The Best Roofing Contractors in Winter Garden, FL: 20 Licensed Firms (2026)
By Shelly Marchetti, Florida homeowner advocate. Reviewed by Hal Winstead, Editor, licensed roofing contractor.
I was on a ladder behind a 1980s two-story on Cold Stream Drive when the rain came throught the trees. The owner had called about a drip in the front bedroom, but the real problem was overhead: the shingles along the ridge had lifted and the nails had rusted flat. That was a Tuesday in September, just before the tropical storm crossed Lake Apopka and headed into Winter Garden. I remember thinking that a house can look solid from the curb and still be a sieve over your head.
So I didn't build this list from yard signs or neighbors' cousins. I sat with the Florida DBPR licence roll and checked every company, one by one. Of the 20 below, 9 came back with an active roofing licence. The other 11 didn't, and I won't vouch for them. If you're tired of guessing, start with every roofing company we list in Winter Garden — those are the ones whose paperwork actualy checks out. That's not a guarantee against every storm, but it's the only honest starting point I know.
Short answer: the 20 best roofing companies in Winter Garden, Florida are led by Hi Low ROOFING & SOLAR, ANC Roofing, Inc and Davis Roofing & Restoration. Of the 20 listed here, 9 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 Garden 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; 9 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 Garden Florida Has to Offer
1. Hi Low ROOFING & SOLAR
Florida licence: CCC1332547 (active) · Google rating: 5 from 319 reviews · Based in: 13330 W Colonial Dr Ste 110, Winter Garden · Phone: +1 407-287-6171
2. ANC Roofing, Inc.
Florida licence: CCC048173 (active) · Google rating: 4.8 from 227 reviews · Based in: 720 Business Park Blvd #10, Winter Garden · Phone: +1 407-654-4500
3. Davis Roofing & Restoration
Florida licence: CCC1332682 (active) · Google rating: 5 from 116 reviews · Based in: 1446 9th St, Winter Garden · Phone: +1 407-759-5729
4. Sunray Roofing and Solar
Florida licence: CCC1333692 (active) · Google rating: 4.9 from 119 reviews · Based in: 861 Vineland Rd, Winter Garden · Phone: +1 407-347-7222
5. Certified Roofing Solutions, LLC
Florida licence: CCC1326502 (active) · Google rating: 4.9 from 81 reviews · Based in: 1220 Winter Garden Vineland Rd #108, Winter Garden · Phone: +1 407-907-4722
6. DeSantis Roofing Inc
Florida licence: CCC1334390 (active) · Google rating: 5 from 33 reviews · Based in: 724 Willett Dr, Winter Garden · Phone: +1 407-765-0305
7. TruTop Roof
Florida licence: CCC1337085 (active) · Google rating: 5 from 27 reviews · Based in: 13340 W Colonial Dr #220, Winter Garden · Phone: +1 407-830-5252
8. Sun State Roofing LLC
Florida licence: CCC1334830 (active) · Google rating: 5 from 19 reviews · Based in: 153 Sugar Belle Dr B #114, Winter Garden · Phone: +1 407-777-6338
9. Ocean Roofing of Florida LLC
Florida licence: CCC1330574 (active) · Google rating: 4 from 32 reviews · Based in: 14422 Shoreside Way, Winter Garden · Phone: +1 407-575-0022
10. Level Roofing
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 390 reviews · Based in: 1401 Beulah Rd Ste 114, Winter Garden · Phone: +1 689-319-8900
11. Ludovici Roofing & Construction
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 107 reviews · Based in: 127 S Dillard St, Winter Garden · Phone: +1 321-437-9965
12. Reliant Roofers and Restoration
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 83 reviews · Based in: 553 W Plant St, Winter Garden · Phone: +1 407-574-8550
13. Trinity Restoration and Roofing Orlando
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 66 reviews · Based in: 1106 Brick Rd, Winter Garden · Phone: +1 689-528-0343
14. Montana Roofing
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.8 from 39 reviews · Based in: 761 Garden Commerce Pkwy C, Winter Garden · Phone: +1 689-808-6745
15. Winter Garden Roof Repair
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 29 reviews · Based in: 3131 Daniels Rd 119 Suite 119, Winter Garden · Phone: +1 689-225-6788
16. Talco Construction
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.7 from 79 reviews · Based in: 17304 C R 378, Winter Garden · Phone: +1 407-654-4426
17. Oakland Guys Roofing Contractors
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 5 from 1 reviews · Based in: 814 Revival Pl, Winter Garden · Phone: +1 689-273-9123
18. Nations Roof
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.3 from 22 reviews · Based in: 691 Garden Commerce Pkwy #170, Winter Garden · Phone: +1 407-649-1333
19. Kim Brothers Roof Repair
Florida licence: not matched in the DBPR roll — ask before hiring · Google rating: 4.9 from 25 reviews · Based in: 15528 W Colonial Dr f a Unit F, Suite A, Winter Garden · Phone: +1 689-288-8333
20. Winter Garden Guys Roofing Contractors
Florida licence: not matched in the DBPR roll — ask before hiring · Based in: 121 Agnes St, Winter Garden · Phone: +1 689-273-9138
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 Winter Garden →