
Get matched with top painters in Winchester, MA
There are 40 highly-rated local painters.
Need a pro for your painting project in Winchester, MA?
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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 November 30, 2025
Find Painters in Winchester

Target Painting & Contracting Inc
Target Painting & Contracting Inc
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
Lighthouse Painting
Lighthouse Painting
With over 40+ years of combined experience throughout our team, Lighthouse Painting is ready to paint your vision! With over 1500+ completed projects, we strive towards providing unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with quality results on your painting project every step of the way. Call or message us today to schedule your complimentary estimate!
"Very professional. job completed per contract specifications. Workers completed tasks with a pleasant “can do”attitude. Maintained a clean work area during the work. Would hire again"
Paul G on June 2025
With over 40+ years of combined experience throughout our team, Lighthouse Painting is ready to paint your vision! With over 1500+ completed projects, we strive towards providing unparalleled customer service - and it starts with communication. Our staff is prompt, courteous, and are ready to provide you with quality results on your painting project every step of the way. Call or message us today to schedule your complimentary estimate!
"Very professional. job completed per contract specifications. Workers completed tasks with a pleasant “can do”attitude. Maintained a clean work area during the work. Would hire again"
Paul G on June 2025

Supreme Painters Inc
Supreme Painters Inc
Supreme Painters & Remodelers Inc. is your trusted partner for all your painting and remodeling needs. With decades of experience, we specialize in delivering exceptional craftsmanship and unmatched customer service to homeowners and businesses alike. Whether you're looking to revitalize your interiors, protect your exteriors, or transform your property with a complete renovation, we have the expertise to bring your vision to life. Our services include interior and exterior painting, drywall repair, cabinet refinishing, power washing, deck staining, and more. We also excel in remodeling projects such as kitchen and bathroom upgrades, flooring installation, and custom carpentry. Our skilled team uses top-quality materials and advanced techniques to ensure lasting results that exceed your expectations. At Supreme Painters & Remodelers Inc., we take pride in our attention to detail, professionalism, and commitment to delivering projects on time and within budget. From the initial consultation to the final walkthrough, we work closely with our clients to ensure their satisfaction every step of the way. Based in Boston, we serve residential and commercial clients throughout the region. Our mission is simple: to enhance the beauty, functionality, and value of your property while making the process stress-free and enjoyable. Discover the Supreme difference today—call us for a free estimate and let us turn your ideas into reality. Your project deserves the best, and that’s exactly what we deliver. Supreme Painters & Remodelers Inc.—where quality meets excellence.
"Lindo is fantastic to work with and his team is excellent. We have had Supreme work on two different projects in our house. The first was ceiling patch work and crown molding installation. This was done very efficiently. His team was always on time, great at communication. The second job was bigger and involved a complete renovation of our master bathroom. The work that was done was high quality and the team was great to work with. I highly recommend Supreme, and am already in discussions for our next project together."
Matthew F on February 2024
Supreme Painters & Remodelers Inc. is your trusted partner for all your painting and remodeling needs. With decades of experience, we specialize in delivering exceptional craftsmanship and unmatched customer service to homeowners and businesses alike. Whether you're looking to revitalize your interiors, protect your exteriors, or transform your property with a complete renovation, we have the expertise to bring your vision to life. Our services include interior and exterior painting, drywall repair, cabinet refinishing, power washing, deck staining, and more. We also excel in remodeling projects such as kitchen and bathroom upgrades, flooring installation, and custom carpentry. Our skilled team uses top-quality materials and advanced techniques to ensure lasting results that exceed your expectations. At Supreme Painters & Remodelers Inc., we take pride in our attention to detail, professionalism, and commitment to delivering projects on time and within budget. From the initial consultation to the final walkthrough, we work closely with our clients to ensure their satisfaction every step of the way. Based in Boston, we serve residential and commercial clients throughout the region. Our mission is simple: to enhance the beauty, functionality, and value of your property while making the process stress-free and enjoyable. Discover the Supreme difference today—call us for a free estimate and let us turn your ideas into reality. Your project deserves the best, and that’s exactly what we deliver. Supreme Painters & Remodelers Inc.—where quality meets excellence.
"Lindo is fantastic to work with and his team is excellent. We have had Supreme work on two different projects in our house. The first was ceiling patch work and crown molding installation. This was done very efficiently. His team was always on time, great at communication. The second job was bigger and involved a complete renovation of our master bathroom. The work that was done was high quality and the team was great to work with. I highly recommend Supreme, and am already in discussions for our next project together."
Matthew F on February 2024

Pontes Painting, Inc.
Pontes Painting, Inc.
Pontes Painting, Inc., is a family owned business. Needless to say, we have the experience you deserve. We specialize in both, exterior and interior, painting projects. At Pontes Painting, Inc., we believe in quality, responsiveness and affordable pricing. We take pride in giving our customers beautiful spaces, for a lot cheaper than our competition. We look forward to serving you. Give us a call today for a free quote.
"The painting was excellent. The carpentry was exact and professional. Work crew was neat and hard working. They were always on time and worked throughout the day. Rafael was a great communicator throughout the project and made sure we were happy with all the work they performed."
David W on October 2025
Pontes Painting, Inc., is a family owned business. Needless to say, we have the experience you deserve. We specialize in both, exterior and interior, painting projects. At Pontes Painting, Inc., we believe in quality, responsiveness and affordable pricing. We take pride in giving our customers beautiful spaces, for a lot cheaper than our competition. We look forward to serving you. Give us a call today for a free quote.
"The painting was excellent. The carpentry was exact and professional. Work crew was neat and hard working. They were always on time and worked throughout the day. Rafael was a great communicator throughout the project and made sure we were happy with all the work they performed."
David W on October 2025

Urbano Painting, Inc.
Urbano Painting, Inc.
Urbano Painting offers over 28 years of industry experience and will provide you with an unmatched level of experience and commitment to your home improvement project. We have earned a solid reputation for a variety of residential home improvement and repair projects to include painting, cabinetry, decks and more. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building long-term relationships with our clients and guarantee your satisfaction! Give us a call today or visit our website below, and let's get started.
"Hired them to paint the interior of my home. Very attentive and courteous team. Excellent communication and updates about their progress. Iâ m happy with their work and would recommend Urbano Painting to others."
Christina A on May 2024
Urbano Painting offers over 28 years of industry experience and will provide you with an unmatched level of experience and commitment to your home improvement project. We have earned a solid reputation for a variety of residential home improvement and repair projects to include painting, cabinetry, decks and more. We pride ourselves on the quality of our work as well as our commitment to outstanding results. We look forward to building long-term relationships with our clients and guarantee your satisfaction! Give us a call today or visit our website below, and let's get started.
"Hired them to paint the interior of my home. Very attentive and courteous team. Excellent communication and updates about their progress. Iâ m happy with their work and would recommend Urbano Painting to others."
Christina A on May 2024

Affordable Painting
Affordable Painting
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
Blake Painting & Remodeling
Blake Painting & Remodeling
Home Improvement Contractor with over 25 years experience in making your house a home. Meticulous attention to detail, clean, neat and punctual.
"Blake is a highly, skilled professional in his field. His work is top quality. He is a professional who takes pride in his work. He walked me and my husband through the entire process, so we knew what to expect. He arrived on time and put his head down and WORKED the entire day. He cleaned up the work area at the end of every day. Our bathroom never looked so good. I will DEFINATELY use his company again for future projects."
Mary B on October 2025
Home Improvement Contractor with over 25 years experience in making your house a home. Meticulous attention to detail, clean, neat and punctual.
"Blake is a highly, skilled professional in his field. His work is top quality. He is a professional who takes pride in his work. He walked me and my husband through the entire process, so we knew what to expect. He arrived on time and put his head down and WORKED the entire day. He cleaned up the work area at the end of every day. Our bathroom never looked so good. I will DEFINATELY use his company again for future projects."
Mary B on October 2025
Kennedy Painting
Kennedy Painting
We are a locally owned and operated fully Licensed, Interior, and Exterior Painting company. We strive for excellence and provide the best for our clients. We also offer wallpaper install, wallpaper removal, stucco as well as cleaning services.
"My first time hiring an Angi Pro and I hit the jackpot. Brian Kennedy of Kennedy Painting exceeded my expectations over and over again. From the start of our correspondence in early August (project delayed due to personal issues on my end) to our conversation in October when Brian asked 'how about Monday at 7:00 AM?" I was introduced to the team that worked so efficiently, moving furniture (living room/dining room and two hallways) cleaned up at the end of each day. Wallpaper stripped, walls repaired, and painted. My project took five complete days with minimal interruptions in my daily life. Very, very professional, efficient organization. "
Robin S on October 2025
We are a locally owned and operated fully Licensed, Interior, and Exterior Painting company. We strive for excellence and provide the best for our clients. We also offer wallpaper install, wallpaper removal, stucco as well as cleaning services.
"My first time hiring an Angi Pro and I hit the jackpot. Brian Kennedy of Kennedy Painting exceeded my expectations over and over again. From the start of our correspondence in early August (project delayed due to personal issues on my end) to our conversation in October when Brian asked 'how about Monday at 7:00 AM?" I was introduced to the team that worked so efficiently, moving furniture (living room/dining room and two hallways) cleaned up at the end of each day. Wallpaper stripped, walls repaired, and painted. My project took five complete days with minimal interruptions in my daily life. Very, very professional, efficient organization. "
Robin S on October 2025

High Definition Painting Inc
High Definition Painting Inc
We are a commercial painting business that provides the best quality painting to keep your business looking fresh. As a business painting company, we can help you give your business the look you have always desired. We are experts in local commercial & house painting, providing both interior & exterior painting at competitive pricing.
"This is the second time that I’ve used High Definition painting - Fernando and his team did an incredible job painting the third floor of my home and outside shutters. The finished product looks incredible and the team is wonderful. Highly recommend."
Kristi C on October 2025
We are a commercial painting business that provides the best quality painting to keep your business looking fresh. As a business painting company, we can help you give your business the look you have always desired. We are experts in local commercial & house painting, providing both interior & exterior painting at competitive pricing.
"This is the second time that I’ve used High Definition painting - Fernando and his team did an incredible job painting the third floor of my home and outside shutters. The finished product looks incredible and the team is wonderful. Highly recommend."
Kristi C on October 2025

North Shore Painting
North Shore Painting
When you need the best painting the area has to offer, turn to us and our 25+ years of experience, as well as our high retention rate with many satisfied customers. Whether you want to build your dream home or you need home improvements, we've got you covered!
"My crew from NSP was amazing. Professional, courteous, kind and on point to get the task done. Large 2 story colonial with addition and ovs garage. I believe it took total of 5 days because of early weather in October 22. No paint chips on ground, very conscious of my shrubs and gardens, you would not even know they were painting. I HIGHLY RECOMMEND this outstanding company and would not hesitate to have them paint my home again. The price was very fair, the warranty good but most of all they always stayed in touch to let me know what was going to happen etc. My team, Frank, Benjamin and Valerio were amazing. Peter the owner and coordinator did a great job. Thank you again. My neighbors stopped to tell me how great my home looks and asked for the name of the painters for them in springtime. Thats says much about Northshore Painting. Great job, great professionalism, great job. VCM Billerica Ma"
Virginia M on December 2022
When you need the best painting the area has to offer, turn to us and our 25+ years of experience, as well as our high retention rate with many satisfied customers. Whether you want to build your dream home or you need home improvements, we've got you covered!
"My crew from NSP was amazing. Professional, courteous, kind and on point to get the task done. Large 2 story colonial with addition and ovs garage. I believe it took total of 5 days because of early weather in October 22. No paint chips on ground, very conscious of my shrubs and gardens, you would not even know they were painting. I HIGHLY RECOMMEND this outstanding company and would not hesitate to have them paint my home again. The price was very fair, the warranty good but most of all they always stayed in touch to let me know what was going to happen etc. My team, Frank, Benjamin and Valerio were amazing. Peter the owner and coordinator did a great job. Thank you again. My neighbors stopped to tell me how great my home looks and asked for the name of the painters for them in springtime. Thats says much about Northshore Painting. Great job, great professionalism, great job. VCM Billerica Ma"
Virginia M on December 2022
The Winchester, MA homeowners’ guide to painting services
From average costs to expert advice, get all the answers you need to get your job done.

The cost to paint vinyl siding depends on the type of paint, square footage, labor, and more. Check out this guide to help you budget for painting vinyl siding.

The average cost to paint shutters is $350, depending on the size, number of shutters, and labor. Read this guide to learn more about shutter costs.

Do you want the color of your exterior doors to really pop? Learn about the labor cost to paint the front door, back door, and other entranceways.

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.

Whether you opt for low-luster or high-gloss depends on budget, skill, aesthetics, and material. Learn how to pick the best sheen for exterior paint projects.

The best time to stain a deck is when it’s dry but not too sunny. How often you restain a deck depends on climate and wood type, but every two to three years is normal.
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- 🌱 "Mow a small front yard"
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