Top-rated exterior painters.

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TRUSTED BY CHESTER, MA HOMEOWNERS

  • Average homeowner rating star icon4.4
    Average homeowner rating
  • Verified reviews icon99
    Verified exterior painting services reviews

Find Exterior painters in Chester

Avatar for Burns & Co.

Burns & Co.

Located In Florence/ Northampton
4.92(
25
)
Approved Pro

Burns & Co.

Located In Florence/ Northampton
4.92(
25
)
Approved Pro
Customers say: True professional
Recommended by 96% of Angi customers
Recommended by 96% of HomeAdvisor customers
55 local quotes requested

Book your Exterior job today.We service the Berkshires and Northern Connecticut. 25 years of experience in Painting and Remodeling. I would love to weatherize your property from the harsh New England weather. I am a firm believer in using Sherman Williams exterior, paints and epoxies to winterize your home, and give it a long lasting weather shield the elements. I absolutely love what I do. Bringing your home back to life with a beautiful Paint Job. I aim to please and all of my customers are ecstatic when the jobs complete. Please feel free to call or text me anytime to schedule your appointment for free estimate. I am a proud recipient of the Angie’s list 2023 and 2024 service award. Feel free to call, text, or email at any time. 413-588-8708 Please leave a message because your call is very important to me and I will get back to you. Thank you and take care I look forward to meeting you

"The work was done very well and on time Mike was reasonably priced. I have asked him to return to do more work for me in the future."

Marita M on October 2025

Book your Exterior job today.We service the Berkshires and Northern Connecticut. 25 years of experience in Painting and Remodeling. I would love to weatherize your property from the harsh New England weather. I am a firm believer in using Sherman Williams exterior, paints and epoxies to winterize your home, and give it a long lasting weather shield the elements. I absolutely love what I do. Bringing your home back to life with a beautiful Paint Job. I aim to please and all of my customers are ecstatic when the jobs complete. Please feel free to call or text me anytime to schedule your appointment for free estimate. I am a proud recipient of the Angie’s list 2023 and 2024 service award. Feel free to call, text, or email at any time. 413-588-8708 Please leave a message because your call is very important to me and I will get back to you. Thank you and take care I look forward to meeting you

"The work was done very well and on time Mike was reasonably priced. I have asked him to return to do more work for me in the future."

Marita M on October 2025


Avatar for The Empire Company

The Empire Company

459 E River St
4.95(
93
)
Approved Pro

The Empire Company

459 E River St
4.95(
93
)
Approved Pro
Customers say: Quality work
Recommended by 98% of Angi customers
Recommended by 98% of HomeAdvisor customers
66 local quotes requested

We know how important it is to choose a company that will meet and exceed your expectations. We work with honesty and partner with our customers, as we're both always seeking 100% satisfaction.We're a family owned business. My wife and I run this to have a better life for our families. We offer interior & exterior painting, all types of handyman work, pressure washing, and housecleaning services.

"Excellent job! Took care of a fair amount of carpentry to get things looking good. Bruno was very responsive to how I wanted things to look and adjusted as necessary. Everyone loves how things came out. Highly recommend!"

Michael T on September 2025

We know how important it is to choose a company that will meet and exceed your expectations. We work with honesty and partner with our customers, as we're both always seeking 100% satisfaction.We're a family owned business. My wife and I run this to have a better life for our families. We offer interior & exterior painting, all types of handyman work, pressure washing, and housecleaning services.

"Excellent job! Took care of a fair amount of carpentry to get things looking good. Bruno was very responsive to how I wanted things to look and adjusted as necessary. Everyone loves how things came out. Highly recommend!"

Michael T on September 2025


Avatar for S&P Paint and Property Maintenance

S&P Paint and Property Maintenance

4.20(
5
)
Approved Pro

S&P Paint and Property Maintenance

4.20(
5
)
Approved Pro
31 local quotes requested
9 years of experience

We specialize in exterior and interior painting, as well as power washing and gutter maintenance. With 10+ years of service to the Berkshires, we strive to leave our customers beyond satisfied and in love with a new look home or Business. Fully insured ⭐

"I hired Seth to do some interior paint work and could not be happier with the results! He took the time to make sure everything was perfect and was always willing to go above and beyond answering all my paint questions. I will be hiring Seth in the future and highly recommend his services to everyone!"

Jessica R on March 2025

We specialize in exterior and interior painting, as well as power washing and gutter maintenance. With 10+ years of service to the Berkshires, we strive to leave our customers beyond satisfied and in love with a new look home or Business. Fully insured ⭐

"I hired Seth to do some interior paint work and could not be happier with the results! He took the time to make sure everything was perfect and was always willing to go above and beyond answering all my paint questions. I will be hiring Seth in the future and highly recommend his services to everyone!"

Jessica R on March 2025


Welcome to Top Hat Services, we look forward to discussing your home improvement project, please reach out to us anytime!


Avatar for T&T remodeling

T&T remodeling

5.00(
12
)

T&T remodeling

5.00(
12
)
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers

Hello, I'm Scott. I've been in the construction services field for over 30 years. I'm happy to help with any of your remodeling needs. At our company, your satisfaction is our top priority. We are committed to completing every job to the highest standards, ensuring exceptional quality and service. Discover our range of services and reach out today to book your free estimate. Let us show you the difference our dedication can make!

"Working with Scott was outstanding. Scott impressed me with his reliability, thoroughness, and exceptional results. He's highly skilled, trustworthy, and even went above and beyond to fix issues he noticed that we were unaware of. I would hire him again without hesitation and enthusiastically recommend him to anyone in need of quality work!"

Jessica H on November 2024

Hello, I'm Scott. I've been in the construction services field for over 30 years. I'm happy to help with any of your remodeling needs. At our company, your satisfaction is our top priority. We are committed to completing every job to the highest standards, ensuring exceptional quality and service. Discover our range of services and reach out today to book your free estimate. Let us show you the difference our dedication can make!

"Working with Scott was outstanding. Scott impressed me with his reliability, thoroughness, and exceptional results. He's highly skilled, trustworthy, and even went above and beyond to fix issues he noticed that we were unaware of. I would hire him again without hesitation and enthusiastically recommend him to anyone in need of quality work!"

Jessica H on November 2024


"I was very impressed working with this company. Communication was superb right off the bat. We went over the job in detail, and it was completed perfectly. The company is very professional and pays attention to every detail. The price was good too! They also cleaned the area thoroughly and my property looks exquisite. Hire this company with confidence. Thank you!"

John C on October 2025

Good work guarantee. I love making our customer's happy

"I was very impressed working with this company. Communication was superb right off the bat. We went over the job in detail, and it was completed perfectly. The company is very professional and pays attention to every detail. The price was good too! They also cleaned the area thoroughly and my property looks exquisite. Hire this company with confidence. Thank you!"

John C on October 2025


Avatar for Alyssa Crabtree

Alyssa Crabtree

No reviews yet

Alyssa Crabtree

No reviews yet
1 years of experience

I offer a variety of services from painting, to drywall, flooring, plumbing, framing, and light carpentry. I am a Registered Home Improvement Contractor, preparing to be a General Contractor. All of my work is extremely detailed, thorough, and professional.

I offer a variety of services from painting, to drywall, flooring, plumbing, framing, and light carpentry. I am a Registered Home Improvement Contractor, preparing to be a General Contractor. All of my work is extremely detailed, thorough, and professional.



Avatar for Dalessandro construction coro

Dalessandro construction coro

No reviews yet

Dalessandro construction coro

No reviews yet

Hello, my name is Lovis Vallecillo, owner of the company Dalessandro Construction Corp. My company has its respective legal document required by Massachusetts law. Dalessandro Construction Corp has been in existence since 2016. Our specialty is general construction.

Hello, my name is Lovis Vallecillo, owner of the company Dalessandro Construction Corp. My company has its respective legal document required by Massachusetts law. Dalessandro Construction Corp has been in existence since 2016. Our specialty is general construction.


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Exterior Painting questions, answered by experts

Newer paint cans often come with an “easy pour” spout with a twist lid. These can be tricky to open, but the key is to grip the spout cover with your fingers and twist it counter-clockwise. There should be a raised ridge in the middle to make it easy to grab. For more standard twist lids, you can try prying the lid off by turning it with your hands, as you would a jar, or running it under warm water.

Fiberglass bathtubs require paint that can withstand repeated exposure to water and humidity. Additionally, they require a high-strength epoxy coating to protect the paint from water. A few brands make appropriate paints, some in spray cans.

However, kits are the best choice because they come with everything you need (with instructions) to ensure a durable finish. These kits may require mixing the paint with a hardener that gives it the strength to withstand repeated water exposure. 

Most high-gloss paint will stick to plastic. However, it’s important to prepare your plastic surface to have the best success with painting it. Even the most plastic-adhering paint can struggle to fully adhere to a surface that no one has properly prepared. Ensure that the surface is clean and free of grease or dirt. If your plastic is very slick, you may also want to lightly sand it to increase the chances of complete adhesion.

It’s a matter of personal preference on whether you want to tip the crew or the lead painter. You can tip the crew as a whole, just the lead painter, or each individual painter. Do what feels right in the context of the job.

DIY is possible with proper preparation and equipment, but a professional painter ensures smoother finishes, especially for intricate cabinetry.

The Chester, MA homeowners’ guide to exterior painting services

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