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Find Asphalt shingle roofing installers and replacers in Oak Bluffs

Avatar for Stuart & Co., LLC

Stuart & Co., LLC

4.95(
10
)
Approved Pro

Stuart & Co., LLC

4.95(
10
)
Approved Pro
Customers say: Terrific value
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
20 years of experience

Stuart & Co., LLC, is a well established business with over 25 years of unmatched expertise. Customer preference and priorities are always first. We're very timely with our work and never lose attention to detail. Stuart & Co., LLC, has built a reputation for quality work with each satisfied customer. Our sense of pride is apparent in every restoration we complete. Call Stuart & Co., LLC, today and we'll be there in your time of need.

"They had my roof done before I knew it. No mess. Very professional. Love the color of the roof Brian helped me choose really makes a difference."

Bonnie W on January 2023

Stuart & Co., LLC, is a well established business with over 25 years of unmatched expertise. Customer preference and priorities are always first. We're very timely with our work and never lose attention to detail. Stuart & Co., LLC, has built a reputation for quality work with each satisfied customer. Our sense of pride is apparent in every restoration we complete. Call Stuart & Co., LLC, today and we'll be there in your time of need.

"They had my roof done before I knew it. No mess. Very professional. Love the color of the roof Brian helped me choose really makes a difference."

Bonnie W on January 2023


Millers Professionals, Inc

New on HomeAdvisorNew on HomeAdvisor
Approved Pro

Millers Professionals, Inc

New on HomeAdvisorNew on HomeAdvisor
Approved Pro
18 years of experience
Free onsite estimate

Millers Profressionals, Inc 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.

Millers Profressionals, Inc 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.


Avatar for Bradford Rothwell

Bradford Rothwell

5.00(
1
)
Approved Pro

Bradford Rothwell

5.00(
1
)
Approved Pro
21 years of experience
Free onsite estimate

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"Brad and his work crew brought my newly purchased home back to life. A full interior/exterior renovation which fit into our budget. Easy to work with, attentive, and professional. Would hire again! - Will Klosinski "

will k on December 2025

We take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer's needs. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

"Brad and his work crew brought my newly purchased home back to life. A full interior/exterior renovation which fit into our budget. Easy to work with, attentive, and professional. Would hire again! - Will Klosinski "

will k on December 2025


Avatar for US ProPaint and Renovation, Inc.

US ProPaint and Renovation, Inc.

4.85(
242
)
Approved Pro

US ProPaint and Renovation, Inc.

4.85(
242
)
Approved Pro
Super Service Award
Customers say: Quality work
637 local quotes requested
23 years of experience

US Pro Paint and Renovation is a full-service home improvement company that has been serving the South Shore, Cape Cod and Greater Boston areas for over 23 years. Owned and operated by JR Reis and Jessica Reis, who have a combined 23 years of experience in construction and renovations, our company specializes in exterior and interior home improvement services including, siding, roofing, painting, windows, doors, flooring, decks, repairs, renovations, remodeling, cabinets refacing and refinishing, additions and expansions, restorations (including mold and water restorations). We are dedicated to providing great quality workmanship, employing a drug-free staff of high moral character, using high-quality products, offering exceptional warranties, and ensuring your satisfaction. - Highly rated and recommended contractor on Angie's List/HomeAdvisor with over 230 reviews. - Rated 4.8 stars on Google with over 170 reviews. - We leave your job site cleaner than when we arrived.

"Good people, did a great job on quote"

Rick C on December 2025

US Pro Paint and Renovation is a full-service home improvement company that has been serving the South Shore, Cape Cod and Greater Boston areas for over 23 years. Owned and operated by JR Reis and Jessica Reis, who have a combined 23 years of experience in construction and renovations, our company specializes in exterior and interior home improvement services including, siding, roofing, painting, windows, doors, flooring, decks, repairs, renovations, remodeling, cabinets refacing and refinishing, additions and expansions, restorations (including mold and water restorations). We are dedicated to providing great quality workmanship, employing a drug-free staff of high moral character, using high-quality products, offering exceptional warranties, and ensuring your satisfaction. - Highly rated and recommended contractor on Angie's List/HomeAdvisor with over 230 reviews. - Rated 4.8 stars on Google with over 170 reviews. - We leave your job site cleaner than when we arrived.

"Good people, did a great job on quote"

Rick C on December 2025


Avatar for PLJ CARPENTRY INC

PLJ CARPENTRY INC

4.86(
11
)
Approved Pro

PLJ CARPENTRY INC

4.86(
11
)
Approved Pro
Customers say: Quick response
9 years of experience
Free onsite estimate

We pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business! Book with us online or feel free to give us a call today!

" Working with the PLJ crew was an excellent experience from start to finish. My deck came out absolutely beautiful?exactly how I envisioned it. The team was super nice and took the time to answer every question I had along the way. I highly recommend PLJ to anyone looking to turn their project into reality. They get a thumbs up and 5 stars all day long!"

ben c on December 2025

We pride our company on reliability, great communication, integrity, and quality work. We are experts in our trade and will do our best to keep you as educated as we can on your particular task or project. We look forward to earning your business! Book with us online or feel free to give us a call today!

" Working with the PLJ crew was an excellent experience from start to finish. My deck came out absolutely beautiful?exactly how I envisioned it. The team was super nice and took the time to answer every question I had along the way. I highly recommend PLJ to anyone looking to turn their project into reality. They get a thumbs up and 5 stars all day long!"

ben c on December 2025


Avatar for Capital Construction Contracting South

Capital Construction Contracting South

4.68(
42
)
Approved Pro

Capital Construction Contracting South

4.68(
42
)
Approved Pro
Customers say: Quality work
1646 local quotes requested
22 years of experience

Capital Construction Contracting Inc. was founded in 2005 as a full service home remodeling company. We provide complete interior and exterior home improvement services specializing in James Hardie siding, including roofing, windows, doors, custom decks and interior remodels. We pride ourselves on fantastic customer service and top notch craftsmanship. We hold numerous certifications in the industry, and we are proud to work with the best products from leading manufacturers. No matter what home improvement needs you have, Capital Construction Contracting Inc. is here to provide you with quality solutions. Our mission is simple : to improve the lives of our customers by providing the highest quality building materials installed by highly skilled, professionally trained crafts persons with the highest level of customer service. Feel free to visit our showroom: 3 Norwood Street, Dorchester MA We value your business!

"Everything was done to perfection."

Cindy M on September 2025

Capital Construction Contracting Inc. was founded in 2005 as a full service home remodeling company. We provide complete interior and exterior home improvement services specializing in James Hardie siding, including roofing, windows, doors, custom decks and interior remodels. We pride ourselves on fantastic customer service and top notch craftsmanship. We hold numerous certifications in the industry, and we are proud to work with the best products from leading manufacturers. No matter what home improvement needs you have, Capital Construction Contracting Inc. is here to provide you with quality solutions. Our mission is simple : to improve the lives of our customers by providing the highest quality building materials installed by highly skilled, professionally trained crafts persons with the highest level of customer service. Feel free to visit our showroom: 3 Norwood Street, Dorchester MA We value your business!

"Everything was done to perfection."

Cindy M on September 2025


Avatar for Vaz Construction, Inc.

Vaz Construction, Inc.

5.00(
3
)
Approved Pro

Vaz Construction, Inc.

5.00(
3
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
11 local quotes requested

Vaz Construction, Inc., 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. We offer a range of services for all of your residential and commercial needs and we're waiting for your call!

"We were really apprehensive as weâ ve had some bad experiences with contractors in the past, but we called anyways because we had some shingles fly off in a rainstorm. The company sent a rep named Elijah out. He recommended we go through insurance because he said it was insurable damage. The insurance awarded us about 6k, but Elijah said he might be able to get us more if we allowed him to try so we agreed. He sent them various emails highlighting areas that they had missed, and to our surprise, the insurance increased their payout to about 18k! We couldnâ t have been more pleased! When the crew came out they were fast, clean, and professional. The roof looks fantastic! Ive had some bad experiences in the past, but they really went above and beyond. Iâ ll forever recommend them to all my family and friends!"

Evan D on March 2024

Vaz Construction, Inc., 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. We offer a range of services for all of your residential and commercial needs and we're waiting for your call!

"We were really apprehensive as weâ ve had some bad experiences with contractors in the past, but we called anyways because we had some shingles fly off in a rainstorm. The company sent a rep named Elijah out. He recommended we go through insurance because he said it was insurable damage. The insurance awarded us about 6k, but Elijah said he might be able to get us more if we allowed him to try so we agreed. He sent them various emails highlighting areas that they had missed, and to our surprise, the insurance increased their payout to about 18k! We couldnâ t have been more pleased! When the crew came out they were fast, clean, and professional. The roof looks fantastic! Ive had some bad experiences in the past, but they really went above and beyond. Iâ ll forever recommend them to all my family and friends!"

Evan D on March 2024


Avatar for Castro Finish Carpentry Inc

Castro Finish Carpentry Inc

5.00(
9
)
Approved Pro

Castro Finish Carpentry Inc

5.00(
9
)
Approved Pro
Super Service Award
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
11 years of experience

Welcome to Castro finish carpentry! We have over 12 years of experience on all: *Remodeling (Interior and Exterior) *Decks *Additions framing *Siding *Roofing *Windows *Doors And so much more!! Castro Finish Carpentry is a full insured company located at Cape Cod, on the field over 12 years. Our crew is formed by high capacity craftsman to guarantee a impeccable job, beyond competence and dedication, we preserve transparency to our costumers!! Feel free to give us a call and email for any question!

"The project went very well. From the initial assessment through unexpected issues to completion, the process was smooth and the work was professional and well done. Steve was very responsive and helpful throughout."

Robert G on May 2025

Welcome to Castro finish carpentry! We have over 12 years of experience on all: *Remodeling (Interior and Exterior) *Decks *Additions framing *Siding *Roofing *Windows *Doors And so much more!! Castro Finish Carpentry is a full insured company located at Cape Cod, on the field over 12 years. Our crew is formed by high capacity craftsman to guarantee a impeccable job, beyond competence and dedication, we preserve transparency to our costumers!! Feel free to give us a call and email for any question!

"The project went very well. From the initial assessment through unexpected issues to completion, the process was smooth and the work was professional and well done. Steve was very responsive and helpful throughout."

Robert G on May 2025


"I contracted Black Stallion Enterprises LLC to replace the roofs on two of my houses. The entire process from the initial estimate to completion was fair, easy, transparent, and professional. They arrived promptly, completed the job on time and within budget. The workers were clean and worked full days with minimal disturbances to our everyday activities. Joe oversaw the job and provided step-by-step updates, explaining what was being done and the reasoning behind it. Additionally, where things were not done properly by the original builder, BSE added the necessary products and fixed it, all within the original price estimate. The roofs look beautiful, and we are already seeing efficiency as a result of the replacement. The BSE team followed up after completion to ensure we were happy. They definitely stand behind their work and materials. I highly recommend BSE for all construction projects and will hire them again."

Erica M on October 2024

We pride ourselves on the quality work we provide, while delivering great customer service. Check out our services offered and call or click to schedule an estimate today!

"I contracted Black Stallion Enterprises LLC to replace the roofs on two of my houses. The entire process from the initial estimate to completion was fair, easy, transparent, and professional. They arrived promptly, completed the job on time and within budget. The workers were clean and worked full days with minimal disturbances to our everyday activities. Joe oversaw the job and provided step-by-step updates, explaining what was being done and the reasoning behind it. Additionally, where things were not done properly by the original builder, BSE added the necessary products and fixed it, all within the original price estimate. The roofs look beautiful, and we are already seeing efficiency as a result of the replacement. The BSE team followed up after completion to ensure we were happy. They definitely stand behind their work and materials. I highly recommend BSE for all construction projects and will hire them again."

Erica M on October 2024


Avatar for Wood Trades LLC

Wood Trades LLC

5.00(
5
)
Approved Pro

Wood Trades LLC

5.00(
5
)
Approved Pro
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
5 years of experience

We guarantee your satisfaction. We pride ourselves on the quality work we provide, while delivering great customer service. This is your one-stop shop for all your home improvement, roofing, and new construction needs. Frame to finish, we do it all!

"I recommend this wonderful company without any hesitation. I first contacted Wood Trades LLC seeking a deck quote in September 2024, and John and Karin came out the very next day. From day one, John and Karin provided impeccable service. I cannot say enough wonderful things about their communication, transparency, honestly, and reliability. All current insurance/contractor licenses were provided up front, and any change in cost was documented through clear contracts. In addition, they patiently navigated me through a difficult permitting process from start to finish. Once the work was started, I had a gorgeous new deck in just over one week. I cannot thank this company enough for gaining, and more importantly, maintaining my trust through this project. I certainly look forward to working with Wood Trades again, and highly recommend their services to anyone seeking high quality results from a wonderful company. Exceeded expectations!"

Lindsay A on December 2024

We guarantee your satisfaction. We pride ourselves on the quality work we provide, while delivering great customer service. This is your one-stop shop for all your home improvement, roofing, and new construction needs. Frame to finish, we do it all!

"I recommend this wonderful company without any hesitation. I first contacted Wood Trades LLC seeking a deck quote in September 2024, and John and Karin came out the very next day. From day one, John and Karin provided impeccable service. I cannot say enough wonderful things about their communication, transparency, honestly, and reliability. All current insurance/contractor licenses were provided up front, and any change in cost was documented through clear contracts. In addition, they patiently navigated me through a difficult permitting process from start to finish. Once the work was started, I had a gorgeous new deck in just over one week. I cannot thank this company enough for gaining, and more importantly, maintaining my trust through this project. I certainly look forward to working with Wood Trades again, and highly recommend their services to anyone seeking high quality results from a wonderful company. Exceeded expectations!"

Lindsay A on December 2024

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FAQs for asphalt shingle roofing installation and replacement projects in Oak Bluffs, MA

Roofing professionals can usually install a medium-sized asphalt shingle roof in two to three days. Installation time increases if your roof is particularly steep or difficult to access or has features like chimneys or skylights that roofers must work around.

Three-tab asphalt shingles usually have the lowest upfront cost of any roofing shingle material. They’re sturdy and typically last 15 to 20 years. However, they may have a shorter lifespan in especially hot or cold climates. Talk to a local roofing professional about the best materials for your climate. In some cases, materials with a higher upfront cost may save you more on repairs or replacements in the long run.

Start by multiplying the length by the width of your roof to calculate the square footage. Most shingle replacement costs $4 to $12 per square foot for materials and labor, depending on factors like the material and the slope of your roof. Once you know the size of your roof, you can calculate a rough estimate of total costs or contact a local roofing professional to provide you with a custom quote.

Asphalt shingles are generally considered to be a low-maintenance item. However, cleaning your asphalt roofing can help prolong the lifespan and keep it looking fresh. If you’re comfortable with DIY and have the proper equipment, you may be able to clean your asphalt shingles yourself. However, if you have an especially high or steep roof, it’s usually safer to hire a professional roof cleaner.

The Oak Bluffs, MA homeowners’ guide to asphalt shingle roofing installations and replacements

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