Exterior Painting in Cheshire, Massachusetts
Looking for a High-Quality Exterior Painter in Cheshire?
Pittsfield Painting Company paints everything! We will paint your siding, shingles, decks, and railings. We can paint your garage, shed, fence, roof, driveway, and light posts. We even paint metal, such as sliding doors, windows, and metal railings. You name it, we can paint it. The skilled Cheshire, Massachusetts exterior painters at Pittsfield Painting Company have over 20 years of experience providing beautiful, long-lasting results for local homeowners. Give us a call today for a free estimate.
Memorial Day Special!
Get 10% OFF Any Exterior Painting Services
expires 05/31/2026
Call for a Free Quote
(413) 414-4636
❝Meticulous in Their Work❞
★★★★★ - "Shane & Keith were meticulous with their work. They were easy to communicate with and were always accommodating. I would highly recommend them!"
Steven Glicksman
_w298.jpg)
Call Cheshire's Exterior Painting Professionals
If you have ever tried painting the exterior of your Cheshire, MA home or business, you know that it's not an easy task. Exterior painting is both a skill and an art. That's why Pittsfield Painting Company's professional exterior painters in Cheshire have over 20 years of experience painting the exteriors of homes and offices, and are familiar with Cheshire's various exterior architectural styles and building materials used in exterior construction over the years. When you need affordable high quality exterior painting that Cheshire residents trust, make Pittsfield Painting Company your painting contractor!
Professional Exterior Painting Prep
The Cheshire exterior painters at Pittsfield Painting Company begin by preparing surfaces, removing old flaking paint, washing dirty areas, filling in cracks and dents, and sanding rough areas. Pittsfield Painting Company painters then apply one, two, or three layers of primer and paint as needed to create a long-lasting, high-quality exterior finish.
Satisfaction Guaranteed
Naturally, Pittsfield Painting Company guarantees that you will be satisfied with your exterior painting in Cheshire. The job will be done to your specification, and we will go the extra mile to ensure you are not only satisfied but actually happy with your newly painted exterior! Call (413) 414-4636 today.
WHAT CUSTOMERS ARE SAYING:
-
★★★★★ - "I was very pleased with Shane and Keith's attention to detail in every aspect of my exterior painting project. They had some cool mornings and October rain to work around, but when it was a good day to paint, they were on the job. Great customer service and nice work. I will definitely use them again."
Daniel DeMoss, Exterior Painting
2025-12-01 -
★★★★★ - "I hired Pittsfield Painting Company to paint my kitchen and living room, also the cabinets in the kitchen; I wasn’t sure what to do with them, as they were old. But Shane and his team came in and totally transformed my kitchen… now it has an updated, warm, inviting feeling that we absolutely love! Also, I had baseboard and Sheetrock that needed to be repaired, that was all taken care of as well with minimum disruption to our daily life and their team's communication was great. I would highly recommend Pittsfield Painting Company for any project big or small! And will definitely use them again! Thanks, guys!"
Danielle Delaney, Cabinet Painting
2026-01-01 -
★★★★★ - "I had my kitchen, hallways, and all the trim painted two times and sanded in many places. The work was done to perfection. I honestly could not ask for a better job. I feel these pictures will do all the talking. Highly recommend Pittsfield Painting for any type of painting you need. Super professional, in on time and completed on time."
Bob Turner, Interior Painting
2026-01-01 -
★★★★★ - "Shane and Keith are great guys, came in and hung two doors very well and quickly, will gladly contract with them again."
groger27, Light Carpentry
2026-01-01 -
★★★★★ - "I contacted Shane to paint our kitchen cabinets. He did an amazing job. He was quick, communicative, professional, and meticulous. Highly recommend!"
Erica Taupier, Cabinet Painting
2026-02-01 -
★★★★★ - "Excellent job painting the ceiling of our church!"
Cathy Chapman, Painting
2026-02-01 -
★★★★★ - "Good work done efficiently at a reasonable price."
Roxanne Montich Reed, Painting
2026-03-01 -
★★★★★ - "Pittsfield painting... a job well done. Everything was top-notch: neat, clean, fast, and professional! Friendly and accommodating. It was a big job, they had it done on time and a beautiful job! Perfect!"
Tina Barnes, Painting
2026-03-01 -
★★★★★ - "Shane and his crew were unbelievable with their dedication and expertise to the job. We couldn’t be happier."
Marie Beron, Painting
2026-03-18 -
★★★★★ - "Very professional and top quality work."
Christine Bialobok, Painting
2026-03-18 -
★★★★★ - "Pittsfield Painting company did an excellent and professional paint job on my family's home."
Keith Smith, House Painting
2026-03-26 -
★★★★★ - "Shane and his crew did a great job, were very professional, and didn’t leave until we were pleased with the job. Highly recommend!"
Gabriel Gracia Maldonado, Painting
2026-03-27 -
★★★★★ - "I had my workout room revamped and it’s one of my favorite rooms now! Pittsfield Painting Co. did a wonderful job, I recommend them highly!"
Bonnie Mitus in Lanesborough, MA
2025-12-08 -
★★★★★ - "Shane and his crew did a fantastic job. Very professional and courteous."
John Farley, Painting
2025-11-18 -
★★★★★ - "I hired Shane and his team to paint my backyard fence. They did an incredible job in a timely manner. Very reliable company, and has shown up on time for every job since! Would recommend!"
Dominik Hall, Painting
2025-11-18 -
★★★★★ - "We had our bathroom painted by Pittsfield Painting after having had wallpaper on the walls for over two decades. Pittsfield Painting carefully smoothed the rough surfaces caused by wallpaper and repainted with a smooth finish. This great work was done in one day. We will have Pittsfield Painting do other painting jobs on our “to-do” list. Highly recommend Pittsfield Painting."
Ann Manns, Interior Painting
2025-11-18 -
★★★★★ - "Beyond exceptional work. These guys refinished and stained my entire deck after another contractor damaged it on a different job. They communicate great, their attention to detail is exceptional, and the final product is well beyond my expectations. I couldn’t be happier. A 35-year-old deck has never looked this good. Literally could not be happier with how this project went."
Michael Winter, Deck Staining
2025-11-18 -
★★★★★ - "Shane & Keith were meticulous with their work. They were easy to communicate with and were always accommodating. I would highly recommend them!"
Steven Glicksman, Painting
2025-11-18 -
★★★★★ - "Shane and his team did a great job on our home. He was professional and kind throughout the quoting process and the job itself. Shane kept us notified along the way about progress and made sure we were completely satisfied with the end product. Highly recommend for any job, big or small!"
Seamus C., Painting in Pittsfield, MA
2025-11-12
