4.7 
280 *The Angi rating for Gutter Cleaning companies in Windermere, FL is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Cleaning needs.
*The HomeAdvisor rating for Gutter Cleaning companies in Windermere, FL is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Cleaning needs.
Last update on January 08, 2026
Serving Windermere, FL and surrounding areas
Approved
In business since 1992
Free estimates
Emergency services offered
"Very communicative, affordable, professional and attentive. We are very pleased with how quickly we were able to get schedule in and are happy with our cleaned gutters!"
+1
Serving Windermere, FL and surrounding areas
Approved
In business since 2018
Free estimates
Warranties offered
"Very professional and pleasant. Arrived early like they said they would, set all the material that was to be used for the job. Went to work immediately and finished just in time for the rain. They did an awesome job on my gutters and cleaned up after themselves when they were done. I would definitely recommend CJT Construction Corp for gutter installation. I love how they turned out and also the areas where they placed the down spouts. I would definitely use them again if needed. My gutters look very neat and flawless. Great job Cesar I really appreciate you and your crew."
+39
Serving Windermere, FL and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Warranties offered
"LeafFilter doesn't clean gutters, they sell and install their LeafFilter Gutter products and only clean the gutters if you buy their product. I can't even begin to afford their product so I wasn't able to get my gutter cleaned by them."
+63
Serving Windermere, FL and surrounding areas
Approved
In business since 2019
Free estimates
Small jobs welcome
"They provided excellent craftsmanship and went above and beyond to make my gutters functional again."
+66
Serving Windermere, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2022
Free estimates
Credit card accepted
"Fantastic job. He was able to clear out about 5 years of leaves, dirt and live plants out of the gutters and they look BEAUTIFUL. A+ work, would recommend him to anyone who needs it!"
+43
Serving Windermere, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2024
Free estimates
Offers commercial services
"I am very satisfied with the work done by Bailey's. He checked andxs cleaned all of my gutters and down spouts to include some molding that had started in one area of my fence. He also did an outstanding job on my driveway and side walks. He took pictures and videos of all areas and explaained the before and after. I am totally satisfied with the work performeds by Bailey's Pure Pressure Waah, and I will surely call him for my future projects."
Serving Windermere, FL and surrounding areas
Approved
In business since 2017
Free estimates
Emergency services offered
Since 2007, PaintSolid LLC has been providing Central Florida with top-notch house painting services. Our extensive list of services includes interior & exterior painting, kitchen cabinet painting, roof painting, flooring installation, pressure washing, and some handyman services. We offer competitive pricing, reliable timelines, commitment to quality, emergency services, free estimates, licensed in trade, and quick response time. \nWe also believe in building relationships based on trust and are committed to our clients even after the project is completed. At PaintSolid, we are dedicated to helping you with all of your home projects, big or small. Let us show you why we are one of Central Florida’s trusted home services providers – contact us today for a free estimate!\n\nRegards, \nArchie at PaintSolid LLC \nPhone: 407-484-5391 \nEmail: [email protected]
+86
Serving Windermere, FL and surrounding areas
Approved
In business since 2000
Free estimates
Credit card accepted
"Not only cleaned the gutters but fixed our outside drainage issue. On time, honest and reliable! Thank you"
Serving Windermere, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2019
Free estimates
Credit card accepted
"Very knowledgeable and professional. Cleaned up very thoroughly. Highly recommend"
Serving Windermere, FL and surrounding areas
Approved
In business since 2020
Free estimates
Warranties offered
"Friendly and fast service. Great quality gutter work. Would hire them for any other project going forward. Thank you!"
+1
From average costs to expert advice, get all the answers you need to get your job done.
This guide to gutter cleaning costs in Orlando, FL provides local estimates for cleaning gutters based on length, type, and number of stories on a home.
The cost of seamless gutters varies based on home size, labor rates, gutter materials, and more. Here’s what you can expect to pay in Orlando, FL.
Wondering how much gutter installation costs? We’ll break down prices by material, gutter type, and other factors impacting overall gutter costs in Orlando, FL.
What is gutter cleaning, and why is it important? From benefits and cost to recommended cleaning frequency, we bring you essential gutter cleaning basics you need to know.
Learn about the downspout cleaning tools to buy to prevent gutter clogs that can cause water to pool near your basement or foundation.
If you’re wondering when the best time to clean gutters is, the answer depends on your climate and the number and type of trees around you. Our guide breaks it all down.
