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TRUSTED BY WINCHESTER, MA HOMEOWNERS

  • 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
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

"They showed up when they said they will and the gutters looks great."
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

"I have been using Hennelly & Son Roofing & Gutters for over 6 years now. Whether it is fixing the gutters, addressing roof problems or simply cleaning gutters, the result is always equally good - great professional job ! What is most amazing is his responsiveness -- Joe as he promises in his voice mail -- always returns your call immediately. In spite of weather not always cooperating he goes the extra mile by working even on Sunday to meet the deadline and make my house ready for an upcoming snow storm !"
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

"Real well, there was some debri left in the yard from the gutter flush"
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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Gutter Cleaning questions, answered by experts

Downspouts channel water from your roof and gutters into the ground following a specific route so water doesn’t accumulate around your house’s foundation. Without a downspout, the standing water will wash away material and disrupt the soil, leading to foundation erosion. The standing water will also form ice around your house during cold weather, causing a safety hazard.

Usually 1-2 hours, depending on gutter length and condition.

Failing to clean your gutters can lead to serious and costly damage. When leaves and other debris cause blockages, water cannot drain properly and will overflow. This can lead to water pooling around your home’s foundation, causing basement flooding and structural damage. The overflow can also damage your roof, siding, and fascia boards, with the constant moisture promoting mold, mildew, and rot. The weight of wet debris can cause gutters to sag or break, while stagnant water creates a breeding ground for pests like mosquitoes and rodents. Additionally, runoff can damage landscaping or freeze on driveways and patios, causing cracks. To prevent these issues, it is recommended to clean your gutters at least once or twice a year.

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.

Once you’ve installed your gutters, you'll need to maintain them. You should clean your gutters once or twice a year to keep them functioning correctly. But if climbing a ladder and scooping out handfuls of wet leaf gunk is just not your thing, you can hire a professional gutter cleaner near you to do the job. 

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