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10 Best Gutter Installation Companies in Chester, NY

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Written By Bradford Cuthrell

Last Updated April 2024

If your gutters are old and worn – or if your home is lacking gutters in the first place – installing new, reliable gutters should be one of your top priorities. Unreliable gutters can eventually end up with recurring leaks and subsequent costly water damage. Annual rainfall in Chester is above average, so having a good gutter system is highly important.

Our comprehensive list of the premier gutter installation providers in the Chester area can help you get started.

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Most Durable
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Best Designed
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Top 10 Best Gutter Installation Companies in Chester

Green Collar Roofing & Exteriors

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259 Dunning Rd, Middletown, NY 10940 (845) 344-2029 greencollarroofing.com

Transparent pricing

Diligent in educating customers

Good customer service

Free assessment

Services Offered

Soffit and fascia
Inspection
Gutter installation

Guaillas Inc. Roofing, Gutters, & Siding

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11 Midland Ave, Middletown, NY 10940 (845) 381-7366 guaillasroofing.com

Diligent in educating customers

Free assessment

Transparent pricing

Good customer service

Services Offered

Maintenance and cleaning
Gutter guards
Gutter installation

Gutter Helmet of Eastern NY

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28 Fair Ave #2, Middletown, NY 10940 (845) 245-2581 gutterhelmetny.com

Good customer service

Diligent in educating customers

Punctual service

Transparent pricing

Free assessment

Services Offered

Seamless gutters
Gutter replacement
Gutter installation
Inspection

VL Roofing and Siding Inc

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402 E Main St, Middletown, NY 10940 (845) 801-2104 vlroofingandsiding.com

Good customer service

Punctual service

Diligent in educating customers

Free assessment

Transparent pricing

Services Offered

Gutter installation
Downspouts
Seamless gutters

Exterior Pro Builders Inc.

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20 Fairlawn Ave, Middletown, NY 10940 (845) 237-4887 exteriorprobuilders.com

Diligent in educating customers

Good customer service

Transparent pricing

Free assessment

Services Offered

Gutter installation
Gutter repair
Inspection

Extera Roofing

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218 Greenwich Ave, Goshen, NY 10924 (845) 500-6757 exteraroofing.com

Free assessment

Transparent pricing

Good customer service

Services Offered

Gutter installation
Inspection

Hudson Valley Roofers Inc.

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822 W Kaisertown Rd, Montgomery, NY 12549 (845) 457-1560 hvroofers.com

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Good customer service

Transparent pricing

Services Offered

Gutter installation

New Jersey Strong Construction, LLC

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624 County Rd 517, Sussex, NJ 07461 (862) 281-8708 new-jersey-strong-construction-llc.business.site

Transparent pricing

Free assessment

Punctual service

Good customer service

Services Offered

Gutter installation

L-Pro Restoration Inc.

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659 Gardnertown Rd, Newburgh, NY 12550 (845) 842-6637 lproroofing.com

Transparent pricing

Punctual service

Good customer service

Free assessment

Services Offered

Gutter installation
Inspection

Segelman Shaw Roofing Siding & Gutters

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1 Executive Blvd Unit 105B, Suffern, NY 10901 (845) 364-8200 letsroof.com

Diligent in educating customers

Good customer service

Transparent pricing

Services Offered

Maintenance and cleaning
Inspection
Gutter installation
Today's Homeowner Ranking Methodology

Today's Homeowner looks at dozens of datapoints on gutter installation companies to come up with our data-driven rankings. It's not possible for a company to pay for preferential treatment in our rankings. We look at the following key factors in determining who should top our list:

  • Company Experience
  • Real User Reviews
  • Company Reputation
  • Accreditations and Licenses
  • Service Area
  • Customer Service
Have questions about our methodology or company ratings? Reach out to FindAPro@TodaysHomeowner.com.

What Services Do Gutter Installation Companies Offer?

By working with a full-service gutter installation company, you'll get the longest lifespan and best value from your system. The Chester companies on our list can do all these jobs and more:

  • Gutter guard installation: Gutter guards will help stop plant matter from clogging your downspouts. No matter the style or age of your gutter system, a local gutter guard company can install the right guards for them.
  • Cleaning: Gutters require routine cleaning. Chester residents have moderate tree cover, and while they experience a lot of rainfall, it probably won't be enough to clear clogs.
  • Installation: An expert technician can help you install a new gutter system safely while protecting your roof's warranty.
  • Repair: Whether you're dealing with cracking, holes, sagging, mold, or loose sections, an experienced Chester gutter professional can identify and resolve your gutter issues quickly.
If you find a local gutter company you like, ask if they offer long-term contracts for installation, cleaning, and repairs. These packages are normally billed either monthly or annually.

Gutter Services

By working with a full-service gutter installation company, you'll get the longest lifespan and best value from your system. The Chester companies on our list can do all these jobs and more:

  • Gutter guard installation: Gutter guards will help stop plant matter from clogging your downspouts. No matter the style or age of your gutter system, a local gutter guard company can install the right guards for them.
  • Cleaning: Gutters require routine cleaning. Chester residents have moderate tree cover, and while they experience a lot of rainfall, it probably won't be enough to clear clogs.
  • Installation: An expert technician can help you install a new gutter system safely while protecting your roof's warranty.
  • Repair: Whether you're dealing with cracking, holes, sagging, mold, or loose sections, an experienced Chester gutter professional can identify and resolve your gutter issues quickly.
If you find a local gutter company you like, ask if they offer long-term contracts for installation, cleaning, and repairs. These packages are normally billed either monthly or annually.

How To Choose a Gutter Installer

Doing comprehensive research on gutter companies ahead of time helps avoid shoddy workmanship and overinflated rates. When assessing gutter installers, look for:

Assess Their Experience

Look for an established local provider with years, or ideally decades, of gutter installation experience. An experienced provider understands your local climate and weather as well as local home architecture styles and can help you find the right gutters for your home. It will also have proven systems for safe and efficient gutter installation.

Verify Proper Licensing and Insurance

Before committing to a contract, verify that the company has the proper credentials. Request to see licensing, bonding, and insurance documentation upfront. Proper credentialing tells you that the company operates above board and helps protect you from issues if an injury or property damage occurs during the project.

Check Reviews and Referrals

Spend time searching online reviews on sites such as Yelp, the Better Business Bureau, and Google to confirm that the company has a proven track record of providing good customer service and great project results. Look for long-term satisfied customers to get a sense of the company's overall reliability. Watch for any red flags, such as poor communication or unfinished jobs. All the providers we recommend have a high number of reviews with a good average rating.

Choose Reputable Brands

Choose a gutter installer with certification from the gutter manufacturer, as this means the provider truly understands the process and knows how to install gutters according to the manufacturer's specifications. This helps you get the best results.

Examine Warranties

Only use contractors that offer strong manufacturer guarantees on supplies as well as their own installation warranties. Look for 5-10 year warranties on basic aluminum gutters and 1-3 years on labor.

Gutter Installation Materials

Pick durable materials like heavy-gauge aluminum that won't decay, warp, or rust over time. The right materials will be able to withstand the weather in Chester. Make sure any paints and finishes will also last a long time.

Questions to Ask

Be sure to ask specific questions when comparing different gutter installers. You'll want to ask questions including these:

  • How long does full installation take? Most providers can usually complete a gutter installation project in around one day's time.
  • What materials are best for my gutters based on my specific home style and the local weather conditions? Consider the pros and cons of each gutter material, accounting for key factors such as Chester's average rainfall, snowfall, and the size and capacity of the gutters.
  • How do you guarantee a smooth integration with my existing roof? Find out whether steps like underlayment replacement are included.
  • What are the specific warranty coverages on materials and workmanship? High-quality materials often come with 5–10 year warranties. Labor is typically back by a 1-3 year warranty.
  • Will you provide a detailed quote for both full gutter replacement and fixes for problem areas? Get estimates in writing to ensure you know the cost of your gutter installation before the job begins.
  • Are you also able to install gutter guards? Putting in gutter guards helps prevent blockages that result from leaves and debris falling into your gutters.
  • How will you make sure that the new gutters have the right pitch and slope to prevent standing water? Proper slope and pitch helps prevent overflow. Your provider should know how to correctly align a gutter system with your home’s roof.
Taking the time to thoroughly research providers helps you select the best gutter installation company. Investing in new gutters now helps avoid much pricier water and structural damage later.

Frequently Asked Questions About Gutters in Chester, NY

One way to verify the reputation of a gutter services company is to read online reviews. When you speak to a company representative, confirm that they have insurance and that they can clearly explain how the job will or won't affect your roof warranty. Lastly, a reliable Chester gutter services company should provide an estimate and a copy of their warranties to you in writing after completing an inspection.

The average Chester homeowner spends between $376-$3,373 for gutter installation, with a cost of about $3.73 per linear foot. This cost will depend on the size of your home (including number of levels) and the gutter materials and whether you’ve opted for sectional or seamless. The best way to determine how much gutter installation is going to cost is to speak with one or more Chester gutter installation companies and ask. Make sure to have a general idea of the material and gutter footage you want when you call.

For all gutter services, the benefits of using a local Chester gutter company include greater safety, better quality of work, and decreased risk of future problems. When it comes to installation, hiring a professional often comes with the added benefit of a warranty for both services and materials. When it comes time to replace your gutters, a gutter services professional can provide materials and later discard both leftover materials and waste, which will help you save time and keep your yard clean.

There are gutter companies that also offer cleaning or repair services for your siding, windows, or roofing. Usually, these services are provided by companies that provide more “all-purpose” home services. If you want to combine multiple services, we suggest contacting several companies from our list to see what packages they offer.

Accessories such as downspout brackets, decorative boots, and fascia brackets can be added to your gutter system to make it look nicer. If you live somewhere, like Chester, that gets more precipitation than average, you could consider adding a conductor head onto your gutters, giving them more time to drain and reducing the risk of overflow. If your roof has a deeper overhang, you could also purchase a rain chain to help drain water directly from your gutters to the ground.

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