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Find Painters in Winchester

Kennedy Painting
5.0(
109
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1990

Free estimates

Emergency services offered

"Brian and his team were great. Not only did they do a great job painting, but Brian had us leave all furniture in place and his team moved it to paint and moved it back in place before we got home. Extremely helpful for those of us that don't have time to be rearranging furniture morning and night. They also assisted determining where some stains were coming from by removing drywall and replacing it, in an awkward area of the ceiling. They repaired and looked like new. Highly recommend Brian and his team."
Response time1 day
Response rate100%
Recommended by92%of homeowners
Avatar for High Definition Painting Inc
High Definition Painting Inc
4.9(
87
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2010

Free estimates

Credit card accepted

"High Definition Painted the entire interior of my home 12 plus rooms. My Wife and I are extremely happy with the results. We also had High Definition paint the exterior of my home several years ago and were very happy with the results. Would highly recommend this Company and will call them for future painting jobs."
Additional Photos
Additional Photos
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+32

Response time8 hrs
Response rate100%
Recommended by97%of homeowners
Avatar for Erivan Da Silva Painting
Erivan Da Silva Painting
4.8(
70
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+16 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 1997

Free estimates

Warranties offered

"Erivan has done a lot of painting over the years for our triple decker - exterior and interior. This summer he painted our rental unit and as usual did a wonderful job - he shows up on time, is very neat, and does a very professional job. He also just power washed and stained our first floor porch, painted some new window trims that we'd just had replaced, and also repainted some of the trim around the porch even though we hadn't asked him to do so. It looks great! Erivan takes great pride in his work and we always feel like he's taking care of our home as if it is his own. He is also a very warm and friendly person."
Painting - Exterior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project
Painting - Interior Project

+846

Response time1 day
Recommended by93%of homeowners
Avatar for ARCH PAINTING
ARCH PAINTING
4.4(
161
)
Interior Painting or Staining: 5 + RoomsExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+14 more

Serving Winchester, MA and surrounding areas

Approved

In business since 1997

Free estimates

Warranties offered

"Work was performed exactly as discussed and agreed to (match existing paint colors) at estimated cost. Start was delayed at our request due to high heat and humidity, with no complaints. Work was further delayed through no fault of Arch Painting due to continuous wet weather. Once a good weather window finally occurred, the work was performed quickly with no impact on us. We were totally satisfied with the quality of the work and the finished product."
BEFORE
AFTER
Before
After
Before

+17

Response time12 hrs
Response rate100%
2 neighbors recently requested a quote
Avatar for North Shore Painting
North Shore Painting
4.8(
59
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Winchester, MA and surrounding areas

Approved

In business since 1990

Free estimates

Warranties offered

"Peter and his team did an excellent job! The house needed a lot of carpentry repair (window frames repair, siding replacement etc.) All carpentry work was addressed. All the work was done with high quality. The house looks beautiful and I would recommend North Shore Painting."
Before
After
Exterior
Stairs
Dining Room

+5

Response time2 days
Recommended by96%of homeowners
Avatar for Pontes Painting, Inc.
Pontes Painting, Inc.
4.9(
100
)
Exterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: MediumExterior Home or Structure - Paint or Stain: Small+9 more

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2014

Free estimates

Emergency services offered

"Rafael and his crew of painters worked with me to complete an exterior transformation of my home in Boxborough. The work included power washing and staining the clapboard southern front and eastern side of the house, as well as painting the house cellular PVC trim and the new front door surround on the southern exposure of the house. The painting was done with care and efficiency, while at the same time ensuring that the work was completed at a high standard. All this was done at a fair price. They will return in the new year, once construction work on the west side of the house is completed, to stain the clapboards on the northern rear of the house and western side, as well as paint the cellular PVC trim. I highly recommend Pontes Painting, they provide a professional painting service at a fair price."
Left side
Peabody
Peabody
Peabody
Peabody

+10

Response time10 hrs
Response rate100%
47 neighbors recently requested a quote
Avatar for KLS Painting and Tiling
KLS Painting and Tiling
4.9(
62
)
Painting or Staining - Small ProjectsExterior Building - Paint or Stain - For BusinessInterior Painting or Staining: 1 - 2 Rooms+2 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2016

Free estimates

Small jobs welcome

"I am very happy with the quality of the paint job that Silas Silva of KLS Painting company performed. He proved to be an excellent choice among 5 other pros who sent the quotes. He was hired for painting exterior of my house and fences. I was especially impressed with how he and his crew meticulously scrapping, sanding &oil primer of all of the imperfection of the existing shingles, replacing and repairing any areas need to be done before the paint job and the result was like I got a brand new house. My house can be considered big enough and aged so the work was very time consuming and thanks to KLS painting professionals. I strongly recommend KLS painting to anyone who needs quality & afforable painting job."
Kitchen cabinets
Kitchen cabinets
Kitchen cabinets
Kitchen cabinets
Response time4 hrs
Response rate95%
1 neighbors recently requested a quote
Avatar for Target Painting & Contracting Inc
Target Painting & Contracting Inc
4.8(
182
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+3 more

Serving Winchester, MA and surrounding areas

Approved

In business since 2009

Free estimates

Warranties offered

"Perfect. This was not a typical job. Normally painters paint flat surfaces. This job was to paint (stain) 62 6-sided boards installed as a pergola. I tried to do it myself but only did 4 boards before I gave up and called Target Painting. (Another company refused the job.) Gene was great, as well as all the crew. At one point, one of the painters went up on the roof to monitor the progress and inspect the hard-to-reach places. Everything was great, including the cleanup."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+92

Recommended by93%of homeowners
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FAQs for painting projects in Winchester, MA

Most homeowners opt for semi-gloss or high-gloss paint to make the baseboards stand out against the walls. If you’d rather keep things subtle, matching the wall sheen with eggshell or satin also works well. When your trim has nicks or dents, reach for a flatter, matte finish—it hides minor imperfections better than a shiny coat.

Stripping old paint from trim costs $1 to $3 per linear foot. Pros use specialized tools and techniques to lift away existing layers without gouging the wood, then prep the surface for a fresh finish. While it adds to your budget, proper removal protects the molding and sets the stage for a smoother, longer-lasting paint job.

Tackling the baseboards first often leads to crisper lines. Painting trim first lets you tape off the boards instead of the walls, so you’re less likely to splatter color where you don’t want it. Any stray marks on the wall get covered when you roll on the final coat, making the whole process faster and tidier.

You can absolutely paint baseboards in place. Leaving them installed avoids the risk of cracking or misaligning the boards when they’re reattached. With thorough cleaning, light sanding, and careful taping, a pro—or an experienced DIYer—can achieve a sharp, factory-smooth finish while saving you the hassle of prying off and reinstalling trim.

Painting almost always beats replacement in cost. Swapping out baseboards runs about $150 in DIY materials or roughly $1,100 with a pro, while repainting costs about $50 in supplies and $1 to $5 per square foot for labor. Unless the boards are warped or severely damaged, a fresh coat delivers the same visual upgrade for a fraction of the price.

Paintable caulk and wood filler are the go-to fixes for nail holes in baseboards. Wood filler sands flush for a glass-smooth surface, while caulk provides a flexible seal that won’t crack as the house settles. Either way, patching those tiny divots before you prime ensures your finished baseboards look seamless.

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.