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10 Best Gutter Installation Companies in Winter Park, FL

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Written By Bradford Cuthrell

Last Updated April 2024

No matter where you live, properly-installed and reliable gutters are critical. Inadequate gutters can eventually lead to damaging leaks and the resulting costly water damage. You may be worried about the cost of gutter installation services, as well as the timeline and whether it may affect your roof warranty. This is where local experts can help.

This curated list of the best gutter installation experts in Winter Park can get you started on fixing all of your gutter problems.

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Most Durable
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Best Designed
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Top 10 Best Gutter Installation Companies in Winter Park

Brian Sikes Roofing

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210 North St, Longwood, FL 32750 (407) 878-3750 briansikesroofing.com

Diligent in educating customers

Free assessment

Good customer service

Transparent pricing

Services Offered

Inspection
Soffit and fascia
Gutter installation

Central Homes Roofing & Solar Services

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1920 Boothe Cir, Longwood, FL 32750 (407) 732-7262 centralhomesroofing.com

Diligent in educating customers

Transparent pricing

Free assessment

Good customer service

Services Offered

Gutter installation
Inspection
Soffit and fascia

Secured Roofing & Solar

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483 Montgomery Pl Suite 104, Altamonte Springs, FL 32714 (407) 439-1200 securedroofingandsolar.com

Diligent in educating customers

Transparent pricing

Good customer service

Free assessment

Services Offered

Gutter installation
Inspection

JCM Roofing & Restoration

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440 Plumosa Ave #1020, Casselberry, FL 32707 (407) 878-6648 jcmroofing-restoration.com

Transparent pricing

Punctual service

Good customer service

Free assessment

Diligent in educating customers

Services Offered

Gutter installation
Inspection

Mr. Gutter - Seamless Gutters

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3550 Old Winter Garden Rd, Orlando, FL 32805 (407) 777-1792 mrgutterfl.com

Free assessment

Diligent in educating customers

Transparent pricing

Punctual service

Good customer service

Services Offered

Gutter guards
Downspouts
Maintenance and cleaning
Seamless gutters
Gutter installation
Gutter repair

New Standard Roofing Orlando

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1040 Belle Ave #1290, Winter Springs, FL 32708 (407) 512-0144 newstandardroofingorlando.com

Transparent pricing

Good customer service

Free assessment

Punctual service

Services Offered

Gutter installation
Soffit and fascia
Inspection

Southern Image Gutters, Inc.

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8250 Cyers Ln, Orlando, FL 32822 (407) 535-0529 southernimageguttersinc.com

Transparent pricing

Good customer service

Diligent in educating customers

Free assessment

Services Offered

Gutter installation
Gutter repair
Gutter guards
Maintenance and cleaning
Seamless gutters
Gutter replacement
Soffit and fascia

Stratus Roofing

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2200 Lucien Way #400, Maitland, FL 32751 (407) 439-1957 stratusroofing.com

Diligent in educating customers

Free assessment

Good customer service

Transparent pricing

Services Offered

Gutter installation
Inspection

Gutter Masters of Central Florida

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4455 Dardanelle Dr Suite D, Orlando, FL 32808 (407) 904-8901 centralfloridagutters.com

Good customer service

Diligent in educating customers

Punctual service

Transparent pricing

Free assessment

Services Offered

Gutter guards
Maintenance and cleaning
Soffit and fascia
Seamless gutters
Gutter repair
Gutter installation

Florida Premier Roofing LLC

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10245 E Colonial Dr, Orlando, FL 32817 (407) 216-2782 flpremierroofing.com

Diligent in educating customers

Free assessment

Transparent pricing

Good customer service

Services Offered

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?

Almost all the Winter Park gutter services companies we recommend are full-service. A few of the many services they provide include the following:

  • Installation: Licensed gutter professionals have the knowledge and resources to cut and install new gutters without damaging your roof.
  • Gutter guard installation: By hiring a professional to install gutter guards, you'll boost your system's efficiency and increase its lifespan by preventing clogs from plant matter. Guards also help stop pests from settling inside your gutters.
  • Repair: Gutter problems can happen to anyone. Whether you're struggling with sagging gutters, cracks, or leaks, a local Winter Park professional can inspect and repair the problem before it gets worse.
  • Cleaning: Routine gutter cleaning is essential for success, especially with the wet weather in Winter Park, but it's not easy or fun to do yourself. A professional can handle the dirty work for you to help prevent overflowing, clogging, and warping.
If you like a particular gutter service provider, many companies offer long-term maintenance plans that cover new installation, routine cleaning, and repairs as needed. You can pay monthly or annually for these packages.

Gutter Services

Almost all the Winter Park gutter services companies we recommend are full-service. A few of the many services they provide include the following:

  • Installation: Licensed gutter professionals have the knowledge and resources to cut and install new gutters without damaging your roof.
  • Gutter guard installation: By hiring a professional to install gutter guards, you'll boost your system's efficiency and increase its lifespan by preventing clogs from plant matter. Guards also help stop pests from settling inside your gutters.
  • Repair: Gutter problems can happen to anyone. Whether you're struggling with sagging gutters, cracks, or leaks, a local Winter Park professional can inspect and repair the problem before it gets worse.
  • Cleaning: Routine gutter cleaning is essential for success, especially with the wet weather in Winter Park, but it's not easy or fun to do yourself. A professional can handle the dirty work for you to help prevent overflowing, clogging, and warping.
If you like a particular gutter service provider, many companies offer long-term maintenance plans that cover new installation, routine cleaning, and repairs as needed. You can pay monthly or annually for these packages.

How To Choose a Gutter Installer

Research gutter installers in great depth first, so you don't end up with poor work or an overinflated bill. When assessing gutter installation companies, look for:

Assess Their Experience

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

Verify Proper Licensing and Insurance

Only hire a provider that's fully licensed, bonded, and insured. Ask to see copies of their license, bonds, and insurance documentation upfront before committing. Proper certification and insurance protects you from liability and shows that the company is operating legally.

Check Reviews and Referrals

Spend time looking through online reviews on sites such as the Better Business Bureau, Google, and Yelp to verify the company's a proven track record of providing good customer service and great project results. Look for long-term satisfied customers to gain insights into the company's overall reliability. Be on the lookout for any red flags, such as poor communication or unfinished jobs. All our recommended providers boast a good average rating across a high number of reviews.

Choose Reputable Brands

Choose a business that's certified through the gutter manufacturer. You'll want a business that has the proper training to complete all gutter installations per the manufacturer's specifications to achieve the best results.

Examine Warranties

Choose contractors that provide robust manufacturer warranties on supplies, as well as their own installation warranties. Look for 5-10 year warranties on regular aluminum gutters and 1 to 3 year warranties on labor.

Gutter Installation Materials

Go for strong materials – for example, heavy-gauge aluminum – that won't warp, rust, or decay over time. Materials that can withstand Winter Park’s weather are key. Be sure any paints and finishes also have a long lifespan.

Questions to Ask

When comparing potential gutter installation companies, be sure to ask these kinds of detailed questions:

  • Are you also able to install gutter guards? Putting in gutter guards helps prevent clogging that results from leaves, twigs, and other debris falling into your gutters.
  • What gutter materials are best for the local weather conditions and my specific home style? Factors such as Winter Park's typical annual rainfall and the risk of inclement weather in your area will affect the size and type of gutter you should get. Learn the pros and cons of each gutter material.
  • How will you make sure there’s smooth integration with my current roof? Look for steps such as underlayment replacement.
  • How long does full installation take? Most companies can complete installations in about 24 hours.
  • What kind of warranties are there for labor and materials? Quality materials typically come with 5–10 year warranties. Labor is normally back by a 1-3 year warranty.
  • Can you provide a detailed quote for both full gutter replacement and problem area fixes? Get written estimates from providers, so you know exactly what the total cost of gutter installation will be before the project starts.
  • How will you ensure the new gutters have the right slope and pitch to reduce standing water? Proper pitch and slope helps prevent overflow. Your provider should know how to align your gutter system with your home’s roofing specifications.
Doing your due diligence to research and compare providers will help you choose the best gutter installation company for your home. Installing new gutters now helps prevent more expensive water and structural damage down the road.

Frequently Asked Questions About Gutters in Winter Park, FL

Browsing online reviews is one of the best ways to learn about the reputation of a gutter services company. When you speak with a representative, verify that the company is properly insured, and ask them to clarify how the procedures will or will not affect your roof warranty. Lastly, a legitimate Winter Park gutter services company should provide in writing both an estimate of the cost and a description of its warranty policy.

The average Winter Park homeowner spends between $387-$3,428 for gutter installation, with a cost of about $3.80 per linear foot. This price depends on the size of your home (including number of stories) and the gutter materials and whether you’ve opted for sectional or seamless. The only way to know for sure how much gutter installation will cost is to speak with one or more Winter Park gutter installation companies and ask. Make sure to have a general idea of the material and gutter footage you are looking for when you call.

Working with a gutter professional in Winter Park gives you higher quality work, increased safety, and lessened risk of future issues. When you're replacing or installing your gutter system, a gutter services professional can offer you a warranty for services and materials. If you need to replace your existing gutters, a gutter services company will provide materials and haul away any leftover materials or debris afterward. This will save you time and hassle and help keep your lawn clean.

Your number one concern when doing DIY gutter maintenance? Safety. Always ensure that you work on a ladder, not from the roof, where falls are more likely. Take care to make sure that the ladder is secure, and wear work gloves. Start by making sure your downspout is clear, so standing water can flow out of the system, and finish the job by using a hose or bucket of water to flush the gutters to confirm that they're draining properly.

Any time you're doing any kind of work on your gutters, check the brackets that attach your gutter system to your house to see if they need to be repaired, tightened, or replaced. You can also look for any holes in your gutters, and seal them when the gutters are dry.

Gutter accessories, including decorative boots, downspout brackets, and fascia brackets, can be added to your gutter system to make it look nicer. If you live somewhere, like Winter Park, that gets more precipitation than average, you could consider attaching a conductor head to your gutters, allowing them more time to drain and reducing the risk of overflow. If your roof has a deeper overhang, you could utilize a rain chain to help drain water directly from your gutters to the ground.

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