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TRUSTED BY WINCHESTER, KY HOMEOWNERS

  • Average homeowner rating star icon3.8
    Average homeowner rating
  • Verified reviews icon95
    Verified gutter cleaning services reviews

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

J&T Pressure Washing
4.8(
76
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, KY and surrounding areas

Approved

Super Service Award Winner

In business since 2022

Free estimates

Offers commercial services

"Doug, you did a fantastic job cleaning my driveway. The next day I walked around and noticed all the extra work you did for my house. You even surprised me by doing my gutters. I am astonished at the appearance and whiteness of your work. You went above and beyond my wildest expectations. The quality of your work is outstanding. Please don't hesitate to hire this team, as you won't be disappointed. Well worth the cost. A rating. Thank you, Doug, for your professionalism, care, and concern."
Response time5 hrs
Response rate97%
32 neighbors recently requested a quote
Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,582
)
Gutters & Downspouts - Clean

Serving Winchester, KY 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

11270 neighbors recently requested a quote
Recommended by81%of homeowners
Avatar for Upward Prowash
Upward Prowash
4.9(
74
)
Gutters & Downspouts - Clean- For Business

Serving Winchester, KY and surrounding areas

Approved

In business since 2017

Free estimates

Credit card accepted

"I had my house, deck and driveway cleaned. He did an excellent job. He took the time need to clean ALL the surfaces thoroughly. I was impressed with how much effort and detail they did, especially on my deck. I would use this company again and I highly recommend them."
My jobs
My jobs
My jobs
My jobs
My jobs

+7

Recommended by90%of homeowners
Avatar for MTC Investment Group LLC.
MTC Investment Group LLC.
5.0(
14
)
Gutters & Downspouts - Clean

Serving Winchester, KY and surrounding areas

Approved

In business since 2019

Free estimates

"Matt and his crew did an outstanding job. Very professional and courteous. They also made sure that everything was cleaned up well. They showed up right on time. I would highly recommend them if you need any guttering work done."
New gutters
New gutters
New gutters
New gutters
New gutters

+4

Response time5 hrs
Response rate100%
3 neighbors recently requested a quote
Avatar for Window Wash Wizards
Window Wash Wizards
4.8(
19
)
Gutters & Downspouts - Clean

Serving Winchester, KY and surrounding areas

Approved

Free estimates

Small jobs welcome

Offers commercial services

"Evan and his helper did a great job on cleaning out the gutters and downspouts on my home ( there was vegetation visibly growing in the gutters) including pipes that run under the yard and sidewalk to the street. Unfortunately, a piece of debris cracked a window pane under the gutter. They had a glass guy at my home before they left, took measurements and promptly replaced the cracked pane. At no charge to me. These guys are pros, I highly recommend them. Plan to have them come back out and have windows clean. A++"
Back patio Pressure Wash
Back patio Pressure Wash
Back patio Pressure Wash
Back patio Pressure Wash
House Wash April 2026

+5

6 neighbors recently requested a quote
Avatar for A. B. H. Decors, Inc.
A. B. H. Decors, Inc.
4.7(
80
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, KY and surrounding areas

Approved

In business since 1994

Free estimates

Warranties offered

"A.B.H. Decors tackled some neglected guttering that I wasn't sure would even be able to be cleaned up, and buried downspout that no longer aligned to the homes gutters. Not only were the downspouts securely reconnected, but steps were taken to make sure all gutters were draining smooth and fully, and the exteriors cleaned up looking as close to new as anyone could have expected. I am exceptionally please with the results of the job, and am already looking to schedule future work. It is a pleasure to know a company that truly strives for complete customer satisfaction."
Upper Scale Homes
Upper Scale Homes
Interiors
Interiors
Response time3 hrs
2 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Eric's Handyman Services
Eric's Handyman Services
5.0(
11
)
Gutters & Downspouts - Clean

Serving Winchester, KY and surrounding areas

Approved

In business since 2020

Free estimates

Credit card accepted

Eric's Handyman Services is committed to excellence in every aspect of our \nbusiness. We uphold a standard of integrity bound by fairness, honesty, \nand personal responsibility. Our distinction is the quality of service \nwe bring to our customers. Accurate knowledge of \nour trade combined with ability is what makes us true professionals. \nAbove all, we are watchful of our customers' interests and make their \nconcerns the basis of our business.

Road and Creek Cleanup
Road and Creek Cleanup
Road and Creek Cleanup
Road and Creek Cleanup
Road and Creek Cleanup

+10

Avatar for AFS PROPERTY SOLUTIONS
AFS PROPERTY SOLUTIONS
5.0(
3
)
Gutters & Downspouts - Clean

Serving Winchester, KY and surrounding areas

Approved

Emergency services offered

Small jobs welcome

Offers commercial services

Experienced. Reliable. Ready to Help.\n\nWith 10+ years of construction experience, I’m a true jack of all trades who takes pride in honest work, fair service, and getting the job done right.\n\nI offer flexible and after-hours scheduling for:\n• Furniture assembly\n• Cabinet installation\n• Pressure washing\n• Gutter & downspout cleaning\n• Minor plumbing repairs\n• General handyman work\n• Home maintenance & repairs\n\nNo job is too small. If it needs fixed, installed, cleaned, or assembled, give me a call—I’ll be happy to take a look!

3 neighbors recently requested a quote
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Gutter Cleaning FAQs, answered by experts

Water should not be dripping behind your gutters. Rain dripping between your gutters and the fascia might indicate that the gutters are misaligned with the fascia board or there are loose screws in the gutters, allowing water to pass through. Start by checking for these issues and make repairs ASAP.

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.

Underground downspouts refer to the sections of downspout extensions that lead away from your home and gutter system. While they cost more than traditional extensions, they can provide several benefits, such as less frequent damage and no need to move them for lawn care tasks. Whether they're worth it or not depends on your budget at installation time and how much convenience they'll add to your situation.

Shingle granules can be cleaned out of gutters using a small scoop or a hose, depending on the quantity of granules and how much other debris is in your gutters. First, clear your gutters of leaves and other debris. This may remove granules in the gutters if they are mixed in with the debris. Use a plastic scoop to remove larger quantities of granules or a hose with a high-powered nozzle for smaller amounts, and collect and dispose of the granules once they’ve been removed.

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.

The Winchester, KY homeowners’ guide to gutter cleaning services

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