Get matched with top exterior painters in Chester, MA
There are 7 highly-rated local exterior painters.
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TRUSTED BY CHESTER, MA HOMEOWNERS
4.4 Average homeowner rating
105 Verified exterior painting services reviews
Verified Reviews for Exterior Painting pros in Chester, MA
*The Angi rating for Exterior Painting companies in Chester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Exterior Painting needs.
*The HomeAdvisor rating for Exterior Painting companies in Chester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Exterior Painting needs.
Last update on December 07, 2025
Find Exterior painters in Chester
The Empire Company
The Empire Company
Super Service Award
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.
"I needed someone to fix a leak and add siding which had rotted. I couldn’t be more pleased. Bruno’s repair crew and painters were excellent."
Walter P on October 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.
"I needed someone to fix a leak and add siding which had rotted. I couldn’t be more pleased. Bruno’s repair crew and painters were excellent."
Walter P on October 2025
Burns & Co.
Burns & Co.
Super Service Award
Customers say: True professional
35 local quotes requested
15 years of experience
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
"A professional job and very reliable. Would highly recommend the services and company to anyone looking for home improvement. Top notch service."
Jimmie A 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
"A professional job and very reliable. Would highly recommend the services and company to anyone looking for home improvement. Top notch service."
Jimmie A on October 2025
S&P Paint and Property Maintenance
S&P Paint and Property Maintenance
36 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
Sentri Homes
Sentri Homes
407 local quotes requested
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.
T&T remodeling
T&T remodeling
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
Alyssa Crabtree
Alyssa Crabtree
1 years of experience
What I do isn’t just about painting walls or fixing things — it’s about creating spaces people feel proud of. From painting projects that brighten your home to repairs that bring peace of mind, every job I take on is powered by purpose and built from the heart. Each project is a reflection of my values, my craftsmanship, and my genuine passion for what I do. Check out my instagram for recent projects. https://www.instagram.com/ancprojects?igsh=c3E0a2ZnM2x0djdx&utm_source=qr
What I do isn’t just about painting walls or fixing things — it’s about creating spaces people feel proud of. From painting projects that brighten your home to repairs that bring peace of mind, every job I take on is powered by purpose and built from the heart. Each project is a reflection of my values, my craftsmanship, and my genuine passion for what I do. Check out my instagram for recent projects. https://www.instagram.com/ancprojects?igsh=c3E0a2ZnM2x0djdx&utm_source=qr
Dalessandro construction coro
Dalessandro construction coro
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.
Evgeny korenevskiy
Evgeny korenevskiy
10 years of experience
Furniture assembly, deck building, painting, fixing, remodeling, window door installation, siding , fences instaling , doing all kinds of stuff
Furniture assembly, deck building, painting, fixing, remodeling, window door installation, siding , fences instaling , doing all kinds of stuff
K browns Property Maintenance
K browns Property Maintenance
Free onsite estimate
K Browns Property maintenence is a locally owned and operated Company in Berkshire County with reliable pricing my areas I cover is and services I offer Handy men work 14 year experience Snow plowing Snow blowing 10 year experience furniture assembly 3 year expensive Any work that you need done around house I am will to help fully licensed and insured Give me call at 413-841-7736 to discuss further on details of stuff you would like done as always stay safe stay blessed and have a great day Richmond ma Pittsfield ma Lanasbroro ma Chesher ma Adams ma And more Depending on job North adams ma
K Browns Property maintenence is a locally owned and operated Company in Berkshire County with reliable pricing my areas I cover is and services I offer Handy men work 14 year experience Snow plowing Snow blowing 10 year experience furniture assembly 3 year expensive Any work that you need done around house I am will to help fully licensed and insured Give me call at 413-841-7736 to discuss further on details of stuff you would like done as always stay safe stay blessed and have a great day Richmond ma Pittsfield ma Lanasbroro ma Chesher ma Adams ma And more Depending on job North adams ma
Exterior Painting questions, answered by experts
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.
Painting a garage door is one of the most impactful projects you can undertake with a smaller budget. Learn what makes up the total cost, as well as tips on how you can save.
The cost of materials and labor all factor into your overall brick staining cost, but what other factors impact the bottom line? Our guide covers this and more.
The cost to paint a house's exterior depends on its size, siding type, and height. The finish and the home's exterior condition also play a role.
Learning how to whitewash brick can make for a brighter, lighter space with a natural appearance. Keep reading to learn how you can whitewash brick yourself.
Ready to take on the home from the outside? Why not start with its exterior paint? These tips help you paint your home's exterior surfaces without making costly mistakes. Learn how to paint the exterior of your home at a professional level.
Breathe new life into your deck by sanding it before adding stain. Follow this guide to learn how to sand a deck and choose the right grit sandpaper.
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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"