--- title: The 3 Best Roofing Contractors in Winter Haven | Local Three url: https://thelocalthree.com/winter-haven/roofing-contractors/ updated: 2026-10-31 --- [Local *Three* Selected, not listed](https://thelocalthree.com/) - [Winter Haven](https://thelocalthree.com/winter-haven/) - [Roofing Contractors](https://thelocalthree.com/roofing-contractors/) - [How we select](https://thelocalthree.com/how-we-select/) - [For businesses](https://thelocalthree.com/claim/) 1. [Home](https://thelocalthree.com/) 2. [Florida](https://thelocalthree.com/florida/) 3. [Winter Haven](https://thelocalthree.com/winter-haven/) 4. Roofing Contractors Winter Haven · Roofing Contractors # The 3 Best Roofing Contractors in Winter Haven 2027 Edition Three roofing contractors in Winter Haven worth calling first, chosen from 5 local companies on their public record. Here is why each one made it. Updated October 31, 2026 By the Local Three editors [How we select](https://thelocalthree.com/how-we-select/) In short Of the 5 roofing contractors we reviewed in Winter Haven, these three had the strongest records: 91 public reviews between them, averaging 4.4 out of 5. Local Three editors · October 31, 2026 Editor's Pick ## [Bob & Jerry's Roofing Inc.](https://thelocalthree.com/business/g-e565ee42c0bdd117/) **4.5** from 46 (2021) reviews Based in Auburndale Coverage Based in Winter Haven ### Why we picked them The strongest overall record of the 5 roofing contractors we reviewed in Winter Haven: rating, review volume, recent activity and years in business, taken together. Checked Oct 2026 - Operating status Request a quote [Call +1 863-965-9595](tel:+18639659595)[Website](https://thelocalthree.com/winter-haven/roofing-contractors/bobandjerrysroofing.com) Selection 02 ## [Imperial Roofing of Polk County Inc](https://thelocalthree.com/business/g-3b7b4f2a2b2f87fd/) **4.6** from 17 (2021) reviews Based in Winter Haven Coverage Based in Winter Haven ### Why we picked them A steady public record: 4.6 from 17 (2021) reviews. Checked Oct 2026 - Operating status Request a quote [Call +1 863-967-9244](tel:+18639679244)[Website](http://www.imperialroof.com/) Reader Favorite ## [1st Class Roofing, Inc.](https://thelocalthree.com/business/g-9529bc19180deffc/) **4.2** from 28 (2021) reviews Based in Auburndale Coverage Based in Winter Haven ### Why we picked them A large, loyal client base: 28 (2021) public reviews, averaging 4.2 out of 5. Checked Oct 2026 - Operating status Request a quote [Call +1 863-324-4043](tel:+18633244043)[Website](https://www.1stclassroofingincfl.com) Beyond the three ## More roofing contractors in Winter Haven Other Winter Haven companies that met our basic bar. We looked at 5 in all for this work. - Robert Binns Roofing Inc. 4.1 · 36 (2021) - Ray's Roofing of Central Florida 4.3 · 27 (2021) At a glance ## The three, side by side Comparison of the selected roofing contractors in Winter Haven | | 01 Bob & Jerry's Roofing Inc. | 02 Imperial Roofing of Polk County Inc | 03 1st Class Roofing, Inc. | |---|---|---|---| | Best for | Editor's Pick | – | Reader Favorite | | Rating | 4.5 · 46 (2021) reviews | 4.6 · 17 (2021) reviews | 4.2 · 28 (2021) reviews | | In business | – | – | – | | Budget | – | – | – | | Free estimate | Ask | Ask | Ask | | License | Not confirmed yet | Not confirmed yet | Not confirmed yet | | Based in | Auburndale | Winter Haven | Auburndale | Methodology ## How we selected these businesses Three is a deliberately small number. It forces us to leave out good companies. [Read the full methodology](https://thelocalthree.com/how-we-select/) 1. **We start with everyone.** 5 roofing contractors in Winter Haven, from public listings and review platforms. 2. **We remove the risky.** No working phone, too few genuine reviews or a weak rating. 3. **We read the record.** Review volume and recency, years in business and the record checks we could confirm. 4. **Editors keep three.** And write down who each one suits best. Selection is never for sale. [How we make money](https://thelocalthree.com/how-we-make-money/). Local facts · Polk ## Winter Haven, by the numbers Public records tell you how busy the trade is and what the rules ask of every job. Read them before you call. Median home value: Median value of owner-occupied homes (ACS table B25077). $269,800 [U.S. Census Bureau, American Community Survey 5-year estimates](https://data.census.gov/table/ACSDT5Y2024.B25077?g=160XX00US1278275) · 2020–2024 Homes built before 1990: 11,806 of 23,431 housing units were built in 1989 or earlier (ACS table B25034, year structure built). 50.4% [U.S. Census Bureau, American Community Survey 5-year estimates](https://data.census.gov/table/ACSDT5Y2024.B25034?g=160XX00US1278275) · 2020–2024 Households in Winter Haven: Occupied housing units (one household per occupied home), ACS table B25003. 20,396 [U.S. Census Bureau, American Community Survey 5-year estimates](https://data.census.gov/table/ACSDT5Y2024.B25003?g=160XX00US1278275) · 2020–2024 Atlantic hurricane season: An average season (1991–2020) has 14 named storms, 7 hurricanes and 3 major hurricanes. June 1 to November 30 [NOAA National Hurricane Center, Tropical Cyclone Climatology](https://www.nhc.noaa.gov/climo/) · 1991–2020 climate period Median year homes were built: Half of all housing units were built before this year (ACS table B25035). 1990 [U.S. Census Bureau, American Community Survey 5-year estimates](https://data.census.gov/table/ACSDT5Y2024.B25035?g=160XX00US1278275) · 2020–2024 Owner-occupied homes: 12,991 of 20,396 occupied homes are lived in by their owners (ACS table B25003). 63.7% [U.S. Census Bureau, American Community Survey 5-year estimates](https://data.census.gov/table/ACSDT5Y2024.B25003?g=160XX00US1278275) · 2020–2024 Public sources, checked October 31, 2026. Local guide ## Hiring roofing contractors in Winter Haven: what to know first ### Check the license Look the company up on your state’s license search, and ask for insurance papers sent by the insurer. ### Compare written quotes Three quotes for the same work, each listing what is not included. ### Ask about the warranty In writing, clear about what it covers, and transferable if you sell. ### Pay in stages Pay for finished, inspected stages, not dates. More in [our Winter Haven cost guide](https://thelocalthree.com/guides/roofing-contractors-cost-winter-haven/). Request a quote ## Ask our three for a price One short form, sent only to the companies you tick. Most reply within one or two working days. Send my request to We never sell your details. A business that answers may pay us a small fee; your price is the same. Questions ## Questions about roofing contractors in Winter Haven How did the editors choose these roofing contractors in Winter Haven? Editors shortlist businesses with strong ratings and enough reviews, check their records, and choose the final picks against the published criteria. We compared 5 roofing contractors for Winter Haven. Paid placements never change the order. Which of these roofing contractors in Winter Haven has the best reviews? Imperial Roofing of Polk County Inc has a 4.6 rating from 17 (2021) (2021) public reviews, the highest on this page. Which of these roofing contractors has the most reviews? Bob & Jerry's Roofing Inc., with 46 (2021) (2021) public reviews. A long review history shows how a business handles many jobs. Are these roofing contractors licensed? 3 of the 3 businesses here had their state license checked against public records. Each profile shows the source and the date of the check. How many quotes should I get for roofing contractors in Winter Haven? Get at least three. Use the quote form on this page: only the businesses you tick receive your request. Related in Winter Haven ## Also selected - [HVAC Contractors](https://thelocalthree.com/winter-haven/hvac-contractors/) - [Air Duct Cleaning Companies](https://thelocalthree.com/winter-haven/air-duct-cleaning-companies/) - [HVAC Repair](https://thelocalthree.com/winter-haven/hvac-repair/) - [HVAC System Replacement](https://thelocalthree.com/winter-haven/hvac-replacement/) - [AC Repair](https://thelocalthree.com/winter-haven/ac-repair/) - [Emergency AC Repair](https://thelocalthree.com/winter-haven/emergency-ac-repair/) - [AC Maintenance & Tune-Up](https://thelocalthree.com/winter-haven/ac-maintenance/) - [AC Installation & Replacement](https://thelocalthree.com/winter-haven/ac-replacement/) Nearby editions ## Roofing Contractors nearby - [Jacksonville](https://thelocalthree.com/jacksonville/roofing-contractors/) - [Miami](https://thelocalthree.com/miami/roofing-contractors/) - [Tampa](https://thelocalthree.com/tampa/roofing-contractors/) - [Orlando](https://thelocalthree.com/orlando/roofing-contractors/) - [Port St. Lucie](https://thelocalthree.com/port-st-lucie/roofing-contractors/) - [St. Petersburg](https://thelocalthree.com/st-petersburg/roofing-contractors/) - [Cape Coral](https://thelocalthree.com/cape-coral/roofing-contractors/) - [Tallahassee](https://thelocalthree.com/tallahassee/roofing-contractors/) Up a level ## More in Winter Haven - [Winter Haven edition](https://thelocalthree.com/winter-haven/) - [Roofing Contractors, every city](https://thelocalthree.com/roofing-contractors/) - [Winter Haven cost guide](https://thelocalthree.com/guides/roofing-contractors-cost-winter-haven/) For businesses ## Own a local business in Winter Haven? 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Ratings and review counts are collected from public review platforms and were last refreshed on October 31, 2026 . Sponsored placements are always labelled and never change who is selected.