
Get matched with top gutter cleaning pros in Winthrop, MA
There are 31 highly-rated local gutter cleaning pros.
Need a pro for your gutter cleaning project in Winthrop, MA?
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Verified Reviews for Gutter Cleaning pros in Winthrop, MA
*The Angi rating for Gutter Cleaning companies in Winthrop, 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 Winthrop, 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 October 04, 2025
Find Gutter cleaning pros in Winthrop

JLM Gutter Cleaning Service
JLM Gutter Cleaning Service
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

Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
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

Melvin Power Wash
Melvin Power Wash
We are a locally owned and operated home improvement and exterior cleaning company based out of Providence, RI and servicing all of Rhode Island, Massachusetts, Connecticut and throughout New England. Our services include: Gutter and Downspout Cleaning, Gutter Repair, Replacement & Installation, Pressure Washing (Roof & House Exterior), Deck Restoration (with Sealant and/or Staining), Deck Maintenance, Window and Screen Cleaning, Carpentry, Exterior Painting, Leaf Removal, Ice & Snow Removal and much more! We are fully licensed & insured and strive to exceed the guidelines established by the Roofing Manufacturers Association. Our mission is to provide the highest quality service to our customers and make it our top priority. We always strive to complete the job to our customers’ requirements and guarantee that it will be done right and on time! Please contact us today to schedule an appointment! 20% OFF from second Home Power wash to Angie's List members. Regularly priced for 2000 feet at $299.00 10% off for Deck maintenance to Angie's List members. Priced regularly 200 feet for $289.00 Call to claim at 401-327-8409
"Melvin responded promptly to all communications and arrived on time to provide a quote. The quote was very reasonable, and the work was done very well and on time. He was accommodating and provided a ladder to access one of the porches."
Roger J on June 2025
We are a locally owned and operated home improvement and exterior cleaning company based out of Providence, RI and servicing all of Rhode Island, Massachusetts, Connecticut and throughout New England. Our services include: Gutter and Downspout Cleaning, Gutter Repair, Replacement & Installation, Pressure Washing (Roof & House Exterior), Deck Restoration (with Sealant and/or Staining), Deck Maintenance, Window and Screen Cleaning, Carpentry, Exterior Painting, Leaf Removal, Ice & Snow Removal and much more! We are fully licensed & insured and strive to exceed the guidelines established by the Roofing Manufacturers Association. Our mission is to provide the highest quality service to our customers and make it our top priority. We always strive to complete the job to our customers’ requirements and guarantee that it will be done right and on time! Please contact us today to schedule an appointment! 20% OFF from second Home Power wash to Angie's List members. Regularly priced for 2000 feet at $299.00 10% off for Deck maintenance to Angie's List members. Priced regularly 200 feet for $289.00 Call to claim at 401-327-8409
"Melvin responded promptly to all communications and arrived on time to provide a quote. The quote was very reasonable, and the work was done very well and on time. He was accommodating and provided a ladder to access one of the porches."
Roger J on June 2025
Rafael's Painting
Rafael's Painting
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

AML Landscaping
AML Landscaping
We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.
"Excellent work! Reasonable price, on time, professional, friendly. Aurelio and team did a great job. We already have discussed future projects and have recommended them to our neighbor. "
Kimberley B on March 2025
We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.
"Excellent work! Reasonable price, on time, professional, friendly. Aurelio and team did a great job. We already have discussed future projects and have recommended them to our neighbor. "
Kimberley B on March 2025

John Hubert Roofing & Home Improvement
John Hubert Roofing & Home Improvement
At John Hubert Roofing & Home Improvement, we will always meet or exceed your expectations. Our associates are skilled, efficient, safe and courteous at all times. We look forward to your next project. Choose the best, call us today.
"Fast response. Very fair price. No â overselling.â"
Fr L on September 2021
At John Hubert Roofing & Home Improvement, we will always meet or exceed your expectations. Our associates are skilled, efficient, safe and courteous at all times. We look forward to your next project. Choose the best, call us today.
"Fast response. Very fair price. No â overselling.â"
Fr L on September 2021

Ned Stevens Gutter Cleaning
Ned Stevens Gutter Cleaning
When you choose Ned Stevens for your gutter cleaning, gutter repair, gutter installation, window cleaning and other services, you can count on exceptional quality of work and outstanding customer service. Our labor staff are all our own employees, and we train them in our state-of-the-art training facility focusing on quality work. Our work is 100% Guaranteed. Your satisfaction is our goal. We want to make your gutter cleaning experience effortless. You never need to be home! We are fully insured and guarantee all of our work. Our family owned company has been cleaning and installing gutters for over 50 years.
"My experience was good. There good communication regarding the job and someone came out and completed the work as soon as the weather allowed"
Geraldine D on September 2025
When you choose Ned Stevens for your gutter cleaning, gutter repair, gutter installation, window cleaning and other services, you can count on exceptional quality of work and outstanding customer service. Our labor staff are all our own employees, and we train them in our state-of-the-art training facility focusing on quality work. Our work is 100% Guaranteed. Your satisfaction is our goal. We want to make your gutter cleaning experience effortless. You never need to be home! We are fully insured and guarantee all of our work. Our family owned company has been cleaning and installing gutters for over 50 years.
"My experience was good. There good communication regarding the job and someone came out and completed the work as soon as the weather allowed"
Geraldine D on September 2025

HM PRO LANDSCAPING INC
HM PRO LANDSCAPING INC
We have the experience and we are committed to providing quality workmanship and superior customer service on all our applications. We strive to maintain our reputation as a high quality, very service oriented company with our main focus being customer satisfaction.
"They did a super job, they are true professionals. I loved the change for my house....Hicieron un súper trabajo son unos verdaderos profesionales Me encantó el cambio para mi casa."
Liliana P on October 2025
We have the experience and we are committed to providing quality workmanship and superior customer service on all our applications. We strive to maintain our reputation as a high quality, very service oriented company with our main focus being customer satisfaction.
"They did a super job, they are true professionals. I loved the change for my house....Hicieron un súper trabajo son unos verdaderos profesionales Me encantó el cambio para mi casa."
Liliana P on October 2025

American Gutter Cleaning & Installations, Inc.
American Gutter Cleaning & Installations, Inc.
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.
"Their company was the best. We told him what we needed and they showed up within two weeks. We couldn’t believe how cheap it was to do the work. I actually got a price from leaf guide for $1500 an American Gutter did the whole job For only $95. I would highly recommend them and will absolutely call upon them for any further needs we have."
Ann F on September 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.
"Their company was the best. We told him what we needed and they showed up within two weeks. We couldn’t believe how cheap it was to do the work. I actually got a price from leaf guide for $1500 an American Gutter did the whole job For only $95. I would highly recommend them and will absolutely call upon them for any further needs we have."
Ann F on September 2025

Boston Window Cleaning
Boston Window Cleaning
Boston Window Cleaning offers fast, friendly and courteous service. We use only the best products and are always eager to answer your questions and concerns. We have built our reputation on our commitment to providing quality service, which has earned us an impressive reputation with many valuable customers. Call us directly to speak to an expert!
"A fabulous job!! Our windows are so clean that you can’t tell there is glass in them! Jay was prompt, thorough and professional. It is wonderful to be able to enjoy our view. We would absolutely recommend Boston Window Cleaning and will be telling all of our neighbors about the wonderful job that was done in our home."
Deborah C on August 2025
Boston Window Cleaning offers fast, friendly and courteous service. We use only the best products and are always eager to answer your questions and concerns. We have built our reputation on our commitment to providing quality service, which has earned us an impressive reputation with many valuable customers. Call us directly to speak to an expert!
"A fabulous job!! Our windows are so clean that you can’t tell there is glass in them! Jay was prompt, thorough and professional. It is wonderful to be able to enjoy our view. We would absolutely recommend Boston Window Cleaning and will be telling all of our neighbors about the wonderful job that was done in our home."
Deborah C on August 2025
FAQs for gutter cleaning projects in Winthrop, MA
Yes, it’s okay to use a pressure washer to clear and clean your gutters. Be careful to avoid the outside of the gutters, as getting too close with the powerwasher can peel away the paint. Also, be careful to avoid causing any damage to seams that may be in the corners or along the length of the gutter.
Gutter cleaning costs about $170 on average, ranging from about $75 to $400. Cost factors include the type, length, and height of your gutters. A multiple-story home with gutters high off the ground and accessible only by ladder or working on a steep roof will cost more than a single-story house with a relatively flat roof.
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.
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 can clean the gutters on a two-story house using gutter tongs on an extension pole. However, cleaning second-story gutters from a ladder or the roof is very dangerous and should be done by a professional.
The Winthrop, MA homeowners’ guide to gutter cleaning services
From average costs to expert advice, get all the answers you need to get your job done.
This guide to gutter cleaning costs provides estimates for cleaning different types of gutters, tips for saving money on gutter cleaning, and answers to how to clean gutters.
Learn how to unclog a downspout to keep your gutters working properly.
What is gutter cleaning, and why is it important? From benefits and cost to recommended cleaning frequency, we bring you essential gutter cleaning basics you need to know.
Gutters clogged with debris can cause your system to leak, sending water down the side of your home and into your foundation. Learn how this problem can lead to soil erosion, slab foundation damage, and basement column damage.
Regular gutter cleaning protects your home from water damage. Find out how often you should clean your gutters and look for signs like accumulated debris.
Harvesting your own rainwater is surprisingly simple. A rain barrel costs very little compared to how much you’ll save—and Mother Earth will thank you, too.
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- 🌱 "Mow a small front yard"
- 🛠 "Fix a leaking pipe under the sink"
- 🏠 "Repair shingles on an asphalt roof"