Get matched with top painters in Winchester, MA
There are 89 highly-rated local painters.
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4.6 
470 Verified Reviews for Painting pros in Winchester, MA
*The Angi rating for Painting companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Painting needs.
*The HomeAdvisor rating for Painting companies in Winchester, MA is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Painting needs.
Last update on May 10, 2025
Painters in Winchester
With over 30+ years of combined experience under our belt, we are ready to paint your vision! Our mission is to provide you with unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with a quality finish to your painting project every step of the way. Call or message us today to schedule an estimate!
"The entire team at Lighthouse painting, especially Nick and Wesley, did an amazing job with our project! The interior painting was meticulous and great care was given to matching our color preferences and completing all of the work in a timely fashion. This is an extremely professional and dedicated team and we could not have been more pleased with the way our painting project turned out!"
Tanja H on February 2025
With over 30+ years of combined experience under our belt, we are ready to paint your vision! Our mission is to provide you with unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with a quality finish to your painting project every step of the way. Call or message us today to schedule an estimate!
"The entire team at Lighthouse painting, especially Nick and Wesley, did an amazing job with our project! The interior painting was meticulous and great care was given to matching our color preferences and completing all of the work in a timely fashion. This is an extremely professional and dedicated team and we could not have been more pleased with the way our painting project turned out!"
Tanja H on February 2025
Strongman Painting specializes in interior and exterior painting. Commercial and Residential. Our teams committed focus is customer satisfaction, Preparation, cleanliness, respect , Last but not least an amazing painting experience and final product you will be very pleased with.
"The crew was great — meticulous, careful, courteous, timely, efficient, friendly, and more. The repaired walls look great on this old home. I will definitely call you again if I need more painting in addition to recommending to whomever asks! Thanks for making this place look 10 years younger!"
Heather w on January 2025
Strongman Painting specializes in interior and exterior painting. Commercial and Residential. Our teams committed focus is customer satisfaction, Preparation, cleanliness, respect , Last but not least an amazing painting experience and final product you will be very pleased with.
"The crew was great — meticulous, careful, courteous, timely, efficient, friendly, and more. The repaired walls look great on this old home. I will definitely call you again if I need more painting in addition to recommending to whomever asks! Thanks for making this place look 10 years younger!"
Heather w on January 2025
Affordable Painting has over 40 years of experience painting and servicing Massachusetts and New Hampshire. e service many of the towns & cities located in the Greater Boston and Central New Hampshire area.
"Mark did an exceptional job on our interior project. He is a hard worker, is there when he said he would be there, very professional, and reasonably priced. We would absolutely hire him again."
Robert D on March 2024
Affordable Painting has over 40 years of experience painting and servicing Massachusetts and New Hampshire. e service many of the towns & cities located in the Greater Boston and Central New Hampshire area.
"Mark did an exceptional job on our interior project. He is a hard worker, is there when he said he would be there, very professional, and reasonably priced. We would absolutely hire him again."
Robert D on March 2024
**SPRING IS HERE AND WE'RE EXCITED TO CONNECT WITH YOU ABOUT YOUR EXTERIOR PAINTING PROJECT!!**We have been serving clients since 2008 with a full range of high-quality exterior and interior painting services with our team of highly trained and dedicated house painters. Our goal is to deliver top-notch quality and a unique customer service experience in business and home owners. Crystal Painting will offer you a free, personalized quote tailored to the individual needs of your project. We provide a broad range of commercial and residential painting services as well as plastering, carpentry, and wallpaper removal.
"Leonardo and his team were extremely professional and hard working. They did an excellent and thorough job painting and restoring the exterior of the house (which was in bad need of repair). We highly recommend their work and plan on hiring them for an indoor project as well."
ALEX B on October 2018
**SPRING IS HERE AND WE'RE EXCITED TO CONNECT WITH YOU ABOUT YOUR EXTERIOR PAINTING PROJECT!!**We have been serving clients since 2008 with a full range of high-quality exterior and interior painting services with our team of highly trained and dedicated house painters. Our goal is to deliver top-notch quality and a unique customer service experience in business and home owners. Crystal Painting will offer you a free, personalized quote tailored to the individual needs of your project. We provide a broad range of commercial and residential painting services as well as plastering, carpentry, and wallpaper removal.
"Leonardo and his team were extremely professional and hard working. They did an excellent and thorough job painting and restoring the exterior of the house (which was in bad need of repair). We highly recommend their work and plan on hiring them for an indoor project as well."
ALEX B on October 2018
ADO Painting is committed to providing our customers in the Greater Boston and Metro West areas outstanding painting services and customer care. We want to help you to reshape your spaces, either residential, commercial, interior, or exterior, with the color of your choice.
"It went very well. Alan was an absolute pleasure to work with. I immediately felt comfortable with him. He answered all my questions and concerns when he first came to give me an estimate on the job. He was flexible on beginning the job. He was able to start in a few days, but I needed a month to fulfill some commitments and to get my place ready. He was very understanding, and we agreed on a date. He arrived on the day we set, and he and his co-worker finished in the time he said he would. I was thrilled with the results. Alan is a hard worker who takes pride in his work and is one of the nicest people too!"
JOYCE K on April 2024
ADO Painting is committed to providing our customers in the Greater Boston and Metro West areas outstanding painting services and customer care. We want to help you to reshape your spaces, either residential, commercial, interior, or exterior, with the color of your choice.
"It went very well. Alan was an absolute pleasure to work with. I immediately felt comfortable with him. He answered all my questions and concerns when he first came to give me an estimate on the job. He was flexible on beginning the job. He was able to start in a few days, but I needed a month to fulfill some commitments and to get my place ready. He was very understanding, and we agreed on a date. He arrived on the day we set, and he and his co-worker finished in the time he said he would. I was thrilled with the results. Alan is a hard worker who takes pride in his work and is one of the nicest people too!"
JOYCE K on April 2024
With over 200 years of combined experience, we have the skills to deliver a quality home renovation for your needs. We do expert work and use only premium products from manufacturers such as Sherwin Williams, Benjamin Moore, California, and Cabot. Don't let just anyone perform your renovations. Our team of professionals is fully insured for your protection. Certificates of insurance are provided to clients and potential clients, upon request.
"Go with Target. I've used several painters, and I have never had the excellent level of quoting and detailed Statement of Work, customer service responsiveness, crew professionalism, quality of prep work and painting, and ability to deliver on my timeline. I am not easily impressed, but Andy, Gabriella, and team knocked it over the Green Monster!"
Rob H on June 2023
With over 200 years of combined experience, we have the skills to deliver a quality home renovation for your needs. We do expert work and use only premium products from manufacturers such as Sherwin Williams, Benjamin Moore, California, and Cabot. Don't let just anyone perform your renovations. Our team of professionals is fully insured for your protection. Certificates of insurance are provided to clients and potential clients, upon request.
"Go with Target. I've used several painters, and I have never had the excellent level of quoting and detailed Statement of Work, customer service responsiveness, crew professionalism, quality of prep work and painting, and ability to deliver on my timeline. I am not easily impressed, but Andy, Gabriella, and team knocked it over the Green Monster!"
Rob H on June 2023
Locally and Family owned painting company , we are here to serve you and treat your projects, your home like our own. Here at Chilel painting you are Family. Call today for a free estimate.
"Fantastic Crew! Ozweldo and his brothers are probably THE most professional, polite, prompt, price conscientious team I've ever worked with in 40 years of Designing and Building. They start every job with absolutely perfect, on-time appointments with clients. Oz starts with polite listening and site review, submitting his Certificate of Insurance and clear, explained, materials costs and labor. When he says he'll be there, They Show Up! On time, start early, stay late and work Saturdays! They prepare and protect your home, your floors, the furniture, the dog... I simply cannot recommend Chilel Painters highly enough. Every client, every job. Oz is so professional, the Very Best."
Colleen L on June 2024
Locally and Family owned painting company , we are here to serve you and treat your projects, your home like our own. Here at Chilel painting you are Family. Call today for a free estimate.
"Fantastic Crew! Ozweldo and his brothers are probably THE most professional, polite, prompt, price conscientious team I've ever worked with in 40 years of Designing and Building. They start every job with absolutely perfect, on-time appointments with clients. Oz starts with polite listening and site review, submitting his Certificate of Insurance and clear, explained, materials costs and labor. When he says he'll be there, They Show Up! On time, start early, stay late and work Saturdays! They prepare and protect your home, your floors, the furniture, the dog... I simply cannot recommend Chilel Painters highly enough. Every client, every job. Oz is so professional, the Very Best."
Colleen L on June 2024
Hi there. I am Steve the owner of Bay State and I have over 25 years of experience in residential repairs. I can help with any Honey-Do-List you can throw at me! Some of my services including but not limited to: Interior & exterior painting (Lead certified), pressure washing: deck, porch, & patio painting/repair/cleaning/restoration, carpentry. No job too big or small. I offer a 10% Senior & Veteran's Discount. Please give me a call today! Buy two rooms get a third room 50% off. Paint five rooms (ceilings walls and trim )and get a sixth room free! Book now to get your spot!and pressure washer
"The service was discussed to me in detail. If an issue was spotted it was explained to me. Items for example: the outdoor tables, chairs, and outside wall with mold, that was not the deck was done without any additional costs. I would hire again next year."
Robert R on July 2024
Hi there. I am Steve the owner of Bay State and I have over 25 years of experience in residential repairs. I can help with any Honey-Do-List you can throw at me! Some of my services including but not limited to: Interior & exterior painting (Lead certified), pressure washing: deck, porch, & patio painting/repair/cleaning/restoration, carpentry. No job too big or small. I offer a 10% Senior & Veteran's Discount. Please give me a call today! Buy two rooms get a third room 50% off. Paint five rooms (ceilings walls and trim )and get a sixth room free! Book now to get your spot!and pressure washer
"The service was discussed to me in detail. If an issue was spotted it was explained to me. Items for example: the outdoor tables, chairs, and outside wall with mold, that was not the deck was done without any additional costs. I would hire again next year."
Robert R on July 2024
Family run business who are ready to start helping owners create the home they have always wanted! We have over 25 years of experience! We get our jobs done as quickly and as efficiently as possible at a reasonable price! Perfection is what we strive for at all times! Our clients satisfaction is what keeps us going throughout our profession. We use the best of the best painting materials along with the best painting brand " Benjamin Moore". Our company is based out of Northborough & Marlborough Massachusetts but we service all of Massachusetts.
"Outstanding! Great people to work with."
Jack K on December 2024
Family run business who are ready to start helping owners create the home they have always wanted! We have over 25 years of experience! We get our jobs done as quickly and as efficiently as possible at a reasonable price! Perfection is what we strive for at all times! Our clients satisfaction is what keeps us going throughout our profession. We use the best of the best painting materials along with the best painting brand " Benjamin Moore". Our company is based out of Northborough & Marlborough Massachusetts but we service all of Massachusetts.
"Outstanding! Great people to work with."
Jack K on December 2024
Please, send a message to us through our website: allonepainting.com We are All in one Painting. A dependable Painting and Cleaning company. We have a lot of testimonial videos about our work on our website, contact us directly, also we have the Best price for you with high quality. Let us introduce our happy job for you. We have Super Service Award, again. If you want a good solution for your project, we are what you need!
"Kaio and the team at All In One Painting are exceptional workers and highly skilled painters. My house had renters in it for 30 years and the walls were in desperate need of repairs and new paint. Kaio was professional and communicative from start to finish. Not missing a single detail and making sure I was satisfied with the progress at every step of the way. His work looks amazing from the cabinets, to the walls to the trim. He left my home in pristine condition. I 100% recommend Kaio and will be using him for any future services. Thank you Kaio for being so caring to your clients and treating us like family."
Emily D on December 2024
Please, send a message to us through our website: allonepainting.com We are All in one Painting. A dependable Painting and Cleaning company. We have a lot of testimonial videos about our work on our website, contact us directly, also we have the Best price for you with high quality. Let us introduce our happy job for you. We have Super Service Award, again. If you want a good solution for your project, we are what you need!
"Kaio and the team at All In One Painting are exceptional workers and highly skilled painters. My house had renters in it for 30 years and the walls were in desperate need of repairs and new paint. Kaio was professional and communicative from start to finish. Not missing a single detail and making sure I was satisfied with the progress at every step of the way. His work looks amazing from the cabinets, to the walls to the trim. He left my home in pristine condition. I 100% recommend Kaio and will be using him for any future services. Thank you Kaio for being so caring to your clients and treating us like family."
Emily D on December 2024
Painting services FAQs
You should paint your home exterior every five to 10 years, on average. Climate and surroundings can affect how well paint holds up. Wood siding will likely need a fresh coat of paint every three to seven years. Paint on brick tends to last about eight to 17 years, on average.
Professional painters charge $20 to $50 per hour, on average. Hourly rate cost factors include the complexity of the paint job, the type of paint, the height of the walls and ceiling, and the type of prep and repairs needed. For example, removing wallpaper costs an additional $3 per square foot because it can be very time consuming and labor intensive. Your location will also impact the hour rate.
To estimate the cost to paint interior walls, multiply the square footage by the average price range to paint interior walls, which is $2 to $6 per square foot. For example, a 12-by-12-foot room with 8-foot tall walls is 384 square feet, meaning that the cost to paint the room will range from $768 to $2,304. Painting the ceiling and any trim will add to the overall cost, as will any repairs.
To calculate the square footage of a home exterior, painters multiply the length of the wall by the height of the wall to be painted. Then they add the total square footage for all of the walls to be painted. To calculate the price, they multiply the total square footage by their cost per square foot to prep and paint. Additional costs may factor in such as repairs, additional trim, and walls higher than the first story.
The cost to paint the exterior of a house ranges from $1,900 to $4,500 or about $1.50 to $4 per square foot, depending on the size, height, and complexity of the home layout. Other cost factors include your location, the type of siding (e.g., wood, aluminum, brick, stucco, etc.), and the kind of paint (e.g. oil-based, latex, acrylic, etc.). Painting the trim a different color or painting intricately designed trim can also increase the cost.
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