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TRUSTED BY PAWLING, NY HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon137
    Verified gutter cleaning services reviews

Top-Rated Gutter cleaning pros in Pawling - Updated Nov 2026

Avatar for Gutter Guy
Gutter Guy
4.7(
395
)
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2001

Free estimates

Emergency services offered

"James and his son did an excellent job and are highly reliable and very accomodating! I would definitely recommend them to anyone looking for gutter cleaning, roofing repairs and installation, siding and gutter leaf guard installation. They also do power washing ."
new gutter
gutter job
80 ft gutter
Response time9 hrs
2 neighbors recently requested a quote
Recommended by93%of homeowners
Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,582
)
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved (Corporate)

In business since 2005

Free estimates

Warranties offered

"LeafFilter doesn't clean gutters, they sell and install their LeafFilter Gutter products and only clean the gutters if you buy their product. I can't even begin to afford their product so I wasn't able to get my gutter cleaned by them."
Free no obligation estimates
Free no obligation estimates
Metal Screen mesh ontop of gutter
Free-flowing water in clean gutters
Debris resistant gutter protection

+63

11178 neighbors recently requested a quote
Recommended by81%of homeowners
Avatar for Black Diamond Home Improvement
Black Diamond Home Improvement
4.9(
9
)
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved

In business since 2015

Free estimates

Emergency services offered

"????? I couldn?t be more satisfied with Black Diamond Home Improvement! I had gutter guards installed on my house, and from beginning to end, the experience was absolutely outstanding. The pricing was honestly mind-blowing. I couldn?t believe how reasonable the price was for the quality of work I received. On top of that, the knowledge, professionalism, and attention to detail this pro brought to the job were beyond impressive. He clearly knows what he?s doing and takes pride in his work. Everything was done professionally, and the finished job looks great. I?m extremely happy that I found Black Diamond Home Improvement on Google. Finding a contractor you can trust isn?t always easy, but I?m very glad I found this company. I would absolutely recommend Black Diamond Home Improvement to anyone looking for quality work at a great price. In fact, I was so impressed that he will definitely be doing my sister?s house next week! Could not be happier with the service. Five stars all the"
Gutter guards
Gutter guards
Gutter guards
Roof cleaning
Roof cleaning

+84

21 neighbors recently requested a quote
Recommended by57%of homeowners
Exact Fit Seamless Gutters Of Westchester, Inc.
4.2(
10
)
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved

In business since 2003

Free estimates

Emergency services offered

"I had a broken gutter that was lying on the ground which was torn down from the last snowstorm. Mark and his team came on the same day I called, and replaced a gutter as well as cleaned all of my gutters and fixed the gutters extensions, so the water would be dispensed away from the house. They did an amazing job. I will definitely use them again and recommend the services."
Response time5 hrs
3 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for All Cleaning & Maintenance LLC
All Cleaning & Maintenance LLC
4.8(
9
)
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved

In business since 2014

Free estimates

Small jobs welcome

We are a locally owned and operated company that values honesty, integrity, and treats your home as if it were our own. We offer a variety of general contractor services that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of each project that we are involved with. We look forward to building lasting relationships, and guarantee your satisfaction! \n

kitchen
kitchen
kitchen
New House
New House

+7

Response time5 hrs
Response rate97%
9 neighbors recently requested a quote
Avatar for Chloe’s Cleaning Co
Chloe’s Cleaning Co
New to Angi
Gutters & Downspouts - Clean

Serving Pawling, NY and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

Hi, I’m Chloe!! I’m a friendly, dependable housekeeper who genuinely enjoys helping people create clean, comfortable, and welcoming homes. I take pride in my work and pay close attention to detail, ensuring every space is cleaned with care and thoroughness. With previous housekeeping experience, I understand the importance of reliability, professionalism, and treating your home with respect. I’m currently growing my housekeeping business and am excited to connect with new clients through this platform. I look forward to earning your trust and helping keep your home looking its best!! Please feel free to reach out to me with any questions, to receive a custom quote or for more information

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Gutter Cleaning FAQs, answered by experts

You may have a clogged gutter. Downspouts can also clog if your gutter collects too much debris. Hire a professional gutter cleaner, and if you still have problems, install a gutter guard (which prevents debris from entering your gutter system) and a downspout extension (which helps drain water further away from your foundation, so it doesn't pool near your house). Follow these tips to keep your gutter downspouts clean.

Yes, gutters can still get clogged even with gutter guards installed. While guards significantly reduce the amount of debris that enters your gutters, they are not 100% effective.

Small debris such as pine needles, seedlings, algae, small leaves, and pebbles can pass through the guard's screen or mesh and accumulate over time. Clogs can also form if the guards themselves are not cleaned and become overwhelmed with debris on top, preventing water from entering the gutter.

If this buildup is neglected, it can lead to clogs, water leaks, mold growth, and even plants sprouting from the gutters. The primary benefit of gutter guards is not the complete elimination of maintenance, but a dramatic reduction in how often you need to perform it, often from several times a year to just once a year or less.

Walking on the roof to clean gutters is unsafe and not recommended due to significant safety risks. It is especially dangerous on steep or slippery roofs, or if the roof is wet or covered in leaves, which increases the chance of a fall. In addition to personal injury, walking on the roof can damage shingles, potentially leading to water leaks. Instead of walking on the roof, use a sturdy ladder positioned on a stable surface to access the gutters. Be aware that using a ladder also carries risks, as it can be difficult to maintain balance while performing the work. You can also use ground-based cleaning tools. For safety reasons and to prevent damage to your roof, hiring a professional to clean your gutters is the best and safest option.

Any small amount of standing water can be damaging to your gutters. It’s recommended that a ¼ inch puddle or more should be addressed. Failure to keep water from pooling in your gutters can result in clogs, algae growth, and pests that damage your gutters over time. 

While you can clean your gutters without geting on a ladder, you won't know just how well you're cleaning them without the use of a telescopic water pole. Some ways to clean gutters from the ground include using telescopic cleaning tools and a leaf blower extension, wet/dry vacuum extension, pressure washer, or garden hose with a curved end.

The Pawling, NY homeowners’ guide to gutter cleaning services

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