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  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon113
    Verified gutter repairs and replacements reviews

Find Gutter repair and replacement pros in Winchester

Avatar for Fortuna Gutters

Fortuna Gutters

Based In
5.00(
13
)
Approved Pro

Fortuna Gutters

Based In
5.00(
13
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
113 local quotes requested

Fortuna Gutters is a professional gutter cleaning service dedicated to providing homeowners and businesses in Massachusetts with reliable, high-quality gutter solutions. Our mission is to offer peace of mind by ensuring your property is protected from water damage. We believe in delivering long-lasting results by approaching each project with the same care and attention we would give our own homes. At Fortuna Gutters, we pride ourselves on being more than just a service provider—we're a partner in maintaining the integrity and safety of your home. Our team is committed to offering sustainable, innovative solutions that not only function efficiently but also blend seamlessly with the beauty of your property. With a foundation built on trust and integrity, we maintain full transparency with our clients throughout every step of the process. We listen closely to your needs, working with you to find the best solution to protect your home. Our focus on innovation means we constantly seek out the latest technologies and techniques to provide the most effective gutter services. Additionally, we prioritize sustainability by using eco-friendly materials and practices, ensuring we not only protect your home but also the environment. Whether you need regular gutter cleaning, repairs, or installations, you can count on Fortuna Gutters to deliver top-notch services that keep your property safe and dry. Call us today at 978-397-2750 to schedule an appointment.

"Good job well"

Dipendra T on September 2025

Fortuna Gutters is a professional gutter cleaning service dedicated to providing homeowners and businesses in Massachusetts with reliable, high-quality gutter solutions. Our mission is to offer peace of mind by ensuring your property is protected from water damage. We believe in delivering long-lasting results by approaching each project with the same care and attention we would give our own homes. At Fortuna Gutters, we pride ourselves on being more than just a service provider—we're a partner in maintaining the integrity and safety of your home. Our team is committed to offering sustainable, innovative solutions that not only function efficiently but also blend seamlessly with the beauty of your property. With a foundation built on trust and integrity, we maintain full transparency with our clients throughout every step of the process. We listen closely to your needs, working with you to find the best solution to protect your home. Our focus on innovation means we constantly seek out the latest technologies and techniques to provide the most effective gutter services. Additionally, we prioritize sustainability by using eco-friendly materials and practices, ensuring we not only protect your home but also the environment. Whether you need regular gutter cleaning, repairs, or installations, you can count on Fortuna Gutters to deliver top-notch services that keep your property safe and dry. Call us today at 978-397-2750 to schedule an appointment.

"Good job well"

Dipendra T on September 2025


Avatar for Torri Enterprises

Torri Enterprises

119 Drum Hill Road
5.00(
7
)
Approved Pro

Torri Enterprises

119 Drum Hill Road
5.00(
7
)
Approved Pro
Customers say: True professional
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
95 local quotes requested

Torri Enterprises have been servicing thousands of residential and commercial clients for over 20 years. Our many years of superior work and dedication to customers have us recognized as a premium gutter service company. Torri Enterprises has two locations to serve you. One located in Dracut, Massachusetts and the other in Myrtle Beach, South Carolina operating under the name Allied Home Services Inc. We pride ourselves on customer satisfaction.

"Excellent work and price! Beat out all 3 of my competitors. Came in and finished the job in about 3 hours. No more water leak in the basement. Thought I needed a French drain that would've been very co$$tly. Would recommend them to anyone."

Bong S on September 2024

Torri Enterprises have been servicing thousands of residential and commercial clients for over 20 years. Our many years of superior work and dedication to customers have us recognized as a premium gutter service company. Torri Enterprises has two locations to serve you. One located in Dracut, Massachusetts and the other in Myrtle Beach, South Carolina operating under the name Allied Home Services Inc. We pride ourselves on customer satisfaction.

"Excellent work and price! Beat out all 3 of my competitors. Came in and finished the job in about 3 hours. No more water leak in the basement. Thought I needed a French drain that would've been very co$$tly. Would recommend them to anyone."

Bong S on September 2024


Avatar for Mighty Dog Roofing of Greater Middlesex

Mighty Dog Roofing of Greater Middlesex

66 Tadmuck Rd
5.00(
7
)
Approved Pro

Mighty Dog Roofing of Greater Middlesex

66 Tadmuck Rd
5.00(
7
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
131 local quotes requested

Our Mission at Mighty Dog Roofing is to be an industry changer, leading the industry with integrity, finding innovative ways to exceed the expectations of our clients and the communities we serve, and providing a customized experience each and every time we care for their home. At Mighty Dog Roofing, we pledge superior service to our customers through excellent communication and customer service. How do we accomplish that? Courteous customer education, community service, and the highest level of integrity and ethics. Mighty Dog Roofing is endorsed by the nation's top manufacturers and distributors, offering our customers the best and most innovative products and services in the industry.

"The job went amazing. I loved our product!!"

Liam D on June 2025

Our Mission at Mighty Dog Roofing is to be an industry changer, leading the industry with integrity, finding innovative ways to exceed the expectations of our clients and the communities we serve, and providing a customized experience each and every time we care for their home. At Mighty Dog Roofing, we pledge superior service to our customers through excellent communication and customer service. How do we accomplish that? Courteous customer education, community service, and the highest level of integrity and ethics. Mighty Dog Roofing is endorsed by the nation's top manufacturers and distributors, offering our customers the best and most innovative products and services in the industry.

"The job went amazing. I loved our product!!"

Liam D on June 2025


B8 Master Build

21 Revere Beach BLVD
No reviews yet

B8 Master Build

21 Revere Beach BLVD
No reviews yet
13 years of experience

Our Services at B8 Master Build At B8 Master Build, we specialize in crafting high-quality, custom solutions for your home. With years of experience in the industry, we offer a range of services designed to enhance the beauty and durability of your property. Whether you’re looking to upgrade your roof, add a new deck, or transform your outdoor living space, we’ve got you covered. • Metal Roofing: We install durable and energy-efficient metal roofs that are built to withstand the elements. Whether you need a replacement or a new installation, we ensure a perfect fit that enhances the style and protection of your home. • Decks: Our custom-built decks are designed to be both beautiful and functional. From material selection to the final touches, we create outdoor spaces that you and your family will enjoy for years to come. • Outdoor Living Spaces: We specialize in creating inviting outdoor areas that blend seamlessly with your home. Whether it’s a new porch, patio, or a complete outdoor living design, we help you build the perfect space to relax and entertain. • Porches & Additions: Looking to expand your living space? Our porches and home additions are tailored to fit your needs and style, adding both function and curb appeal to your home. We pride ourselves on providing personalized service and delivering results that exceed expectations. Every project is treated with care, and we work closely with our clients to bring their visions to life.

Our Services at B8 Master Build At B8 Master Build, we specialize in crafting high-quality, custom solutions for your home. With years of experience in the industry, we offer a range of services designed to enhance the beauty and durability of your property. Whether you’re looking to upgrade your roof, add a new deck, or transform your outdoor living space, we’ve got you covered. • Metal Roofing: We install durable and energy-efficient metal roofs that are built to withstand the elements. Whether you need a replacement or a new installation, we ensure a perfect fit that enhances the style and protection of your home. • Decks: Our custom-built decks are designed to be both beautiful and functional. From material selection to the final touches, we create outdoor spaces that you and your family will enjoy for years to come. • Outdoor Living Spaces: We specialize in creating inviting outdoor areas that blend seamlessly with your home. Whether it’s a new porch, patio, or a complete outdoor living design, we help you build the perfect space to relax and entertain. • Porches & Additions: Looking to expand your living space? Our porches and home additions are tailored to fit your needs and style, adding both function and curb appeal to your home. We pride ourselves on providing personalized service and delivering results that exceed expectations. Every project is treated with care, and we work closely with our clients to bring their visions to life.


Couto Construction Inc.

2500 Main Street
No reviews yet

Couto Construction Inc.

2500 Main Street
No reviews yet
33 local quotes requested

Most people stress over home improvements. We make it easy and affordable. The exterior home experts at Couto Construction have been beautifying homes across Massachusetts, Cape Cod and Rhode Island for more than 30 years. We've helped thousands of homeowners, and we're here for you.

Most people stress over home improvements. We make it easy and affordable. The exterior home experts at Couto Construction have been beautifying homes across Massachusetts, Cape Cod and Rhode Island for more than 30 years. We've helped thousands of homeowners, and we're here for you.


Skyfall Gutters

Hampshire Drive
No reviews yet

Skyfall Gutters

Hampshire Drive
No reviews yet
1 years of experience

With a focus on customer satisfaction and personalized service, we specialize in gutter cleaning, repair, and installation, using the latest techniques and high-grade materials to protect your home from water damage. Our experienced team understands the unique needs of homes in the region and takes pride in offering reliable, professional solutions tailored to each property's specific requirements.

With a focus on customer satisfaction and personalized service, we specialize in gutter cleaning, repair, and installation, using the latest techniques and high-grade materials to protect your home from water damage. Our experienced team understands the unique needs of homes in the region and takes pride in offering reliable, professional solutions tailored to each property's specific requirements.



Winegar Custom

10 Stevens Street
5.00(
13
)

Winegar Custom

10 Stevens Street
5.00(
13
)
Customers say: Quality work
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Family owned business! We offer all your home improvement needs including remodeling. Kitchens, bathrooms, siding, roofing, framing, interior /exterior carpentry, general electric, painting and basic plumbing repairs . As well as general handyman Fix-It repairs no job too small.

"The work was completed quickly and with great care for the property. They did a fantastic and thorough job! Would definitely recommend them and use them again ."

Paul B on May 2025

Family owned business! We offer all your home improvement needs including remodeling. Kitchens, bathrooms, siding, roofing, framing, interior /exterior carpentry, general electric, painting and basic plumbing repairs . As well as general handyman Fix-It repairs no job too small.

"The work was completed quickly and with great care for the property. They did a fantastic and thorough job! Would definitely recommend them and use them again ."

Paul B on May 2025


United Exterior Siding

123 Main St.
5.00(
2
)

United Exterior Siding

123 Main St.
5.00(
2
)
Customers say: Quick response
2 years of experience

At United Exterior Siding Inc., we specialize in siding replacement, ensuring your home looks its best while providing maximum protection. Our expert team also offers top-quality services in roofing, gutters, trim, and decks. With a commitment to excellence and customer satisfaction, we invite you to experience our professional services firsthand.

"The work crew with efficient and completed the work within the time that it was promised. I will definitely hire again."

Andy V on July 2024

At United Exterior Siding Inc., we specialize in siding replacement, ensuring your home looks its best while providing maximum protection. Our expert team also offers top-quality services in roofing, gutters, trim, and decks. With a commitment to excellence and customer satisfaction, we invite you to experience our professional services firsthand.

"The work crew with efficient and completed the work within the time that it was promised. I will definitely hire again."

Andy V on July 2024


ID Flat Roof

234 W Newton St APT 2
No reviews yet

ID Flat Roof

234 W Newton St APT 2
No reviews yet
25 years of experience

Repair, replacement, and installation of flat roofs, low-pitched roofs, regular roofs, and decks.Residential and Commercial roofs. Rubber roofs, asphalt shingles roofs, metal roofs, and PVC roofs. We Have More than 21 Years of experience and a Lifetime Warranty. We accept credit cards and have all insurance and licenses. If you want to make your next roof your last roof, call us today, and let us provide you with the final solution to your roof or deck problems.

Repair, replacement, and installation of flat roofs, low-pitched roofs, regular roofs, and decks.Residential and Commercial roofs. Rubber roofs, asphalt shingles roofs, metal roofs, and PVC roofs. We Have More than 21 Years of experience and a Lifetime Warranty. We accept credit cards and have all insurance and licenses. If you want to make your next roof your last roof, call us today, and let us provide you with the final solution to your roof or deck problems.

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Gutter Repair and Replacement questions, answered by experts

Repairs typically take 1-3 hours, depending on the complexity and location.

There are a handful of things you can look for to determine if you need to pay for gutter repairs, including the following:

  • Water leaking from the underside of your gutters during rainfall

  • Visible gaps between your gutters and your roof

  • Frequent issues with gutters overflowing or holding standing water

  • Gutters that sag or pull away from the house

  • Water damage to soffits, fascia boards, or other building materials

  • Mold growth on your exterior walls

  • Soil erosion underneath your roof overhang

  • Foundation leaks or inward bowing of foundation walls

Whether it’s better to repaint or replace gutters will depend on their overall state. One or two small damages can easily be fixed and covered up with a fresh coat of paint for minimal additional costs. On the other hand, you’ll likely pay less to install a new set-up rather than fixing one that’s heavily damaged.

Whether you need to remove your home's gutters before installing a drip edge depends entirely on their installation. In most cases, you can work around the gutters and not have to remove them. This process is straightforward because the drip edge should extend past the back edge of the gutter. However, if your gutter placements are high on the fascia, you may have to take them down to install the drip edge properly. 

Yes, professionals can spot and rectify downspout issues such as clogs, leaks, or disconnections during cleaning. They ensure proper water flow, protecting the building's foundation and preventing water damage or erosion.

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The Winchester, MA homeowners’ guide to gutter repairs and replacements

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