Best Roofers in Winter Springs FL - 20 Licensed Firms (2026)

By Shelly Marchetti, Florida homeowner advocate. Reviewed by Hal Winstead, Editor, licensed roofing contractor.

I was standing in a flooded yard on a cul-de-sac just off Tuskawilla Road, near Winter Springs Boulevard, the morning after a squall tore throught. The owners of that two-story house had watter dripping from a hallway light fixture, and they didn’t know which roofer to call. I’m not a roofer; I’m the one who helps homeowners sort out the trustworthy from the smooth talkers.

To put this list together, I went to the Florida DBPR licence roll and checked every company I’d noted down. That’s not a quick website skim; it’s pulling each license, matching the name on the paperwork to the one on the truck. Five of the 20 below came back with an active roofing licence, and those are the ones I’d let onto your driveway. You can review every roofing company we list in Winter Springs and check that record for yourself, because a license is the easiest thing to pretend to have and the hardest thing to argue with.

Short answer: the 20 best roofing companies in Winter Springs, Florida are led by Raptis Roofing, New Standard Roofing Orlando and Pro Roofing Contractors. Of the 20 listed here, 5 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 Winter Springs roofing companies directory page — this post is the 20 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; 5 of 20 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 20 Best Roofing Companies Winter Springs Florida Has to Offer

1. Raptis Roofing

Florida licence: CCC1335172 (active) · Google rating: 4.9 from 141 reviews · Based in: 1255 Belle Ave #171, Winter Springs · Phone: +1 321-444-6484

2. New Standard Roofing Orlando

Florida licence: CCC1333388 (active) · Google rating: 5 from 113 reviews · Based in: 170 W State Rd 434, Winter Springs · Phone: +1 407-512-0144

3. Pro Roofing Contractors

Florida licence: CCC1331019 (active) · Google rating: 4.8 from 47 reviews · Based in: 518 Lombardy Rd, Winter Springs · Phone: +1 407-901-1733

4. Gold Eagle Roofing

Florida licence: CCC1329437 (active) · Google rating: 4.8 from 46 reviews · Based in: 3625 FL-419, Winter Springs · Phone: +1 321-407-7663

5. Local Roofing Contractor LLC

Florida licence: CCC1335834 (active) · Google rating: 5 from 2 reviews · Based in: 1170 Tree Swallow Dr 201 201, Winter Springs · Phone: +1 321-524-2962

6. Citrus Contracting LLC

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.5 from 198 reviews · Based in: 201 W State Rd 434 Ste A, Winter Springs · Phone: +1 407-969-6868

7. Roof Top Services of Central Florida, Inc.

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.6 from 123 reviews · Based in: 1150 Belle Ave #1060, Winter Springs · Phone: +1 407-696-7663

8. Hogan Roofing Orlando

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 58 reviews · Based in: 358 Roberts Family Ln, Winter Springs · Phone: +1 407-917-4049

9. Crafted Roofing Co

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 2 reviews · Based in: 1130 E Florida 434, Winter Springs · Phone: +1 689-304-5550

10. Roof Care of Central Florida

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.8 from 6 reviews · Based in: 5840 Red Bug Lake Rd #1513, Winter Springs · Phone: +1 407-984-4440

11. JM Specialty Contractors LLC

Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 1 reviews · Based in: 236 Buttonwood Ave, Winter Springs · Phone: +1 407-327-8505

12. Winter Springs Guys Roofing Contractors

Florida licence: not matched in the DBPR roll — ask before hiring · Based in: 302 San Rafael St, Winter Springs · Phone: +1 321-677-5104