Best roofers in Winter Haven, Fla.

Winter Haven’s warm climate and long storm season can be tough on roofs, especially with constant sun, heavy summer rain and the risk of tropical storms. Over time, those conditions can cause roofing materials to wear down faster than expected. Small issues like loose shingles or minor leaks can also turn into bigger problems if they are not addressed early, but finding the right roofer for the job is easier said than done. That’s why we researched the best roofers in Winter Haven by reviewing licensing, customer reviews, pricing details and Better Business Bureau (BBB) accreditation information to help you find the best fit.

Top Winter Haven roofers

The best roofing company in Winter Haven for YOU

Before picking a roofer, you have to consider what type of service you need, your budget, timeline and preferences for a local or national company. We recommend getting quotes from three to five roofers in your area to compare customer service, pricing and material quality. Availability also matters, especially during storm season, when reputable roofers can book out weeks in advance.

If you want a locally focused company with in-house crews, strong warranties and an ongoing maintenance option, RIG Roofing is our top pick in Winter Haven. It stands out for its long track record in the area and hands-on approach throughout the project. If you prefer a company with decades of experience, no deposit requirement and a wide range of services, Bob & Jerry’s Roofing is a strong alternative.

Best roofing companies in Winter Haven, Fla.

RIG Roofing is the best overall Winter Haven roofing company

RIG Roofing has been serving Winter Haven and around Central Florida since 2005. It is known for its consistent workmanship and customer-first approach. The company is family-owned and led by founder and president James Curtis. Its name stands for "results, integrity and grounded." These values show up in how the team communicates, works on job sites and supports you throughout the roofing process.

RIG Roofing offers both residential and commercial roofing services across 11 counties in Central Florida. When you request an estimate, the team collects basic information and schedules an on-site inspection rather than giving ballpark pricing over the phone. This allows it to assess materials, storm damage and any rotted wood that may need replacement to offer an accurate estimate.

A 50% deposit is required to begin work. You can pay by check, ACH transfer or credit card, though credit card payments include a 3% fee. Financing is available, including 12 months same as cash, with additional options depending on your needs.

Services offered

• Roof replacement

• Repairs

• Maintenance

• Insurance claim assistance

• Emergency tarping

Beyond replacements and repairs, RIG Roofing offers an annual roof maintenance program designed for Florida’s tropical climate. The plan costs $194 per year when you choose the biannual payment plan. Maintenance visits include debris removal, gutter cleaning, inspection of roof penetrations, securing loose shingles and repairing nail pops to help prevent costly issues down the road.

Cleanup is included in every estimate. Crews use a catch-all system to collect debris, place an on-site dumpster that is hauled away after the job and run magnets across the yard to pick up nails.

All employees are full-time, background-checked and have worked with the company for at least 10 years. RIG Roofing provides a 10-year workmanship warranty along with a two-year roof maintenance warranty that includes two complimentary checkups per year. If weather interferes with a scheduled job, the team monitors conditions closely and reschedules when needed. It also keeps roofs protected with tarps if rain occurs during the project.

RIG Roofing is BBB-accredited with an A+ rating. It has six complaints in the past three years, but all have been answered or resolved by the company. It holds a strong 4.8 rating on Google (583 reviews), 4.3 on Angi (eight reviews) and a 2.5 on Yelp (13 reviews).

The office is located at 2001 Havensale Blvd. Northwest, Winter Haven, Fla., 33881. Since it offers 24/7 emergency services, you can call at any time of day. Its phone number is 863-294-4477 or you can visit the company’s website to request a quote online.

Customer testimonial

We had an incredible experience with RIG Roofing in replacing our residential roof and dock roof. The team provided exceptional customer service from first contact all the way through final inspection. The technicians, sales staff, administrative support, and delivery personnel were friendly, courteous, and professional. This project was a large investment for us, and having a company we can trust to do the work with quality and integrity was paramount to our peace of mind. A huge thank you to Angelina Bowen and Ryan Sackett for their above-and-beyond service during this process. - Rebecca M., Google reviews (⭐⭐⭐⭐⭐)

* See Google reviews * See Yelp reviews

Bob & Jerry’s Roofing is our top alternative roofing company

Bob & Jerry’s Roofing is a family-owned roofing company that has served Winter Haven and the surrounding Central Florida community for more than 40 years. Based nearby in Auburndale, it brings national-level experience and systems while still operating with a local, hands-on approach. The company focuses on residential roofing and gutter services.

When you request an estimate, Bob & Jerry’s Roofing schedules an on-site visit rather than providing ballpark pricing over the phone. The estimator goes on the roof and takes measurements and photos. Based on your roof’s condition and requested materials, the estimator prepares a detailed quote. This process helps avoid surprises and ensures pricing reflects the full scope of work.

Unlike many roofing companies in Winter Haven, Bob & Jerry’s Roofing does not require a deposit to get started. You can pay by cash, check, credit or debit card. There is no credit card fee.

Services offered

• Roof installation

• Replacement

• Repairs

• Gutters

• Skylights

• Inspections

Your estimate includes cleanup, meaning the crew uses tarping and catch systems to protect landscaping, driveways and walkways. After your roof is complete, it does a magnetic sweep to remove nails and debris.

Office staff are full-time company employees who undergo background checks. Roofing crews work as subcontractors but are supervised at all times by a full-time superintendent who works on-site. Workmanship warranties range from five to 10 years, depending on the roofing system selected. The company also offers an extended maintenance warranty for an additional cost. Your estimator will go over the options in your quote.

The company closely monitors weather conditions and waits as long as possible to reschedule if storms are expected. Decisions are typically made the day before or the morning of the job and projects are rescheduled on the next available day to prevent delays.

Bob & Jerry’s Roofing is accredited by the BBB with an A+ rating and has no complaints on the site. It has solid customer reviews, including a 4.9 rating on Google (389 reviews), 4.1 on Angi (five reviews) and a 3.7 on Yelp (nine reviews).

Its office is located at 219 Orange Street, Auburndale, Fla., 33823. You can stop by or call 863-965-9595 between 8 a.m. and 4 p.m. Monday through Friday. The office is closed on the weekends. Call or send a message online to start your roofing estimate.

Customer testimonial

Best roofing company to work with. They replaced my 20 year old roof that had several leaks and was long overdue for a replacement. From the start the process was smooth sailing. They have an excellent, dedicated team who kept me informed along the way. Harris went above and beyond to make sure I understood all of my options and kept me updated from start till finish. Daniel, Jason, and Steve ensured I had a quality finished product while Tiffany and Kelly helped me get all the paperwork in order. If your looking for an affordable quality roof replacement, choose Bob and Jerry's Roofing. - Jason O., Google reviews (⭐⭐⭐⭐⭐)

* See Google reviews * See Yelp reviews

Best Choice Roofing is the best national roofer serving Winter Haven

Yahoo Local is here to help people make informed decisions with confidence. While supporting local businesses is important, there are situations where a national roofing company may be the better option. If you’re choosing between the two, our guide on local vs. national roofers can help clarify the differences. For homeowners considering a nationwide provider, Best Choice Roofing is our top national pick for the Southeast.

Based in Tennessee, Best Choice Roofing operates dozens of offices throughout the Southeast and serves customers nationwide. The company has 90 locations across 30 states, spanning from Los Angeles to New York. As a full-service roofing contractor, it provides roofing, gutter and skylight services both within the Southeast and beyond. Founded in 2009, this Tennessee-based company is now the nation’s largest Owens Corning Platinum Preferred Contractor. It holds a 4.2-star average rating on Google from over 200 reviews. On Yelp, Best Choice averages one star, though that rating is based on just two reviews and does not accurately represent its overall service.

Most Best Choice Roofing locations specialize in asphalt shingle roofing systems, though some offices can accommodate specialty material requests, including metal roofing. Each project includes a standard five-year labor warranty, with the option to upgrade to a lifetime warranty. As an Owens Corning Platinum Preferred Contractor, Best Choice also offers a 50-year materials warranty on Owens Corning products.

Services offered

• Roof repair, replacement and installation

• Free roof inspections

• Roof cleaning

• Gutter services

• Skylight installation and repair

In line with other national roofing providers, Best Choice does not share pricing details over the phone. Instead, customers schedule a free on-site inspection. During the visit, a Best Choice “solutionist” reviews pricing, deposits, financing and payment structure. A company representative explained that these details vary significantly by job and location, making an in-person estimate the only reliable way to receive accurate information. Free inspections are typically available within 24 hours of the first call.

Financing is the most common payment method, though other options, such as card or check, may be available and can be discussed with your Best Choice representative during the inspection.

Best Choice Roofing is accredited by the BBB with an A+ rating and has received about 121 complaints over the past three years. Inspectors and project managers are employed directly by the company, while installation crews are subcontracted, which is standard practice for large national roofing companies. All in-house employees undergo criminal background checks before hiring, though findings do not automatically disqualify candidates.

For additional details, call 407-993-2209 or request a free inspection online. Best Choice Roofing operates in 30 states nationwide, and its nearest office is located at 22 W. Monument Ave., Suite 2, Kissimmee, Fla., 34741. Its office hours are Monday through Friday, from 8 a.m. to 5 p.m.

For more details on this recommended roofer, read our in-depth Best Choice Roofing review .

Customer testimonial

We had a great experience with Best Choice Roofing. We love our new roof. The whole process was easy from start to finish. The team that came in were very respectful and professional. They did an excellent job of cleaning up after they were finished. I would highly recommend them for any of your roof replacement needs. - Carri T., Google reviews (⭐⭐⭐⭐⭐)

* See Google reviews * See Yelp reviews

More best Winter Haven roofers

You can count on Yahoo Local roofing advice, and this is why

Yahoo has spent decades evaluating and reporting on local businesses. Even after all these years, our goal remains the same. Each guide we create is designed to provide clear and reliable information about local services. We explain how our rankings are created rather than asking you to take our word for it. Our system uses customer reviews from multiple established sources and weighs them to create balanced rankings. We also share the factors behind our decisions so you can decide which companies you trust. Our selections are never sponsored and we do not accept payment for placement or rankings. You can learn more on our full methodology page .

Here is everything that went into the rankings for our list of the best roofing companies in Winter Haven:

• 37 roofers evaluated

• 3,371 customer reviews and ratings from five sources

• Eight ranking criteria incorporated

• Interviewed or connected with three featured roofers

• Independent price quotes sought from three featured roofing companies

• Independently researched and fact-checked by Yahoo

• Recommendations are maintained and updated regularly

Florida roofing FAQs

How much does the average roof replacement cost in Florida?

According to This Old House , the average cost of a roof replacement in Florida is about $6,680, with most paying between $5,281 and $16,635. Where you land in that range depends on roof size, materials and whether storm damage or rotted decking is found. Florida roofs also need to stand up to strong sun, heavy rain, high humidity and hurricane-force winds. This means you may need higher-quality materials, which increases the cost. Many Florida roofers perform an on-site inspection to provide an accurate quote.

How do I know if my roof needs repairs or a full replacement?

There are several signs your roof needs service, such as missing shingles, leaks, sagging areas or water stains on your ceiling. These signs don’t always mean you need a full replacement, especially if your roof is still young. Once a roof hits 15 to 20 years, a full replacement might be the better option if there is widespread damage. Roofers on this page, including RIG Roofing and Bob & Jerry’s Roofing , use onsite inspections to decide whether repairs or a full replacement is needed.

Are there roofing regulations or permits required in Florida?

Roofing companies must be licensed through the Florida Department of Business and Professional Regulation , which helps protect you from unqualified or unlicensed contractors. Most roof replacements also require a permit from your local city or county. These rules are especially important in Florida due to hurricane and wind-resistance standards. Reputable roofers, including the companies on this page, typically handle licensing verification and permits for you. Learn more in our guide to Florida roofing and licensing regulations .

How long does a roof typically last in Florida?

Your roof’s lifespan in Florida can be shorter than average due to intense sun exposure, high humidity, heavy rain and frequent storms. Asphalt shingle roofs in Florida typically last about 15 to 20 years, while metal roofs often last 40 to 70 years when properly installed and maintained. Regular inspections and maintenance can help extend the life of any roofing material. Learn more in our guide to how long a roof lasts .

What is the best time of year to replace a roof in Florida?

Spring and early summer are often good times to replace a roof in Florida because the weather tends to be more predictable. Spring usually brings fewer daily storms and slightly cooler temperatures, which can help keep projects on schedule. Roof replacements can still be done in summer, but frequent afternoon rain and extreme heat may cause delays. Hurricane season runs from June 1 through November 30, so try to schedule work before then. These guides explain the pros and cons of replacing a roof in spring and summer .

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