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There are 30 highly-rated local gutter cleaning pros.

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TRUSTED BY WINNETKA, IL HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon796
    Verified gutter cleaning services reviews

Find Gutter cleaning pros in Winnetka

Avatar for Amruss Inc Home Improvement Company

Amruss Inc Home Improvement Company

1040 S Milwaukee Ave
4.52(
4,270
)
Approved Pro

Amruss Inc Home Improvement Company

1040 S Milwaukee Ave
4.52(
4,270
)
Approved Pro
Customers say: Super punctual
125 local quotes requested
26 years of experience

Amruss Home Improvement has been in business for more than 25 years. Everybody knows us for our professional Window washing and Gutter cleaning services. But besides those, we also provide a whole variety of other services like Power Washing, Deck Restoration, Garage Cleaning, Caulking, and Holiday light installation services. We offer fast, high-quality, and professional services at affordable prices. We value every customer and strive to provide the best service possible. Award-winning. Licensed & Insured. Additional DBA - Amruss Inc. Cost is determined by the job.

"They never contacted us. At least, I could have received an estimate by text. In fact, it was a very poor response by any business on this site. I would not do this again."

Anna C on November 2024

Amruss Home Improvement has been in business for more than 25 years. Everybody knows us for our professional Window washing and Gutter cleaning services. But besides those, we also provide a whole variety of other services like Power Washing, Deck Restoration, Garage Cleaning, Caulking, and Holiday light installation services. We offer fast, high-quality, and professional services at affordable prices. We value every customer and strive to provide the best service possible. Award-winning. Licensed & Insured. Additional DBA - Amruss Inc. Cost is determined by the job.

"They never contacted us. At least, I could have received an estimate by text. In fact, it was a very poor response by any business on this site. I would not do this again."

Anna C on November 2024


Avatar for Above Water & Beyond

Above Water & Beyond

5.00(
11
)
Approved Pro

Above Water & Beyond

5.00(
11
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
41 local quotes requested

5 years of experience, Above Water & Beyond gets the job done RIGHT! We stand on our values firm on our values, service before self, integrity first, excellence in all we do! We are owner operator as we look to grow and expand in the community. We look forward to helping you get the service you need done!

"All went great. Deck and brick pavers look great"

Diana M on July 2025

5 years of experience, Above Water & Beyond gets the job done RIGHT! We stand on our values firm on our values, service before self, integrity first, excellence in all we do! We are owner operator as we look to grow and expand in the community. We look forward to helping you get the service you need done!

"All went great. Deck and brick pavers look great"

Diana M on July 2025


Avatar for Cardena Window & Associates

Cardena Window & Associates

New on AngiNew on Angi
Approved Pro

Cardena Window & Associates

New on AngiNew on Angi
Approved Pro
40 local quotes requested
3 years of experience

Cardena Window & Associates in Prospect Heights, IL provides comprehensive pressure washing services to enhance the appearance and upkeep of your property. Our services include window cleaning, power washing, gutter cleaning, house cleaning, and office cleaning. With a focus on quality and detail, Cardena Window & Associates ensures your home or business looks its best. For more information, call us now! We serve in Prospect Heights, IL, Riverwoods Village IL; Deerfield Village IL; Winnetka Village IL; West Deerfield Township IL; Glencoe Village IL; and the surrounding areas. Pressure Washing Services, Pressure Washing Company, Commercial Pressure Washing, Home Pressure Washing, House Pressure Washing Power Washing, Pressure Washing For more information visit our website: https://pressurewashing-il.com/ We also accept the following payment methods: Cash

Cardena Window & Associates in Prospect Heights, IL provides comprehensive pressure washing services to enhance the appearance and upkeep of your property. Our services include window cleaning, power washing, gutter cleaning, house cleaning, and office cleaning. With a focus on quality and detail, Cardena Window & Associates ensures your home or business looks its best. For more information, call us now! We serve in Prospect Heights, IL, Riverwoods Village IL; Deerfield Village IL; Winnetka Village IL; West Deerfield Township IL; Glencoe Village IL; and the surrounding areas. Pressure Washing Services, Pressure Washing Company, Commercial Pressure Washing, Home Pressure Washing, House Pressure Washing Power Washing, Pressure Washing For more information visit our website: https://pressurewashing-il.com/ We also accept the following payment methods: Cash


Avatar for Prime Time Window & Gutter Cleaning Inc

Prime Time Window & Gutter Cleaning Inc

1806 W Cuyler Ave
3.77(
372
)
Approved Pro

Prime Time Window & Gutter Cleaning Inc

1806 W Cuyler Ave
3.77(
372
)
Approved Pro
Customers say: Quality work
252 local quotes requested
29 years of experience

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


Avatar for Joe and Tony Landscaping LLC

Joe and Tony Landscaping LLC

89 Lee Rd
4.62(
195
)
Approved Pro

Joe and Tony Landscaping LLC

89 Lee Rd
4.62(
195
)
Approved Pro
Customers say: Super punctual
74 local quotes requested
Free onsite estimate

Joe and Tony Landscaping LLC is entering it’s 45th year, as a maintenance and design/build company providing the Northshore with professional, experienced, award winning landscape services. Our continued commitment to employee training and product knowledge assures you the highest industry standards and product installation techniques are being utilized on your landscape project. Take advantage of our landscape design and installation experience to give your home the look that complements you and your lifestyle.

"it went EXCELLENT - everything went exactly as planned - would definitely recommend them to everyone - they are the best !!!!"

Bob S on December 2021

Joe and Tony Landscaping LLC is entering it’s 45th year, as a maintenance and design/build company providing the Northshore with professional, experienced, award winning landscape services. Our continued commitment to employee training and product knowledge assures you the highest industry standards and product installation techniques are being utilized on your landscape project. Take advantage of our landscape design and installation experience to give your home the look that complements you and your lifestyle.

"it went EXCELLENT - everything went exactly as planned - would definitely recommend them to everyone - they are the best !!!!"

Bob S on December 2021


Avatar for Bubbles Window Washing & Gutter Cleaning

Bubbles Window Washing & Gutter Cleaning

2037 W Belle Plaine Ave
4.59(
1,056
)
Approved Pro

Bubbles Window Washing & Gutter Cleaning

2037 W Belle Plaine Ave
4.59(
1,056
)
Approved Pro
Customers say: Quality work
159 local quotes requested
22 years of experience

Bubbles Window Washing & Gutter Cleaning specializes in window washing, gutter cleaning, and pressure washing services, and has been serving the Chicagoland area for 20 years! Our up-front, accountable service guarantees that you will be blown away not only by our professionalism, but by our expert service. Our window washers, gutter cleaners, and power washers have all been trained directly to company specifications and have years of experience in the field. Their training gives them an unmatched attention to detail and the quality of each service reflects this. We are licensed, bonded, and insured to make sure that your home and your interests are protected above all else. Because of our dedication to superior service, we have been the recipients of the Angie's List Super Service Award since 2008! When you choose Bubbles Window Washing & Gutter Cleaning, you choose the company trusted by your friends, family, and neighbors. Contact us today to receive your free quote!

"I highly recommend Bubbles Window Washing and Gutter Cleaning. I called them to schedule service to clean all my windows (inside and out), screens and tracks. They were able to schedule me for the next morning. Domingo arrived at my home promptly and was extremely courteous and very thorough. My windows have never been cleaner and I will be using them again in the Spring and Fall of next year."

Amy N on September 2025

Bubbles Window Washing & Gutter Cleaning specializes in window washing, gutter cleaning, and pressure washing services, and has been serving the Chicagoland area for 20 years! Our up-front, accountable service guarantees that you will be blown away not only by our professionalism, but by our expert service. Our window washers, gutter cleaners, and power washers have all been trained directly to company specifications and have years of experience in the field. Their training gives them an unmatched attention to detail and the quality of each service reflects this. We are licensed, bonded, and insured to make sure that your home and your interests are protected above all else. Because of our dedication to superior service, we have been the recipients of the Angie's List Super Service Award since 2008! When you choose Bubbles Window Washing & Gutter Cleaning, you choose the company trusted by your friends, family, and neighbors. Contact us today to receive your free quote!

"I highly recommend Bubbles Window Washing and Gutter Cleaning. I called them to schedule service to clean all my windows (inside and out), screens and tracks. They were able to schedule me for the next morning. Domingo arrived at my home promptly and was extremely courteous and very thorough. My windows have never been cleaner and I will be using them again in the Spring and Fall of next year."

Amy N on September 2025


Avatar for Ramon and Ramon Landscaping Inc

Ramon and Ramon Landscaping Inc

14889 W Rte 173
4.23(
13
)
Approved Pro

Ramon and Ramon Landscaping Inc

14889 W Rte 173
4.23(
13
)
Approved Pro
Customers say: Terrific value
102 local quotes requested
30 years of experience

We are a family owned business & operated. We have been proudly serving the Lake and Cook County North shore since 1995. We have built and kept a reputation of great service and dedication. We started as a landscaping company that would gain the skills and confidence to run a hardscape company. please calls us TODAY for a FREE Estimate .(847)417-4208 mobile phone for immediate response

"From the very beginning they did not show up as promised. They did show up the next day after I contacted them. I"

Patricia M on August 2020

We are a family owned business & operated. We have been proudly serving the Lake and Cook County North shore since 1995. We have built and kept a reputation of great service and dedication. We started as a landscaping company that would gain the skills and confidence to run a hardscape company. please calls us TODAY for a FREE Estimate .(847)417-4208 mobile phone for immediate response

"From the very beginning they did not show up as promised. They did show up the next day after I contacted them. I"

Patricia M on August 2020


Avatar for RV Landscaping and Snow Removal

RV Landscaping and Snow Removal

9588 Terrace Place
5.00(
12
)
Approved Pro

RV Landscaping and Snow Removal

9588 Terrace Place
5.00(
12
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
583 local quotes requested

Discover Seasonal Perfection with RV Landscaping & Snow Removal. Where professional landscaping and efficient snow removal converge to transform your property year-round. Trust in our skilled team to deliver both aesthetics and practical solutions, ensuring your outdoor spaces are safe and clean in any weather.

"Excellent service at a reasonable price. Really great."

Tanya L on August 2025

Discover Seasonal Perfection with RV Landscaping & Snow Removal. Where professional landscaping and efficient snow removal converge to transform your property year-round. Trust in our skilled team to deliver both aesthetics and practical solutions, ensuring your outdoor spaces are safe and clean in any weather.

"Excellent service at a reasonable price. Really great."

Tanya L on August 2025


Avatar for Chicago Service Source, Inc.

Chicago Service Source, Inc.

2500 W 36th St
4.25(
16
)
Approved Pro

Chicago Service Source, Inc.

2500 W 36th St
4.25(
16
)
Approved Pro
Customers say: Terrific value
823 local quotes requested
38 years of experience

Chicago Service Source, Inc (A Women Owned property maintenance company) has over 35 years experience serving the Chicagoland area, as well as the entire State of Illinois and NW Indiana. We are committed to excellence in building, property construction and maintenance. Leading provider in sealcoat and concrete and landscape services. We have the experience, knowledge, motivation, equipment and manpower to serve your needs. We have a staff of over 150 individuals all trained and ready to service your property. We can service your property needs quickly and efficiently with the high level of service and reliability that you expect and deserve. All of our staff members are uniformed and trained for the specific job at hand. We are dedicated to customer service. We believe that our company can provide quality service at competitive rates.

"Provided competitive quote and performed the work needed promptly"

Dan B on September 2025

Chicago Service Source, Inc (A Women Owned property maintenance company) has over 35 years experience serving the Chicagoland area, as well as the entire State of Illinois and NW Indiana. We are committed to excellence in building, property construction and maintenance. Leading provider in sealcoat and concrete and landscape services. We have the experience, knowledge, motivation, equipment and manpower to serve your needs. We have a staff of over 150 individuals all trained and ready to service your property. We can service your property needs quickly and efficiently with the high level of service and reliability that you expect and deserve. All of our staff members are uniformed and trained for the specific job at hand. We are dedicated to customer service. We believe that our company can provide quality service at competitive rates.

"Provided competitive quote and performed the work needed promptly"

Dan B on September 2025


C R EBERT JR INC

2268 COMMONWEALTH AVE
5.00(
1
)
Approved Pro

C R EBERT JR INC

2268 COMMONWEALTH AVE
5.00(
1
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
49 years of experience

Our company was a family roofing business started 79 years ago and has evolved into so much more. C.R. Ebert Jr, Inc. has a team of professionals who specialize in providing you with the best results in roofing installation, siding repair and installation, new gutter installation, soffit, trim and general exterior work. Located in North Chicago, IL, C.R. Ebert Jr, Inc. has been serving the North Shore for over 80 years.

"was done same day in couple hrs what i was looking to get done"

WILLIAM P on November 2023

Our company was a family roofing business started 79 years ago and has evolved into so much more. C.R. Ebert Jr, Inc. has a team of professionals who specialize in providing you with the best results in roofing installation, siding repair and installation, new gutter installation, soffit, trim and general exterior work. Located in North Chicago, IL, C.R. Ebert Jr, Inc. has been serving the North Shore for over 80 years.

"was done same day in couple hrs what i was looking to get done"

WILLIAM P on November 2023

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FAQs for gutter cleaning projects in Winnetka, 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 Winnetka, IL homeowners’ guide to gutter cleaning services

From average costs to expert advice, get all the answers you need to get your job done.

What do you need done? We’ll find top pros.
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