Top-rated gutters & downspouts cleaners.

Get matched with top gutters & downspouts cleaners in Chestnut Hill, MA

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

Find Gutters & downspouts cleaners in Chestnut Hill

Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
697
)

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2000

Free estimates

Warranties offered

"Hennelly & Son sent Jack and Mike and they went above and beyond! They not only cleaned the gutters but also took time and care to listen to my concerns and addressed as needed. Whenever I asked them to look at an area again, they did so without any hesitation and said their goal was to make sure I was satisfied. It is hard to explain the excellent level of service they provided in words. There is good customer service, then there is great customer service, then there is best customer service and then there is Hennelly and Son! And they are so friendly to talk to. I would hire Hennelly & Son again and also highly recommend Jack and Mike. If there was a higher rating than A I would choose that."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

Response time12 hrs
7 neighbors recently requested a quote
Recommended by94%of homeowners
Avatar for Sun Bright Window Cleaning
Sun Bright Window Cleaning
4.9(
128
)

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"I agree with all the other reviewers. Everardo was prompt, professional and extremely thorough in power washing our house. He meticulously got every part of the house from top to bottom sparkling clean. The price was resonable for such a complete job and we are thrilled with the results. We will definitely hire him again. He is going to come back to clean the gutters as well."
House power washing
During the power washing
After work is done
Before Cleaning
After cleaning

+13

Response time2 hrs
Response rate98%
1 neighbors recently requested a quote
Avatar for AAA Sparkling Window & Gutter Cleaning
AAA Sparkling Window & Gutter Cleaning
4.9(
353
)

Serving Chestnut Hill, MA and surrounding areas

Approved

In business since 1925

Free estimates

Warranties offered

"They have been cleaning my gutters for years and always do a great job. They are thorough and don't leave a mess behind. They are coming out in the next week or so do some additional work with the gutters and windows. <br />"
Response time2 days
5 neighbors recently requested a quote
Recommended by96%of homeowners
...
Showing 1-10 of 717
FAQs for gutters & downspouts cleaning service projects in Chestnut Hill, MA

You’ll want to clean gutters once or twice a year—in early spring and again in fall—to keep water flowing and avoid pricey leaks. Homes tucked beneath tall trees or hit with heavy debris may need two to four visits instead. Staying on schedule protects your roof, siding, and foundation from costly water damage.

Even with gutter guards, plan on an occasional cleaning—just not as often as homes without guards. Installing gutter guards blocks leaves, but grit and shingle granules still slip through and pile up over time. A quick sweep keeps water moving and stops overflow that can damage your roof or foundation.

Watch for overflowing water, slow or silent downspouts, sagging sections, or debris peeking over the gutter edge. You might also spot water stains, weeds, or an increasing number of ants in certain areas. Any of these red flags means it’s time to call a gutter cleaning pro for service before minor clogs turn into major leaks.

Skip cleanings for too long and gutters overflow, sending water under shingles, down siding, and toward the foundation. The result can be mold, rotted fascia, basement leaks, and repair bills that dwarf the price of a quick cleaning. It can also mean that future cleanings will be more expensive as it will take pros longer to deep clean gutters that are full of heavy debris. Staying on schedule saves money and headaches.

Plan on gutter cleaning service to take an average of one hour for an average single-story home and two to three hours for taller houses. Add extra time if gutter guards need to come off or clogs are packed in. Pros work methodically, clearing every linear foot so water can flow freely again.

The Chestnut Hill, MA homeowners’ guide to gutters & downspouts cleaning services

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