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TRUSTED BY WEST ROXBURY, MA HOMEOWNERS

  • Average homeowner rating star icon4.2
    Average homeowner rating
  • Verified reviews icon1.1k+
    Verified gutter cleaning services reviews

Top-Rated Gutter cleaning pros in West Roxbury - Updated Nov 2026

Avatar for JLM Gutter Cleaning Service
JLM Gutter Cleaning Service
4.4(
533
)
Gutters & Downspouts - Clean

Serving West Roxbury, MA and surrounding areas

Approved

In business since 1998

Free estimates

Small jobs welcome

For over 25 years, JLM Gutter Cleaning Service has remained locally Family Owned & Operated, specializing in all things Gutter-related. Cost is determined by the job. Call (800) 362-0933 to schedule an Estimate or an Appointment. Mailing Address: PO Box 553 Stoughton, MA 02072.

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2 neighbors recently requested a quote
Recommended by88%of homeowners
Avatar for Hennelly & Son Roofing & Gutters
Hennelly & Son Roofing & Gutters
4.8(
740
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving West Roxbury, MA and surrounding areas

Approved

In business since 2000

Offers commercial services

Customers say: Quality work

"I have been using Hennelly & Son Roofing & Gutters for over 6 years now. Whether it is fixing the gutters, addressing roof problems or simply cleaning gutters, the result is always equally good - great professional job ! What is most amazing is his responsiveness -- Joe as he promises in his voice mail -- always returns your call immediately. In spite of weather not always cooperating he goes the extra mile by working even on Sunday to meet the deadline and make my house ready for an upcoming snow storm !"
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+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 West Roxbury, 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 GUTTER MASTER SERVICE LLC
GUTTER MASTER SERVICE LLC
5.0(
7
)
Gutters & Downspouts - Clean

Serving West Roxbury, MA and surrounding areas

Approved

Free estimates

Credit card accepted

Offers commercial services

We are committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade, combined with ability, is what makes us true professionals. Above all, we are watchful of our customers' interests and make their concerns the basis of our business \n \n

6 neighbors recently requested a quote
Avatar for Gotta Get A Gutter
Gotta Get A Gutter
4.4(
17
)
Gutters & Downspouts - Clean

Serving West Roxbury, MA and surrounding areas

Approved

In business since 1986

Free estimates

Emergency services offered

Welcome to Gotta Get A Gutter! We are committed to exceeding your expectations. As experts, we will handle your needs with the high quality expertise that your home or business deserves. We offer competitive prices and customer satisfaction is our number one priority. Call us directly today at 781-727-7915!

Roof & Gutters
Roof & Gutters
Roof & Gutters
Roof
Roof

+29

Response time6 hrs
Response rate94%
15 neighbors recently requested a quote
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Gutter Cleaning FAQs, answered by experts

Gutter cleaning in West Roxbury should follow a seasonal schedule: clear out leaves and twigs after spring storms, inspect for loose brackets and leaks in summer, and thoroughly clean gutters during the fall. In winter, monitor for ice dams and remove any blockages promptly. With older homes and mature trees common in the area, pay special attention to downspout extensions and look for signs of pest nesting or water overflow.

Helpful?

In West Roxbury, overlooking regular pruning of mature street trees, waiting too long after peak leaf fall, and ignoring downspout elbows can quickly lead to gutter blockages. Failing to check gutters after nor’easters or heavy spring rains, and not addressing early signs of ice dam formation, can also cause debris buildup and water damage, reducing the effectiveness of your gutter cleaning efforts.

Helpful?

In West Roxbury, gutters beneath mature street trees—especially those facing the road—tend to collect the most debris. North-facing gutters and roof valleys are more prone to moss and ice buildup, while downspout connections can clog from clay soil and seasonal freeze-thaw cycles. Pay close attention to gutters over driveways, roof corners, and low-lying additions, as these areas often require more frequent cleaning and inspection.

Helpful?

Before tackling gutter cleaning in West Roxbury, schedule your project just after peak leaf drop or major storms for best results. Confirm your insurance covers exterior maintenance, and discuss timing with neighbors if your homes are close together. Check for any unique features on historic homes, plan for yard waste disposal according to local guidelines, and always inspect for overhead wires or tight access points to keep the project safe and efficient.

Helpful?

If your West Roxbury home has gutters that overflow during rain, visible streaks or stains on siding, or ice dams in winter, it’s time for cleaning. Homes with large trees nearby, steep or intersecting rooflines, or clay soil are at higher risk for clogs. Older or multi-story homes especially benefit from regular gutter maintenance to prevent water intrusion and foundation issues.

Helpful?

The West Roxbury, MA homeowners’ guide to gutter cleaning services

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