof to ceiling. The end result is a skylight that looks like it was always part of the house.
"5 Stars – Highly Recommend Wilson Roofing and Renovation! I recently had the pleasure of working with Wilson Roofing and Renovation, and I couldn't be happier with the results."
See our profileAdd a Skylight While We're Already Up There
If you're planning a roof replacement or a new metal roof install, adding a skylight at the same time is significantly more cost-effective than doing it as a standalone project. The roof is already being stripped and rebuilt, so the framing, flashing, and waterproofing are integrated into the new system from day one — no cutting into finished work, no patching existing shingles around a new opening. It's the cleanest install possible and saves you the labor cost of a second service call down the road. Many of our roof replacement customers add one or two skylights once they see how affordable it is during the same project.
"They contacted me within a day of inquiry, Randy came and provided an accurate estimate with a fair price. They ordered the supplies and had them delivered promptly."
See our profileSkylights Installed by Roofing Professionals
A skylight is a roof penetration first and a window second. That's why a licensed roofer — not a window installer — is the right contractor for the job.
- Full step-flashing and counter-flashing integration
- Ice-and-water shield membrane at every opening
- Verified drainage paths before the skylight goes in
- Licensed, insured, and locally operated
- 100+ verified five-star Google reviews
Skylight Installation FAQ
In most cases, yes. Skylights can be installed on shingle roofs, metal roofs, and flat or low-slope roofs (with the appropriate curb-mounted unit). The installation method and flashing approach varies by roof type, which is why having a licensed roofer handle the job matters. We'll assess your roof and recommend the right skylight type during the estimate.
Not when it's installed properly. Skylight leaks are almost always caused by improper flashing or skipped waterproofing steps during installation. Wilson Roofing uses a complete flashing system — step flashing, counter flashing, ice-and-water shield — integrated directly into your roofing material. We verify drainage paths and test the installation before we leave.
A standalone skylight installation typically takes one to two days, depending on the roof type and whether interior framing or drywall work is needed for the light shaft. If the skylight is being added during a roof replacement, it's folded into the overall project timeline with no additional days required.
We install major skylight brands including VELUX and other industry-standard manufacturers. Fixed, vented, and solar-powered options are all available. We'll recommend the right unit based on your goals — whether that's purely natural light, added ventilation, or both — and walk you through the options during the estimate.
Significantly. During a roof replacement, the roofing material is already being removed and rebuilt, so integrating a new skylight opening is far less labor-intensive than cutting into a finished roof. You save on labor, materials, and the patching work that a standalone install requires. If a new roof is in your plans, it's the ideal time to add skylights.
This company is awesome. The crews were very professional, always had one English speaking supervisor on the job. Worked extremely hard and did an exceptional job protecting plants.
Related Roofing Services
Skylight Repair
Existing skylight leaking? We diagnose the cause and fix it permanently — flashing, seals, or full unit replacement.
Learn MoreMetal Roofs
Adding a skylight to a new metal roof? Standing seam metal at shingle prices — the perfect time to include skylights in the build.
Learn MoreAttic & Roof Ventilation
Skylights and ventilation work together. Proper attic airflow keeps your home cooler and extends the life of your roof.
Learn MoreWhy Homeowners Trust Wilson Roofing
Licensed & Insured
Fully licensed Florida roofing contractor with workers' comp and liability coverage on every project.
100+ Five-Star Reviews
Perfect 5.0 rating from over one hundred verified Google reviews. Our reputation is earned, not bought.
Locally Operated
Based in Tampa and Sarasota. Local roots mean we stand behind every skylight we install.
Certified Professionals
CertainTeed and GAF certified, BBB A+ accredited. Credentials that back our workmanship.
Flashing-First Approach
Every skylight gets full step and counter flashing integrated with your roof — not surface-sealed with caulk.
Transparent Pricing
Detailed written estimates. No hidden fees. If adding a skylight during a reroof saves you money, we'll show you the numbers.
Areas We Serve
Get a Skylight Installed the Right Way
Wilson Roofing installs skylights with full flashing integration, not surface sealant. Whether you're adding one to your existing roof or including it in a new build, we'll make sure it stays leak-free for decades.
Call or Request a Quote
Call 941-422-1737 or submit the form. Tell us about the project and we'll schedule a free on-site estimate.
We Plan the Install
We assess your roof, recommend the right skylight unit and placement, and provide a detailed written estimate.
Enjoy Natural Light
We install, flash, seal, and verify. Your new skylight is part of the roof system — not just bolted on top.