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TRUSTED BY CHESTER, VT HOMEOWNERS

  • Average homeowner rating star icon4.3
    Average homeowner rating
  • Verified reviews icon50
    Verified roofing services reviews

Find Roofers in Chester

Avatar for Clear Choice Home Improvements

Clear Choice Home Improvements

4.73(
349
)
Approved Pro

Clear Choice Home Improvements

4.73(
349
)
Approved Pro
Customers say: Quality work
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
21 years of experience

Clear Choice Home Improvements is New Hampshire's largest and New England's fastest growing Home Improvement Company. Family owned and operated, we provide truly personalized home remodeling services. At Clear Choice, we pride ourselves on presenting the best quality replacement windows, vinyl siding, roofing, bathroom systems, and gutter guards. Clear Choice will ALWAYS install these products in your home as if we were putting them into our own. Should those products ever need service, Clear Choice will ALWAYS be there to take care of any problems. We're confident that the home improvement products we install in your home are the absolute best in the industry.

"This company should not be in business. By far the worst interaction I’ve ever had with a sales person for my entire life. Do not use this company."

John O on September 2024

Clear Choice Home Improvements is New Hampshire's largest and New England's fastest growing Home Improvement Company. Family owned and operated, we provide truly personalized home remodeling services. At Clear Choice, we pride ourselves on presenting the best quality replacement windows, vinyl siding, roofing, bathroom systems, and gutter guards. Clear Choice will ALWAYS install these products in your home as if we were putting them into our own. Should those products ever need service, Clear Choice will ALWAYS be there to take care of any problems. We're confident that the home improvement products we install in your home are the absolute best in the industry.

"This company should not be in business. By far the worst interaction I’ve ever had with a sales person for my entire life. Do not use this company."

John O on September 2024


"The project was done last Spring in a timely manner and we love the roof! We'll see it it will stand up to the test of a Vermont winter"

Jonathon H on September 2025

Welcome to East Coast Metal Roofing, LLC! We take pride in our reliability, great communication, integrity and quality work. We are experts in home improvement and will do our best to keep you educated on your project. We look forward to earning your business!

"The project was done last Spring in a timely manner and we love the roof! We'll see it it will stand up to the test of a Vermont winter"

Jonathon H on September 2025


"Excellent work"

Jean C on September 2024

Watkins Building & Remodeling offers excellent quality and superior customer service. We are on the job on time and ensure your satisfaction with our work. Call today for an appointment.

"Excellent work"

Jean C on September 2024


Avatar for J White Contracting

J White Contracting

4.89(
14
)
Approved Pro

J White Contracting

4.89(
14
)
Approved Pro
Customers say: True professional
26 years of experience
Free onsite estimate

With over 40 years of experience in the roofing industry, J White Contracting is your industry leader state wide. We pride ourselves on our extreme professionalism and attention to detail. As a family owned and operated business, you can trust we will treat your project as we would treat our own. Our satisfaction guarantee will assure you that we will not leave your property until you are completely satisfied with our work. Give us a call today, we look forward to working with you!

"Great experience all around!!!!"

Jason B on July 2024

With over 40 years of experience in the roofing industry, J White Contracting is your industry leader state wide. We pride ourselves on our extreme professionalism and attention to detail. As a family owned and operated business, you can trust we will treat your project as we would treat our own. Our satisfaction guarantee will assure you that we will not leave your property until you are completely satisfied with our work. Give us a call today, we look forward to working with you!

"Great experience all around!!!!"

Jason B on July 2024


"Hired subcontractors to do the work, hardly here themselves to manage the project. Tire existing roof off and let it downpour on my house where water ended up in my kitchen. would not hire again."

dawn e on January 2025

North American Roofs : we install remove and repair architectural shingle roofs and standing seam metal

"Hired subcontractors to do the work, hardly here themselves to manage the project. Tire existing roof off and let it downpour on my house where water ended up in my kitchen. would not hire again."

dawn e on January 2025


Avatar for Stevens Roofing & Siding

Stevens Roofing & Siding

4.46(
35
)
Approved Pro

Stevens Roofing & Siding

4.46(
35
)
Approved Pro
Customers say: Quick response
25 years of experience
Free onsite estimate

We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We specialize in asphalt shingle roofing we pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!

"Great job did what asked at a fair price good honest hard working people great family owned business "

walter g on March 2025

We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We specialize in asphalt shingle roofing we pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building lasting relationships and guarantee your satisfaction!

"Great job did what asked at a fair price good honest hard working people great family owned business "

walter g on March 2025


Avatar for ACG Construction Group LLC

ACG Construction Group LLC

4.67(
6
)
Approved Pro

ACG Construction Group LLC

4.67(
6
)
Approved Pro
2 years of experience
Free onsite estimate

ACG Construction Group 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. With services to fit any budget.

"ACG did a brand new roof for me. Insurance gave me three weeks to get it finished and they completed it efficiently and well before the deadline. Very communicative, responsive & professional. Job looks great, absolutely would recommend using ACG. "

Evan R on November 2025

ACG Construction Group 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. With services to fit any budget.

"ACG did a brand new roof for me. Insurance gave me three weeks to get it finished and they completed it efficiently and well before the deadline. Very communicative, responsive & professional. Job looks great, absolutely would recommend using ACG. "

Evan R on November 2025


Avatar for Christopher's Handyman

Christopher's Handyman

5.00(
2
)
Approved Pro

Christopher's Handyman

5.00(
2
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
15 years of experience

Christopher's Handyman is the premier handyman company of the Windam area. With more than a decade of experience working on all kinds of repairs projects. Christopher's Handyman is unrivaled in their commitment to customer service and will always offer the most competitive pricing. Give Christopher's Handyman a call today and get the best work for you dollar! Estimates will cost a minimum of $100.00.

"Christopher is doing a nice job repairing some water damage in my kitchen and refinishing my hard wood floors. I have a few more projects that I will be doing in the near future and will not hesitate calling Chris for these as well."

Carol M on September 2021

Christopher's Handyman is the premier handyman company of the Windam area. With more than a decade of experience working on all kinds of repairs projects. Christopher's Handyman is unrivaled in their commitment to customer service and will always offer the most competitive pricing. Give Christopher's Handyman a call today and get the best work for you dollar! Estimates will cost a minimum of $100.00.

"Christopher is doing a nice job repairing some water damage in my kitchen and refinishing my hard wood floors. I have a few more projects that I will be doing in the near future and will not hesitate calling Chris for these as well."

Carol M on September 2021


Avatar for Sentri Homes

Sentri Homes

New on AngiNew on Angi
Approved Pro

Sentri Homes

New on AngiNew on Angi
Approved Pro
2 years of experience
Free onsite estimate

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.

Sentri Homes is a full-service contractor delivering high-end home additions, whole-home remodels, new custom builds, luxury kitchens, structural framing, roof replacements, and every major renovation. We assign a dedicated project manager to every job, deliver meticulous craftsmanship with clear communication, and back our work with an industry-leading warranty to ensure complete peace of mind on your largest investments. Our in-house team of licensed builders and master craftsmen consistently earns 5-star reviews by turning big visions into stunning, high-value homes—when you need one trusted partner who truly does it all, we’re the proven choice.


Avatar for JR Quality Construction Inc

JR Quality Construction Inc

New on AngiNew on Angi
Approved Pro

JR Quality Construction Inc

New on AngiNew on Angi
Approved Pro
4 years of experience
Free onsite estimate

Our mission is to be a provider that brings back the personal touch with our customers. We will build a relationship that will last a lifetime after you see our quality work. As a locally owned and operated business, we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today!

Our mission is to be a provider that brings back the personal touch with our customers. We will build a relationship that will last a lifetime after you see our quality work. As a locally owned and operated business, we feel invested in our clients and constantly strive for customer satisfaction. Call or message us to schedule an estimate today!

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Roofing questions, answered by experts

The installation may have been done correctly. However, improperly installed gutter guards can easily damage your shingles. Also, cheap gutter guards rarely come with installation fixtures. In the worst cases, they simply ask you to nail the guards in, which would sabotage your roof’s water resistance and thus void the warranty. To be sure, always check with your home warranty provider before making any modifications.

DIY is not recommended, as slate requires specialized handling and proper underlayment installation for durability.

A gable roof with steep pitches covered in asphalt shingles or wood shakes is the most popular roof for Cape Cod homes. Asphalt shingles started gaining popularity in the early 1900s, so wood shake roofs, which were popular in the 1700s when Cape Cod homes were first built, are the traditional option. You can further modernize your Cape Cod home by raising the roof in the front, back, or both to add living space and change up the traditional single-gable roof with doghouse dormers.

While it’s technically possible to repoint a chimney without scaffolding, it’s not recommended, especially for taller chimneys. Scaffolding provides a stable platform that allows for safer and more precise work. Without it, you might find yourself in a risky situation, and the quality of the repointing could suffer.

Roof repairs average around $1,100 but can easily exceed that for larger repairs. The cost of roof replacement depends on the size of your home and the materials used but averages between $4,000 and $24,000.

The Chester, VT homeowners’ guide to roofing services

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

What do you need done? We’ll find top pros.
  • 🌱 "Mow a small front yard"
  • 🛠 "Fix a leaking pipe under the sink"
  • 🏠 "Repair shingles on an asphalt roof"