Top-rated gutter cleaning pros.

Best gutter cleaning pros near Holliston, MA

Enter your zip and get matched with up to 5 pros

Need a pro for your gutter cleaning project in Holliston, MA?

Select your specific project to find the pro for you.

TRUSTED BY HOLLISTON, MA HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon543
    Verified gutter cleaning services reviews

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

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

Serving Holliston, MA and surrounding areas

Approved

In business since 2000

Offers commercial services

Customers say: Quality work

"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%
5 neighbors recently requested a quote
Avatar for Sun Bright Window Cleaning
Sun Bright Window Cleaning
4.9(
134
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Holliston, MA and surrounding areas

Approved

In business since 2017

Free estimates

Offers commercial services

From everything from window cleaning, to gutter cleaning, to power washing, we are the experts you need to take care of your home or business. We provide fast and detailed service and look to treat every home or business as we would our own. We look forward to working with you!

4 neighbors recently requested a quote
Recommended by100%of homeowners
Avatar for Gotta Get A Gutter
Gotta Get A Gutter
4.4(
17
)
Gutters & Downspouts - Clean

Serving Holliston, MA and surrounding areas

Approved

In business since 1986

Free estimates

Emergency services offered

"Christian was wonderful. He went beyond our expectations to ensure our gutters were repaired and in great working condition. So happy we chose to work with him!"
Roof & Gutters
Roof & Gutters
Roof & Gutters
Roof
Roof

+29

Response time6 hrs
Response rate94%
15 neighbors recently requested a quote
Avatar for Nova Top Roofing & Siding
Nova Top Roofing & Siding
5.0(
9
)
Gutters & Downspouts - Clean

Serving Holliston, MA and surrounding areas

Approved

In business since 2015

Free estimates

Emergency services offered

We pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business! Book with us online or feel free to give us a call today! \n \n \n \n

...
Showing 1-10 of 297
Gutter Cleaning FAQs, answered by experts

Gutter cleaning in Holliston directly improves home comfort by preventing water intrusion in basements, which is a frequent concern due to the area’s high water table and clay-rich soil. Clean gutters also help deter pests like mosquitoes and carpenter ants, protect your home’s foundation, and minimize landscape erosion. Regular maintenance ensures quieter rainstorms and preserves curb appeal, especially in neighborhoods with dense maple and pine tree coverage.

Helpful?

In Holliston, unexpected costs during gutter cleaning often arise when technicians discover issues like warped gutters from heavy oak or maple leaf buildup, or blockages in underground drainage systems common in older neighborhoods. Additional charges may apply for removing pine needles, handling excess debris from mature trees, or addressing ice dam remnants after harsh winters. Emergency visits following Nor’easters can also increase overall project complexity.

Helpful?

Gutter cleaning in Holliston becomes more complex for homes with steep colonial roofs, mature hardwood trees, or custom copper gutters often found in historic districts. Properties bordering conservation land may have restricted access, while underground drainage and seasonal ice buildup require specialized tools. Multi-story homes and dense foliage also demand extra safety precautions and can extend project timelines, especially during peak leaf fall.

Helpful?

In Holliston, gutter cleaning maintenance should include scheduling cleanings each spring and fall to manage heavy leaf and pine needle accumulation. After major storms or snowmelt, inspect for clogs, check for ice dam formation, and ensure downspouts flow freely. Regularly examine gutter guards if present, tighten fasteners, and trim overhanging branches from local hardwoods. Annual professional assessments help address issues unique to the area’s climate and foliage.

Helpful?

After gutter cleaning in Holliston, keep detailed service receipts, before-and-after photos, and a log of any repairs or gutter guard installations. Maintain a seasonal maintenance checklist tailored to your property’s tree types, such as oaks or pines. Recording debris disposal methods and noting recommendations for future upkeep can be helpful for insurance claims, especially after severe weather events typical in the region.

Helpful?

The Holliston, MA homeowners’ guide to gutter cleaning services

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