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TRUSTED BY CHESAPEAKE, VA HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon402
    Verified gutter cleaning services reviews

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

Avatar for Gutters Matter
Gutters Matter
4.8(
21
)
Gutters & Downspouts - Clean- For Business

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2013

Free estimates

Emergency services offered

"I give Gutters Matter top grades for promptness, courtesy, quality of work and materials, and fair pricing. When I posted a requirement for a small gutter installation job, Gutters Matter called within the hour offering to come out the same afternoon to scope the work and provide a written estimate. By the time they arrived 2 hrs later, 3 other companies had responded to my post but turned down the work because the job was "too small." Gutters Mattter provided a fair estimate which I accepted. We scheduled a start the next day and they were on time to the minute with a crew of four who installed the new gutters ordered in less that three hours, cleaned up after themselves, and even cleaned out my existing gutters ... a task which I had not ordered and which had not been included in their estimate."
Gutter Services
Gutter Services
Gutter Services
Gutter Services
Gutter Services

+78

Response time12 hrs
Response rate90%
14 neighbors recently requested a quote
Avatar for LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,588
)
Gutters & Downspouts - Clean

Serving Chesapeake, VA 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 R&R Pressure Washing
R&R Pressure Washing
5.0(
27
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2017

Free estimates

Warranties offered

"R&R Pressure washing did a great job! Very professional and my home was thoroughly cleaned without any damage to surfaces. Additionally, Mr. Romano pointed out a couple of areas on our exterior that needed attention. Will hire again for next year!"
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+37

Response time11 hrs
Response rate99%
9 neighbors recently requested a quote
Avatar for Shine
Shine
4.9(
27
)
Gutters & Downspouts - Clean- For Business

Serving Chesapeake, VA and surrounding areas

Approved

In business since 1999

Free estimates

Customers say: Quick response

"You responded immediately after I requested quotes for service from gutter cleaners online. I was charged exactly the rate quoted over the phone. I was scheduled for service right away and was very happy with the results! Thank you, Jackie Hughes [email protected]"
2 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Restrepos Solutions
Restrepos Solutions
5.0(
18
)
Gutters & Downspouts - Clean

Serving Chesapeake, VA and surrounding areas

Approved

In business since 2021

Free estimates

Small jobs welcome

"It was a pleasure to interact with David snd he did great work on my parents gutters. My mom was so impressed with him that she hired him on the spot to also do the windows. Don’t hesitate to contact him!"
25 neighbors recently requested a quote
Recommended by73%of homeowners
Avatar for Ember and Grace
Ember and Grace
5.0(
4
)
Gutters & Downspouts - Clean

Serving Chesapeake, VA and surrounding areas

Approved

Small jobs welcome

"I can’t say enough good things about Miranda and Marla! These ladies did a phenomenal job deep cleaning my home. When I say they didn’t leave anything untouched, I mean NOTHING! 😂 They were very professional, thorough, and paid close attention to every little detail. You can definitely tell they take pride in their work. When I woke up this morning, it honestly felt like I was waking up in a new house again. Everything looked, smelled, and felt so fresh and clean. That feeling alone was worth it! I’ve already recommended Miranda and Marla to several of my friends and coworkers, and I will continue to recommend them. If you’re looking for someone who is dependable, professional, and actually takes the time to do the job right, these are your ladies! 10/10 BOOK THEM! You will not be disappointed. I will definitely be adding them to the rotation. Thanks ladies, see you soon❣️"
Kitchen clean
Kitchen clean
Kitchen clean
Kitchen clean
Kitchen clean

+8

26 neighbors recently requested a quote
Avatar for Ocean Roofing, LLC
Ocean Roofing, LLC
5.0(
5
)
Gutters & Downspouts - Clean- For Business

Serving Chesapeake, VA and surrounding areas

Approved

Free estimates

Warranties offered

Offers commercial services

At Ocean Roofing, we are a family-owned and operated company with over 20 years of experience serving homeowners and businesses throughout the Hampton Roads area. We specialize in residential and commercial roofing, gutter repairs and replacements, and we proudly offer free estimates on every project. \n\nOur commitment is to deliver quality workmanship and exceptional customer service from start to finish. We take the time to understand your needs, keep you informed throughout every step of the process, and ensure every job is completed with precision and care. Our goal is to provide lasting results you can trust and be proud of for years to come.

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

In Chesapeake, homeowners often overlook securing ladders on sandy or uneven ground, leading to safety risks. Cleaning gutters during stormy weather or hurricane season is another frequent error. Many forget to wear gloves and eye protection, miss hidden wildlife nests, or fail to clear heavy leaf buildup from local trees. Ignoring drainage problems and using high-pressure washers incorrectly can also cause gutter or siding damage.

Helpful?

In Chesapeake, consider that clay soil and low elevation can cause water to linger near your foundation if gutters aren’t clear. Frequent storms and high humidity increase the risk of mold and gutter deterioration. Watch for wildlife nesting in gutters, and check the local schedule for yard debris pickup. Homes in older neighborhoods with large trees may need more frequent cleaning due to heavier seasonal debris.

Helpful?

Regular gutter cleaning in Chesapeake immediately helps prevent water damage, protects landscaping, and reduces mosquito breeding by eliminating standing water. Over time, it preserves your roof, siding, and foundation, lowering maintenance needs and supporting property value. Clean gutters also help manage stormwater runoff, protecting both your home and the Chesapeake Bay watershed, and keeping your neighborhood attractive and resilient year-round.

Helpful?

Before cleaning gutters in Chesapeake, check the weather for a dry, calm day and avoid peak storm seasons. Gather sturdy ladders with stabilizers for soft soil, gloves, and debris bags. Inspect gutters for loose sections, animal nests, or blockages. Review any HOA guidelines or neighborhood restrictions. Let someone know you’ll be working outside for added safety, especially if your home is set back from the street.

Helpful?

Your Chesapeake home likely needs gutter cleaning if you notice overflowing gutters, visible leaf or pine needle buildup, or water pooling near the foundation. Signs like sagging gutters, exterior water stains, or dampness in crawl spaces are strong indicators. Homes surrounded by mature trees or those that have experienced recent storms should be scheduled for cleaning to prevent water damage and maintain proper drainage.

Helpful?

The Chesapeake, VA homeowners’ guide to gutter cleaning services

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