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  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon649
    Verified gutter cleaning services reviews

Verified Reviews for Gutter Cleaning pros in Winchester, MA

*The Angi rating for Gutter Cleaning companies in Winchester, 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 Winchester, 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 August 14, 2026

Find Gutter cleaning pros in Winchester

Avatar for JLM Gutter Cleaning Service
JLM Gutter Cleaning Service
4.4(
533
)
Gutters & Downspouts - Clean

Serving Winchester, MA and surrounding areas

Approved

In business since 1998

Free estimates

Small jobs welcome

For over 25 years, JLM Gutter Cleaning Service has remained locally Family Owned & Operated, specializing in all things Gutter-related. Cost is determined by the job. Call (800) 362-0933 to schedule an Estimate or an Appointment. Mailing Address: PO Box 553 Stoughton, MA 02072.

Gallery
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2 neighbors recently requested a quote
Recommended by88%of homeowners
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Avatar for AAA Sparkling Window & Gutter Cleaning
AAA Sparkling Window & Gutter Cleaning
4.6(
389
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 1925

Free estimates

Warranties offered

"Scheduled my house very quickly after I called. They did a great job of cleaning gutters and downspouts.
"
Response time2 days
Response rate100%
2 neighbors recently requested a quote
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Avatar for Elite Gutter Cleaning Service
Elite Gutter Cleaning Service
5.0(
28
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2022

Free estimates

Offers commercial services

"Cleanest my gutters have ever been. I switched this year and I am very happy"
Response time20 mins
Response rate100%
Recommended by100%of homeowners
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Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
739
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2000

Free estimates

Warranties offered

"Prompt quoting; prompt service; completed on time; cleaned up; identified some additional concerns that they corrected in the quoted price. Everything they did was properly and neatly done."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

Response time12 hrs
Response rate100%
7 neighbors recently requested a quote
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Avatar for Valley View Gutter Cleaning LLC
Valley View Gutter Cleaning LLC
5.0(
14
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2019

Free estimates

Credit card accepted

"Showed a video of the process.. Cleaned debris. Very easy to work with"
Gutters Cleaning
Gutters Cleaning
Gutters Cleaning
Gutters Cleaning
Gutters Cleaning

+11

1 neighbors recently requested a quote
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Avatar for Sun Bright Window Cleaning
Sun Bright Window Cleaning
4.9(
134
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"Sunbright cleaned our interior and exterior windows and also cleaned our gutters . We were 100% pleased with their promptness, their communication and the work they performed. The staff wore masks and booties while working inside. Very careful and professional! I strongly recommend this company."
House power washing
During the power washing
After work is done
Before Cleaning
After cleaning

+13

Response time2 hrs
Response rate98%
1 neighbors recently requested a quote
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Avatar for Gutter Kings
Gutter Kings
4.3(
527
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"They came, they gave me a date, they did their thing and I gave them a check. They did a good job. They got rid of all the debris that were all over the gutters. I would recommend them and I would use them again."
30 neighbors recently requested a quote
Recommended by83%of homeowners
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Avatar for American Gutter Cleaning & Installations, Inc.
American Gutter Cleaning & Installations, Inc.
4.9(
31
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1990

Free estimates

Warranties offered

"Very polite and thorough cleaning of gutters"
After Cleaning
Before Cleaning
Before Cleaning
Gutter Install
Gutter Install

+4

Response time9 hrs
Response rate98%
202 neighbors recently requested a quote
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Avatar for Boston Window Cleaning
Boston Window Cleaning
5.0(
12
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, MA and surrounding areas

Approved

In business since 2021

Free estimates

Small jobs welcome

"Boston Window Cleaning responded very promptly to my gutter and downspout cleaning request and came the same day. Jay was friendly, professional, worked efficiently, and did a great job on our house, which has some tight spaces for accessing the gutters. And the price was very good. Will definitely use these guys again."
Power washing
Power washing
Power washing
Power washing
Power washing

+4

29 neighbors recently requested a quote
Recommended by8%of homeowners
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Showing 1-10 of 352
Gutter Cleaning questions, answered by experts

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.

Yes, gutter cleaning methods without using a ladder are available, including:

  • A curved wand attachment for your hose 

  • Gutter tongs on an extension pole

  • A leaf blower gutter cleaning kit

  • Vacuum designed for cleaning gutters

Just be sure that your downspouts are connected and can direct water away from the house if you’re using a water-powered method. This will keep the water from dumping next to the house.

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.

No—gutters should be designed and properly installed so they are ready to handle any level of rainflow from your roof. If you notice pooling water around your gutters or on the roof, it’s imperative that you contact a gutter repair pro near you—the slope of your gutters could be off and need adjusting.

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

The Winchester, 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