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

Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,588
)
Gutters & Downspouts - Clean

Serving Winchester, IN 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

10993 neighbors recently requested a quote
Recommended by80%of homeowners
Avatar for D.A. Quality Roofing
D.A. Quality Roofing
4.9(
6
)
Gutters & Downspouts - Clean- For Business

Serving Winchester, IN and surrounding areas

Approved

In business since 2015

Free estimates

Credit card accepted

We are a locally owned and operated company that values honesty and integrity in all aspects of our business. Our major focus is on the quality our work and producing outstanding results. We are committed to creating a level of value unmatched by any of our competitors. We look forward to building lasting relationships with our clients and guarantee your satisfaction!

Response time1 day
Response rate97%
31 neighbors recently requested a quote
Avatar for Kenneth Dietz
Kenneth Dietz
New to Angi
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, IN and surrounding areas

Approved

Credit card accepted

Offers commercial services

Hi, my name is Riley. I’m 22 years old and working hard to build my path as a general contractor. I take pride in honest work, reliability, and doing every job the right way. My goal is to provide quality craftsmanship people can trust while continuing to grow my business through hard work and dedication.

Accent Wall
Accent Wall
Accent Wall
Quality First Construction LLC
New to Angi
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, IN and surrounding areas

Approved

Just like the name suggests, quality always comes first. With 10 years of both residential and commercial carpentry, there is a wide range of projects that we have experience in. We highly value customer/contractor relations, and aim to leave our clients pleased with a job well done in a timely manner.

2 neighbors recently requested a quote
All Star Building Corp
4.4(
28
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winchester, IN and surrounding areas

In business since 2001

Free estimates

Emergency services offered

"All Star did a great job on all aspects of the job. I was given my choice of colors for the roof and siding with samples to hold together to see the match. The roofers showed up early and stayed late to get as much done as possible the first day. They showed early the second day and stayed until all work was complete and clean-up was done. The roof is beautiful. The siding guys had it a little tougher due to weather but did the job in a timely manner and did excellent work. The siding is beautiful, and the fascia work is just great. It really looks like a new house. The 6 inch white gutters really set off the whole appearance of the house. The gutter guys added some extended downspouts for me that were not in the original estimate and that really helps get the water away from the house. The appearance of my house before was not too bad, but now it really looks like a new house. I really love the work done and professionalism of everyone involved."
Recommended by87%of homeowners
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Gutter Cleaning FAQs, answered by experts

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.

Although having gutter guards and hoods dramatically reduces the number of times you will have to clean out your gutters, it doesn't necessarily mean that you won't ever have to clean your gutters. Experts recommend cleaning your gutters at least once every two years, even with gutter guards and hoods installed. If you don’t want to clean them yourself, you can hire a gutter cleaning company near you to complete the job.

If you don't want to install gutter guards, the most common and inexpensive alternative is regular gutter cleaning, either annually, biannually, or as soon as they start to fill up. Using a leaf blower attachment can make this process easier. Other products designed to reduce cleanings include gutter screens (made of wire mesh, nylon, or foam), which are typically less expensive than a full gutter guard installation. You can also find guards and inserts designed specifically to protect your downspouts or opt for a whole gutter system like LeafGuard, which integrates the gutter and guard into a single product.

The best times of year to clean your gutters are typically in the spring and fall. Cleaning in the fall is crucial for removing leaves and debris that have accumulated, which helps prevent clogs. A spring cleaning ensures your gutters are clear and prepared for seasonal rainfall.

As a general guideline, experts recommend cleaning your gutters at least twice a year. However, the optimal frequency depends on several factors, such as local weather patterns, the type of gutters you have, and the number of trees on your property. If your home is surrounded by many large trees or pine trees, you may need to clean your gutters as often as every three to four months. If you have few or no trees nearby, twice a year is likely sufficient. In some cases, you may need to clean them a couple of times during the fall and spring to keep them clear and allow water to flow freely.

The cost to install a downspout extension or reroute a downspout generally falls between $30 and $200. The final price depends on factors like whether you DIY the project or hire a gutter professional, the complexity of your gutter system, and the length of the new extension. A simple, above-ground DIY installation can cost as little as $30 for materials. In contrast, a more complex project involving professional installation and digging trenches for underground piping could cost over $1,000. This is still a significant saving compared to replacing your entire gutter system, which costs around $1,900 on average.

The Winchester, IN homeowners’ guide to gutter cleaning services

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