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Find Painters in Cheshire

T C B Painting
5.0(
19
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain: LargeExterior Home or Structure - Paint or Stain: Medium+2 more

Serving Cheshire, CT and surrounding areas

Approved

Emergency services offered

Customers say: True professional

"Terry and his crew were very professional from the estimate to the last minute they spent in my home. They used quality paint, I know this because there was no horrible paint smell after the job was completed. Speaking of completed, they completed the job in one day. I am very impressed."
Response time1 day
Recommended by72%of homeowners
Avatar for Pro Painters
Pro Painters
4.7(
320
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+5 more

Serving Cheshire, CT and surrounding areas

Approved

Super Service Award Winner

In business since 2006

Free estimates

Warranties offered

"Jacob and crew were excellent. This is the second bigger project they've done for us. They were precise, prompt and polite throughout the process. Additionally, they are very neat. Everything looks perfect. Jacob will be staining our front porch, pillars, and door when the weather warms. We're planning to have Pro Painters handle another big project next year. If you have an upcoming painting project, I highly recommend using Pro Painters."
Painting - Interior Project
Additional Photos
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Additional Photos

+369

Response time1 day
Response rate100%
Recommended by93%of homeowners
Avatar for NHV Painters
NHV Painters
4.9(
96
)
Exterior Home or Structure - Paint or Stain: LargeInterior Painting or Staining: 5 + RoomsExterior Building - Paint or Stain - For Business+9 more

Serving Cheshire, CT and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Warranties offered

"Glenn and his team did an AMAZING job painting the interior of my house. They were able to answer any questions that I had about the project and finished the job on time. My house looks better than ever! I will definitely hire New Haven Painters again for any future painting projects."
Exterior Painting
Interior Painting
Cabinet Refinishing
Commercial Painting
Painters In Action!

+118

Response time2 hrs
2 neighbors recently requested a quote
Recommended by43%of homeowners
Avatar for Challenger Construction, LLC
Challenger Construction, LLC
4.8(
100
)
Exterior Home or Structure - Paint or Stain: Large

Serving Cheshire, CT and surrounding areas

Approved

In business since 2002

Free estimates

Emergency services offered

"I called for a quote when shopping around for my exterior paint/stain project. Leoâ s price was competitive but I ultimately went with another company since I had received their quote first. That was a mistake. I called Leo to see if he had availability to come look at fixing the job that the first company started. The first company had failed to sand any of the trim and the paint was immediately peeling after day 1. Leo came right out, looked at the job once more and his team started the next day. They took their time and did a great job with the prep work and fixing what the first company had done. This was not a three day project like the first company was aiming for. They really took their time and did it correctly. He also guided me in selecting which colors should be used in certain areas. My home looks brand new. I would recommend Challenger Construction for any and all painting needs."
1
1
1
1
Trumbull  job

+101

Response time11 hrs
19 neighbors recently requested a quote
Recommended by96%of homeowners
Avatar for Ambrocio's Painting
Ambrocio's Painting
4.7(
43
)
Exterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or StainExterior Home or Structure - Paint or Stain: Large+18 more

Serving Cheshire, CT and surrounding areas

Approved

In business since 2001

Free estimates

Customers say: Super punctual

"I hired Ambrocio's to paint our barn following a roofing and repair job. They completed in job in 4 days, pressure washing the entire structure, staining the siding and painting all the trim. They did a thorough job, were fairly neat on the job site, and the barn looked brand new after the job. A couple of problem areas were also brought to my attention so I could address them as needed in the future. I would happily hire them again."
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Recommended by97%of homeowners
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FAQs for painting projects in Cheshire, CT

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 Cheshire, CT homeowners’ guide to painting services

From average costs to expert advice, get all the answers you need to get your job done.