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TRUSTED BY CHESHIRE, MA HOMEOWNERS

  • Average homeowner rating star icon4.5
    Average homeowner rating
  • Verified reviews icon30
    Verified gutter cleaning services reviews

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

Avatar for Advanced Seamless Gutters
Advanced Seamless Gutters
4.4(
210
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Cheshire, MA and surrounding areas

Approved

In business since 1999

Free estimates

Emergency services offered

"I used advanced seamless gutters for gutters on my house and they did a wonderful job. Also they were able to take care of my leaky basement faster than anyone could even come out to give an estimate.They were clean and professional and reasonably priced."
BASEMENT RE-FINISHING
MOLD CERTIFICATION
Hatchway
Footer
Hatchway Foundation Walls

+63

Response time1 day
Response rate86%
165 neighbors recently requested a quote
Avatar for CJ's Gutter and Glass
CJ's Gutter and Glass
3.4(
5
)
Gutters & Downspouts - Clean

Serving Cheshire, MA and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We offer a variety of General Contractor services that are customizable to each individual project. You will find us to be competitively priced, paying close attention to the details of each and every project that we are involved with. We look forward to building lasting relationships and guarantee your satisfaction! \n

101 neighbors recently requested a quote
Oak and ivory cleaning co
New to Angi
Gutters & Downspouts - Clean

Serving Cheshire, MA and surrounding areas

Approved

Hi! I’m Shelbea, the owner of Oak & Ivory Cleaning Co. 🤍✨\n\nI started my cleaning business with one simple goal: to help make life a little easier by giving my clients a clean, comfortable, and welcoming space to come home to. I take pride in being dependable, detail-oriented, and treating every home as if it were my own.\n\nWhether you need a routine cleaning, deep clean, move-in/move-out service, or just some extra help getting your space back in order, I’d love the opportunity to help! 🧹🫧\n\nThank you for supporting my small business — I can’t wait to make your space shine! 🤍

2 neighbors recently requested a quote
Integrity Property Solutions
New to Angi
Gutters & Downspouts - Clean

Serving Cheshire, MA and surrounding areas

Approved

Hi! I'm a hardworking, dependable professional who takes pride in doing quality work and treating every home with respect. I offer painting, cleanouts, yard cleanups, and general odd jobs. I believe in being honest, showing up on time, communicating clearly, and leaving every job looking its best. Whether it's a small project or a bigger cleanup, I work hard to get the job done right and make sure my customers are satisfied. I look forward to helping you with your next project!

Avatar for Robert Roofing & Gutters
Robert Roofing & Gutters
4.1(
127
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Cheshire, MA and surrounding areas

In business since 1980

Free estimates

Emergency services offered

"Robert Roofing and Gutters did an excellent job!  My husband and I had a leak in the living room of our home and decided we would give Angie's List a try. After reading through the reviews, we decided on Robert Roofing. We contacted them, and fortunately, they were able to come out the next day!  The owner was very upfront about the costs and they did not charge us a penny over what was quoted.  They replaced our shingles - they look great and no leaks!  Comments:  professional, prompt and courteous.  Would recommend.
"
FRONT
SIDE
BACK
FRONT
SIDE

+2

Recommended by86%of homeowners
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Gutter Cleaning FAQs, answered by experts

Gutter guards and covers can minimize debris accumulation.

Water overflow, foundation damage, and mold growth are risks.

You may have a clogged gutter. Downspouts can also clog if your gutter collects too much debris. Hire a professional gutter cleaner, and if you still have problems, install a gutter guard (which prevents debris from entering your gutter system) and a downspout extension (which helps drain water further away from your foundation, so it doesn't pool near your house). Follow these tips to keep your gutter downspouts clean.

It’s recommended that you clean your gutters after a severe storm, however, regular storms don’t raise the same concerns. Look for signs your gutter might need cleaning after a harsh storm. Do you see broken branches and excessive leaves all over your yard? Chances are your gutters caught quite some debris. Also, ensure a few drying days before cleaning your gutters. Dry debris is much easier to clean.

The kind of gutter guards you have will affect how often you need to clean them. The more basic type of gutter screen requires cleaning once or twice a year. With a micromesh screen, you may be able to extend the time between cleanings to every two years or so.

However, if you have trees near your roof, you’ll need to clean your gutters more frequently, especially if you have chicken-wire or colander-type gutter guards. If you have pine trees near your roof, you may even need to clean your gutters quarterly, as tiny pine needles can get through any type of gutter guard.

The Cheshire, MA homeowners’ guide to gutter cleaning services

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