5 Best Painters Near Chester, NY Ranked by Chooz Score

Homeowners in Chester, NY have access to several highly rated painting contractors, many of whom serve the broader Orange County and Hudson Valley region. Reviews across these companies consistently highlight crew professionalism, thorough prep work, and strong communication from start to finish.

The last time we conducted our Chooz Score analysis, Willow Tree Painting & Home Improvement LLC had nearly 100 Google reviews with a perfect 5.0-star rating. They earned a Chooz Score of 90.8%, the highest among contractors serving the Chester, NY area. They also hold 5.0 stars on Yelp and Google Guaranteed status. If you own an older home with challenging exterior surfaces, Willow Tree is a strong choice. Multiple customers describe trusting the crew enough to leave while work was in progress, and several highlight how the team guided them away from paint colors or finishes that would not hold up over time.

• Customers frequently mention that the crew completed full interior and exterior jobs in a single engagement, including power washing, board replacement, and deck staining alongside the painting itself
• Owner James is cited across reviews for providing phone estimates before in-person visits, giving homeowners a price range early in the process
• The team handles specialty projects like cedar fence staining, custom wood door restoration, and horse barn refinishing alongside standard residential painting

"Our house was in serious need of an exterior repaint. The team at Willow Tree did an amazing job at correcting the poor original caulking and gave our house an amazing new refresh. The guys really were up and above my expectations." - Kevin Burrows, Google Review

For homeowners focused on getting the best value across multiple bids, Ryan's Painting stands out. They earned a Chooz Score of 88.6% with over 110 Google reviews and a 4.9-star rating. Ryan's Painting is also 100% recommended on Facebook and holds 5.0 stars on Yelp. With 5 years in business and an A+ rating with the Better Business Bureau, this company has grown quickly through word of mouth. If you are comparing quotes from several contractors, Ryan's competitive pricing and transparent communication make them a solid pick.

• Several reviewers describe receiving four or five bids before choosing Ryan's, noting that while not always the cheapest option, the combination of communication and quality made the difference
• Crew foreman Dave is named repeatedly for staying on site from start to finish, and customers note that Ryan himself checks in daily on larger jobs
• Color consultation comes up often, with customers praising Ryan's help in selecting paint colors that complement their home's style

"I worked with Ryan and his team to stain my deck and fence. I received four quotes for the project, and while Ryan was not the cheapest or most expensive option, he was the best option." - Michael Wilkinson, Google Review

Repeat customers and referrals tell the story for CertaPro Painters of Orange County, NY. They earned a Chooz Score of 87.6% with over 175 Google reviews and a 4.8-star rating. With over 12 years in business operating from their Warwick office, CertaPro also holds 4.9 stars on Angi with over 20 reviews and over 15 Yelp reviews. If you have multiple projects planned over the coming years, CertaPro's track record of long-term customer relationships is worth noting.

• Multiple reviewers describe using CertaPro for four, five, or even more separate projects across different years, returning for everything from deck staining to cabinet painting to full exterior work
• Commercial clients, including businesses with multiple buildings, cite consistent quality and minimal disruption to their operations

"We moved to Warwick sixteen years ago. CertaPro Painters of Warwick are the only painters we've used multiple times over multiple years because there's no drama, just a great paint job." - Jerry Zimmerman, Google Review

A hands-on, owner-operated company, Pro Painting Plus earned a Chooz Score of 87.6% with over 50 Google reviews and a perfect 4.9-star rating. Owner Rob McRae is described by customers as personally present on job sites daily, checking in on progress and asking if homeowners are satisfied. If you want direct access to the business owner throughout your project, Pro Painting Plus delivers that experience.

• The company takes on unusual projects that other contractors pass on, including an 1865 tin roof restoration and historic home exteriors with specialty finishes
• Crew members Herbie, Juan, Dario, and Eric are named by customers for careful wall repair work before painting begins
• Several customers mention that Rob accepted small jobs other companies were not interested in, like a single mudroom or accent wall

"Rob quickly assessed and identified my needs and wants during the estimate and the next day Dario and Eric executed the job beautifully. It was a joy to return home and see the finished product." - Taryn Dibble, Google Review

Rounding out the top contractors serving Chester, NY, KB Quality Painting earned a Chooz Score of 83.2% with over 120 Google reviews and a perfect 5.0-star rating across every single review. Owner Kevin is praised for helping customers choose the right colors, often steering them toward options they had not considered. If you need guidance on color selection along with quality execution, KB Quality Painting is a good fit.

• Customers consistently describe Kevin as personally involved in every project, from the initial walkthrough to the final touch-ups
• The company maintains an active Instagram portfolio with over 190 project posts, giving potential customers a visual preview of completed work

"I hired Kevin to paint my living room and kitchen. He helped me to pick the right color, which I really appreciated. It turned out that I really needed his insight. He did an amazing job!" - Luciana Freitas, Google Review

~Review Snippet Sources: Google, Yelp, Facebook

Painting quality is the most frequently praised aspect across contractors serving Chester, NY. Customers describe results that exceed expectations, with particular emphasis on flawless edges, smooth finishes, and careful attention to trim and detail work. KB Quality Painting receives consistent praise for precision, with customers like Tom O'keefe noting Kevin's pride in each project. Willow Tree Painting & Home Improvement LLC is highlighted for handling complex projects on older homes, where careful surface preparation makes the difference in the final result. "The quality of their craftsmanship really shows, and our house now looks absolutely beautiful." - Daniel Gundersen, Google Review. Ryan's Painting customers frequently describe results on kitchen cabinets and interior trim that look factory-finished. "They were professional, accommodating, organized and worked extremely hard to make our house look brand new." - Daniel Golembiewski, Google Review.

Pro Painting Plus stands out for taking on challenging materials like cedar, teak, and pine siding, with owner Rob ensuring each wood type gets the right treatment. "Rob told me he would make my house beautiful, but I could never believe what they have done with my cedar house and different woods." - Mike Jergensen, Google Review. CertaPro Painters of Orange County, NY earns praise for consistent quality across both small touch-ups and large-scale projects, with repeat customers confirming the same standard of work year after year. "Any time we have used them they always did an excellent job." - Ray Wasnieski, Google Review.

~Review Snippet Sources: Google

Communication and professionalism rank among the top themes in reviews for painting contractors near Chester, NY. Customers consistently praise responsiveness during the estimate phase and clear updates throughout the project. Ryan's Painting is described as easy to reach from the first inquiry, with Ryan personally returning calls and texts quickly. "Ryan was great to work with, communicates well, best price and did a perfect job." - Glenn Kamp, Google Review. Willow Tree Painting & Home Improvement LLC runs a structured office operation, with Kelly and Lisa handling scheduling and logistics while project manager Peter provides daily on-site updates. "From the moment I met James it has been a wonderful experience! Peter, Ron and the crew have done impeccable. They couldn't be more accommodating." - Laura Newkirk, Google Review.

Certified Painting LLC owner Brian Shannon is frequently praised for sending progress photos to out-of-state homeowners and responding to messages quickly. "Brian was very thorough and did an excellent job on a huge project. His communication throughout was excellent." - Dawn Bennett, Google Review. CertaPro Painters of Orange County, NY customers note that Brendan McManus handles estimates and follows through on scheduling commitments without last-minute changes. KB Quality Painting earns similar praise, with customers highlighting Kevin's clear upfront pricing and realistic timelines. "Excellent communication when it came to setting expectations about how much the work would cost as well as when they'd be able to complete it by." - Darnell Dorce, Google Review.

~Review Snippet Sources: Google

Value and fair pricing come up frequently in reviews for painting contractors serving Chester, NY. Many customers describe comparing multiple bids before making a decision, and several contractors are praised for offering competitive rates without sacrificing quality. Ryan's Painting is frequently chosen after customers compare four or five quotes, with reviewers noting the pricing felt fair for the level of work delivered. "The estimate was very reasonable. They came on time as planned and did a beautiful job." - J Weatherstone, Google Review. Willow Tree Painting & Home Improvement LLC is described as the most reasonably priced option by customers who interviewed multiple companies, and several reviewers mention receiving a price range over the phone before committing to an in-person estimate.

KB Quality Painting consistently receives praise for excellent pricing relative to the finished quality. "Great pricing, very clean after the fact and Kevin is such a nice guy." - Rich Agnello, Google Review. Pro Painting Plus customers highlight that Rob provides detailed, honest invoices with no surprise charges. CertaPro Painters of Orange County, NY is described as offering very fair pricing given the longevity and professionalism of the operation. Across the board, reviewers serving the Chester, NY area indicate that quality painting does not require overpaying.

~Review Snippet Sources: Google

Punctuality and schedule reliability are consistently praised across contractors near Chester, NY. Ryan's Painting customers describe crews arriving on time every day of multi-day projects, with one reviewer noting three rooms completed in a single day. "Ryan's painting was fantastic. They showed up on time, were respectful and ready to work. They got three rooms done for me in 1 day." - Mike Lehmann, Google Review. Willow Tree Painting & Home Improvement LLC is praised for completing projects on time and on budget, with reviewers like John Taguer noting this level of reliability is rare in the industry today.

CertaPro Painters of Orange County, NY customers describe the team honoring scheduled start dates and finishing within the estimated timeline, even on large projects. "They honored the schedule set, and were considerate in tidying up around my home." - Mary Williamson, Google Review. Certified Painting LLC owner Brian is noted for fitting customers in quickly, even for smaller jobs, and sticking to promised timelines. Pro Painting Plus crews are described as arriving on time and staying until the work is done, with owner Rob checking in daily to keep projects moving.

~Review Snippet Sources: Google

Cleanup and neatness are among the most frequently mentioned positives in reviews for Chester, NY area painters. Customers consistently describe crews covering furniture, protecting floors, and leaving homes spotless after the job is complete. Certified Painting LLC customers praise Brian and his team for thorough prep work and clean execution on both interior and exterior jobs. "Brian showed up on time, prepped the walls, ceiling, and baseboards thoroughly, and painted beautifully. Not a drop of paint anywhere it shouldn't be." - Cecile Callan, Google Review. KB Quality Painting earns similar praise, with multiple reviewers describing Kevin's crew as covering everything and leaving spaces spotless after completing the work.

Willow Tree Painting & Home Improvement LLC is described as exceptionally clean by customers who had full interior jobs completed while living in the home. "We are extremely pleased with the painting job performed by Willow Tree from the initial consultation to the final walkthrough. The quality of their craftsmanship really shows." - Daniel Gundersen, Google Review. Ryan's Painting crews are noted for covering furniture carefully and cleaning up at the end of each work day, not just at project completion. Pro Painting Plus customers highlight that the crew took great care to keep surrounding areas clean during the work.

~Review Snippet Sources: Google

Repeat business and word-of-mouth referrals are a strong pattern across painting contractors serving Chester, NY. CertaPro Painters of Orange County, NY leads in this area, with multiple reviewers describing four, five, or more separate projects over the years. One customer describes a sixteen-year relationship with the company. "I've used CertaPro multiple times over the years for deck cleaning and staining, power washing the house, etc., and have always been very satisfied." - Guy Callari, Google Review. Certified Painting LLC also has a strong repeat customer base, with reviewers describing second and third projects with owner Brian.

Ryan's Painting customers frequently mention plans to hire again, with several reviews already describing return engagements. "On time professional friendly workers very neat excellent work would highly recommend and I will be using them again for other areas of my home." - Carole Incantalupo, Google Review. Willow Tree Painting & Home Improvement LLC reviewers describe recommending the company to neighbors and family after their own experience, and several note they have already booked follow-up projects. Pro Painting Plus also earns repeat business, with one customer noting this was their second time hiring Rob's team and praising the consistent quality each time.

~Review Snippet Sources: Google