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TRUSTED BY ROSLINDALE, MA HOMEOWNERS

  • Average homeowner rating star icon4.3
    Average homeowner rating
  • Verified reviews icon818
    Verified gutter cleaning services reviews

Verified Reviews for Gutter Cleaning pros in Roslindale, MA

*The Angi rating for Gutter Cleaning companies in Roslindale, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Cleaning needs.

*The HomeAdvisor rating for Gutter Cleaning companies in Roslindale, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Gutter Cleaning needs.

Last update on July 18, 2025

Find Gutter cleaning pros in Roslindale

Avatar for AAA Sparkling Window & Gutter Cleaning
AAA Sparkling Window & Gutter Cleaning
4.6(
389
)

Serving Roslindale, 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.
"
Response time2 days
Response rate100%
2 neighbors recently requested a quote
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Avatar for Third Generation Window & Gutter Cleaning
Third Generation Window & Gutter Cleaning
4.8(
110
)

Serving Roslindale, MA and surrounding areas

Approved

In business since 2005

Free estimates

Warranties offered

"We just had all our window cleaned, both interior and exterior. Karl and his team did an immaculate job; the windows sparkle, any furniture that had to be moved was put back exactly in place and they were fully prepared to maintain with masks, gloves, booties and safe distancing. I’ve used Third Generation for many years."
Additional Photos
Additional Photos
Additional Photos
Gutter Repairs
Additional Photos

+6

2 neighbors recently requested a quote
Recommended by98%of homeowners
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Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
738
)

Serving Roslindale, 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
Response rate100%
3 neighbors recently requested a quote
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Avatar for Sun Bright Window Cleaning
Sun Bright Window Cleaning
4.9(
134
)

Serving Roslindale, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"Everado reached out to me right away. He was very professional and friendly. They were on time and did a good job. I am satisfied and have arranged for another gutter cleaning before the winter. I would recommend this company."
House power washing
During the power washing
After work is done
Before Cleaning
After cleaning

+13

Response time2 hrs
Response rate98%
Recommended by100%of homeowners
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Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,526
)

Serving Roslindale, MA and surrounding areas

Approved (Corporate)

In business since 2005

Free estimates

Warranties offered

"I simply want my gutters cleaned and an opinion re the gutter and roof status. Not interested in gutter replacement at this time."
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

10295 neighbors recently requested a quote
Recommended by83%of homeowners
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Avatar for Ned Stevens Gutter Cleaning
Ned Stevens Gutter Cleaning
4.1(
3,399
)

Serving Roslindale, MA and surrounding areas

Approved

In business since 1965

Free estimates

Credit card accepted

"They did an awesome job cleaning my gutters. The job was done quickly and they cleaned up and disposed all of the debris."
Our work
Our work
Our work
Our work
Our work

+1

Response time11 hrs
Response rate100%
4751 neighbors recently requested a quote
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Avatar for Rooster Maintenance Services LLC
Rooster Maintenance Services LLC
5.0(
45
)

Serving Roslindale, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2021

Free estimates

Small jobs welcome

"Rooster Maintenance did an outstanding job cleaning my windows. I also had them clean my gutters.. Fantastic job was done on windows and gutters. Definitely would recommend this company"
Response time1 day
Response rate93%
21 neighbors recently requested a quote
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Showing 1-10 of 321
Gutter Cleaning questions, answered by experts

Absolutely—and lots of it. Overflowing water from your gutters can damage your siding and your roof. All of the moisture getting into the cracks and crevices of your home can lead to mold or mildew problems down the line. In addition, when water pools around your home, it needs a place to go—and sometimes it ends up inside the house, creating a very unwanted flood.

The most common problem with gutters is clogging from debris like leaves, blossoms, and seeds from surrounding trees. This debris can block downspouts, leading to improper drainage and water overflow.

Other common issues include:

  • Leaks and holes, which can often be repaired with gutter sealant or caulk.

  • Rust, sagging, or detachment from the roofline.

  • Damage from strong storms.

  • Improperly pitched gutters that don't drain correctly.

Regular cleaning in the spring and fall is the best way to prevent most of these problems. You may need to clean them more often during periods of heavy leaf fall.

Water should not be dripping behind your gutters. Rain dripping between your gutters and the fascia might indicate that the gutters are misaligned with the fascia board or there are loose screws in the gutters, allowing water to pass through. Start by checking for these issues and make repairs ASAP.

On a typical three-bedroom home, gutter cleaning takes about one hour. For larger homes, especially those with multiple stories, the job can take two to three hours. The time required may increase if the gutters need extensive cleaning, the roof is steep, the gutters are hard to reach, or if gutter guards need to be uninstalled and reinstalled.

While both underground and above-ground downspout extensions are a step up from no downspout extensions, underground downspouts are better for those looking for a more discreet option. Underground downspouts are hidden away—out of sight, out of mind. You won't be bumping into the extended sections with your lawn mower, nor will you see the downspouts sticking out like a sore thumb.

The Roslindale, MA homeowners’ guide to gutter cleaning services

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

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