Winter Haven · Cost guide

Cost Guide: Roofing Contractors in Winter Haven

What shapes the price, what to check, and who locals recommend.

Updated October 31, 2026

See Winter Haven's favorite roofing contractors

Overall FavoriteBob & Jerry's Roofing Inc.
★ 4.5 · 46 (2021) reviews
Imperial Roofing of Polk County Inc
★ 4.6 · 17 (2021) reviews
1st Class Roofing, Inc.
★ 4.2 · 28 (2021) reviews

Before you sign

Four things to check with any business

Check the license with your state's licensing board.
Get three itemised quotes so you compare like with like.
Confirm who pulls the permit: it should be in the business's name.
Tie payments to stages and get the warranty in writing.

For a fair price, compare three itemised quotes for the same job. Ask the favorites for a quote

Who to call

Winter Haven's favorite roofing contractors

Why each one earned its label

Overall FavoriteBob & Jerry's Roofing Inc.
★ 4.5 · 46 (2021) reviews
FavoriteImperial Roofing of Polk County Inc
★ 4.6 · 17 (2021) reviews
Favorite1st Class Roofing, Inc.
★ 4.2 · 28 (2021) reviews
Customer FavoriteRobert Binns Roofing Inc.
★ 4.1 · 36 (2021) reviews
FavoriteRay's Roofing of Central Florida
★ 4.3 · 27 (2021) reviews

Local facts

Winter Haven, by the numbers

Official figures that shape what the job costs here.

$269,800
Median home value (Median value of owner-occupied homes (ACS table B25077).)
U.S. Census Bureau, American Community Survey 5-year estimates · 2020–2024
50.4%
Homes built before 1990 (11,806 of 23,431 housing units were built in 1989 or earlier (ACS table B25034, year structure built).)
U.S. Census Bureau, American Community Survey 5-year estimates · 2020–2024
20,396
Households in Winter Haven (Occupied housing units (one household per occupied home), ACS table B25003.)
U.S. Census Bureau, American Community Survey 5-year estimates · 2020–2024
June 1 to November 30
Atlantic hurricane season (An average season (1991–2020) has 14 named storms, 7 hurricanes and 3 major hurricanes.)
NOAA National Hurricane Center, Tropical Cyclone Climatology · 1991–2020 climate period
1990
Median year homes were built (Half of all housing units were built before this year (ACS table B25035).)
U.S. Census Bureau, American Community Survey 5-year estimates · 2020–2024
63.7%
Owner-occupied homes (12,991 of 20,396 occupied homes are lived in by their owners (ACS table B25003).)
U.S. Census Bureau, American Community Survey 5-year estimates · 2020–2024

Questions

Cost questions answered

How is the top 5 ranking of roofing contractors in Winter Haven calculated?

Each business gets a score from its rating, review volume, recent reviews, years in business, profile completeness and record checks. The highest scores make the list. 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?

5 of the 5 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.