
Get matched with top gutter cleaning pros in Sleepy Hollow, IL
There are 21 highly-rated local gutter cleaning pros.
Need a pro for your gutter cleaning project in Sleepy Hollow, IL?
TRUSTED BY SLEEPY HOLLOW, IL HOMEOWNERS
4.5
Average homeowner rating755
Verified gutter cleaning services reviews
Verified Reviews for Gutter Cleaning pros in Sleepy Hollow, IL
*The Angi rating for Gutter Cleaning companies in Sleepy Hollow, IL 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 Sleepy Hollow, IL 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 Sleepy Hollow

Prime Time Window & Gutter Cleaning Inc
Prime Time Window & Gutter Cleaning Inc
Over 50,000 satisfied customers since 1996, we are the premier home improvement company in Chicago and the surrounding areas. Prime Time Window Cleaning provides the best residential home and commercial property services at the most competitive price. Our goal is to make each customer a raving fan and to earn not only their business, but also that of their friends, neighbors, and relatives. If you are not satisfied with our service to your home, you simply do not have to pay! Contact Prime Time Window Cleaning for your window washer, Chicago services, as well as other exterior projects, such as gutter cleaning gutter repair power washing and soft washing. We look forward to helping your home look its best! Book an appointment today at 800-480-1360.
"DO NOT support this business, nor recommend their services! I ecently entrusted this business to clean my gutters. During the cleaning I was approached by one of their employees who indicated that a concrete resurfacing and sealing was needed underneath one of my gutter spouts. Due to the fact that I (like many of you) believed in their reviews, I had no reason to distrust this representative of the company. The employee (Cristobal Flores) quoted me a total price of $1600 for the job. To my dismay, this guy never completed the job, and I have not heard back after making NUMEROUS attempts at retrieving my money back. The owner has acknowledge this fraudulent act, and refuses to make this situation right. He denies that Flores works for his company, but admits he was "helping out" that day. Sounds like an employee to me! This business does not back their customers. Instead, allows their employees to side-hustle the customers, and we are left out to dry with no concerns of this victimization. More time is actually spent attempting to reverse negative reviews, when it seems that they are extremely warranted. BEWARE!"
Kal H on June 2025
Over 50,000 satisfied customers since 1996, we are the premier home improvement company in Chicago and the surrounding areas. Prime Time Window Cleaning provides the best residential home and commercial property services at the most competitive price. Our goal is to make each customer a raving fan and to earn not only their business, but also that of their friends, neighbors, and relatives. If you are not satisfied with our service to your home, you simply do not have to pay! Contact Prime Time Window Cleaning for your window washer, Chicago services, as well as other exterior projects, such as gutter cleaning gutter repair power washing and soft washing. We look forward to helping your home look its best! Book an appointment today at 800-480-1360.
"DO NOT support this business, nor recommend their services! I ecently entrusted this business to clean my gutters. During the cleaning I was approached by one of their employees who indicated that a concrete resurfacing and sealing was needed underneath one of my gutter spouts. Due to the fact that I (like many of you) believed in their reviews, I had no reason to distrust this representative of the company. The employee (Cristobal Flores) quoted me a total price of $1600 for the job. To my dismay, this guy never completed the job, and I have not heard back after making NUMEROUS attempts at retrieving my money back. The owner has acknowledge this fraudulent act, and refuses to make this situation right. He denies that Flores works for his company, but admits he was "helping out" that day. Sounds like an employee to me! This business does not back their customers. Instead, allows their employees to side-hustle the customers, and we are left out to dry with no concerns of this victimization. More time is actually spent attempting to reverse negative reviews, when it seems that they are extremely warranted. BEWARE!"
Kal H on June 2025

F and A Window Cleaning
F and A Window Cleaning
When you call F & A Window Cleaning, Alex or Federico will be the ones answering the phone and going to your home to ensure everything is done right. With a combined experience of over 30 years servicing all of Chicagoland area, we can handle any job from window cleaning, gutter cleaning and pressure washing. We take pride in what we do! F and A Window Cleaning provides the best residential home services at the most competitive price. Our goal is to make each customer a raving fan and to earn not only their business, but that of their friends, neighbors and relatives.
"Professional and great service! Would hire again."
Christina S on September 2023
When you call F & A Window Cleaning, Alex or Federico will be the ones answering the phone and going to your home to ensure everything is done right. With a combined experience of over 30 years servicing all of Chicagoland area, we can handle any job from window cleaning, gutter cleaning and pressure washing. We take pride in what we do! F and A Window Cleaning provides the best residential home services at the most competitive price. Our goal is to make each customer a raving fan and to earn not only their business, but that of their friends, neighbors and relatives.
"Professional and great service! Would hire again."
Christina S on September 2023

JB Deck and Fence Renewal
JB Deck and Fence Renewal
**WE DO NOT DO MAJOR REPAIRS OR BUILDS** JB Deck and Fence Renewal your premiere choice for all your interior and exterior painting and staining services! Locally operated in Elgin IL and family owned, we are committed to providing superior finishes, with a friendly client centered approach. Our services include: Deck Sealing – Patio/Concrete Sealing and Washing – Gazebo or Pergola Sealing – Fence Painting – Exterior Painting - Gutter Cleaning. **WE DO NOT DO MAJOR REPAIRS OR BUILDS** In a nutshell, if you have a portion of your home that needs a revamp, we’re here and happy to help. Give us a call or text today for a free estimate on your next project! **WE DO NOT DO MAJOR REPAIRS OR BUILDS**
"Working with JB Deck and Fence was a great experience. Samantha responded promptly to my request for a quote and gave us a detailed estimate. She was very helpful with her knowledge of staining options. The job was started on time, performed professionally, and looks amazing."
Kevin D on August 2025
**WE DO NOT DO MAJOR REPAIRS OR BUILDS** JB Deck and Fence Renewal your premiere choice for all your interior and exterior painting and staining services! Locally operated in Elgin IL and family owned, we are committed to providing superior finishes, with a friendly client centered approach. Our services include: Deck Sealing – Patio/Concrete Sealing and Washing – Gazebo or Pergola Sealing – Fence Painting – Exterior Painting - Gutter Cleaning. **WE DO NOT DO MAJOR REPAIRS OR BUILDS** In a nutshell, if you have a portion of your home that needs a revamp, we’re here and happy to help. Give us a call or text today for a free estimate on your next project! **WE DO NOT DO MAJOR REPAIRS OR BUILDS**
"Working with JB Deck and Fence was a great experience. Samantha responded promptly to my request for a quote and gave us a detailed estimate. She was very helpful with her knowledge of staining options. The job was started on time, performed professionally, and looks amazing."
Kevin D on August 2025

JCV Landscape
JCV Landscape
Landscaping business locally owned and operated we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today!
"They did the BEST job. Would call them again!"
Earlene L on April 2025
Landscaping business locally owned and operated we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today!
"They did the BEST job. Would call them again!"
Earlene L on April 2025

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
Allproroofingservices
Allproroofingservices
APR Roofing Services is your locally owned and operated roofing construction company in Chicago, IL. Since our incorporation as APR Contracting, LLC, our goal has been and continues to be providing incomparable roofing services. The quality of our work and our attention to detail is unmatched. We pride ourselves on being the best value for our customers, providing affordable roofing solutions and unmatched craftsmanship. Our professional team has Installed and repaired 100's of Commercial & Industrial Roofs. We have experience with commercial & industrial roofing, residential properties, and multi-story buildings. We have a wide variety of roofing solutions available to choose from, which ensure maximum efficiency for your all your roofing needs.
"Ashton Miller from APR roofing services was very professional and guided me step-by-step on how he would do the project, me and my fiancé agreed with the price and decided to schedule the work. The work was completed upon due date on time. And cleaned up after nicely. Went smooth, highly recommend"
Mia W on March 2025
APR Roofing Services is your locally owned and operated roofing construction company in Chicago, IL. Since our incorporation as APR Contracting, LLC, our goal has been and continues to be providing incomparable roofing services. The quality of our work and our attention to detail is unmatched. We pride ourselves on being the best value for our customers, providing affordable roofing solutions and unmatched craftsmanship. Our professional team has Installed and repaired 100's of Commercial & Industrial Roofs. We have experience with commercial & industrial roofing, residential properties, and multi-story buildings. We have a wide variety of roofing solutions available to choose from, which ensure maximum efficiency for your all your roofing needs.
"Ashton Miller from APR roofing services was very professional and guided me step-by-step on how he would do the project, me and my fiancé agreed with the price and decided to schedule the work. The work was completed upon due date on time. And cleaned up after nicely. Went smooth, highly recommend"
Mia W on March 2025
Natys Landscaping & Construction
Natys Landscaping & Construction
Hello! Natys landscaping for any service you would like! Really professional! We don’t only show our love and passion but we take care of you like it’s our house. We have the best affordable price around town. We do a lot of types of jobs, we have 9 years of experience. • •Gutter cleaning • Weed removal& preventing • Tree/Shrub removal, •Planting or trimming bushes •Snow removal or Pressure washing • Seed/ Sod installation, • Mulch installations •Week and bi-weekly lawn maintenance, •Paver or stones patios, • Driveway, sidewalks repairs , resettling or re-sanding,• Concrete slabs (100% fully insured) Free estimate And a lot more just ask!
Hello! Natys landscaping for any service you would like! Really professional! We don’t only show our love and passion but we take care of you like it’s our house. We have the best affordable price around town. We do a lot of types of jobs, we have 9 years of experience. • •Gutter cleaning • Weed removal& preventing • Tree/Shrub removal, •Planting or trimming bushes •Snow removal or Pressure washing • Seed/ Sod installation, • Mulch installations •Week and bi-weekly lawn maintenance, •Paver or stones patios, • Driveway, sidewalks repairs , resettling or re-sanding,• Concrete slabs (100% fully insured) Free estimate And a lot more just ask!
Prestige Soft-Washing
Prestige Soft-Washing
At Prestige Soft-Washing, we specialize in harnessing the power of pressure washing techniques to restore and rejuvenate the appearance of residential, commercial, and industrial properties. Our team of skilled technicians is dedicated to delivering exceptional results, utilizing state-of-the-art equipment and eco-friendly cleaning agents to tackle even the toughest grime, dirt, and stains. Whether it's revitalizing driveways, sidewalks, decks, or facades, we take pride in transforming surfaces and enhancing curb appeal. Customer satisfaction is at the core of everything we do. From the moment you reach out to us for a consultation to the completion of the job, we prioritize clear communication, reliability, and professionalism. We understand that every property is unique, which is why we tailor our services to meet your specific needs and exceed your expectations. Experience the difference with Prestige-Soft Washing and let us elevate the cleanliness and attractiveness of your property. Contact us today to schedule your next cleaning project and discover why we're the trusted choice for pressure washing excellence.
At Prestige Soft-Washing, we specialize in harnessing the power of pressure washing techniques to restore and rejuvenate the appearance of residential, commercial, and industrial properties. Our team of skilled technicians is dedicated to delivering exceptional results, utilizing state-of-the-art equipment and eco-friendly cleaning agents to tackle even the toughest grime, dirt, and stains. Whether it's revitalizing driveways, sidewalks, decks, or facades, we take pride in transforming surfaces and enhancing curb appeal. Customer satisfaction is at the core of everything we do. From the moment you reach out to us for a consultation to the completion of the job, we prioritize clear communication, reliability, and professionalism. We understand that every property is unique, which is why we tailor our services to meet your specific needs and exceed your expectations. Experience the difference with Prestige-Soft Washing and let us elevate the cleanliness and attractiveness of your property. Contact us today to schedule your next cleaning project and discover why we're the trusted choice for pressure washing excellence.
First choice gutters
First choice gutters
Hello dear customers: we are offering gutter cleaning service prices range from 110 to 225
Hello dear customers: we are offering gutter cleaning service prices range from 110 to 225
Forever Green Lawncare
Forever Green Lawncare
Landscaping business locally owned and operated we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today! Facebook: IG: forevergreen2019
"Victor and his crew did fantastic! He worked with us very well and would verify everything right before planting the plants and flowers to make sure we were happy with the placement. He gave suggestions and lawn care advice without being overbearing and his calm and kind personality made him great to work with. Neighbors were keeping an eye out and liked our results so much that they asked for his card for help with their yards. We will definitely use him again. Thank you Victor and crew!"
Christopher H on May 2025
Landscaping business locally owned and operated we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today! Facebook: IG: forevergreen2019
"Victor and his crew did fantastic! He worked with us very well and would verify everything right before planting the plants and flowers to make sure we were happy with the placement. He gave suggestions and lawn care advice without being overbearing and his calm and kind personality made him great to work with. Neighbors were keeping an eye out and liked our results so much that they asked for his card for help with their yards. We will definitely use him again. Thank you Victor and crew!"
Christopher H on May 2025
FAQs for gutter cleaning projects in Sleepy Hollow, IL
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 Sleepy Hollow, IL 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.
Learn about the downspout cleaning tools to buy to prevent gutter clogs that can cause water to pool near your basement or foundation.
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"