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TRUSTED BY SOUTHOLD, NY HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon66
    Verified gutter cleaning services reviews

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

Avatar for Pro Master Construction, Inc.
Pro Master Construction, Inc.
5.0(
126
)
Gutters & Downspouts - Clean

Serving Southold, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2020

Warranties offered

Credit card accepted

"Luan provided a written free quote which was reasonable. He is very personable and did not pressure to get the job. His work was excellent. He was very methodical and wanted me to be satisfied before accepting payment. He always did a thorough clean up each day. I would hire him again and highly recommend him."
Response time8 hrs
Response rate92%
126 neighbors recently requested a quote
Avatar for TOP FIX CONSTRUCTION INC.
TOP FIX CONSTRUCTION INC.
5.0(
13
)
Gutters & Downspouts - Clean

Serving Southold, NY and surrounding areas

Approved

In business since 2025

Free estimates

Credit card accepted

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

Molding
Roofing
Roofing
Roofing
New siding

+15

3 neighbors recently requested a quote
Avatar for Wash King
Wash King
5.0(
5
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Southold, NY and surrounding areas

Approved

In business since 2022

Free estimates

Emergency services offered

Wash King is 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.

Response time6 hrs
Response rate98%
Recommended by100%of homeowners
Avatar for Ned Stevens Gutter Cleaning- Commercial
Ned Stevens Gutter Cleaning- Commercial
4.0(
1
)
Gutters & Downspouts - Clean- For Business

Serving Southold, NY and surrounding areas

Approved

In business since 1965

Free estimates

Credit card accepted

When you choose Ned Stevens for your gutter cleaning, gutter repair, gutter installation, window cleaning and other services, you can count on exceptional quality of work and outstanding customer service. Our labor staff are all our own employees, and we train them in our state-of-the-art training facility focusing on quality work. Our work is 100% Guaranteed. Your satisfaction is our goal. We want to make your gutter cleaning experience effortless. You never need to be home! We are fully insured and guarantee all of our work. Our family owned company has been cleaning and installing gutters for over 60 years.

Our Work
Our Work
Our Work
Our Work
Our Work

+1

5 neighbors recently requested a quote
Avatar for Sebonac Creek Landscape
Sebonac Creek Landscape
4.6(
9
)
Gutters & Downspouts - CleanGutters & Downspouts - Clean- For Business

Serving Southold, NY and surrounding areas

Approved

In business since 2012

Free estimates

Emergency services offered

We offer only the best in quality workmanship and professional courtesy. We specialize in all phases of commercial and residential landscaping. We are committed to quality work and outstanding results & are strongly involved in local community activities. We look forward to working with you! \n

Response time7 hrs
Response rate93%
7 neighbors recently requested a quote
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Gutter Cleaning FAQs, answered by experts

Properly installed gutters should be able to function normally in heavy rains. Allowing water to overflow can cause water damage around your home's basement or foundation. If the overflow is caused by a simple clog, paying a gutter cleaning cost of $125 to $250 may be enough to get the gutters running clear again. If there's a larger issue, you may need to repair or replace your gutters.

Water should not be dripping behind your gutters. Rain dripping between your gutters and the fascia might indicate that the gutters are misaligned with the fascia board or there are loose screws in the gutters, allowing water to pass through. Start by checking for these issues and make repairs ASAP.

Icicles don't necessarily mean your gutters are clogged or bad, but they can indicate an underlying issue. While clogged gutters can cause icicles to form, the problem could also be an ice dam on your roof from poor insulation. In that case, melting snow can refreeze in the gutter even without a clog. Regardless of the cause, the weight of the ice can damage your gutters or even rip them completely off the house. If you are unsure of the underlying problem, it's best to call a roofing company to assess the issue and implement a permanent solution.

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.

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.

The Southold, NY homeowners’ guide to gutter cleaning services

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