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10 Best Gutter Installation Companies in Winchester, CT

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Written By Bradford Cuthrell

Last Updated April 2024

If your gutters are getting old and worn – or if your home is lacking gutters in the first place – installing new, reliable gutters should be a top priority. Without adequate protection from the elements, your home is at risk of costly unfixable leaks and water damage. If you’re a resident of Winchester, you might already spend more time than most people thinking about your gutters, as the town has more trees than the rest of the U.S.

This curated list of the premier gutter installation providers in and around Winchester can help you get started.

Our Recommended Providers

Top Pick
4.6/5
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  • Diligent in educating customers
  • Transparent pricing
Most Durable
3.8/5
  • Transparent pricing
  • Durable product
  • Timely and professional service
Best Designed
4.7/5
  • Free assessment
  • Best product design
  • Excellent customer education

Top 10 Best Gutter Installation Companies in Winchester

Leafguard Gutter Protection

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227 Progress Dr, Manchester, CT 06042 (203) 463-5978 leafguard.com

Diligent in educating customers

Punctual service

Free assessment

Good customer service

Services Offered

Gutter guards
Seamless gutters
Gutter installation

EPB Roofing & Remodeling

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29 Albrecht Rd, Torrington, CT 06790 (860) 482-5218 epbroof.com

Transparent pricing

Good customer service

Services Offered

Gutter installation
Maintenance and cleaning

Rhino-Back Roofing

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524 Hopmeadow St, Simsbury, CT 06070 (860) 217-1424 rhinobackroofing.com

Diligent in educating customers

Transparent pricing

Good customer service

Free assessment

Services Offered

Inspection
Gutter installation

Jules Poirier Company LLC

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31 E Main St Second Floor, Avon, CT 06001 (860) 604-7660 jpoirier.com

Free assessment

Punctual service

Diligent in educating customers

Transparent pricing

Good customer service

Services Offered

Gutter installation

Pierpont's Rain Gutter Specialists

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856 N Main St, Thomaston, CT 06787 (860) 283-9729 pierpontsraingutter.com

Diligent in educating customers

Good customer service

Transparent pricing

Free assessment

Services Offered

Downspouts
Gutter installation
Gutter guards

Casanova Remodeling

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269 Main St, Terryville, CT 06786 (877) 283-8158 casanovaremodeling.com

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Transparent pricing

Diligent in educating customers

Good customer service

Services Offered

Gutter repair
Gutter installation

JP Carroll Roofing

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135 W Dudley Town Rd, Bloomfield, CT 06002 (860) 467-1639 jpcarrollroofing.com

Good customer service

Transparent pricing

Free assessment

Services Offered

Inspection
Gutter guards
Maintenance and cleaning
Downspouts
Gutter installation

Major Home Improvements

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22 Verona St, Westfield, MA 01085 (413) 636-6046 majorhomeimprovements.com

Diligent in educating customers

Transparent pricing

Punctual service

Free assessment

Good customer service

Services Offered

Gutter installation
Downspouts
Soffit and fascia
Gutter guards

Weathertite Sales, LLC

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550 Main St S, Bethlehem, CT 06751 (203) 528-4727 weathertitesales.com

Free assessment

Transparent pricing

Punctual service

Good customer service

Diligent in educating customers

Services Offered

Maintenance and cleaning
Gutter repair
Gutter installation
Gutter guards
Inspection

O'Donnell Bros

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17 Divinity St, Bristol, CT 06010 (860) 589-5155 odonnellbros.com

Transparent pricing

Good customer service

Free assessment

Diligent in educating customers

Services Offered

Gutter installation
Downspouts
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?

Full-service gutter installation companies provide homeowners with the best value. Each Winchester provider we recommend can support you with many services, including the following:

  • Cleaning: Routine gutter cleaning is essential for success, especially with the wet weather in Winchester, but it's not easy or fun to do yourself. A professional can handle the cleaning for you to help prevent clogging, overflowing, and warping.
  • Repair: Winchester homeowners can face gutter issues anytime, from sagging and cracks to mildew and mold. A local gutter professional can repair your gutters in no time, and without breaking the bank.
  • Installation: Whether you're buying sectional gutters or custom-cut seamless ones, an expert provider will have the necessary training to install your new gutter system safely.
  • Gutter guard installation: Gutter guards help stop plant matter from clogging your downspouts. No matter the age or style of your gutter system, a local gutter guard company can install the right guards for them.
If you find a gutter services provider you want to stick with, many offer long-term maintenance plans that cover new installation, routine cleaning, and repairs as needed. There are options to pay by the month or year for these packages.

Gutter Services

Full-service gutter installation companies provide homeowners with the best value. Each Winchester provider we recommend can support you with many services, including the following:

  • Cleaning: Routine gutter cleaning is essential for success, especially with the wet weather in Winchester, but it's not easy or fun to do yourself. A professional can handle the cleaning for you to help prevent clogging, overflowing, and warping.
  • Repair: Winchester homeowners can face gutter issues anytime, from sagging and cracks to mildew and mold. A local gutter professional can repair your gutters in no time, and without breaking the bank.
  • Installation: Whether you're buying sectional gutters or custom-cut seamless ones, an expert provider will have the necessary training to install your new gutter system safely.
  • Gutter guard installation: Gutter guards help stop plant matter from clogging your downspouts. No matter the age or style of your gutter system, a local gutter guard company can install the right guards for them.
If you find a gutter services provider you want to stick with, many offer long-term maintenance plans that cover new installation, routine cleaning, and repairs as needed. There are options to pay by the month or year for these packages.

How To Choose a Gutter Installer

Research gutter installers in great depth first, so you don't overpay or get bad service. When evaluating gutter installation companies, look for:

Assess Their Experience

When searching for a gutter installation expert, try to choose a local company that's been operating for many years or decades. This experience indicates that the company understands your area's weather and climate, as well as common local home designs, which helps them choose the best gutters for your house. Additionally, these companies have proven techniques for safe, efficient gutter installation.

Verify Proper Licensing and Insurance

Make sure to choose a company with the right certifications. Ask to see licensing, bonding, and insurance documentation before committing to a contract. Current credentials mean that a company follows best practices and local regulations, giving you peace of mind.

Check Reviews and Referrals

Spend time reading online reviews on sites such as Yelp, Google, and the Better Business Bureau. Verify that the provider has a proven record of excellent work and good customer service. Look for long-term satisfied customers to gain insights into a provider’s reliability. Watch out for red flags like poor communication or unfinished jobs. All our recommended providers have a high number of reviews with a good average rating.

Choose Reputable Brands

Pick a gutter installer with manufacturer certification. These businesses that are formally trained are trained to install gutters per the manufacturer's specifications for the best results.

Examine Warranties

You should only pick companies that offer solid manufacturer warranties on materials, plus their own installation warranties. Look for 5 to 10 year guarantees on basic aluminum gutters and 1 to 3 years of labor coverage.

Gutter Installation Materials

Look for durable, long-lasting materials such as heavy gauge aluminum that are unlikely to decay, warp, or rust over time. The right materials will hold up under your local weather in Winchester. You'll want to make certain that any paints and finishes also have a long lifespan and don't peel or fade prematurely.

Questions to Ask

To properly evaluate potential gutter companies, you'll need to take the time to ask key questions such as these:

  • Can you also install gutter guards? Installing gutter guards helps prevent clogs that result from debris such as leaves getting into your gutters. This is particularly important in a place like Winchester with lots of trees.
  • What materials are recommended for my gutters based on the local weather conditions and my specific home style? Consider the benefits and drawbacks of each gutter material, taking into account important factors such as Winchester's typical snowfall, rainfall, and the weight and volume of the gutters.
  • Can you provide a detailed quote for both full gutter replacement and problem area fixes? Get quotes in writing to ensure you understand the price of your gutter installation before the work begins.
  • How do you make sure there’s smooth integration with my current roofing? See whether steps like underlayment replacement are included.
  • How long does the installation process take? Most companies can complete installations in around one day.
  • What are the specific warranty details for labor and materials? High-quality materials are often backed by 5–10 year warranties. Labor is normally back by a 1-3 year warranty.
  • What steps do you take to ensure my new gutters have the optimal pitch and slope to avoid standing water? Correct slope and pitch greatly lower overflow risk. Your gutter installation provider should know how to properly align your gutter system on your roof.
Taking the time to thoroughly research providers helps you choose the right gutter installer. Investing in new gutters now helps avoid much pricier water and structural damage in the future.

Frequently Asked Questions About Gutters in Winchester, CT

One way to verify that a gutter services company is trustworthy is to look for online reviews. When you speak with someone from the company, confirm that they have insurance and that they can walk you through how the job will or won't affect your roof warranty. Finally, a trustworthy Winchester gutter services company should provide information about their warranties as well as an estimate to you in writing after performing an inspection.

The average cost of gutter installation in Winchester is between $420-$3,597, or about $4.00 per linear foot. The size of your house and the number of stories it has will affect the cost, as will the material you choose and whether you need seamless or sectional gutters. The only surefire way to estimate the cost of gutter installation in Winchester is to talk to one or more gutter installation companies to ask for a free estimate. When you speak with a company, you should already have a basic idea of what gutter material you want, and how long the system will need to be.

For all gutter services, the benefits of hiring a local Winchester gutter company include better quality of work, improved safety, and decreased risk of future problems. For installation, hiring a professional usually means getting a warranty for both services and materials. When it comes time to replace your gutters, a gutter services professional can both supply materials and haul away waste, which will save you time and help keep your lawn clean.

Top priorities for home gutter maintenance include regular cleaning and inspection. This lets you identify problems before they get out of hand, and lowers the risk of debris buildup that can crack, clog, or strain your gutters. Problems should be fixed as soon as possible, either yourself or with the help of a local Winchester gutter services company. You could also consider investing in gutter guards, which cut down on the amount of time and money spent on cleaning and maintaining your gutters.

Some gutter companies may also offer repair or cleaning services for your siding, windows, or roofing. Usually, these services are provided by more "all-purpose" home service companies. If you want to combine multiple services, we recommend contacting several companies from our list to ask about what packages they offer.

When repairing or cleaning gutters on your own, the most important thing is to be safe. Work while standing on a ladder (not your roof, where you're more likely to fall), be sure that the ladder is stable, and wear gloves. Verify that the downspout is unblocked, to let standing water exit the system, and when you’re finished use a hose to flush the gutters to ensure that they're draining properly.

When you're already on a ladder looking at your gutters, check the gutter brackets that attach to the house to ensure that they're still working properly and don't need tightening or replacing. Also look for any holes in your gutters, and seal them when the gutter is dry.

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