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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."
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+3

Response time12 hrs
Response rate100%
5 neighbors recently requested a quote
Avatar for New England Home Performance Kings
New England Home Performance Kings
4.3(
529
)
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
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Gutter Cleaning FAQs, answered by experts

Icicles don't necessarily mean your gutters are clogged or bad, but they can indicate an underlying issue. While clogged gutters can cause icicles to form, the problem could also be an ice dam on your roof from poor insulation. In that case, melting snow can refreeze in the gutter even without a clog. Regardless of the cause, the weight of the ice can damage your gutters or even rip them completely off the house. If you are unsure of the underlying problem, it's best to call a roofing company to assess the issue and implement a permanent solution.

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.

Clean regularly, inspect for rust or damage, and apply sealant to joints as needed.

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

Gutters should be cleaned at least twice a year, in the spring and in the fall, to remove the debris from trees that can clog the eavestroughs and downspouts. Debris like leaves, twigs, and seed pods can build up and cause your gutters to overflow, potentially causing damage to your roof and foundation. Water backing up under the shingles can rot the edge of your roofline. Overflow water falling next to your foundation can end up leaking into your basement or crawl space.

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.