Stewart Painting
Chooz Score Insights
The Same Crew Every Time
The Chooz Score's in-house crews component shows consistency: the same crew names appear across multiple reviews spanning months. Tim and Rabi handle house washing, Wayne leads painting crews, Jeremy and Matt handle carpentry, and Earl manages larger exterior projects. Customers don't get random subcontractors - they get familiar faces:
- Tim and Rabi mentioned in over a dozen reviews for house washing work
- Wayne's crew praised repeatedly for exterior painting projects
- Matt and Gabe specifically named for carpentry precision
"The entire Stewart Painting team has been incredibly professional across the board - communication, scheduling, organization, prep work, punctuality, craftsmanship, attention to detail, and cleanup." - Maggie C., Google Review
Built on Loyalty
If you're looking for a contractor you can call for years to come, this company has built serious loyalty. Stewart Painting uses their own W2 employees rather than contract painters - a distinction several reviewers specifically call out. The Chooz Score's customer retention indicators show repeat customers planning future projects before current ones end:
- Multiple customers describe using Stewart for over five years across different projects
- Reviewers note crews "take pride in their craft" and return for touch-ups without hesitation
- Paint it Forward community program demonstrates local investment
"We had such a great experience with Stewart Painting at our summer cottage that we decided to hire them for work on our main property too." - Maggie C., Google Review
A Name People Trust
The last time we conducted our Chooz Score analysis, Stewart Painting had over 350 Google reviews across their Cape Cod and South Shore locations with a 4.8-star rating. This company earned a Chooz Score of 87.7%. With over 40 years in business since 1980, they've built an operation that spans generations:
- A+ rating with the Better Business Bureau
- MA HIC License No. 175254 verified active
- $2M liability insurance, OSHA certified, EPA compliant, Sherwin-Williams partnership
"Earl's crew was courteous and meticulous in painting the original wood, trim and shutters. It has been 29 years since it received a fresh coat, and it looks like a new house again!" - Richard T., Google Review
Questions to Ask Stewart Painting
Timeline and communication expectations
Stewart Painting operates with multiple specialized crews - wash, carpentry, and paint - which can create coordination challenges on complex projects. Several reviewers mentioned delays and communication gaps, particularly during busy season. Ask directly: "What's the realistic timeline for my project, and who will be my main point of contact if questions come up during the work?"
"I signed on with them in early May. The work was supposed to be completed in July. It took until October 17 for them to finish. I often went weeks without hearing from them." - Jack M., Google Review (no owner reply)
Find out more about how we Stewart Painting
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Additional Questions Answered
Does Stewart Painting use their own employees or subcontractors for painting projects?
Stewart Painting employs full-time, professionally trained painters and carpenters rather than subcontractors. Reviews consistently mention the same crew leaders by name across multiple projects. One customer noted the team was "so professional, keeping me informed and making sure that everything was exactly as I wanted it." Crew leaders like Earl, Rocky, Wayne, and Gilson appear repeatedly in customer feedback, demonstrating consistent staffing.
How does Stewart Painting's house washing team perform according to customers?
Tim and Rabi receive frequent praise for their house washing work. Customers describe results where "shingles look brand new" and note the team takes "good care of all my plants in the process." One reviewer mentioned the gutters and downspouts looked great with no damage to landscaping. The duo appears in numerous reviews as a dedicated washing team known for thorough, careful work.
What do customers say about Stewart Painting's cleanup after completing projects?
Cleanup receives consistent praise across reviews. Customers describe the process as "immaculate" and note there were "virtually no signs of them having been there when they left." Multiple reviewers mention crews maintaining neat work environments throughout projects. One customer specifically praised the crew for protecting belongings and grounds during exterior work.
Does Stewart Painting honor their two-year warranty when issues arise?
Reviews indicate the company stands behind their warranty commitment. One customer reported that when "house stain did peel within that time limit," Stewart Painting "came back and repainted the house without question." Another reviewer noted that when touch-ups were needed, issues "were addressed and it looks excellent." The warranty covers workmanship on all completed projects.
How does Stewart Painting handle carpentry and custom woodwork projects?
The carpentry division tackles projects ranging from simple repairs to custom builds. When one customer needed custom shed doors after a break-in, carpenters Matt and Robby "arrived yesterday to hand make the new doors" despite "cold and wind" and "did a fantastic job." Reviews mention window replacements, crown molding installation, rotted wood repair, and trim work handled by the dedicated carpentry team.
What do reviews reveal about communication and scheduling with Stewart Painting?
Customer experiences with communication vary. Many praise the office staff, with one noting Carissa and Liam were "very helpful and responsive with good follow up to our questions on scheduling." Estimators like Zach receive recognition for being "very prompt, thorough and informative." However, some reviews mention scheduling challenges and suggest confirming timelines directly with project coordinators.
How do customers describe Stewart Painting crew leader Earl and his team?
Earl appears frequently in positive reviews as a respected crew leader. One customer stated "Earl and his team are true professionals" and noted "the quality of their work is excellent." Reviews describe thorough final walk-throughs and attention to detail. Customers report Earl's crews arrive on time, maintain clean work areas, and address concerns promptly during projects.
What is Stewart Painting's Paint It Forward program for veterans?
Stewart Painting runs an annual Paint It Forward program providing free painting, house washing, and carpentry services to deserving veterans. One memorable project involved a veteran's wife winning the contest, with "40 volunteers" contributing to transform their home. Owner Sheldon Stewart participates in the Handyman Hotline podcast and serves on the Pops by the Sea steering committee, reflecting the company's community involvement.
How Stewart Painting Was Evaluated
Every painting company listed on Chooz Painters is evaluated using our multi-step quality framework. We combine structured data analysis with human review to understand how Stewart Painting performs across the key signals that matter most to property owners.
How the Chooz Score Works
The Chooz Score is a 100-point rating based on four core pillars:
- Platform reviews & ratings from sources such as Google, Facebook, Yelp, Angi, BBB, and others
- Review quality & engagement, including depth of customer feedback, photos, and how the company responds to reviews
- Website and digital presence, which helps indicate professionalism, transparency, and communication quality
- Business authority & operations, including years in business, licensing, insurance, and other operational standards
Each contractor is evaluated using the same framework nationwide, and the score reflects Stewart Painting’s performance within its local market.
A Chooz Score represents real-world performance, verified signals, and human-reviewed context.
Chooz Score Award Levels
Scores are determined through more than 40 evaluation factors across our four pillars.
If you want a deeper explanation of how our scoring system works, you can view the full breakdown on our Chooz Scoring page.