4.9 
131 *The Angi rating for Gutter Cleaning companies in Winter Park, 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 Winter Park, 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 11, 2026
Serving Winter Park, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2019
Free estimates
Credit card accepted
"Marcus explained all the work he was going to do ahead of time, then did a great job. Iâ d definitely recommend Shineâ s Gutter Repair to anyone needing their gutters cleaned or repaired."
+55
Serving Winter Park, 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 Winter Park, FL and surrounding areas
Approved
In business since 2018
Free estimates
Warranties offered
"Nice gutter installed with leafguard. Thank you."
+39
Serving Winter Park, FL and surrounding areas
Approved
In business since 2018
Free estimates
Emergency services offered
"Did an excellent job cleaning the gutters. As an aside a clogged drain line was found and cleared."
+27
Serving Winter Park, 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 Winter Park, FL and surrounding areas
Approved
In business since 2019
Free estimates
Small jobs welcome
"The professionals at Seamless Gutters were fantastic! They were hored to clear my gutters and downspouts of leaves and came prepared to delicately climb onto the roof and perform a very much needed service. The owner of Seamless Gutters also istalls new gutter and relevant systems. I would highly recommend the work that they did with no mess or fuss. Job done under two hours!"
+72
Serving Winter Park, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2022
Free estimates
Credit card accepted
"Had my back brick patio area and driveway done first. Excellent service. Today had my roof cleaned. Wow. My roof shingles look like new. Excellent work. Very professional. Will use again and I recommend you do too."
+43
Serving Winter Park, FL and surrounding areas
Approved
Super Service Award Winner
In business since 2024
Free estimates
Offers commercial services
Bailey's Pure Pressure Wash, LLC is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business.\n
Serving Winter Park, 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 Winter Park, 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"
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.
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Learn who to hire to clean your gutters to find the right local professional for gutter cleaning quotes.
