4.2 
37 *The Angi rating for Gutter Repair And Replacement companies in Chester, CT is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Repair And Replacement needs.
*The HomeAdvisor rating for Gutter Repair And Replacement companies in Chester, CT is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Repair And Replacement needs.
Last update on July 30, 2026
Serving Chester, CT and surrounding areas
Approved (Corporate)
In business since 2005
Free estimates
Credit card accepted
"Replacement of old gutters with Leaffilter's gutter. The pricing was reasonable, the work was scheduled and performed in due time, and I believe we got a good service at a good price."
Serving Chester, CT and surrounding areas
Approved
In business since 2014
Free estimates
Credit card accepted
"Left the yard cleaner then when they arrived! Did a full roof and gutters in 2 days time I couldnâ t be happier!"
Serving Chester, CT and surrounding areas
Approved
In business since 2006
Free estimates
Credit card accepted
"Ray was very experienced and helpful and eager to help me with my gutter drainage issues. He didn’t just install brand new gutters—he examined the entire exterior of my house and made recommendations for downspout placement that would drain most of the rainwater away from my house. He made other non-gutter suggestions to help with my drainage issues as well. I had four contractors come to my house for this work and I gave them all the same direction. He was the only one who actually addressed my questions. I would use him again and recommend him highly to others looking for a consultative approach to their gutter project."
+4
Serving Chester, CT and surrounding areas
Approved
In business since 2022
Free estimates
Credit card accepted
"They were only interested in selling their gutter guard product, not in helping me complete my project. Did not hire. If you don't have a specific brand / style of gutter in mind, these folks might work for you, but despite reaching out to me promptly, they were not right for my project."
Serving Chester, CT and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"Did a great job cleaning the gutters. Pouring rain the next day. Gutters worked great."
+1
Serving Chester, CT and surrounding areas
Approved
In business since 2004
Free estimates
Emergency services offered
"Everything was handled very well, gutters look great!"
+42
Serving Chester, CT and surrounding areas
Approved
In business since 1965
Free estimates
Credit card accepted
"Quick to schedule and finish the job (gutter cleaning), though their estimate to repair/replace sections was pricey."
Serving Chester, CT and surrounding areas
Approved
In business since 2004
Free estimates
Emergency services offered
"I had a great experience from initial phone call inquiring about gutter repairs and roof repairs on my home. After contacting a few companies for estimates. I decided the customer care, warranty, and pricing was best with Home Genius. I had my roof and gutters replaced with gutter guards, the crew was efficient, neat, but most importantly everything looks great! Thank you to Alex, Andrew, Becca, and Taylor they were all knowledgeable and answered my random questions almost immediately."
+44
Serving Chester, CT and surrounding areas
Approved
In business since 1993
Free estimates
Credit card accepted
LeafGuard is a market-leading, unique, customized gutter protection system for your home. It carries water away from your property faster, protecting it from water damage associated with clogged, or faulty gutters. The system is 20% thicker than regular gutters and provides added strength against the elements. \n \nLeafGuard is the only gutter brand to offer a Lifetime, No-Clog Warranty. What does this mean? Simple--your gutters are guaranteed not to clog for as long as they're installed on your home. If they do, we'll clean them out for free!
+1
Serving Chester, CT and surrounding areas
Approved
Super Service Award Winner
In business since 2023
Free estimates
Emergency services offered
We have the experience, and we are committed to providing quality workmanship and superior customer service on all our applications. We at Outstanding Pressure Washing Service strive to maintain our reputation as a high quality, very service-oriented company with our main focus being customer satisfaction.
+9
From average costs to expert advice, get all the answers you need to get your job done.
Gutter repair costs may not be as high as you think—but it depends on the type of damage you're addressing. Learn why you need to hire a gutter pro for this work.
Wondering how much gutter installation costs? We’ll break down prices by material, gutter type, and other factors impacting overall gutter costs.
Are gutter guards worth it? The average gutter guard installation cost is $650 to $2,000 but varies depending on types, materials, home height, and other factors.
Gutters have a huge responsibility to protect your home from water damage. These simple DIY gutter repair tips will keep rainwater flowing and your home happy.
Repair your gutters to reduce potential water damage and basement flooding. Review these gutter repair questions for when you talk with a pro.
Are your gutters sagging or leaking? Learn about gutter repair costs, warning signs of water damage, and how to hire the right local pro to fix your system.
