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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

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.

Regular inspections, occasional rinsing, and removing large debris ensure long-term functionality.

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.

Installing a leaf protection system that keeps leaves and pine needles out of your gutter downspout is the best way to prevent clogs. Additionally, you may want to remove any trees or branches that are hanging over your downspouts to prevent leaves and branches from making their way into your gutter system. Of course, routine downspout cleaning and inspection can also help you stay ahead of clogs that create water damage at your home.

Downspouts channel water from your roof and gutters into the ground following a specific route so water doesn’t accumulate around your house’s foundation. Without a downspout, the standing water will wash away material and disrupt the soil, leading to foundation erosion. The standing water will also form ice around your house during cold weather, causing a safety hazard.

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.