Top-rated gutter cleaning pros.

Best gutter cleaning pros near Littleton, MA

Enter your zip and get matched with up to 5 pros

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

Select your specific project to find the pro for you.

TRUSTED BY LITTLETON, MA HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon332
    Verified gutter cleaning services reviews

Top-Rated Gutter cleaning pros in Littleton - Updated Nov 2026

Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
740
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Littleton, MA and surrounding areas

Approved

In business since 2000

Offers commercial services

Customers say: Quality work

"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
Response rate100%
5 neighbors recently requested a quote
Avatar for Gutter Kings
Gutter Kings
4.3(
528
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Littleton, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"Received estimate on 11/14/16 from Wayne. Was told that it would be a week out before scheduling, Crew showed up on 11/15/16 to take care of the job. All in all, unless the lack of service from East Coast Gutter - Hollis, NH, Gutter Kings was very responsive, professional, and quick with the repair. Will be hiring them for a bigger job this coming Spring."
27 neighbors recently requested a quote
Recommended by83%of homeowners
Avatar for GUTTER MASTER SERVICE LLC
GUTTER MASTER SERVICE LLC
5.0(
7
)
Gutters & Downspouts - Clean

Serving Littleton, MA and surrounding areas

Approved

Free estimates

Credit card accepted

Offers commercial services

We are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade, combined with ability, is what makes us true professionals. Above all, we are watchful of our customers' interests and make their concerns the basis of our business \n \n

14 neighbors recently requested a quote
Avatar for Top Tier Construction
Top Tier Construction
5.0(
12
)
Gutters & Downspouts - Clean

Serving Littleton, MA and surrounding areas

Approved

In business since 2025

Free estimates

Emergency services offered

"Top Tier Construction did an amazing job on my roof replacement. From the initial call Jimmy was super professional, he explained every detail and helped us choose the perfect roof for us. Jimmy was very polite, professional and courteous. He explained his price, answered any questions I had and showed up when he said he would. They are gaf certified contractors which gives you access to exclusive warranties. They showed up on time and completed my roof in one day. Everything was cleaned up super well and the following morning Jimmy came back to make sure the crew didn't miss any nails. My roof looks fantastic. I couldn't be happier. I highly recommend them!"
Garage Roof Replacement
Garage Roof Replacement
Garage Roof Replacement
Garage Roof Replacement
6 neighbors recently requested a quote
...
Showing 1-10 of 243
Gutter Cleaning FAQs, answered by experts

Underground downspouts refer to the sections of downspout extensions that lead away from your home and gutter system. While they cost more than traditional extensions, they can provide several benefits, such as less frequent damage and no need to move them for lawn care tasks. Whether they're worth it or not depends on your budget at installation time and how much convenience they'll add to your situation.

Hiring a local gutter cleaner costs an average of $119 to $228. For many homeowners, it’s worth bringing in a pro to make sure there’s a regular cleaning schedule and that the job is done thoroughly. A pro can also inspect your gutters and roofline and flag any issues before you start experiencing costly mold, rot, or water damage.

Although having gutter guards and hoods dramatically reduces the number of times you will have to clean out your gutters, it doesn't necessarily mean that you won't ever have to clean your gutters. Experts recommend cleaning your gutters at least once every two years, even with gutter guards and hoods installed. If you don’t want to clean them yourself, you can hire a gutter cleaning company near you to complete the job.

At least twice a year, or more if surrounded by trees.

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 Littleton, MA homeowners’ guide to gutter cleaning services

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