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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
Showing 1-10 of 38
Gutter Cleaning FAQs, answered by experts

It is not recommended to clean gutters, or do any work on your roof for that matter, without the use of a ladder. Please make sure you have a spotter and avoid slippery surfaces when performing this task.

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.

Clean regularly, inspect for rust or damage, and apply sealant to joints as needed.

Gutters overflow in heavy rain for several reasons. The main reasons why your gutters could be overflowing in heavy rain include:

  • Not enough downspouts to effectively remove water from your gutters

  • Too small of a gutter width—the average gutter size is four to six inches

  • Clogged gutters

  • Incorrect slope

If you believe your gutters were installed incorrectly, it’s a good idea to know who to call for gutter leaks. Speak with a local gutter specialist to get to the bottom of your gutter system to stop water from flooding your property or yard ASAP.

Once you’ve installed your gutters, you'll need to maintain them. You should clean your gutters once or twice a year to keep them functioning correctly. But if climbing a ladder and scooping out handfuls of wet leaf gunk is just not your thing, you can hire a professional gutter cleaner near you to do the job. 

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.