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

Avatar for James Roofing, LLC
James Roofing, LLC
4.8(
54
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Prineville, OR and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"Rarely does a person find a service that rates above 5 stars. If it was possible, we would give James Roofing 10 stars for the work they did for us when they re-roofed our house. For us, what started out as a small leak in the ceiling turned out to be caused by other factors. Not only did the shingles start failing, but the roof was never properly installed when the house was originally built, and again 20 plus years ago, when it was re-roofed. James Roofing responded to our request for a estimate for the leak in a timely manner. Not only that, they arrived early and worked every day until the job was done. The initial estimate was for what appeared to be a problem for one section of the roof. On further inspection, they realized that the whole roof had some serious issues. Along with the shingles failure, it was never vented properly. James Roofing was very good at explaining what was wrong and what needed to be done. I believe their charges where very fair. Their crew was hard working and courteous. When it was all over, the house looked great. Their extra effort to clean up the debris was appreciated. Thank you James Roofing and crew for your excellent service. The Fergusons"
Complete with ventridge ventilation
Complete roofing system
Proper ladder placement and an excellent roof
Back of house
Front of house

+23

Response time2 days
4 neighbors recently requested a quote
Recommended by93%of homeowners
Avatar for JK Cleanup and Hauling LLC
JK Cleanup and Hauling LLC
5.0(
1
)
Gutters & Downspouts - Clean

Serving Prineville, OR and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

Hi, we’re Jose and Dakota, co-owners of JK Cleanup & Hauling LLC, proudly born and raised in Prineville and serving all of Central Oregon.\n\nWe specialize in junk removal, property cleanups, hauling, light demolition, handyman work, yard debris removal, moving services, and more. Whether it’s a garage cleanout, rental turnover, fascia repair, trim work, gravel touch-ups, or helping move heavy furniture — we show up ready to work and get it done right.\n\nWe’re licensed & insured, locally owned, and hands-on with every job. When you hire JK, you’re working directly with us — not a big crew you’ve never met. We take pride in clear communication, fair pricing, and leaving your property cleaner than we found it.\n\nIf you’re looking for dependable, hardworking local guys who stand behind their work — we’d be happy to help.

1 neighbors recently requested a quote
Avatar for Ryan's Property Maintenance
Ryan's Property Maintenance
New to Angi
Gutters & Downspouts - Clean

Serving Prineville, OR and surrounding areas

Approved

Free estimates

Small jobs welcome

Offers commercial services

Solo owner/Operator with 8 years experience. I was a golf course assistant Superintendent then promoted to Landscape Manager at the beautiful Brasada Ranch Resort. Both of those positions require a very keen eye, knowledge, hardwork, dependability and taking pride in your work. I love what I do and it shows in the quality of the finished product. People deserve to have the beautiful landscape they want. Let's envision togther and make it happen! Services I provide include: mowing, trimming, edging, leaf/debris clean up, high powered backpack blowing, pruning, weeding, fertilizing (nutrients only, no pestcides) aerify, dethatch and pressure washing. Look forward to meeting you and exceeding your expectations.\n\nThank you,\nRyan

Avatar for Cascade Power Clean, LLC
Cascade Power Clean, LLC
4.9(
10
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Prineville, OR and surrounding areas

In business since 2019

Free estimates

Credit card accepted

"Highly recommend. He did amazing work getting everything clean for the home we were putting on the market. He was even able to get off some soot stains on paint that a prior cleaner said they couldnâ t remove. The house looked the best it had in years. He also looked out for the birds nest with some baby birds under the covered patio :). He easy to get ahold of, was timely, scheduled quickly and affordable."
Response time7 hrs
Response rate85%
Recommended by100%of homeowners
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Gutter Cleaning FAQs, answered by experts

At least twice a year, or more if surrounded by trees.

Yes, there are several downsides to installing rain chains. For one, rain chains have a lower flow capacity than a typical gutter and downspout system. This means that if there is a rainstorm, the rain chain can stop working completely. Rain chains also cannot redirect rainwater away from your house. In homes with a sloped yard, this could cause water damage in your foundation or basement. 

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.

Usually 1-2 hours, depending on gutter length and condition.

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 Prineville, OR homeowners’ guide to gutter cleaning services

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