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Best gutter repair and replacement pros near Winsted, CT

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Top-Rated Gutter repair and replacement pros in Winsted - Updated Nov 2026

Avatar for The Gutter Shutter of CT
The Gutter Shutter of CT
4.4(
514
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallSeamless Metal Gutters - Repair+4 more

Serving Winsted, CT and surrounding areas

Approved

In business since 2006

Free estimates

Credit card accepted

"Ray was very knowledgeable and explained a good deal. He and his coworker completed the job rapidly and left everything clean afterward. The gutters look great and should be a big improvement. Would recommend Ray and his ptoducts"
Gutters
Gutters
Gutters
Gutters
Additional Photos

+4

48 neighbors recently requested a quote
Recommended by98%of homeowners
Avatar for Northland Roofing LLC
Northland Roofing LLC
4.9(
12
)
Seamless Metal Gutters - InstallSeamless Metal Gutters - Repair

Serving Winsted, CT and surrounding areas

Approved

In business since 2010

Free estimates

Emergency services offered

About Northland Roofing\n\nNorthland Roofing proudly serves Fairfield and Litchfield Counties, providing high-quality roofing, siding, and window installations that protect your home and add lasting value. We believe homeowners deserve honesty, craftsmanship, and peace of mind — not sales pressure or surprises. From your first estimate to final cleanup, our team focuses on clear communication, dependable scheduling, and quality workmanship that stands the test of time. Every project is completed using trusted materials and installed by professionals who care about your home as much as you do. At Northland Roofing, protecting your home is our priority — and we do it right the first time.

Roofing project
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+12

Response time2 days
Response rate100%
Recommended by54%of homeowners
Avatar for Home Genius Exteriors
Home Genius Exteriors
4.9(
522
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+3 more

Serving Winsted, 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."
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing
Asphalt Roofing

+44

Recommended by71%of homeowners
Avatar for The Builders & Cleaners
The Builders & Cleaners
4.9(
122
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Winsted, CT and surrounding areas

Approved

In business since 2018

Free estimates

Emergency services offered

"Excellent service! Highly recommend! David was prompt and very professional. We had damage to our gutters from strong wind gusts. David sent a handy man the same day we called, they repaired the damage quickly, and it was excellent work! Highly reliable!"
Dust out from the ductwork
Dust out from the ductwork
Clean vent
Clean vent
Dust in the return

+1836

Response time1 day
Response rate92%
Recommended by85%of homeowners
Avatar for Leafguard
Leafguard
4.2(
311
)
Seamless Metal Gutters - InstallGutter Covers and Accessories - Install or Replace

Serving Winsted, 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!

Leafguard gutter inside
Leafguard
A new leaf guard system
Leaves going over gutter
Angled view of Leaf Guard

+1

48 neighbors recently requested a quote
Recommended by89%of homeowners
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Gutter Repair and Replacement FAQs, answered by experts

In most cases, it makes more sense to repair leaking or damaged gutters than it will to replace them. You’ll spend an average of $400 to repair your gutters, while full replacement will cost around $2,000 or more, depending on the gutter material and style and the size of your home. If your gutters are nearing the end of their lifespan—usually around 20 years for aluminum or vinyl gutters or up to 50 years for copper or steel—then it might make sense to replace them, as it could cost you less in the long run.

Most repairs take 2-4 hours, but extensive repairs or full section replacements may take an entire day.

Yes, it is okay to knock down icicles yourself. Just make sure to take the proper safety precautions. If you’re not comfortable doing it yourself, contact a roofing professional.

Any small amount of standing water can be damaging to your gutters. It’s recommended that a ¼ inch puddle or more should be addressed. Failure to keep water from pooling in your gutters can result in clogs, algae growth, and pests that damage your gutters over time. 

When it comes to which gutter material is better, the choice really boils down to what you're looking for in a gutter system. If saving money is the most important factor, then your best option is to go for aluminum gutters. If longevity and durability are more important to you, then copper gutters could be the best fit. If you want to customize the color of your gutters, aluminum takes the cake, but if you're looking for a more natural appearance, copper might be a better choice.

The Winsted, CT homeowners’ guide to gutter repairs and replacements

From average costs to expert advice, get all the answers you need to get your job done.