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Best gutter repair and replacement pros near Winchester, IL

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

Avatar for D&D gutters
D&D gutters
New to Angi
Gutter Covers and Accessories - Install or ReplaceGalvanized Gutters - RepairPVC Gutters - Repair+4 more

Serving Winchester, IL and surrounding areas

Approved

Free estimates

Emergency services offered

Warranties offered

Hey everyone! My name is William Desollar, and I’m from Pleasant Plains. I’ve been working in the gutter business for the past 6 years, and over that time I’ve had the opportunity to work on just about everything when it comes to gutters.\n\nI’ve always believed that doing good work and treating people right goes a long way. I take pride in helping homeowners keep their homes protected and looking their best.\n\nWhether you need a gutter repair, replacement, cleaning, or just want someone to take a look, feel free to reach out. I’m always happy to help and provide a free estimate.\n\nThanks for your support. I truly appreciate every opportunity to earn your business!

3 neighbors recently requested a quote
Next-Gen Concrete & Construction LLC
4.4(
4
)
Seamless Metal Gutters - Repair

Serving Winchester, IL and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

We're a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. Our services are customized to the individual project, paying close attention to the details of each project that we're involved with. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guaranteeing your satisfaction!

3 neighbors recently requested a quote
Avatar for All About Gutters, Inc.
All About Gutters, Inc.
4.4(
39
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+2 more

Serving Winchester, IL and surrounding areas

In business since 1999

Free estimates

Emergency services offered

"One thing I really like was that they didn't try to sell me other things like gutter guards. They gave me a good solid price and mention down the road they could add guards but did not push the issue. Rob also notice a piece of facia that had blown off and offered to put it back on at no charge. A real good experience with a lifetime warranty."
 Small repairs are no problem.
 soffitastic!
 copper seamless gutters, copper gutter protection
 EPA Lead-Safe Certified Firm
 6 " Seamless

+20

Recommended by93%of homeowners
Avatar for LeafShield Pro Gutter Solutions
LeafShield Pro Gutter Solutions
4.9(
69
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - Install

Serving Winchester, IL and surrounding areas

In business since 2020

Free estimates

Warranties offered

"Brian followed-up from my Angi's recommendation. He was on-time for our appointment. He didn't try to over sell products that we didn't need like gutters/down pours. He explained how his products was beneficial to our needs. He had videos of potential problems that other similar products could cause. We previously had gutter guards snapped into our gutters that didn't last. He explained how his product is installed, how it allowed the rain to drain and how it was installed to prevent them from popping off. He also offers a great workmanship and factory warranty. The prices was very affordable. Our installation was done within 2 days. His worker arrived on-time, introduced himself and started working Brian stopped by to check on the installation. We had a follow-up question after the installation and Brian responded right away. We definitely recommend this product and company."
Micro Mesh
Micro Mesh
Micro Mesh
24 neighbors recently requested a quote
Recommended by85%of homeowners
Avatar for Illinois Gutter Pros
Illinois Gutter Pros
5.0(
6
)
Gutter Covers and Accessories - Install or ReplaceSeamless Metal Gutters - InstallSeamless Metal Gutters - Repair

Serving Winchester, IL and surrounding areas

In business since 2025

Free estimates

Emergency services offered

"Illinois gutter pros installed seamless black gutters on our newly remodeled home. They were quick and efficient and got the job done well. The gutters have saved our basement from flooding in these heavy rains in July. I would recommend them to anyone looking for gutter repair or installation."
Avatar for Bath Planet of Springfield
Bath Planet of Springfield
4.8(
18
)
Copper Gutters - RepairGalvanized Gutters - RepairGutter Covers and Accessories - Install or Replace+5 more

Serving Winchester, IL and surrounding areas

In business since 1999

Free estimates

Credit card accepted

"HIGH QUALITY job. The estimate was the highest one I received, but the materials were far superior to all others. These look great, SOLID INSTALLATION.  Took away existing gutter that was installed.  Professional from the estimate to the install.  Showed me that he had worker's comp insurance on his workers as well as being licensed and bonded.  Home owner's insurance does not cover hired workers on home improvement projects.  Very important."
Tub to Shower Conversions
Shower Remodeling
Bathtub Remodeling
Bathtub Remodeling
Tub to Shower Conversions

+25

Recommended by92%of homeowners
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Gutter Repair and Replacement FAQs, answered by experts

There are gutter repair experts who specialize in gutter maintenance. These professionals can help with clogging, leaks, sagging, or other issues. An experienced pro should also be able to tell you when a repair won’t be enough and a full replacement will be necessary. Keeping your gutters in great shape is how you prevent bigger problems from forming.

On average, gutters need to be replaced every 20 years. Unprotected gutters in more extreme weather conditions are more prone to breaking and may need to be replaced sooner. Meanwhile, proper maintenance can extend your gutter’s life span even further. That said, proper installation, gutter hangers to provide additional support, and gutter guards or helmets all play an important role in how long your gutters last.

Buried downspouts can freeze during cold weather as cold water runs through them. If you’ve discovered your downspouts are frozen, you can carefully pour hot water down the top of the downspout to defrost them. If that doesn’t work, you may need to dig your downspout back up. Avoid trying to break the ice from the exterior using a hammer as this can cause cracks and damage to your downspout.

To avoid freezing the future, consider adding a heating cable to the exterior, which can adjust heat based on the surrounding temperature.

The average cost to install or replace gutters is around $2,000, with typical project costs ranging from $900 to $7,000. Most companies charge between $4 and $30 per linear foot. The total price depends on several factors, including the size of your home, the complexity of its footprint, the gutter material (e.g., vinyl, metal), and the gutter style (e.g., half-round, custom-built). Additional elements like downspouts, corners, and optional add-ons like gutter guards can also increase the price. The condition of your roof is another consideration, as new gutters cannot be installed on a rotting or sloping roof. While it can be an expensive upfront cost, new gutters are a worthwhile, long-lasting investment for protecting your home's exterior. You can save up to half on labor costs by installing them yourself.

The most common problem with gutters is clogging from debris like leaves, blossoms, and seeds from surrounding trees. This debris can block downspouts, leading to improper drainage and water overflow.

Other common issues include:

  • Leaks and holes, which can often be repaired with gutter sealant or caulk.

  • Rust, sagging, or detachment from the roofline.

  • Damage from strong storms.

  • Improperly pitched gutters that don't drain correctly.

Regular cleaning in the spring and fall is the best way to prevent most of these problems. You may need to clean them more often during periods of heavy leaf fall.

The Winchester, IL homeowners’ guide to gutter repairs and replacements

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