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TRUSTED BY WINTHROP, MA HOMEOWNERS

  • Average homeowner rating star icon4.1
    Average homeowner rating
  • Verified reviews icon149
    Verified gutter cleaning services reviews

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

Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
740
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winthrop, MA and surrounding areas

Approved

In business since 2000

Free estimates

Warranties offered

"Perfect experience. Claimed an Angie's List deal for gutter cleaning. Joe called within the hour and got me on their schedule on the same day. Guys arrived promptly and thoroughly cleaned all of our gutters. There is a steep hill on one side of our house which has prevented other gutter cleaning companies from getting to the gutter over that area, but Joe's crew got up on the roof and cleaned that area, too. They cleaned up well afterwards, as well. Couldn't have asked for a better experience. Will definitely have them back in the fall."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+3

Response time12 hrs
Response rate100%
6 neighbors recently requested a quote
Avatar for Boston Window Cleaning
Boston Window Cleaning
5.0(
12
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winthrop, MA and surrounding areas

Approved

In business since 2021

Free estimates

Small jobs welcome

"Boston Window Cleaning responded very promptly to my gutter and downspout cleaning request and came the same day. Jay was friendly, professional, worked efficiently, and did a great job on our house, which has some tight spaces for accessing the gutters. And the price was very good. Will definitely use these guys again."
Power washing
Power washing
Power washing
Power washing
Power washing

+4

22 neighbors recently requested a quote
Recommended by8%of homeowners
Avatar for Eddi's Construction, Inc.
Eddi's Construction, Inc.
5.0(
32
)
Gutters & Downspouts - Clean

Serving Winthrop, MA and surrounding areas

Approved

In business since 2017

Free estimates

Small jobs welcome

"He came up with a better idea than I had, he added more support anchors and screws. He was very easy going and polite. Very neat, cleaned up after and he replaced and exterior thermostat that was attached to the old part of the deck. I would hire Eddi again."
Decks
Decks
Decks
Decks
Decks

+10

Recommended by88%of homeowners
Avatar for Services & More LLC
Services & More LLC
4.8(
31
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Winthrop, MA and surrounding areas

Approved

Free estimates

Emergency services offered

Warranties offered

"I hired this company for spring cleanup, and when they got here they were able to do so much more They edged all my beds. They mulched everything. They filled my new raised beds with loam. They cleaned my two ponds. They went way over and above what I expected, I would recommend them highly to anyone. They .were professional. They were courteous. They left nothing behind. It was absolutely the best experience I’ve had hiring someone in a long time. I couldn’t be happier. I would highly recommend them to anyone for any projects."
Furniture Assembly
Bathroom Remodel
Bathroom Remodel
Bathroom Remodel
Bathroom Remodel

+4

18 neighbors recently requested a quote
Avatar for Square Services
Square Services
4.6(
29
)
Gutters & Downspouts - Clean- For Business

Serving Winthrop, MA and surrounding areas

Approved

In business since 2017

Free estimates

Emergency services offered

"I had a front deck refinished. Carmen was fantastic, always answered the phone when I called and returned emails promptly. She s very professional and an asset to her business. Work guys were very polite, on time and kept work area very clean. Job was satisfactorily done."
Response time2 days
Response rate86%
Recommended by100%of homeowners
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Gutter Cleaning FAQs, answered by experts

To clean the tops of gutter guards, use a soft-bristle brush or a leaf blower to remove debris like leaves, twigs, or dirt. For stubborn grime, spray the guards with a garden hose, directing water downward to avoid forcing debris into the gutter. If the guards are removable, take them off and rinse thoroughly before reattaching. Regular cleaning, especially during fall or after storms, will help maintain their effectiveness.

Shingle granules can be cleaned out of gutters using a small scoop or a hose, depending on the quantity of granules and how much other debris is in your gutters. First, clear your gutters of leaves and other debris. This may remove granules in the gutters if they are mixed in with the debris. Use a plastic scoop to remove larger quantities of granules or a hose with a high-powered nozzle for smaller amounts, and collect and dispose of the granules once they’ve been removed.

Yes, gutter cleaning methods without using a ladder are available, including:

  • A curved wand attachment for your hose 

  • Gutter tongs on an extension pole

  • A leaf blower gutter cleaning kit

  • Vacuum designed for cleaning gutters

Just be sure that your downspouts are connected and can direct water away from the house if you’re using a water-powered method. This will keep the water from dumping next to the house.

Whether or not you can use a pressure washer to clean your gutter guards depends on the type of gutter guard you have and the strength of the pressure washer. Most gutter guards can handle a low-pressure setting but check first. If you’re unsure if your gutter guard is designed for pressure washing, check your manufacturer’s instructions, ask a pro, or use a garden hose to clean the gutter guard instead. As gutter guards age, they become less resistant to the strong forces of a power washer, so treat older gutter guards with more care.

Yes, gutters can still get clogged even with gutter guards installed. While guards significantly reduce the amount of debris that enters your gutters, they are not 100% effective.

Small debris such as pine needles, seedlings, algae, small leaves, and pebbles can pass through the guard's screen or mesh and accumulate over time. Clogs can also form if the guards themselves are not cleaned and become overwhelmed with debris on top, preventing water from entering the gutter.

If this buildup is neglected, it can lead to clogs, water leaks, mold growth, and even plants sprouting from the gutters. The primary benefit of gutter guards is not the complete elimination of maintenance, but a dramatic reduction in how often you need to perform it, often from several times a year to just once a year or less.

The Winthrop, MA homeowners’ guide to gutter cleaning services

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