Best Painters Near Pine Plains, NY Ranked by Chooz Score

The painting contractors serving Pine Plains, NY work across a wide range of project types - from historic farmhouses and century-old exteriors to kitchen cabinet refinishing and full interior repaints. Customers in this area consistently highlight careful prep work, proactive communication, and finished results that hold up over time.

The last time we conducted our Chooz Score analysis, Ryan's Painting had over 110 Google reviews with a 4.9-star rating, along with 5.0 stars on Angi with over 30 reviews and 100% recommended on Facebook. The company holds a Chooz Score of 88.6% and is accredited with the Better Business Bureau. What stands out across customer accounts is how much ground Ryan's team covers beyond basic painting: multiple reviewers describe the crew handling drywall repairs, skim-coating, crown molding, tile, and light fixture installation as part of the same job. Homeowners managing projects from out of state consistently report no issues with communication or results, and several describe Ryan flagging problems they didn't know they had - including a roof exhaust issue spotted during a painting visit. Foreman Dave is mentioned across multiple reviews for his steady presence on larger jobs from start to finish. If you want a contractor who brings problem-solving and color expertise alongside skilled paint work, Ryan's Painting is a strong fit.

• The crew has completed work in demanding settings including a church from 1831 and a Second Empire home from 1869, where custom pigment matching was required on-site to get the colors exactly right.
• Reviewers describe Ryan offering color guidance throughout the project - suggesting adjustments, bringing samples, and adding small finishing touches that elevated the final result.
• Repeat customers appear across many reviews, with some returning for second and third projects across different areas of the same home.

"This has been the most positive experience I have had with a contractor in my whole life. I rate Ryan's Painting as the #1 option for any paint job, small or big. And the price was right too." - Ann Davison, Google Review

With over 19 years in business and over 30 years of hands-on painting experience, owner Matt Mason of Firefly Painting Inc has built a client base that keeps returning year after year. The company earned a Chooz Score of 83.9% and maintains a perfect 5.0-star rating across over 85 Google reviews, with 100% recommended on Facebook. The business runs as a family operation - Matt's wife Sarah handles scheduling and communications, while Matt and crew member John handle the work on-site. Customers with older homes, historical features, and complex jobs - cabinet refinishing, wallpaper removal, challenging prep surfaces - describe results that went beyond what they expected. Matt is noted for asking detailed questions before the job begins and providing transparent, itemized quotes that lay out exactly what will be done and what it will cost. If you're looking for an experienced team with deep local roots and a thoughtful, relationship-driven approach, Firefly Painting is a well-established choice.

• Multiple customers have returned for their fourth project or more with Matt and John, and at least one client relationship spans over 18 years of consecutive work.
• Reviews consistently note thorough daily cleanup, with a full vacuum at project completion and job sites left in good order every evening.
• The company's reputation extends beyond direct referrals - one reviewer described Firefly being mentioned by name at a local paint store by staff who knew the work firsthand.
• Surface prep is thorough and deliberate, with imperfections addressed before any painting begins - customers with damaged or challenging walls describe that step as a highlight of the experience.

"I will call them for any future painting needs - no need for me to consider other contractors or get multiple estimates." - Pat Boerman, Google Review

Rounding out the top contractors serving Pine Plains, NY, Certified Painting LLC holds a Chooz Score of 82.6% backed by over 100 Google reviews with a perfect 5.0-star rating and 100% recommended on Facebook. A distinguishing pattern in Certified Painting's reviews is the trust customers place in owner Brian Shannon when they can't be on-site themselves. Out-of-state homeowners describe Brian sending progress photos throughout the job without being asked, and several reviewers note leaving Brian to lock up independently - a level of confidence that reflects consistent, honest work over many projects. Crew members Caitlin and Gavin are mentioned by name alongside Brian for careful edges, thorough prep, and friendly service throughout. In over 4 years in business, Brian has taken on everything from NYC apartments to the exterior of a historic estate main house built in the 1700s. If you're planning a large or multi-phase project and want a team that communicates proactively and handles the details without needing to be reminded, Certified Painting is worth a call.

• Brian's written estimates are detailed and itemized by room or project element, with no billing surprises when the job is complete.
• Cabinet refinishing draws consistent praise - customers describe finished kitchens looking brand new, with Brian guiding color and hardware choices throughout the process.
• When unexpected rotten boards and damaged porch materials came up mid-job on a historic exterior, Brian's crew made the repairs and kept moving without additional delays or disputes.

"We live out of state and Brian sent photos periodically to keep us updated on the project. Who does that? Brian does. We highly recommend Certified Painting, LLC for any size job. You won't regret it!" - Terry Wolfson, Google Review

~Review Snippet Sources: Google

Quality of workmanship is the most frequently cited theme across reviews for painting contractors serving Pine Plains, NY. Customers of Ryan's Painting describe finished results that went well beyond what they pictured at the start - skim-coated ceilings repaired so thoroughly that original damage became invisible, colors hand-mixed on-site until they matched exactly, and small finishing touches added without being asked. The crew completed a full sanctuary repaint for a church dating to 1831, working carefully around the building's historical details and delivering a result the client described as stunning. Multiple reviewers describe finding the finished project better than what they had envisioned before the work began.

Firefly Painting Inc and Certified Painting LLC draw similar praise. For Firefly, customers with complex projects - very tall ceilings, historical architectural features, cabinet refinishing, and extensive wallpaper removal - describe results that consistently exceeded their expectations from a team they describe as genuinely skilled. Certified Painting customers describe Brian's crew spraying surfaces and then going back over every inch by hand to ensure full coverage, finishing edge work with a small artist's brush on exterior projects. A property manager overseeing the repaint of a 1700s estate main house described it as the best contracting decision made in over 16 years on the property.

"The quality of work is top-notch - unmatched in the area! Communication is fantastic, and the pricing is also very reasonable. We will continue to use Brian for all of our painting needs!" - Amanda Stapels, Google Review"The results were flawless. We are so happy and cannot stop smiling. The reviews online do not lie. Firefly is obviously well known around the Hudson Valley and we understand why." - JC, Google Review

~Review Snippet Sources: Google

Responsive communication and reliable scheduling are patterns that appear across reviews for all three painting contractors serving Pine Plains, NY. At Ryan's Painting, customers describe Ryan as accessible from the first inquiry through the final day on-site - answering questions promptly, offering suggestions mid-project, and following up when something needed to be corrected. One reviewer described Ryan spotting an imperfection in a job-site photo while on vacation and sending the crew back to address it. For homeowners managing projects from out of state, the crew's ability to work independently while maintaining clear communication is noted as a meaningful strength.

Firefly Painting Inc functions as a family operation: owner Matt Mason handles the fieldwork, while his wife Sarah manages scheduling and customer communications, keeping responses timely and the process running smoothly from first contact through completion. Matt's pre-job process is frequently praised - he asks detailed questions, prepares transparent written quotes, and sets clear expectations before any work begins. Certified Painting LLC's owner Brian Shannon personally handles all communications himself, from initial inquiry through the final walkthrough. Customers describe Brian arriving on time for estimates, confirming schedules ahead of the start date, and sending proactive progress updates - including photos - to clients who can't be on-site during the work.

"Brian was excellent communicating the scheduling and timing of the project as well as the daily times we could expect him and his team to arrive. There were no surprises." - Skip Weisman, Google Review"He came for the consultation super quickly and made special arrangements to get the job done in time for the furniture to be delivered!!" - Betsy Porter, Google Review

~Review Snippet Sources: Google

Thorough prep work and consistent daily cleanup are themes that come up across reviews for painting contractors serving Pine Plains, NY. Customers of Ryan's Painting describe the crew covering furniture, floors, and outdoor landscaping each day, cleaning up at the end of every workday, and leaving the space in good order throughout a multi-day project. Drywall repairs, spackle, and skim-coating are frequently handled as part of the scope before painting begins. On an exterior project at a historic home, the team covered a pond and surrounding plantings each day to protect them throughout the painting work.

At Firefly Painting Inc, customers with challenging prep conditions - damaged walls, wallpaper removal, uneven or historic surfaces - describe the crew addressing imperfections carefully before a brush touches the paint. End-of-day cleanup is mentioned consistently across reviews, with crew members doing a full vacuuming once the project is complete. Certified Painting LLC earns similar observations: Brian and his crew are described as moving and replacing furniture, protecting surrounding areas from drips, and leaving job sites cleaner than they found them. One reviewer noted that materials were organized neatly at the end of each day in preparation for the following morning's work, and another described not being able to tell the crew had ever been on-site except for the finished result on the walls.

"At the end of each day they cleaned up and while working, everything was covered and protected. They took down wall borders in my bathrooms and even painted my baseboard heat registers." - Joan Nissen, Google Review"I was also very impressed by how clean they were - no drips anywhere to be seen. Brian and his team also did a smaller interior project and did floors, ceilings, and so many windows. Excellent work on all of that too." - Zander McKernan, Google Review

~Review Snippet Sources: Google

Pricing and value come up consistently in reviews for painters serving Pine Plains, NY, and the pattern is similar across all three companies featured here. At Ryan's Painting, multiple reviewers describe comparing several estimates before choosing Ryan, with many noting that his pricing was competitive without being the lowest bid. What tipped the decision was the combination of clear communication, a fair quote, and a willingness to walk through the scope in detail. Projects consistently stay on budget, with no additional charges or billing surprises at the end of the job. One reviewer described getting four quotes for a deck and fence project and selecting Ryan based on pricing, communication style, and his willingness to come out and do stain samples in person before any work started.

Firefly Painting Inc earns a similar reputation for honest, transparent pricing. Reviewers describe Matt's quotes as detailed and itemized - clearly breaking down what is being done and why it costs what it does. For customers who want to understand exactly what they are paying for before signing on, that level of specificity carries real weight. Certified Painting LLC customers describe Brian's estimates as competitive and itemized by room or project area, with no gaps between what was quoted and what was invoiced. Multiple reviewers compared Certified against other bids and found Brian's combination of pricing, professionalism, and detail made the decision easy.

"I received four quotes for the project, and while Ryan was not the cheapest or most expensive option, he was the best option - easy to communicate with, very detailed in explaining what to expect, and he stands by his work." - Michael Wilkinson, Google Review"Also the re-finishing was a great deal. I bid the job with a few other vendors and Brian beat all other prices." - Nancy Jacobsen, Google Review

~Review Snippet Sources: Google