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  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon193
    Verified gutter cleaning services reviews

Verified Reviews for Gutter Cleaning pros in Chestnut Hill, MA

*The Angi rating for Gutter Cleaning companies in Chestnut Hill, 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 Chestnut Hill, 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 January 04, 2026

Find Gutter cleaning pros in Chestnut Hill

Avatar for Sun Bright Window Cleaning

Sun Bright Window Cleaning

4.93(
128
)
•Approved Pro

Sun Bright Window Cleaning

4.93(
128
)
•Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
9 years of experience

From everything from window cleaning, to gutter cleaning, to power washing, we are the experts you need to take care of your home or business. We provide fast and detailed service and look to treat every home or business as we would our own. We look forward to working with you!

"Would like them to come back NOW. Ellen Mass 617 290-4864"

Ellen M on September 2024

From everything from window cleaning, to gutter cleaning, to power washing, we are the experts you need to take care of your home or business. We provide fast and detailed service and look to treat every home or business as we would our own. We look forward to working with you!

"Would like them to come back NOW. Ellen Mass 617 290-4864"

Ellen M on September 2024

Avatar for Hennelly & Son Roofing & Gutters

Hennelly & Son Roofing & Gutters

4.95(
665
)
•Approved Pro

Hennelly & Son Roofing & Gutters

4.95(
665
)
•Approved Pro
Customers say: Quality work
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
26 years of experience

Hennelly & Son Roofing and Gutters is locally owned and operated, specializing in roofing, gutter installation, gutter cleaning, snow removal on roofs, and much more. Customer satisfaction is our top priority. Call us today for your free estimate!

"Great! Just one of the best home improvement vendors I’ve ever worked with. Excellent service and great work. Joe was super attentive to spotting and troubleshooting problem and worked incredibly well with our neighbors (we live in a brownstone). He worked quickly."

Brian L on September 2025

Hennelly & Son Roofing and Gutters is locally owned and operated, specializing in roofing, gutter installation, gutter cleaning, snow removal on roofs, and much more. Customer satisfaction is our top priority. Call us today for your free estimate!

"Great! Just one of the best home improvement vendors I’ve ever worked with. Excellent service and great work. Joe was super attentive to spotting and troubleshooting problem and worked incredibly well with our neighbors (we live in a brownstone). He worked quickly."

Brian L on September 2025

Avatar for Third Generation Window & Gutter Cleaning

Third Generation Window & Gutter Cleaning

4.91(
104
)
•Approved Pro

Third Generation Window & Gutter Cleaning

4.91(
104
)
•Approved Pro
Customers say: True professional
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
21 years of experience

Third Generation Window & Gutter Cleaning is a third generation family owned and operated business. Karl the owner is a third generation window and gutter cleaner who learned the business by working with his grandfather and later his father. With over 15 years experience we are the subject matter experts in our field. We take pride in our work and strive for excellence. In addition to window and gutter cleaning we are also a licensed construction company that is able to handle all of your remodeling needs. We service residential and commercial. We are also a 2015, 2016, 2017, 2018, 2019 & 2020 Angie's List Super Service Award Company!

"They kept us waiting for almost three weeks. Then they denied that getting the pine needles off the roof was part of the quote, I had to resend them the email that they sent stating it was. We ended up having to hire another company. "

Alyssa K on December 2025

Third Generation Window & Gutter Cleaning is a third generation family owned and operated business. Karl the owner is a third generation window and gutter cleaner who learned the business by working with his grandfather and later his father. With over 15 years experience we are the subject matter experts in our field. We take pride in our work and strive for excellence. In addition to window and gutter cleaning we are also a licensed construction company that is able to handle all of your remodeling needs. We service residential and commercial. We are also a 2015, 2016, 2017, 2018, 2019 & 2020 Angie's List Super Service Award Company!

"They kept us waiting for almost three weeks. Then they denied that getting the pine needles off the roof was part of the quote, I had to resend them the email that they sent stating it was. We ended up having to hire another company. "

Alyssa K on December 2025

Avatar for Rooster Maintenance Services LLC

Rooster Maintenance Services LLC

4.96(
42
)
•Approved Pro

Rooster Maintenance Services LLC

4.96(
42
)
•Approved Pro
Super Service Award
Customers say: Quick response
5 years of experience
Free onsite estimate

Rooster Maintenance is a locally owned and operated company that values honesty and integrity in all aspects of our business. Our dedicated team of professionals have over 10 years of hands on experience, to provide innovative ideas and suggestions tailored to your projects. Our services are customized to your individual needs, paying close attention to the details of each project that we are involved with. Please feel free to contact us today!

"Juan and Ken came right on time and were professional and pleasant, as well as efficient. They did a great job on all of our windows and screens, both inside and out. I recommend them highly."

Ilene S on October 2025

Rooster Maintenance is a locally owned and operated company that values honesty and integrity in all aspects of our business. Our dedicated team of professionals have over 10 years of hands on experience, to provide innovative ideas and suggestions tailored to your projects. Our services are customized to your individual needs, paying close attention to the details of each project that we are involved with. Please feel free to contact us today!

"Juan and Ken came right on time and were professional and pleasant, as well as efficient. They did a great job on all of our windows and screens, both inside and out. I recommend them highly."

Ilene S on October 2025

Avatar for EP LANDSCAPE DEMO & SERVICES LLC

EP LANDSCAPE DEMO & SERVICES LLC

4.97(
37
)
•Approved Pro

EP LANDSCAPE DEMO & SERVICES LLC

4.97(
37
)
•Approved Pro
Super Service Award
1 years of experience
Free onsite estimate

EP Landscape Demo & Services LLC Serving Boston & Surrounding Communities At EP Landscape Demo & Services LLC, we believe your outdoor space should be an inviting, low-stress extension of your home or business not a constant chore. We specialize in transforming tired yards, overgrown grounds, and underperforming landscapes into beautiful, functional environments you can be proud of.

"I highly recommend working with EP Landscape Demo & Services LLC - Boston. I needed help with snow removal and EP the owner spent the time to answer all my questions. He is very responsive, professional, kind, honest and hardworking. The snow removal he did on my property was well done with attention to details and he salts generously after he is done. And yes! They clean your car of snow as well if you ask them. That is great service. You don't need to go outside at all in the cold if you don't want to. Just hire EP Landscape Demo & Services LLC - Boston and you will see magic happen. My front walkway and the sidewalk and the driveway and the part in the street that typically has a mountain of snow from the city plows - all of that got cleared. EP took the time to do a great job and it was by hand too because there were too few inches to use the snowblower. I think it was heavy snow because it was sleeting too with mixed precipitation. Great service and thank you!"

Sarah N on January 2026

EP Landscape Demo & Services LLC Serving Boston & Surrounding Communities At EP Landscape Demo & Services LLC, we believe your outdoor space should be an inviting, low-stress extension of your home or business not a constant chore. We specialize in transforming tired yards, overgrown grounds, and underperforming landscapes into beautiful, functional environments you can be proud of.

"I highly recommend working with EP Landscape Demo & Services LLC - Boston. I needed help with snow removal and EP the owner spent the time to answer all my questions. He is very responsive, professional, kind, honest and hardworking. The snow removal he did on my property was well done with attention to details and he salts generously after he is done. And yes! They clean your car of snow as well if you ask them. That is great service. You don't need to go outside at all in the cold if you don't want to. Just hire EP Landscape Demo & Services LLC - Boston and you will see magic happen. My front walkway and the sidewalk and the driveway and the part in the street that typically has a mountain of snow from the city plows - all of that got cleared. EP took the time to do a great job and it was by hand too because there were too few inches to use the snowblower. I think it was heavy snow because it was sleeting too with mixed precipitation. Great service and thank you!"

Sarah N on January 2026

Avatar for AAA Sparkling Window & Gutter Cleaning

AAA Sparkling Window & Gutter Cleaning

4.85(
353
)
•Approved Pro

AAA Sparkling Window & Gutter Cleaning

4.85(
353
)
•Approved Pro
Customers say: Super punctual
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
101 years of experience

We are a fully insured family run window and gutter cleaning company, with almost 100 years in the business. We take pride in our customer service and community reputation. We clean windows and gutters for any residential, condos, and businesses. We provide free estimates, and can often do so over the phone. Window cleaning is priced per window. Gutter cleaning depends on the height of house and the amount of gutters. We would love to add your home added to our client list.

"They are very responsive, they listen well and they did a great job."

Rick H on September 2019

We are a fully insured family run window and gutter cleaning company, with almost 100 years in the business. We take pride in our customer service and community reputation. We clean windows and gutters for any residential, condos, and businesses. We provide free estimates, and can often do so over the phone. Window cleaning is priced per window. Gutter cleaning depends on the height of house and the amount of gutters. We would love to add your home added to our client list.

"They are very responsive, they listen well and they did a great job."

Rick H on September 2019

Avatar for A-Z Cleaning Services

A-Z Cleaning Services

4.87(
55
)
•Approved Pro

A-Z Cleaning Services

4.87(
55
)
•Approved Pro
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
13 years of experience

Specializing in Gutter Cleaning, Window Cleaning and Pressure Washing, locally owned and operated A to Z Cleaning Services is your one stop shop for all of your cleaning needs. With an emphasis on customer service, our mission is always to ensure the satisfaction of our customers, offering excellent work, punctual and always using the best products on the market. The A to Z team is highly qualified and equipped with safety equipment so that our clients can rest assured that we take all measures to ensure that our work is always carried out under all the safety regulations of the State of Massachusetts. Contact us today and be amazed by our services. We look forward to earning your business! www.azcleaningservicesma.com

"Great communication beforehand. Arrived on time. Perfect cleaning job. Very fair price. Highly recommended."

Christopher B on February 2022

Specializing in Gutter Cleaning, Window Cleaning and Pressure Washing, locally owned and operated A to Z Cleaning Services is your one stop shop for all of your cleaning needs. With an emphasis on customer service, our mission is always to ensure the satisfaction of our customers, offering excellent work, punctual and always using the best products on the market. The A to Z team is highly qualified and equipped with safety equipment so that our clients can rest assured that we take all measures to ensure that our work is always carried out under all the safety regulations of the State of Massachusetts. Contact us today and be amazed by our services. We look forward to earning your business! www.azcleaningservicesma.com

"Great communication beforehand. Arrived on time. Perfect cleaning job. Very fair price. Highly recommended."

Christopher B on February 2022

Avatar for American Gutter Cleaning & Installations, Inc.

American Gutter Cleaning & Installations, Inc.

5.00(
25
)
•Approved Pro

American Gutter Cleaning & Installations, Inc.

5.00(
25
)
•Approved Pro
Super Service Award
Customers say: Terrific value
36 years of experience
Free onsite estimate

American Gutter Cleaning & Installations, Inc., is a family owned and operated company, founded in 1990 by the Rocha family. Who still run the company along with a highly trained, reliable and fully insured staff. We specialize in Gutter Cleaning, Gutter Repair, New Gutter Installations and Gutter Protections.

"They are very easy to communicate. The service is high quality."

Lei H on December 2025

American Gutter Cleaning & Installations, Inc., is a family owned and operated company, founded in 1990 by the Rocha family. Who still run the company along with a highly trained, reliable and fully insured staff. We specialize in Gutter Cleaning, Gutter Repair, New Gutter Installations and Gutter Protections.

"They are very easy to communicate. The service is high quality."

Lei H on December 2025

Better View Cleaning Services

4.71(
236
)
•Approved Pro

Better View Cleaning Services

4.71(
236
)
•Approved Pro
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
20 years of experience

For sparkling, crystal clear windows & spotless post construction clean-up, call Better View Cleaning Services. Our expert staff employs new equipment & thorough techniques to ensure your satisfaction.

"they did a good job."

William D on November 2025

For sparkling, crystal clear windows & spotless post construction clean-up, call Better View Cleaning Services. Our expert staff employs new equipment & thorough techniques to ensure your satisfaction.

"they did a good job."

William D on November 2025

Avatar for J&E Landscape and Construction

J&E Landscape and Construction

4.82(
104
)
•Approved Pro

J&E Landscape and Construction

4.82(
104
)
•Approved Pro
Customers say: Quality work
Recommended by 97% of Angi customers
Recommended by 97% of HomeAdvisor customers
25 years of experience

2016 Super Service Award Winner with 10% OFF for All Angie's List Members! J&E Landscape provides the following services: Landscaping, Hardscaping-Paver Patios-Walkways-Driveways, Retaining Walls, Lawn Maintenance, Landscape Maintenance, Lawn Mowing, Leaf Removal, Bed Clean Up, Edging, Mulching, Seasonal Flower Installation, Weeding, Bush/Shrub Maintenance, Seasonal Snow Removal.

"Did a great job on my spring cleanup and mulching. Very efficient and competitive price. Will continue to employ for ongoing work."

George C on May 2025

2016 Super Service Award Winner with 10% OFF for All Angie's List Members! J&E Landscape provides the following services: Landscaping, Hardscaping-Paver Patios-Walkways-Driveways, Retaining Walls, Lawn Maintenance, Landscape Maintenance, Lawn Mowing, Leaf Removal, Bed Clean Up, Edging, Mulching, Seasonal Flower Installation, Weeding, Bush/Shrub Maintenance, Seasonal Snow Removal.

"Did a great job on my spring cleanup and mulching. Very efficient and competitive price. Will continue to employ for ongoing work."

George C on May 2025

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Showing 1-10 of 707
Gutter Cleaning questions, answered by experts

Spring and fall tend to be the best times of the year to clean gutters. Fall is when all of the leaves drop into your gutters, so you'll want to clear that out to prevent clogs from becoming worse. Once spring comes, you'll also want to make sure that your gutters are clear of debris for in preparation for rainfall.

Clean your gutters at least twice a year if you don't have any trees near your home. If you have many large trees or pine trees, then you'll want to clean your gutters every three to four months.

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.

The best time to replace gutters is before they experience enough damage or leaking to cause water problems to the home they protect. Seasonally, springtime is the most popular time to replace gutters after a harsh winter causes damage. However, gutter replacement deals are more common later in the year and into autumn when demand for the project is lower. 

Shingle granules can be cleaned out of gutters using a small scoop or a hose, depending on the quantity of granules and how much other debris is in your gutters. First, clear your gutters of leaves and other debris. This may remove granules in the gutters if they are mixed in with the debris. Use a plastic scoop to remove larger quantities of granules or a hose with a high-powered nozzle for smaller amounts, and collect and dispose of the granules once they’ve been removed.

Icicles can form if your gutters are clogged, but that’s not always the issue. You could also have an ice dam on your roof from poor insulation inside. In that case, the melting snow can refreeze in the gutter even if there isn’t a clog. If you’re unsure of the underlying problem, call in a roofing company to assess the issue and implement a permanent solution for you.

The Chestnut Hill, 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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