Top-rated painters.

Get matched with top painters in Cheshire, CT

Enter your zip and get matched with up to 3 pros

Matching on HomeAdvisor

Share some details icon
Share some details about your home project.
Match with local pros icon
Within moments, match with highly-rated local pros.
Compare quotes icon
Compare quotes and choose the best pro for the job.

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

"Excellent painting with attention to detail! Very professional, polite, careful and they were very good with clean up! We had our main level done and it’s beautiful!"
Response time1 day
Recommended by72%of homeowners
Request Quote
Avatar for Pro Painters
Pro Painters
4.7(
321
)
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
Additional Photos
Additional Photos
Additional Photos

+369

Response time1 day
Response rate100%
Recommended by93%of homeowners
Request Quote
Avatar for STAR PAINTERS LLC
STAR PAINTERS LLC
4.9(
117
)
Interior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + Rooms

Serving Cheshire, CT and surrounding areas

Approved

In business since 2005

Free estimates

Emergency services offered

"From start to finish it was a great experience to work with Star Painters. Demir did a walk through on Sunday and by Tuesday we had signed the quote and agreed on a starting date the Monday after. First day was prep day and the following 3 days they painted 5 rooms (all different colors) and trim. They put down plastic throughout to prevent paint spatter. Like I mentioned a great experience. I will hire them again."
Painting - Interior Project
Samples of our decorative painting
Painting and decorating
Painting - Interior Project
Painting - Interior Project

+95

Response time7 hrs
1 neighbors recently requested a quote
Recommended by93%of homeowners
Request Quote
Avatar for Affordable Painting Services
Affordable Painting Services
4.7(
46
)
Interior Painting or Staining: 3 - 4 RoomsInterior Painting or Staining: 5 + RoomsExterior Home or Structure - Paint or Stain

Serving Cheshire, CT and surrounding areas

Approved

In business since 2005

Free estimates

Warranties offered

"James is a true craftsman; his workmanship and professionalism are outstanding. The room he painted for us turned out beautifully, and he also did excellent work on patching and priming two other ceilings for us. James was prompt, courteous, supportive, and very fair with his pricing. He gave us the best estimate that we had received and then - to my astonishment - reduced the agreed-upon price when some of the work took less time than he expected. I would strongly recommend James and Affordable Painting to anyone."
Exterior
Target Optical Store
After Repair
Taarget optical Store
Before Repair

+5

Response time7 hrs
18 neighbors recently requested a quote
Recommended by100%of homeowners
Request Quote
Avatar for A M Painting
A M Painting
4.9(
15
)
Exterior Home or Structure - Paint or Stain: SmallInterior Painting or Staining: 1 - 2 RoomsInterior Painting or Staining: 3 - 4 Rooms+2 more

Serving Cheshire, CT and surrounding areas

Approved

In business since 2005

Free estimates

Credit card accepted

"It was such a pleasure to work with Anthony. He was on time, communicated effectively and knows his craft. I highly recommend his business for painting or staining services."
Cabinets in Southington
Cabinets in Southington
Cabinets in Southington
Cabinets in Southington
Wallpaper removal

+5

Response time4 hrs
Response rate94%
18 neighbors recently requested a quote
Request Quote
Avatar for NHV Painters
NHV Painters
4.9(
96
)
Interior Painting or Staining: 5 + RoomsExterior Building - Paint or Stain - For BusinessExterior Home or Structure - Paint or Stain+9 more

Serving Cheshire, CT and surrounding areas

Approved

Super Service Award Winner

In business since 2015

Free estimates

Warranties offered

"Great job,for a good price, wonderful painting with attention to detail"
Exterior Painting
Interior Painting
Cabinet Refinishing
Commercial Painting
Painters In Action!

+118

Response time2 hrs
1 neighbors recently requested a quote
Recommended by43%of homeowners
Request Quote
Avatar for Supreme Painting and Maintenance
Supreme Painting and Maintenance
4.8(
53
)
Exterior Home or Structure - Paint or Stain: SmallExterior Home or Structure - Paint or Stain: Medium

Serving Cheshire, CT and surrounding areas

Approved

Super Service Award Winner

In business since 2009

Free estimates

Warranties offered

"Floyd and his team were absolutely great. We hired him for an interior paint job. He was timely, professional, and did an amazing job. We will be using Supreme Painting and Maintenance again in the Spring to perform power-washing services on my house. With this experience, Supreme Painting and Maintenance will be my go-to company for my home needs moving forward!"
Response time6 hrs
Response rate99%
53 neighbors recently requested a quote
Request Quote
Avatar for All Care Painting LLC
All Care Painting LLC
5.0(
21
)
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

In business since 2019

Free estimates

Emergency services offered

"Excellent painters, excellent communication, I loved the work they did in my house and I recommended them to paint my sister house."
Exterior
Exterior
Exterior
Exterior
Exterior

+94

Response time1 day
Recommended by66%of homeowners
Request Quote
Avatar for General Painting and Decorating, LLC
General Painting and Decorating, LLC
4.6(
68
)
Exterior Home or Structure - Paint or Stain: LargeExterior Building - Paint or Stain - For Business

Serving Cheshire, CT and surrounding areas

Approved (Corporate)

In business since 2003

Free estimates

Warranties offered

"They did a great job painting the exterior of our house. Very prompt, professional and efficient. Recommend very highly."
Exterior Painting
Deck Stain
Exterior House
Yard Sign
Exterior

+122

Response time11 hrs
Response rate95%
66 neighbors recently requested a quote
Request Quote
...
Showing 1-10 of 917

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.

See all articles