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 By the Local Three editors How we select

Editor's Pick

Bob & Jerry's Roofing Inc.

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 +1 863-965-9595Website

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 Florida4.3 · 27 (2021)

At a glance

The three, side by side

01Bob & Jerry's Roofing Inc.02Imperial Roofing of Polk County Inc031st Class Roofing, Inc.
Best forEditor's Pick–Reader Favorite
Rating4.5 · 46 (2021) reviews4.6 · 17 (2021) reviews4.2 · 28 (2021) reviews
In business–––
Budget–––
Free estimateAskAskAsk
LicenseNot confirmed yetNot confirmed yetNot confirmed yet
Based inAuburndaleWinter HavenAuburndale

Methodology

How we selected these businesses

Three is a deliberately small number. It forces us to leave out good companies.

Read the full methodology

  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.

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 · 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 · 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 · 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 · 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 · 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 · 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.

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.

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