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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."
26 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

You may have a clogged gutter. Downspouts can also clog if your gutter collects too much debris. Hire a professional gutter cleaner, and if you still have problems, install a gutter guard (which prevents debris from entering your gutter system) and a downspout extension (which helps drain water further away from your foundation, so it doesn't pool near your house). Follow these tips to keep your gutter downspouts clean.

Water overflow, foundation damage, and mold growth are risks.

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.

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.

There are several ways to tell if your gutter downspout drain is backed up. The most obvious sign is when you see water flowing over your gutter edges. This can occur during everything from light rain to a rainstorm. Additional signs can include peeling paint around your downspout, visible dirt around your downspout, and moisture on the side of the house. If you're having ongoing problems with clogs caused by a poorly designed or worn-out gutter system, consider getting a quote for gutter replacement cost.

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.