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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 LeafFilter Gutter Protection
LeafFilter Gutter Protection
3.9(
2,588
)
Gutters & Downspouts - Clean

Serving Southold, NY and surrounding areas

Approved (Corporate)

In business since 2005

Free estimates

Warranties offered

"LeafFilter doesn't clean gutters, they sell and install their LeafFilter Gutter products and only clean the gutters if you buy their product. I can't even begin to afford their product so I wasn't able to get my gutter cleaned by them."
Free no obligation estimates
Free no obligation estimates
Metal Screen mesh ontop of gutter
Free-flowing water in clean gutters
Debris resistant gutter protection

+63

10953 neighbors recently requested a quote
Recommended by80%of homeowners
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 and his son were great! Friendly, on time and did a beautiful job replacing our front stoop. Good price and cleaned up when they were done each day. We highly recommend them. I wish I could share before and after pics"
Response time8 hrs
Response rate92%
135 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

4 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

4 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%
5 neighbors recently requested a quote
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Gutter Cleaning FAQs, answered by experts

While you can clean your gutters without geting on a ladder, you won't know just how well you're cleaning them without the use of a telescopic water pole. Some ways to clean gutters from the ground include using telescopic cleaning tools and a leaf blower extension, wet/dry vacuum extension, pressure washer, or garden hose with a curved end.

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.

Gutters should be cleaned at least twice a year, in the spring and in the fall, to remove the debris from trees that can clog the eavestroughs and downspouts. Debris like leaves, twigs, and seed pods can build up and cause your gutters to overflow, potentially causing damage to your roof and foundation. Water backing up under the shingles can rot the edge of your roofline. Overflow water falling next to your foundation can end up leaking into your basement or crawl space.

Yes, you can use a pressure washer to effectively clean debris, dirt, and grime from your gutters, but it must be done with caution to avoid damage. Always use a low-pressure setting, with a recommended range between 1,200 and 1,800 PSI. Excessive pressure can bend or dent aluminum gutters, damage seams, peel paint, or even knock shingles off your roof, potentially leading to leaks and moisture issues. For a safer alternative, consider soft washing or cleaning them by hand. When using a pressure washer, it is safer to use gutter elbow extensions from the ground rather than climbing a ladder, as the force can cause instability. Due to the risks, you may want to hire a licensed and insured contractor for the job.

At least twice a year, or more if surrounded by trees.

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.