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TRUSTED BY CHESTNUT HILL, MA HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon181
    Verified gutter cleaning services reviews

Find Gutter cleaning pros in Chestnut Hill

Avatar for AAA Sparkling Window & Gutter Cleaning

AAA Sparkling Window & Gutter Cleaning

158 Prospect St
4.59(
384
)
Approved Pro

AAA Sparkling Window & Gutter Cleaning

158 Prospect St
4.59(
384
)
Approved Pro
Customers say: Quality work
47 local quotes requested
100 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

110 Meeting House Path
4.80(
56
)
Approved Pro

A-Z Cleaning Services

110 Meeting House Path
4.80(
56
)
Approved Pro
Customers say: True professional
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
78 local quotes requested

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 JLM Gutter Cleaning Service

JLM Gutter Cleaning Service

PO Box 553
4.40(
521
)
Approved Pro

JLM Gutter Cleaning Service

PO Box 553
4.40(
521
)
Approved Pro
Customers say: Quality work
76 local quotes requested
27 years of experience

For Over 25 Years, JLM Gutter Cleaning has remained Local Family Owned & Operated • Specializing in all things Gutters! • 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.

"It went well. They were quick and tidy."

Michael D on June 2025

For Over 25 Years, JLM Gutter Cleaning has remained Local Family Owned & Operated • Specializing in all things Gutters! • 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.

"It went well. They were quick and tidy."

Michael D on June 2025


Avatar for Hennelly & Son Roofing & Gutters

Hennelly & Son Roofing & Gutters

14 Erin Way
4.83(
697
)
Approved Pro

Hennelly & Son Roofing & Gutters

14 Erin Way
4.83(
697
)
Approved Pro
Customers say: Quality work
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
58 local quotes requested

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 J&E Landscape and Construction

J&E Landscape and Construction

73 Oak Street
4.57(
115
)
Approved Pro

J&E Landscape and Construction

73 Oak Street
4.57(
115
)
Approved Pro
Customers say: Quality work
Recommended by 90% of Angi customers
Recommended by 90% of HomeAdvisor customers
189 local quotes requested

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.

"Efficient and professional"

Meng Z on July 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.

"Efficient and professional"

Meng Z on July 2025


Avatar for Third Generation Window & Gutter Cleaning

Third Generation Window & Gutter Cleaning

1 Lanes End
4.95(
105
)
Approved Pro

Third Generation Window & Gutter Cleaning

1 Lanes End
4.95(
105
)
Approved Pro
Customers say: True professional
Recommended by 99% of Angi customers
Recommended by 99% of HomeAdvisor customers
59 local quotes requested

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!

"Beautiful result. Respectful team. Efficient and effective"

Bill H on July 2021

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!

"Beautiful result. Respectful team. Efficient and effective"

Bill H on July 2021


Avatar for Roberto's Affordable Landscaping

Roberto's Affordable Landscaping

109 Nichols Ave Apt #2
3.98(
764
)
Approved Pro

Roberto's Affordable Landscaping

109 Nichols Ave Apt #2
3.98(
764
)
Approved Pro
Customers say: Super punctual
312 local quotes requested
18 years of experience

Roberto Affordable Landscaping proudly serves Waltham, MA. Are you tired of spending time and money trying to keep your grass green to no avail? Let us give it a try! We specialize in providing quality, beautiful landscapes for your home or business. In every job, we strive for 100% customer satisfaction. Our staff will take the time to listen to you and then create a landscape that is designed to meet your individual needs and desires. Meeting and exceeding customer expectations is how “Roberto Affordable Landscaping” has grown to one of the region’s most respected landscaping service firms. Our focus on customer service gives you confidence that your property will be designed, installed, and maintained to industry standards and beyond. With 12 years of experience we know how to get it done right. Please Email or Text us today to schedule an appointment!

"Roberto and his crew did an outstanding job! We usually do all of our hedge abs shrub trimming ourselves, but with a few other projects going on we hadn’t gotten them all season long and they were seriously overgrown. Since we COULD do it ourselves, we had a limit on what we were willing to pay, so we were getting several quotes … most of which were higher than we had hoped. Roberto worked with us on the pricing, which was good news because now it was off of our plate! His crew was there the early next day … fast, friendly, courteous, conscientious and neat! We are now looking to have Roberto and his crew back to take a few more projects off of our plate too! If you want a great job, at great price, by a great crew … we highly recommend Roberto’s Affordable Lands aping!"

James L on September 2025

Roberto Affordable Landscaping proudly serves Waltham, MA. Are you tired of spending time and money trying to keep your grass green to no avail? Let us give it a try! We specialize in providing quality, beautiful landscapes for your home or business. In every job, we strive for 100% customer satisfaction. Our staff will take the time to listen to you and then create a landscape that is designed to meet your individual needs and desires. Meeting and exceeding customer expectations is how “Roberto Affordable Landscaping” has grown to one of the region’s most respected landscaping service firms. Our focus on customer service gives you confidence that your property will be designed, installed, and maintained to industry standards and beyond. With 12 years of experience we know how to get it done right. Please Email or Text us today to schedule an appointment!

"Roberto and his crew did an outstanding job! We usually do all of our hedge abs shrub trimming ourselves, but with a few other projects going on we hadn’t gotten them all season long and they were seriously overgrown. Since we COULD do it ourselves, we had a limit on what we were willing to pay, so we were getting several quotes … most of which were higher than we had hoped. Roberto worked with us on the pricing, which was good news because now it was off of our plate! His crew was there the early next day … fast, friendly, courteous, conscientious and neat! We are now looking to have Roberto and his crew back to take a few more projects off of our plate too! If you want a great job, at great price, by a great crew … we highly recommend Roberto’s Affordable Lands aping!"

James L on September 2025


Avatar for Ruiz Landscaping

Ruiz Landscaping

6 Garden Ln
4.36(
25
)
Approved Pro

Ruiz Landscaping

6 Garden Ln
4.36(
25
)
Approved Pro
Customers say: Super punctual
181 local quotes requested
8 years of experience

We are a professional landscaping service covering the Boston metropolitan area. Our services include: Landscaping, Lawn & Yard Work, Tree Services, Lawn Clean-Ups, Gutter Cleanings, General Lawn Maintenance and much more! Please call us today to schedule an appointment!

"I am a regular customer of this company. The do my spring cleanup, fall cleanup, trim, mulching, and lawn maintenance. I am always amazed at how great the yard looks after they are done. They keep the edges sharp and provide the little extras that other companies do not. They show up on time, are professional and thorough. If you want a great looking yard for a reasonable price, hire this company. Their work is excellent."

Alease B on March 2025

We are a professional landscaping service covering the Boston metropolitan area. Our services include: Landscaping, Lawn & Yard Work, Tree Services, Lawn Clean-Ups, Gutter Cleanings, General Lawn Maintenance and much more! Please call us today to schedule an appointment!

"I am a regular customer of this company. The do my spring cleanup, fall cleanup, trim, mulching, and lawn maintenance. I am always amazed at how great the yard looks after they are done. They keep the edges sharp and provide the little extras that other companies do not. They show up on time, are professional and thorough. If you want a great looking yard for a reasonable price, hire this company. Their work is excellent."

Alease B on March 2025


Rafael's Painting

16 Fuller Street, Apartment 1
5.00(
2
)
Approved Pro

Rafael's Painting

16 Fuller Street, Apartment 1
5.00(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
5 years of experience

Rafael's Painting has over a decade of experience servicing the professional residential interior painting needs of local Boston Metro area residents. We specialize in an array of expertise for all of your professional painting needs. No job is too big or small, and we treat them all with the same personal degree of care and attention to detail. We go above and beyond what's normally expected of painting companies, cleaning all services before and after, and actually going so far as moving each and ever piece of furniture to definitively ensure nothing is missed or damaged during the job. And all of our employees are screened. So whether you're looking to have one room or your entire house painted, we've got the experience, know-how, and professionalism you're looking for to ensure that your health, safety, and investment are all well protected by a true professional.

"Rafael went above and beyond! His work ethic is impeccable , Iâ m hiring him to do more jobs around the house! Highly recommend him"

Jean C on September 2020

Rafael's Painting has over a decade of experience servicing the professional residential interior painting needs of local Boston Metro area residents. We specialize in an array of expertise for all of your professional painting needs. No job is too big or small, and we treat them all with the same personal degree of care and attention to detail. We go above and beyond what's normally expected of painting companies, cleaning all services before and after, and actually going so far as moving each and ever piece of furniture to definitively ensure nothing is missed or damaged during the job. And all of our employees are screened. So whether you're looking to have one room or your entire house painted, we've got the experience, know-how, and professionalism you're looking for to ensure that your health, safety, and investment are all well protected by a true professional.

"Rafael went above and beyond! His work ethic is impeccable , Iâ m hiring him to do more jobs around the house! Highly recommend him"

Jean C on September 2020


Avatar for R & J Painting

R & J Painting

30 Bay Colony
4.71(
50
)
Approved Pro

R & J Painting

30 Bay Colony
4.71(
50
)
Approved Pro
Customers say: Quick response
Recommended by 94% of Angi customers
Recommended by 94% of HomeAdvisor customers
19 local quotes requested

With over 20 years experience, R & J Painting proudly serves its customers with pride, integrity and attention to the details that matter most to you. YOUR perfection is OUR perfection! This is one of the many things that sets us apart from the rest. We are family owned and operated. Give us a call today!

"Very professional. Provided quality work and were flexible with add on requests. Very satisfied and we will have them return for additional jobs."

Small A on May 2024

With over 20 years experience, R & J Painting proudly serves its customers with pride, integrity and attention to the details that matter most to you. YOUR perfection is OUR perfection! This is one of the many things that sets us apart from the rest. We are family owned and operated. Give us a call today!

"Very professional. Provided quality work and were flexible with add on requests. Very satisfied and we will have them return for additional jobs."

Small A on May 2024

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Gutter Cleaning questions, answered by experts

Water overflow, foundation damage, and mold growth are risks.

If you want to replace your home's existing underground downspout, you have options. One is to connect a rain barrel to the downspout. During a storm, water travels from the downspout into the barrel. You can then use the water to irrigate your garden or lawn. 

Another option is to install a downspout extension above ground. The extension will direct water away from your home, but potentially not as far away as an underground system.

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.

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.

Yes, many installers provide seamless options to reduce leaks and improve durability.

By submitting this question, I acknowledge and agree that Angi may publicly display my name, city, state, and question on the website for professionals and others to see.

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.