Top-rated gutter repair and replacement pros.

Get matched with top gutter repair and replacement pros in Chestertown, NY

Enter your ZIP and get matched with up to 5 pros

Need a pro for your gutter repair and replacement project in Chestertown, NY?

Select your specific project to find the pro for you.

Verified Reviews for Gutter Repair And Replacement pros in Chestertown, NY

*The Angi rating for Gutter Repair And Replacement companies in Chestertown, NY 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 Chestertown, NY 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 November 12, 2025

Find Gutter repair and replacement pros in Chestertown

Avatar for Kimble Services LLC

Kimble Services LLC

No reviews yet

Kimble Services LLC

No reviews yet
2 years of experience

We specializing in Property Management, Remodeling, Decks, Sheds, and Lawn Care. Bringing 25+ years of Union Carpentry experience to deliver the most professional product possible.

We specializing in Property Management, Remodeling, Decks, Sheds, and Lawn Care. Bringing 25+ years of Union Carpentry experience to deliver the most professional product possible.

Avatar for Top Gen Roofing

Top Gen Roofing

No reviews yet

Top Gen Roofing

No reviews yet
10 years of experience

We have the experience and dedication to get the job done right! Specializing in Gutter Repair and Replacement services; We guarantee your satisfaction, and we won't leave until the job is done right. We pride ourselves on the quality work we provide, while delivering great customer service! Call or click for your FREE estimate today!

We have the experience and dedication to get the job done right! Specializing in Gutter Repair and Replacement services; We guarantee your satisfaction, and we won't leave until the job is done right. We pride ourselves on the quality work we provide, while delivering great customer service! Call or click for your FREE estimate today!

Compass Contracting & Property Services, LLC

No reviews yet

Compass Contracting & Property Services, LLC

No reviews yet
4 years of experience

We are a small, family-run business that specializes in residential remodels, improvements and maintenance. Whether you're looking for a home renovation or addition, or for 'handyman' repair services, our 10+ years of experience and unwavering attention-to-detail ensures you'll get the job done right the first time, and on time.

We are a small, family-run business that specializes in residential remodels, improvements and maintenance. Whether you're looking for a home renovation or addition, or for 'handyman' repair services, our 10+ years of experience and unwavering attention-to-detail ensures you'll get the job done right the first time, and on time.

Latham Roofing & Siding

No reviews yet

Latham Roofing & Siding

No reviews yet
Free onsite estimate

A dependable company that handles roofing and siding. We offer competitive pricing, fantastic service and an overall great experience for homeowners and businesses. Please feel free to reach out for a free quote today!

A dependable company that handles roofing and siding. We offer competitive pricing, fantastic service and an overall great experience for homeowners and businesses. Please feel free to reach out for a free quote today!

Avatar for Gunner Roofing

Gunner Roofing

4.86(
57
)

Gunner Roofing

4.86(
57
)
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers

Gunner Roofing knows your home is everything. That’s why Gunner was founded with one clear mission: to bring your home improvement project to life with exceptional quality, a personalized experience, and innovative tech to make your project easier than ever. We’re the first roofing company to service nationally as well as the first to offer accurate online quotes in under an hour meaning no more hours on the phone or juggling appointments to meet a dodgy contractor. Gunner is here to make it easy for you - we even help you navigate financing your project through Wells Fargo and assist with permitting. We’re proud to be your go-to roofing, siding, windows, and gutter installer, working with only the industry’s most trusted suppliers like Andersen Windows, Brava Roof Tile, GAF, and James Hardie. Whether you want to upgrade your home’s exterior or ensure your house will protect your family through the next storm, Gunner is excited to work with you as your trusted partner. Skeptical? We get it, this is no small decision. Check out our hundreds of 5-star reviews on google and find us on Inc. 5000 Fastest Growing Companies List, Fast Company’s Most Innovative Companies List, Good Housekeeping Home Reno Award Winners Page, Architectural Digest and more! If you’re curious about how much your project would cost, get your free roofing quote at https://www.gunnerroofing.com/ today - no commitment necessary.

"I am sure that all positive reviews for this company are fake. Nothing that was promised to me was delivered. My siding project is still ongoing for over 1 month. Was told that it would be done in week. Had one rain day. They have system like this: 1) sales person who never installed anything he will promise you things that obviously are not true, 2) crew that is subcontracted but not Gunner, mine was driving for over 2 hours away, 3) person who oversees the project but has little control over anything, no supply, doesn't know the crew, crew does not listen to him, main office does not listen to him, 4) main office does not reply to you. They just tell me to talk to project manager who has no control. So you understand that if there are any issue you are on your own. Quality or work is not good. Many times I had to point to the crew what's wrong, planks are broken yet they were still installing it, caulking is done they way that I can do it better, they cut wires to awning etc"

Eduard S on September 2025

Gunner Roofing knows your home is everything. That’s why Gunner was founded with one clear mission: to bring your home improvement project to life with exceptional quality, a personalized experience, and innovative tech to make your project easier than ever. We’re the first roofing company to service nationally as well as the first to offer accurate online quotes in under an hour meaning no more hours on the phone or juggling appointments to meet a dodgy contractor. Gunner is here to make it easy for you - we even help you navigate financing your project through Wells Fargo and assist with permitting. We’re proud to be your go-to roofing, siding, windows, and gutter installer, working with only the industry’s most trusted suppliers like Andersen Windows, Brava Roof Tile, GAF, and James Hardie. Whether you want to upgrade your home’s exterior or ensure your house will protect your family through the next storm, Gunner is excited to work with you as your trusted partner. Skeptical? We get it, this is no small decision. Check out our hundreds of 5-star reviews on google and find us on Inc. 5000 Fastest Growing Companies List, Fast Company’s Most Innovative Companies List, Good Housekeeping Home Reno Award Winners Page, Architectural Digest and more! If you’re curious about how much your project would cost, get your free roofing quote at https://www.gunnerroofing.com/ today - no commitment necessary.

"I am sure that all positive reviews for this company are fake. Nothing that was promised to me was delivered. My siding project is still ongoing for over 1 month. Was told that it would be done in week. Had one rain day. They have system like this: 1) sales person who never installed anything he will promise you things that obviously are not true, 2) crew that is subcontracted but not Gunner, mine was driving for over 2 hours away, 3) person who oversees the project but has little control over anything, no supply, doesn't know the crew, crew does not listen to him, main office does not listen to him, 4) main office does not reply to you. They just tell me to talk to project manager who has no control. So you understand that if there are any issue you are on your own. Quality or work is not good. Many times I had to point to the crew what's wrong, planks are broken yet they were still installing it, caulking is done they way that I can do it better, they cut wires to awning etc"

Eduard S on September 2025

Avatar for White-j contracting and services

White-j contracting and services

No reviews yet

White-j contracting and services

No reviews yet
10 years of experience

We replace and install windows and doors,kitchens and baths,flooring and tile,custom trim,repair and install drywall.interior painting.

We replace and install windows and doors,kitchens and baths,flooring and tile,custom trim,repair and install drywall.interior painting.

Build Right LLC

No reviews yet

Build Right LLC

No reviews yet
10 years of experience

The Build Right team goes to every job with over 20 years of experience under their belt. We pride ourselves on our experience, quality, and craftsmanship. Our customers can always rely on us being honest, reliable and prompt; together, these values make up the foundation of our business. We focus on providing high-quality service and customer satisfaction and we will do everything we can to exceed your expectations. Call us today for an free estimate.

The Build Right team goes to every job with over 20 years of experience under their belt. We pride ourselves on our experience, quality, and craftsmanship. Our customers can always rely on us being honest, reliable and prompt; together, these values make up the foundation of our business. We focus on providing high-quality service and customer satisfaction and we will do everything we can to exceed your expectations. Call us today for an free estimate.

Showing 1-10 of 46
Gutter Repair and Replacement questions, answered by experts

Repairs typically take 1-3 hours, depending on the complexity and location.

Leaks, corrosion, sagging sections, and loose fasteners are common problems that need fixing.

If your gutters get overwhelmed every time it rains, adding an extra downspout is a solution. First, you'll need to decide where to add the downspout. If your current setup only has a single downspout, one option is to place a new one at the opposite end of the gutter. If you already have a downspout at each end, adding a third one in the middle can help to lighten the load. 

You can hire a professional to add a downspout yourself by cutting into the existing gutter and attaching the necessary parts, such as an outlet and brackets.

Zinc gutters can truly last a lifetime. As one of the strongest materials used for roofing and gutter systems, zinc can last up to 90 years. Even copper gutters don't last as long as zinc gutters. Zinc gutters are a long-lasting investment in both the value and appearance of your home.

Frequently, when water flows over gutters, it indicates a potential clog, necessitating cleaning. For instance, if a twig becomes lodged in the downspout, it can lead to a traffic jam, causing more leaves and sticks to accumulate. Another potential issue is an incorrect pitch, as gutters should channel water toward the downspout. If you observe water overflowing the end cap or leaking through it, it suggests that your gutters are improperly tilted.

The Chestertown, NY homeowners’ guide to gutter repairs and replacements

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

See all articles