8 Roofing Companies in Wildwood, Florida Worth Calling (2026)
By Shelly Marchetti, Florida homeowner advocate. Reviewed by Hal Winstead, Editor, licensed roofing contractor.
One sticky afternoon after Hurricane Idalia had moved off, I was on a driveway along County Road 44A near the old train depot in Wildwood. A ranch-style house had a live oak branch throught the shingles. The homeowner came out and asked if I thought her insurance would cover it. I said I couldn’t know that. But I knew she needed a roofer with a current Florida license, not just the first number that showed up on her phone.
To put this list together, I did the least glamorous thing possible: I checked evrey company that serves Wildwood against the Florida DBPR license roll. Only 2 of the 8 below came back with an active roofing license. That’s the whole point of every roofing company we list in Wildwood. If a name is there, it passed the same check.
Short answer: the 8 best roofing companies in Wildwood, Florida are led by Sky Light Roofing Inc, Bowles Roofing and New Image Roofing Florida. Of the 8 listed here, 2 hold a verified Florida DBPR roofing licence, which is the single check worth doing before anyone climbs on your roof. Rankings below use licence status, review volume, rating and photo evidence — all public, all reproducible.
If you would rather browse the full list rather than my shortlist, every one of them is on the Wildwood roofing companies directory page — this post is the 8 I would call first.
How this list was ranked. Every company here was cross-checked against the Florida Department of Business and Professional Regulation licence roll; 2 of 8 returned an active roofing licence (type CCC or RC), and the licence number is printed on each entry so you can verify it yourself. After licence status, ordering uses Google review count (capped so a big chain cannot buy the top spot on volume alone), star rating, and whether the company has photos and published hours. Nobody paid to appear on this list.
The 8 Best Roofing Companies Wildwood Florida Has to Offer
1. Sky Light Roofing Inc.
Florida licence: CCC1332541 (active) · Google rating: 4.8 from 43 reviews · Based in: 336 S Main St, Wildwood · Phone: +1 352-552-4766
2. Bowles Roofing
Florida licence: CCC058119 (active) · Google rating: 5 from 2 reviews · Based in: 105 Hall St, Wildwood · Phone: +1 352-748-6050
3. New Image Roofing Florida
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 23 reviews · Based in: 5732 C.Thomas Rd, Wildwood · Phone: +1 352-316-6008
4. Roofing the Villages
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 13 reviews · Based in: 810 N Main St, Wildwood · Phone: +1 352-293-2449
5. Nailed Down Roofing
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.8 from 28 reviews · Based in: 703 Mission Dr, Wildwood · Phone: +1 863-592-3404
6. Wildwood Roofing Experts
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4 from 41 reviews · Based in: 203 Curry St, Wildwood · Phone: +1 352-488-9960
7. Chatham roofing contractor repair & installation
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 3.8 from 8 reviews · Based in: Wildwood Ave, Wildwood · Phone: +1 862-289-7205
8. WORRY FREE ROOFING LLC
Florida licence: not matched in the DBPR roll — ask before hiring · Based in: , WILDWOOD
How to check any Florida roofer's licence yourself
Search the licence number at the Florida DBPR licence portal. A roofing contractor holds a CCC (certified) or RC (registered) licence. If the number does not return an active record, that is the end of the conversation.
See all roofing companies in Wildwood →