Top-rated gutter cleaning pros.

Get matched with top gutter cleaning pros in Chester, MA

Enter your zip and get matched with up to 5 pros

Need a pro for your gutter cleaning project in Chester, MA?

Select your specific project to find the pro for you.

Find Gutter cleaning pros in Chester

Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,524
)
Gutters & Downspouts - Clean

Serving Chester, MA 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."
Free no obligation estimates
Free no obligation estimates
Metal Screen mesh ontop of gutter
Free-flowing water in clean gutters
Debris resistant gutter protection

+63

10157 neighbors recently requested a quote
Recommended by83%of homeowners
Avatar for Advanced Seamless Gutters
Advanced Seamless Gutters
4.4(
210
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"Removed old gutters, installed new, seamless gutters, downspouts and gutter guards. Needed to work around an awning for the downspout with excellent looking results. Polite workers and cleaned up the yard after work was completed. Patty C."
BASEMENT RE-FINISHING
MOLD CERTIFICATION
Hatchway
Footer
Hatchway Foundation Walls

+63

Response time3 days
67 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for SOS Powerwash
SOS Powerwash
5.0(
12
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Chester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2022

Free estimates

Small jobs welcome

"My house and roof look fantastic. The chemical used for treating the moss on a portion of my roof also affected some of my surround plants on the ground. I'm sure they will come back fine next spring. It was worth it to have a clean house and roof."
What We Do...
What We Do...
What We Do...
What We Do...
Front Steps

+42

Response time3 hrs
Response rate89%
28 neighbors recently requested a quote
Avatar for CJ's Gutter and Glass
CJ's Gutter and Glass
4.0(
4
)
Gutters & Downspouts - Clean

Serving Chester, MA and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We offer a variety of General Contractor services that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of each and every project that we are involved with. We look forward to building lasting relationships and guarantee your satisfaction!\n

10 neighbors recently requested a quote
Avatar for Chloe’s Cleaning Co
Chloe’s Cleaning Co
New to Angi
Gutters & Downspouts - Clean

Serving Chester, MA and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

Hi, I’m Chloe!! I’m a friendly, dependable housekeeper who genuinely enjoys helping people create clean, comfortable, and welcoming homes. I take pride in my work and pay close attention to detail, ensuring every space is cleaned with care and thoroughness. With previous housekeeping experience, I understand the importance of reliability, professionalism, and treating your home with respect. I’m currently growing my housekeeping business and am excited to connect with new clients through this platform. I look forward to earning your trust and helping keep your home looking its best!! Please feel free to reach out to me with any questions, to receive a custom quote or for more information

Avatar for Gutters & More
Gutters & More
4.2(
27
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Chester, MA and surrounding areas

In business since 1996

Free estimates

Emergency services offered

"They responded to my request for an estimate right away. They cleaned my gutters, replaced my gutter leaf guards, and removed and replaced a section of gutter and the attached downspout.They worked efficiently and did a great job. I was very pleased with the value I received and the workmanship and professionalism of the crew"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+7

Recommended by90%of homeowners
...
Showing 1-10 of 58
Gutter Cleaning questions, answered by experts

Yes, professionals can spot and rectify downspout issues such as clogs, leaks, or disconnections during cleaning. They ensure proper water flow, protecting the building's foundation and preventing water damage or erosion.

It’s best to schedule regular gutter cleanings before there’s a major issue, but sometimes life gets in the way. Luckily, a few telltale signs will let you know when to clean your gutters ASAP:

  • You notice built-up debris in your gutters.

  • Your gutters overflow with water when it rains.

  • Water doesn’t readily flow from your downspouts.

  • Your gutters are damaged or visibly leaking.

  • You notice evidence of leaking along your roof, siding, yard, or pavement.

  • Your gutters have pulled away from your roofing or exterior walls.

  • You see water damage on your soffits or fascia.

  • You have weeds growing in your gutters.

  • You start to see ants or other insects around your gutters or in your home.

  • You suddenly have issues with leaks in your crawl space or basement.

Whether or not you can use a pressure washer to clean your gutter guards depends on the type of gutter guard you have and the strength of the pressure washer. Most gutter guards can handle a low-pressure setting but check first. If you’re unsure if your gutter guard is designed for pressure washing, check your manufacturer’s instructions, ask a pro, or use a garden hose to clean the gutter guard instead. As gutter guards age, they become less resistant to the strong forces of a power washer, so treat older gutter guards with more care.

The cost to install a downspout extension or reroute a downspout generally falls between $30 and $200. The final price depends on factors like whether you DIY the project or hire a gutter professional, the complexity of your gutter system, and the length of the new extension. A simple, above-ground DIY installation can cost as little as $30 for materials. In contrast, a more complex project involving professional installation and digging trenches for underground piping could cost over $1,000. This is still a significant saving compared to replacing your entire gutter system, which costs around $1,900 on average.

It’s recommended that you clean your gutters after a severe storm, however, regular storms don’t raise the same concerns. Look for signs your gutter might need cleaning after a harsh storm. Do you see broken branches and excessive leaves all over your yard? Chances are your gutters caught quite some debris. Also, ensure a few drying days before cleaning your gutters. Dry debris is much easier to clean.

The Chester, MA homeowners’ guide to gutter cleaning services

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