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10 Best Roofers in Chester, NY

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Written By David Cusick

Last Updated April 2024

Caring for your roof is critical to protecting you and your home, but isn't always an easy task. Especially during the rainier parts of the year, the roof on your Chester home may be prone to damage.

For any issues, large or small, there's a local roofing contractor who can help. Our guide can help connect you with one of the top roofers in Chester.

Top 10 Best Roofers in Chester

Erie Home

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19 Industrial Ave, Mahwah, NJ 07430 (845) 202-3862 eriehome.com

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Free inspections

Quality customer service

Services Offered

Roof repair
Quality inspection
Asphalt roofs
Replacement
Metal roofs

Precision Roofing Inc.

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22 Kerr Ln, Southfields, NY 10975 (845) 351-2009 precisionroofinginc.com

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Honors appointment windows

Quality customer service

Free inspections

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Locally owned

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Preventive services

Services Offered

Roof repair
Skylights
Wood roofs
Quality inspection
Slate
Replacement

Green Collar Roofing & Exteriors

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

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Asphalt roofs
Roof repair
Solar panel installation
Quality inspection
Metal roofs
Flat roofs
Replacement
Skylights

Guaillas Inc. Roofing, Gutters, & Siding

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

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Quality customer service

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Flat roofs
Roof repair
Asphalt roofs
Roof cleaning
Skylights
Ventilation
Wood roofs
Metal roofs
Replacement

Frank Stevens & Sons Roofing, Inc.

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56 Smith Clove Rd, Central Valley, NY 10917 (845) 928-2161 frankstevensroofing.com

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Preventive services

Free inspections

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Customer education

Quality customer service

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Roof repair
Replacement
Flat roofs

Exterior Pro Builders Inc.

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

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Quality customer service

Services Offered

Roof repair
Quality inspection
Replacement

Upstate Roofing and Siding

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149 Elm St Unit 101, Monroe, NY 10950 (845) 781-4848 upstateroofingandsiding.com

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Preventive services

Customer education

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Replacement

Home Pro Exteriors, Inc.

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541 NY-17M, Middletown, NY 10940 (845) 343-1777 homeproexteriorsinc.com

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Preventive services

Reputation for timeliness

Quality customer service

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Roof repair
Replacement
Skylights
Ventilation

Hudson Valley Roofers Inc.

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

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Quality customer service

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Roof repair
Wood roofs
Metal roofs
Rubber roofs
Replacement
Asphalt roofs

Level Up Construction

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15 Ash St, New Windsor, NY 12553 (845) 245-9357 hudsonvalleylevelup.com

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Free inspections

Reputation for timeliness

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Replacement
Today's Homeowner Ranking Methodology

Today's Homeowner looks at dozens of datapoints on roofers 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.

How Much Does a New Roof Cost in Chester?

For a project as involved as roof replacement, price is important. Below is the typical price range to replace a roof on a 1,500 square foot home in Chester. We also compare costs for popular roofing materials.

How To Choose a Roofing Company

A new roof installation is a major home renovation that can run tens of thousands of dollars. It's crucial to research and find a top-rated, trusted roofing company for the job. Here are some important considerations for hiring a roofer.

  • Detailed written estimate: Trustworthy roofing contractors will offer a comprehensive written estimate. This estimate should outline the complete work scope, materials required, and total price with no hidden fees. Steer clear of unclear bids, or ones that seem much too high or low.
  • Experience and credentials: Companies operating for over a decade have a proven history and track record of expert service and happy clients. Only consider companies that are properly licensed, bonded, and insured. Inquire about professional certifications, such as those from the National Roofing Contractors Association.
  • Roofing materials and products: Quality roofing materials from top brands are able to handle Chester's weather and last for decades. Beware of contractors who push extremely low-cost or generic products. Inspect shingle samples before deciding.
  • Warranties and guarantees: A reliable roofer will provide robust manufacturer warranties that cover shingles for 30+ years along with at least a 5-year workmanship warranty on labor. Be wary of shorter warranty periods.
  • References and reviews: Research companies carefully by examining their Google, Yelp, or Better Business Bureau (BBB) profiles to look for years of consistently positive feedback. Also ask for recent local references.
  • Responsiveness and communication: From quote to project completion, your contractor should keep in consistent contact with you, respond to all questions, and resolve any concerns.

Signs Your Roof Needs Repair or Replacement

You may not think about your roof every single day, but it protects your home in important ways. Look out for these common signals that your roof needs to be inspected and repaired by a professional roofer.

Roof Age

The age and material of your roof are important. Asphalt shingles, the most popular residential roofing material, typically last 20–25 years before needing to be replaced. If your roof is approaching or past this lifespan, have it evaluated to determine if full replacement is needed.

Leaks or Water Stains in Your Home

One of the most obvious signs of a roof issue is leaking. Stains on ceilings, insulation, and walls — or in your attic — usually mean that water is seeping through deteriorating shingles. Don't ignore small leaks, because even these can encourage mold growth and roof damage.

Exposed Roof Decking Underneath Shingles

Visible roof decking or sheathing under your shingles is a sign that those shingles are severely curling or losing their seal. This means it's time for replacement. Shingles should lie flat to stop water from getting into your home.

Cracked, Broken, or Missing Shingles

Inspect your roof shingles from the ground or a steady ladder. Look for cracking or missing granules. Storms that bring strong winds can cause surface damage over time. To keep your roof in good shape, replace any shingles that have come loose or have open gaps.

Flashing Deterioration Around Roof Penetrations

Roof flashing makes a watertight seal around chimneys, vents, valleys, and other areas where water can penetrate your roof. Cracked, peeling or deteriorated flashing can allow leaks. We recommend promptly resolving any flashing issues that come up.

Sagging Roof Line

An uneven roofline may indicate a structural issue that requires professional evaluation. Without properly addressing and resolving the issue, a sagging roof will get worse over time.

Frequently Asked Questions About Roofing in Chester, NY

The best type of roofing material for your home in Chester will depend on a number of factors, including your budget and how often you want to do maintenance.

Asphalt is more budget-friendly, while materials like metal are more expensive but last longer. You also might choose a material like wood for its environmentally friendly nature.

New York does not require roofing contractors to hold a state-level license, however there may be local requirements. Be sure to verify that your contractor meets any local licensing requirements before signing a contract.

It generally takes between one and five days to replace a roof. Variables that could influence the timeline include the accessibility of your roof, its size, and the weather in Chester during the timeframe. Chester tends to see a lot of rain, which might delay the project.

Your roof can absolutely impact how energy-efficient your home is. For example, a good roof helps you spend less energy heating your home during the winter months. Some materials (like metal) are more energy-efficient than others.

A professional will either pressure wash or "soft wash" your roof, depending on the material and how much cleaning is needed. Power washing is not recommended for certain roof types like asphalt shingles. When soft washing your roof, your contractor might use chemicals like bleach and detergent, and tools such as brooms and brushes.

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