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  1. Home
  2. Florida
  3. Winter Garden
  4. Roofing & Gutters

The Best Roofing & Gutters Company in Winter Garden

Compare top-rated roofing & gutters providers in Winter Garden. Profiles include verified reviews, service details, and direct contact options.

Service providers

DeSantis Roofing Inc

DeSantis Roofing Inc

4.9

From $50

Up to $500

Closed until Sun, 7:00 AM

At DeSantis Roofing Inc in Winter Garden, we specialize in top-tier roofing solutions for residential properties. Our expertise lies in providing …

0 local residents requested quote requests

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Hi Low ROOFING & SOLAR

Hi Low ROOFING & SOLAR

5

From $50

Up to $500

Closed until Mon, 8:00 AM

In Winter Garden, we are Hi Low ROOFING & SOLAR - your go-to partner for all things related to roofing and solar energy solutions. Our mission is …

0 local residents requested quote requests

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Verified Roofing & Gutters in Winter Garden, FL

We show only active businesses that pass moderation. Results are specific to Winter Garden and nearby service areas, and inactive profiles are removed to keep the list current.

Real reviews for roofing & gutters

Ratings and reviews come from customers who used the service. Compare roofing & gutters pros in Winter Garden by experience, responsiveness, and value before you reach out.

Local-first search in Winter Garden

Filter by neighborhood, check locations on the map, and find providers close to home or work in Winter Garden. Listings are refreshed regularly — August 2026.

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Roofing & Gutters near me in Winter Garden, FL - August 2026

Looking for roofing & gutters in Winter Garden? This page lists verified local providers with ratings, reviews, and contact options. We show active businesses only — profiles are moderated and updated by owners.

Compare pros by experience, price range, and customer feedback. Many providers offer free estimates or same-day service for common requests. Use filters and the map to find someone close to your address.

Before you hire

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  • Ask about licensing and insurance when required for this trade.
  • Get a written estimate for work over a few hundred dollars.
  • Confirm availability and any trip or emergency fees upfront.

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What Winter Garden customers say about local pros

  • State Farm Insurance Shannon Till
    State Farm Insurance Shannon Till

    Thanks Hi Low! I was very impressed with the knowledge, professionalism and communication of the entire office of Hi Low Roofing. They replaced my roof and gutters on my rental property for the LOWEST PRICE!!!

  • Miele Tolentino
    Miele Tolentino

    I worked with Larry Sanders, and he provided phenomenal service. We had damage from the hurricane, and my friend recommended Hi Low Roofing but I also contacted couple roofing companies, the professionalism is the reason we picked Hi Low Roofing. They went on my roof, took pictures of the damage and was very honest. Finding a company you can trust with a job is fantastic.

  • Jack Oakes
    Jack Oakes

    So glad I chose these guys to inspect my roof after Hurricane Milton. Tony and Jeff inspected my roof the very next day after I called them. They told me my roof had no damage. With them not having an inspection fee, I was afraid they might try to charge me to fix something that didn't need fixing. But they didn't. They were honest, quick, and very nice. I highly reccomend. I'll call them after every hurricane from now on and be sure to choose them when I do need repairs.

  • Kevin Stewart
    Kevin Stewart

    Hi-Low Roofing has been stellar from the start. Larry came out and met me at my property and walked the property with me. He informed me of all the things to look out for and even shared with me the upgrades and told me which things would likely not be to my benefit, even though I had been considering them. He was very honest and extremely knowledgeable, answering all my questions in detail and saying that if there was something he didn’t know he would find out. As it happened, he knew everything I inquired about and I am more than happy with the work they did. I walked the property after they left and could not find more than one handful of debris. I was floored! The last time I had a roof put on by a different contractor I was finding debris and nails turning up in the yard and planters for a few years! Larry was also very helpful. He informed me that my dryer vent was clogged and had the crew clear it out for me so that my dryer would run more efficiently. He was very thoughtful and facilitated communication between myself and the crew. Miguel was amazing as well. He really cared about how happy I was and communicated very well with the crew. He even checked behind his crew after they left to ensure that I was satisfied. I could not have asked for a better experience, especially after expecting what I experienced from another company the last time I had my roof replaced. Hi-Low Roofing gets 5 Stars and I have already recommended them! Their number and names are already in my contacts. Big thanks to the whole team!

  • Andrea Creagh
    Andrea Creagh

    I cannot recommend Hi Low Roofing enough. Tony, Josh and Jeff came to my house two days after the storm hit and were able to repair my roof right away. Great people and very reasonably priced compared to others we have gotten quotes from. We are very blessed and appreciative of their quick response. Thank you again Tony, Josh and Jeff.

  • Laura King
    Laura King

    Laura and Joe went through explaining the process very well. Was set up quickly for delivery of material & installation. Roof was completed in one day & took about 6 hours.

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