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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.
"
3 neighbors recently requested a quote
Recommended by96%of homeowners
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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
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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

"Perfect experience. Claimed an Angie's List deal for gutter cleaning. Joe called within the hour and got me on their schedule on the same day. Guys arrived promptly and thoroughly cleaned all of our gutters. There is a steep hill on one side of our house which has prevented other gutter cleaning companies from getting to the gutter over that area, but Joe's crew got up on the roof and cleaned that area, too. They cleaned up well afterwards, as well. Couldn't have asked for a better experience. Will definitely have them back in the fall."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

3 neighbors recently requested a quote
Recommended by97%of homeowners
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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(
2,524
)

Serving Roslindale, MA and surrounding areas

Approved (Corporate)

In business since 2005

Free estimates

Warranties offered

"I was tired of cleaning my gutters so I had the gutters cleaned out, sealed, and LeafFilter Gutter Guards installed. Excellent job!"
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

10144 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(
3,396
)

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

4569 neighbors recently requested a quote
Recommended by86%of homeowners
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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 rate92%
21 neighbors recently requested a quote
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Showing 1-10 of 321
Gutter Cleaning questions, answered by experts

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.

The cost to install a downspout extension or reroute a downspout generally falls between $30 and $200. The final price depends on factors like whether you DIY the project or hire a gutter professional, the complexity of your gutter system, and the length of the new extension. A simple, above-ground DIY installation can cost as little as $30 for materials. In contrast, a more complex project involving professional installation and digging trenches for underground piping could cost over $1,000. This is still a significant saving compared to replacing your entire gutter system, which costs around $1,900 on average.

Regular cleaning, applying rust-resistant coatings, and checking for leaks help extend their lifespan.

It’s best to schedule regular gutter cleanings before there’s a major issue, but sometimes life gets in the way. Luckily, a few telltale signs will let you know when to clean your gutters ASAP:

  • You notice built-up debris in your gutters.

  • Your gutters overflow with water when it rains.

  • Water doesn’t readily flow from your downspouts.

  • Your gutters are damaged or visibly leaking.

  • You notice evidence of leaking along your roof, siding, yard, or pavement.

  • Your gutters have pulled away from your roofing or exterior walls.

  • You see water damage on your soffits or fascia.

  • You have weeds growing in your gutters.

  • You start to see ants or other insects around your gutters or in your home.

  • You suddenly have issues with leaks in your crawl space or basement.

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 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.

See all articles