Top-rated painters.

Get matched with top painters in Winchester Center, 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 Winchester Center

Avatar for J & S Painting Plus Inc
J & S Painting Plus Inc
4.7(
332
)

Serving Winchester Center, CT and surrounding areas

Approved

In business since 1977

Free estimates

Warranties offered

"This was the second time I worked with Shecki and Jose. The first was painting the house exterior and it's still holding up well 5 years later. The second time was a re-staining of the deck. Work was done beautifully. Paint was neat, no streaks, carpentry was done well and we're very pleased with the end result. Pricing was a little high this time around. Hope that stabilizes in the future, would definitely look to work again with Shecki and Jose."
Additional Photos
Additional Photos
Before & After
Additional Photos
Additional Photos

+3

1 neighbors recently requested a quote
Recommended by95%of homeowners
Avatar for Ambrocio's Painting
Ambrocio's Painting
4.7(
42
)

Serving Winchester Center, 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."
Additional Photos
Additional Photos
Additional Photos
Recommended by100%of homeowners
Avatar for Challenger Construction, LLC
Challenger Construction, LLC
4.8(
99
)

Serving Winchester Center, 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 time1 day
21 neighbors recently requested a quote
Recommended by97%of homeowners
Avatar for Fresh Coat of Hartford County
Fresh Coat of Hartford County
4.3(
46
)

Serving Winchester Center, CT and surrounding areas

Approved

In business since 2006

Free estimates

Warranties offered

"The painter arrived on time, and had all his own supplies, including protective covering for floors and furniture.  He took the time to review the job details with me, and when he realized the job would not take the full amount of time paid for, he suggested repainting my entry door also (no additional charge).  I was very pleased as it needed painting, but I hadn't budgeted for doing it.  He was very neat and professional, and the quality of work was excellent.  It has now been 4 months since the service, and the kitchen still looks like it was just painted.  My entry door now looks great too!
"
Ceiling
Kitchen
Mural
Siding
Deck

+18

Recommended by86%of homeowners
Avatar for Carlos Suscal Painting
Carlos Suscal Painting
4.6(
34
)

Serving Winchester Center, CT and surrounding areas

Approved

In business since 2001

Free estimates

Warranties offered

"Great experience with Carlos and his crew painting my 1872 Victorian in Ridgefield. They spent several days prepping and sanding the exterior down to the wood. They re-glazed windows, removed and painted the wooden-framed window screens, and removed and painted the shutters as well. There was one section of wood rot that they replaced - all while staying within budget. No surprises. We went over all the details and expectations beforehand and I could not be happier with how my house is looking now. HIGHLY RECOMMEND if you have a daunting paint job. My house required several extremely tall ladders and these guys were up and down like it was nothing. Great crew, great work - top notch."
19 Black man Rd
Response time9 hrs
8 neighbors recently requested a quote
Recommended by96%of homeowners
...
Showing 1-10 of 1701

FAQs for painting projects in Winchester Center, 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 Winchester Center, CT homeowners’ guide to painting services

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