Top-rated painters.

Get matched with top painters in Chester, NY

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 Chester

Avatar for Antnee's Painting
Antnee's Painting
4.7(
108
)

Serving Chester, NY and surrounding areas

Approved

Super Service Award Winner

Free estimates

Warranties offered

Credit card accepted

"⭐️⭐️⭐️⭐️⭐️ Outstanding craftsmanship and professionalism! Anthony’s experience shows in every part of the project. He sent me to several suppliers to pick out paint colors, and everywhere I went people spoke very highly of him. His crew was just as professional — skilled, detail-oriented, and very clean. The results are excellent, and I intend to hire him for more interior trim, sanding, staining, and construction projects. Highly recommend!"
Painting - Interior Project
Exterior
Greenwood lake exterior
Before and after
Cabinet painting

+91

Response time1 day
Recommended by85%of homeowners
Avatar for Javier Ruiz Hardwood Flooring and Painting
Javier Ruiz Hardwood Flooring and Painting
4.9(
96
)

Serving Chester, NY and surrounding areas

Approved

In business since 2001

Free estimates

Emergency services offered

"My wife and I recently purchased a house. Javier and his crew undertook the interior painting and hardwood floor refinishing before we moved in. His approach to the project and the manner in which the work was undertaken was both professional, efficient and of good quality. I would highly recommend Javier and his crew for both interior painting and refinishing of hardwood floors."
Hardwood Flooring Sales/Installation/Refinishing Project
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+59

Response time6 hrs
Recommended by96%of homeowners
Avatar for WARD HOME & COLOR CONCEPTS, LLC
WARD HOME & COLOR CONCEPTS, LLC
5.0(
7
)

Serving Chester, NY and surrounding areas

Approved

In business since 2021

Free estimates

Customers say: True professional

We specialize in interior and exterior painting services, drywall services, cabinet painting, staining, and more! We guarantee your satisfaction, and we won?t leave until the job is done right. We pride ourselves on the quality work we provide, while delivering great customer service! Check out all the services we offer below and call -or- click to schedule a free estimate today! \n

My jobs
My jobs
My jobs
My jobs
My jobs

+38

Recommended by71%of homeowners
Avatar for Pro Painting Plus
Pro Painting Plus
4.7(
16
)

Serving Chester, NY and surrounding areas

Approved

In business since 2007

Free estimates

Offers commercial services

"Bobby and his crew were a pleasure to work with. Put the final touches on the home. Exceptional painting for exterior and interior. Was finished in the time frame he gave us."
During
Finished
common room
Entryway
Upstairs

+4

Response time7 hrs
Recommended by92%of homeowners
Avatar for Nice Guys Painting NY LLC
Nice Guys Painting NY LLC
4.6(
10
)

Serving Chester, NY and surrounding areas

Approved

In business since 2009

Free estimates

Credit card accepted

"Isaac is a master class painting professional. He is quick, thorough, and honest. The painting work was very skillful with great attention to detail. The clean up work at the end of each painting session was very thorough. We love the results and we are very happy with the reasonable price we were charged."
Entrance and Living room
Clean
Response time1 day
8 neighbors recently requested a quote
Recommended by62%of homeowners
Avatar for New York's Clean Team by Angela & Denis Home Improvement
New York's Clean Team by Angela & Denis Home Improvement
4.8(
80
)

Serving Chester, NY and surrounding areas

Approved

Super Service Award Winner

In business since 2013

Free estimates

Emergency services offered

"Angela and Denis did a fantastic job. They were professional, kind and thorough with the cleaning. My home has never looked better! I appreciated their attention to detail and most of all their kindness. Great people, great job! Look forward to working with them again."
Upholstery Cleaning Project
Pressure Washing Project
Organization - Home & Garage Project
Upholstery Cleaning Project
Pressure Washing Project

+237

Response time1 day
Recommended by67%of homeowners
Avatar for L Pro Paint
L Pro Paint
4.9(
6
)

Serving Chester, NY and surrounding areas

Approved

In business since 2022

Free estimates

Credit card accepted

"Got an estimate and the job was done a few days later. Satisfied with the job and complete cleanup afterwards. Luis provided good, pleasant customer service."
Response time5 hrs
Response rate95%
10 neighbors recently requested a quote
Avatar for Brothers Construction
Brothers Construction
4.7(
181
)

Serving Chester, NY and surrounding areas

Approved

In business since 2015

Free estimates

Small jobs welcome

"Urgent painting service, our house needed old doors and drywall repainted. I recently hired SwiftHand Painting Team for a painting job and I'm glad I did. Their attention to detail was impeccable and they made sure my house's doors and drywall were painted very well. They completed the job on time and I am very happy with the results. I would highly recommend them for any painting service; You will not be disappointed!"
Response time2 days
Response rate87%
Recommended by97%of homeowners
...
Showing 1-10 of 679

FAQs for painting projects in Chester, NY

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 Chester, NY homeowners’ guide to painting services

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