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
)

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

10064 neighbors recently requested a quote
Recommended by83%of homeowners
Avatar for Advanced Seamless Gutters
Advanced Seamless Gutters
4.4(
210
)

Serving Chester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"I used advanced seamless gutters for gutters on my house and they did a wonderful job. Also they were able to take care of my leaky basement faster than anyone could even come out to give an estimate.They were clean and professional and reasonably priced."
BASEMENT RE-FINISHING
MOLD CERTIFICATION
Hatchway
Footer
Hatchway Foundation Walls

+63

Response time1 day
82 neighbors recently requested a quote
Recommended by92%of homeowners
Avatar for MPC General Cleaning LLC
MPC General Cleaning LLC
5.0(
14
)

Serving Chester, MA and surrounding areas

Approved

In business since 2021

Free estimates

Warranties offered

"Excellent. Both the house and gutters were pristine when completed! They arrived on time. They were very respectful of property."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+19

Response time1 day
2 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for SOS Powerwash
SOS Powerwash
5.0(
12
)

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 time7 hrs
Response rate91%
29 neighbors recently requested a quote
Avatar for CJ's Gutter and Glass
CJ's Gutter and Glass
3.7(
3
)

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

5 neighbors recently requested a quote
Avatar for Chloe’s Cleaning Co
Chloe’s Cleaning Co
New to Angi

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
)

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 59
Gutter Cleaning questions, answered by experts

Regular cleaning, checking for leaks, and ensuring that downspouts direct water away from the foundation help prolong gutter life.

You can clean the gutters on a two-story house using gutter tongs on an extension pole. However, cleaning second-story gutters from a ladder or the roof is very dangerous and should be done by a professional.

The best times of year to clean your gutters are typically in the spring and fall. Cleaning in the fall is crucial for removing leaves and debris that have accumulated, which helps prevent clogs. A spring cleaning ensures your gutters are clear and prepared for seasonal rainfall.

As a general guideline, experts recommend cleaning your gutters at least twice a year. However, the optimal frequency depends on several factors, such as local weather patterns, the type of gutters you have, and the number of trees on your property. If your home is surrounded by many large trees or pine trees, you may need to clean your gutters as often as every three to four months. If you have few or no trees nearby, twice a year is likely sufficient. In some cases, you may need to clean them a couple of times during the fall and spring to keep them clear and allow water to flow freely.

Walking on the roof to clean gutters is unsafe and not recommended due to significant safety risks. It is especially dangerous on steep or slippery roofs, or if the roof is wet or covered in leaves, which increases the chance of a fall. In addition to personal injury, walking on the roof can damage shingles, potentially leading to water leaks. Instead of walking on the roof, use a sturdy ladder positioned on a stable surface to access the gutters. Be aware that using a ladder also carries risks, as it can be difficult to maintain balance while performing the work. You can also use ground-based cleaning tools. For safety reasons and to prevent damage to your roof, hiring a professional to clean your gutters is the best and safest option.

Yes, gutters can still get clogged even with gutter guards installed. While guards significantly reduce the amount of debris that enters your gutters, they are not 100% effective.

Small debris such as pine needles, seedlings, algae, small leaves, and pebbles can pass through the guard's screen or mesh and accumulate over time. Clogs can also form if the guards themselves are not cleaned and become overwhelmed with debris on top, preventing water from entering the gutter.

If this buildup is neglected, it can lead to clogs, water leaks, mold growth, and even plants sprouting from the gutters. The primary benefit of gutter guards is not the complete elimination of maintenance, but a dramatic reduction in how often you need to perform it, often from several times a year to just once a year or less.

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.