Get matched with the best Roofing & Gutter Service pros in Chestnut Hill, MA

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Centerpoint Painting - Roofing & Gutter Services in Abington, MA

Centerpoint Painting

★ ★ ★ ★ ★ 4.6 (17 reviews)

Abington, MA 02351

5 projects

Centerpoint Painting has proudly served the Duxbury, MA area since 2006, specializing in high-quality painting services. Our offerings include professional interior painting, expert toilet installatio...

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Power Construction Roofing and Siding Corp. - Roofing & Gutter Services in Natick, MA

Power Construction Roofing And Siding Corp.

★ ★ ★ ★ ★ 4.7 (15 reviews)

Natick, MA 01760

1 project

Power Construction Roofing and Siding Corp. has provided exceptional roofing services for over 12 years. We specialize in new roofs, replacements, and repairs for residential and commercial properties...

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Senco Home Services - Roofing & Gutter Services in Tewksbury, MA

Senco Home Services

★ ★ ★ ★ ★ 4.6 (15 reviews)

Tewksbury, MA 01876

2 projects

Senco Home Services provides comprehensive home improvement solutions, covering everything from basement to roof. Our expert teams ensure your home remains in excellent condition through effective com...

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A Gomez Company - Roofing & Gutter Services in Lynn, MA

A Gomez Company

★ ★ ★ ★ ★ 4.5 (15 reviews)

Lynn, MA 01902

8 projects

A Gomez Company is your reliable partner for a wide range of services, including roofing, gutter installation and repair, chimney services, siding, painting, and deck work. We pride ourselves on excep...

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Delarosa Roofing - Roofing & Gutter Services in Salem, MA

Delarosa Roofing

★ ★ ★ ★ ★ 4.7 (14 reviews)

Salem, MA 01970

14 projects

Delarosa Roofing in Salem, MA, offers professional roofing solutions to ensure your home is protected during storms. Our experienced team specializes in roofing installation, replacement, rubber roofi...

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Fairway Roofing & Maintenance LLC - Roofing & Gutter Services in Bellingham, MA

Fairway Roofing & Maintenance LLC

★ ★ ★ ★ ★ 4.7 (14 reviews)

Bellingham, MA 02019

12 projects

Fairway Roofing & Maintenance LLC specializes in roofing, gutters, and property maintenance for commercial, residential, and industrial properties. Fully insured and family-owned, we offer 24-hour eme...

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Classic Metal Roofs, LLC - Roofing & Gutter Services in Stow, MA

Classic Metal Roofs, LLC

★ ★ ★ ★ ★ 4.7 (14 reviews)

Stow, MA 01775

11 projects

Classic Metal Roofs, LLC specializes in standing seam and metal shingle roofing across MA, CT, NH, and RI. With over 50 years of experience and a commitment to quality, our family-owned business offer...

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Platinum Exteriors - Roofing & Gutter Services in Braintree, MA

Platinum Exteriors

★ ★ ★ ★ ★ 4.7 (14 reviews)

Braintree, MA 02184

6 projects

Platinum Exteriors is a premier contractor specializing in roofing, siding, and windows, dedicated to customer satisfaction. Our experienced team delivers exceptional service and quality workmanship,...

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Leighton Construction - Roofing & Gutter Services in Waltham, MA

Leighton Construction

★ ★ ★ ★ ★ 4.8 (13 reviews)

Waltham, MA 02453

8 projects

Founded in 1993 by Wesley Leighton, Leighton Construction specializes in high-quality repairs and renovations while ensuring projects are completed on time and within budget. Committed to superior cra...

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Peter Buzzelle Custom Carpentry Inc. - Roofing & Gutter Services in Jamaica Plain, MA

Peter Buzzelle Custom Carpentry Inc.

★ ★ ★ ★ ★ 4.8 (13 reviews)

Jamaica Plain, MA 02130

7 projects

Peter Buzzelle Custom Carpentry Inc. has proudly served the Boston area since 2010, specializing in the renovation of historic homes. Our dedicated team collaborates closely with clients to ensure exc...

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Verified Reviews for Roofing & Gutter Services pros in Chestnut Hill, MA

*The Growcycle rating for Roofing & Gutter Services companies in Chestnut Hill, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Roofing & Gutter Services needs.

Last update on July 10, 2026

James Morgan

Reviewed in October 2025

I had a great experience with the roofing team. They were efficient and left my yard clean when they finished. Highly recommend their services for any roofing needs.

Over The Top Roofing Request a quote

Sarah Thompson

Reviewed in September 2025

Great service from start to finish. The team was knowledgeable, and they worked hard to make sure everything was done right. Very satisfied with my new roof.

Power Construction Roofing and Siding Corp. Request a quote

Michael Smith

Reviewed in June 2025

Can Roof Construction Llc provided excellent service and quality materials. The crew was friendly and worked efficiently. My roof looks amazing now!

CAN Roof Construction LLC Request a quote

Jessica Taylor

Reviewed in October 2025

From the initial estimate to the final inspection, everything was handled professionally. Their attention to detail really impressed me, and the roof looks amazing now.

Cool Flat Roofing MA Request a quote

Lawrence Wade

Reviewed in November 2025

I had a great experience with my roof replacement. The team was professional, timely, and the quality of work exceeded my expectations. Highly recommend!

IMA Construction Corp Request a quote

Cost Guide

How much does Roofing & Gutter Services cost in Chestnut Hill, MA?

Typical roofing & gutter services projects in Chestnut Hill, MA range from $5,000 to $15,000, with most homeowners paying around $8,500.

$5,000

$8,500 Typical cost in Chestnut Hill, MA

$15,000

LOWHIGH

Prices vary by project scope, materials, and local labor rates.

Per Sq Ft $4–$8

Per Roof Vent $150–$300

Per Gutter Foot $3–$5

Last updated: April 2026

Roofing and gutter services in Chestnut Hill typically cost between $5,000 and $15,000, with an average cost around $8,500. The price range is influenced by the roofing material selected, the size of the roof, and the complexity of the installation.

Local contractors in Chestnut Hill charge between $75 and $150 per hour for roofing services, reflecting the demand for skilled labor in the area. Homeowners should also consider permit requirements from the Chestnut Hill Building Department, which can involve additional fees and time for approval.

When comparing quotes from Chestnut Hill contractors, be sure to look for detailed breakdowns of materials, labor, and any warranties offered. This will help you assess the value of each quote and ensure you choose the best option for your roofing needs.

When comparing roofing and gutter service quotes in Chestnut Hill, always request itemized estimates to understand the scope of work and materials involved.

What affects the cost in Chestnut Hill, MA?

Chestnut Hill Labor Rates

Licensed roofing contractors in Chestnut Hill charge $75–$150/hr, depending on the complexity of the job and experience level. These rates reflect the local demand for skilled roofing professionals.

Permits & Inspections

Most roofing projects in Chestnut Hill require permits from the Chestnut Hill Building Department, which can add costs and time. Inspections may also be necessary to ensure compliance with local regulations.

Material Selection & Quality

Material choice can swing a roofing project by 20–30%, with options ranging from asphalt shingles to metal roofing. Higher-quality materials often lead to longer-lasting roofs and better warranties.

Seasonal Demand & Scheduling

The best time to schedule roofing services in Chestnut Hill is during the late spring and early fall. These seasons typically offer favorable weather conditions, reducing delays and ensuring a smooth installation process.

Frequently Asked Questions About Roofing & Gutter Services in Chestnut Hill, MA

How can I improve the drainage of my gutters?

Improving the drainage of your gutters in Chestnut Hill is crucial to prevent water damage to your home. Start by ensuring your gutters are clean and free of debris, as blockages can cause water to overflow. Installing gutter guards can also help keep leaves and dirt out. Additionally, check the slope of your gutters to ensure they direct water towards downspouts. If they’re not sloped correctly, you may need to adjust their position. If your gutters are still not draining properly, it may be time to consult with a local professional to assess and rectify the issue, ensuring proper water management around your home.

How often should I have my roof inspected?

In Chestnut Hill, it’s advisable to have your roof inspected at least once a year, especially after severe weather conditions such as heavy snow or storms. Regular inspections help identify potential issues early, such as missing shingles, leaks, or damage caused by debris. Additionally, if your roof is older or has experienced significant weathering, more frequent inspections may be warranted. A professional roofing service can provide a thorough evaluation and recommend necessary repairs or maintenance. Keeping up with inspections can extend the life of your roof and prevent costly repairs down the line.

What are the signs I need a new roof?

Several indicators suggest that you may need a new roof in Chestnut Hill. Look for missing or damaged shingles, significant granule loss, or signs of water damage inside your home, such as stains or mold. If your roof is over 20 years old, it may be nearing the end of its lifespan, depending on the material. Additionally, if you notice sagging areas or excessive moss or algae growth, these can be signs of underlying issues. Consulting with a local roofing professional can provide a comprehensive assessment to determine whether a roof replacement is necessary.

What should I do if my gutters are leaking?

If you discover that your gutters are leaking in Chestnut Hill, it’s essential to address the issue promptly to prevent further water damage to your home. Start by inspecting the gutters for visible cracks, holes, or loose joints that may be the source of the leaks. In some cases, simple repairs, such as sealing cracks with a waterproof sealant or reattaching loose sections, may suffice. However, if the damage is extensive or if your gutters are old and rusted, it might be more beneficial to consider a full replacement. Consulting with a local gutter service can provide you with the best options for resolving the leaks effectively.

What types of roofing materials are best for my home?

Choosing the right roofing materials for your home in Chestnut Hill depends on factors such as your budget, aesthetic preferences, and local climate. Common options include asphalt shingles, which are cost-effective and easy to install; metal roofing, known for its durability and energy efficiency; and slate or tile, which offers a classic look but at a higher price point. Each material has its advantages and disadvantages, so consider factors like lifespan, maintenance needs, and insulation properties. Consulting with a local roofing expert can help guide your decision based on your specific circumstances.

Common Roofing & Gutter Services services and their costs

Typical pricing in Chestnut Hill, MA by service type.

Roof Installation

Complete roofing services

Method	Cost Range
Asphalt Shingle Roof The most common roofing choice for homes.	$5,000–$10,000
Metal Roof Durable and energy-efficient, with a longer lifespan.	$10,000–$15,000
Tile Roof Offers a distinct look and excellent durability.	$12,000–$20,000
Flat Roof Ideal for modern designs and commercial buildings.	$6,000–$12,000

Gutter Services

Essential gutter installation and repair

Method	Cost Range
Gutter Installation Installing new gutters to ensure proper drainage.	$1,000–$2,500
Gutter Repair Fixing leaks and damage to existing gutters.	$250–$800
Gutter Cleaning Removing debris to prevent clogs and water damage.	$150–$300
Gutter Guard Installation Installing guards to reduce cleaning frequency.	$500–$1,500

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Price ranges are estimates compiled from publicly available data and may vary with project scope.

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Verified Reviews for Roofing & Gutter Services pros in Chestnut Hill, MA

James Morgan

Sarah Thompson

Michael Smith

Jessica Taylor

Lawrence Wade

How much does Roofing & Gutter Services cost in Chestnut Hill, MA?

What affects the cost in Chestnut Hill, MA?

Frequently Asked Questions About Roofing & Gutter Services in Chestnut Hill, MA

Common Roofing & Gutter Services services and their costs

Roof Installation

Gutter Services

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