Owner Terry Goble doesn't just provide quotes, he works alongside his crew on every project. The Chooz Score's owner engagement indicators are strong: Terry is personally mentioned in the majority of reviews, and customers consistently describe his hands-on approach:
"Terry is not just a salesman providing a quote; Terry is the company owner who remained onsite working at all times. Outstanding quality of work!" - Mike Y., Google Review
If you're looking for a contractor you can call for years to come, this company has built serious loyalty. High marks on the Chooz Score's customer retention indicators: reviewers describe returning for multiple projects over many years:
"I've used Terry and his team a number of times now and it's always great results. From hanging shutters on my house to painting the front door and fixing wood trim, they always do a great job!" - Brie K., Google Review
The last time we conducted our Chooz Score analysis, Annapolis Coatings had over 90 Google reviews with a perfect 5.0-star rating. With 46 years in business, this company earned a Chooz Score of 87.0%:
"We could not have been any more pleased with the extensive painting done by Terry and his crew. They were friendly, meticulous, professional and non-disruptive every step of the way. Best painters we've ever had." - Mary Ellen C., Google Review
100% Recommended (8 Reviews)
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Get StartedFREE SERVICEWhat sets Santana Painting apart is the attention to surface preparation that most contractors skip. Owner Dominic treats prep work as foundational rather than an inconvenient delay, recognizing that behind every painting project is a homeowner who deserves work done properly the first time:
"The walls had lots of nail pops, cracked corners from settling and they needed a lot of attention prior to painting. The walls now look pristine with no imperfections." - Peggy B., Google Review
The last time we conducted our Chooz Score analysis, Santana Painting Company had over 125 Google reviews with a perfect 5.0-star rating. This company earned a Chooz Score of 86.2%. Reviews span multiple platforms with consistent praise:
"Absolutely thrilled with the work done by SantanaPaintingCo! From start to finish, the level of professionalism and attention to detail was truly impressive. Dominic is a true perfectionist, any small imperfection was meticulously addressed without hesitation." - Jonathan V., Google Review
Owner Dominic runs Santana Painting Company with hands-on involvement in every project, from initial estimates through final walk-throughs. The Chooz Score's owner engagement indicators are strong, with Dominic personally mentioned in the majority of reviews:
"Dom and his team are nothing short of amazing, prompt, professional, and a true pleasure to work with from start to finish. They completely transformed my home, giving it a fresh, like-new feel that exceeded my expectations." - Rosie J., Google Review
What sets this company apart is their consistent crew. The Chooz Score's in-house crews component shows the same crew names appearing across multiple reviews, suggesting trained, dedicated employees rather than rotating subcontractors:
"I cannot say enough positive things about my experience with Chesapeake Painting. From getting an estimate all the way through completing the job, the communication was outstanding as was the quality of work." - Kathy K., Google Review
The last time we conducted our Chooz Score analysis, Chesapeake Painting Services had over 380 Google reviews with a 4.9-star rating. This company earned a Chooz Score of 85.8%. Reviews span multiple platforms with consistently strong ratings:
"Great experience from the beginning of the process with reaching out for an estimate, getting a timely response, cost, and then scheduling the team to paint the main floor of our home." - Elyse E., Google Review
Customers consistently mention attention to detail and thorough preparation. The company handles everything from cabinet refinishing to exterior work on historic homes:
"The team was timely, professional, flexible and did an outstanding job on our 100 year old cedar shake home. Project manager stopped by frequently to check in." - Barry D., Google Review
Most reviews praise this company's work, but a couple of detailed reviews mentioned concerns about final walkthrough procedures and follow-up on quality issues. Before signing, it's worth clarifying expectations. Ask them directly: "Can we schedule a final walkthrough together before the crew leaves, and what's the process if I find issues after they're gone?"
"We specifically asked for a walkthrough before the crew left, but were told to just call if we had issues. When we called them back, they only addressed the specific items we pointed out instead of inspecting their own work." - Elizabeth C., Google Review
96% Recommended (22 Reviews)
Owner-operated means something here. Don Howard personally handles estimates, oversees projects, and works closely with customers from start to finish. The Chooz Score's owner engagement indicators are strong: Don is mentioned by name throughout reviews as personally invested in every project:
"Don came out himself for the estimate. Great job painting and matching old colors. Owner works closely with you to get your job accomplished." - Doug G., Google Review
Over 65 Google reviews with a perfect 5.0-star rating don't happen by accident. The last time we conducted our Chooz Score analysis, Don Howard Painting earned a Chooz Score of 85.6%. With over 26 years in business serving Maryland's Eastern Shore, this company has built deep roots:
"From start to finish Don Howard and his crew exceeded our expectations. Our entire 3 story house was soft washed, all trim and siding was re-caulked, with minimal disruption to our family." - Rhonda A., Google Review
If you're looking for a painter you can call for years to come, this company has built serious loyalty. Multiple reviewers describe returning again and again for new projects:
"I've used Howard Painting three times now and they have always done a fantastic job. Workmanship is very professional and their knowledge of the best products to use is great." - Ed G., Google Review
100% Recommended (9 Reviews)
Reviews consistently mention the same crew names across multiple projects, a strong indicator of in-house employees rather than rotating subcontractors. The Chooz Score's in-house crews component shows consistency: Juan Carlos leads projects personally, while specialists like Karla handle ceiling work and Carlos manages cabinet refinishing:
"Juan Carlos and his crew do great work! They work hard and their prices are very competitive. This is the second time they've done work for us, highly recommend!" - MDVA Properties, Google Review
If you're looking for a painter you can call for years to come, this company has built serious loyalty. High marks on the Chooz Score's customer retention indicators: reviewers consistently mention returning for second and third projects:
"First of all had my house painted four times before and none of the other companies was even close in terms of attention to detail as Seven Oaks. Great communication. Great work done, have used them again and recommended them to all my friends." - Mike H., Google Review
The last time we conducted our Chooz Score analysis, Seven Oaks Painting Services had over 85 Google reviews with a 5.0-star rating, plus 5.0 stars on Yelp with 5 reviews. This company earned a Chooz Score of 83.4%. Perfect ratings with zero negative reviews across all platforms is exceptional:
"Seven Oaks Painting was very professional and efficient. They were on time every morning and cleaned up every evening perfectly like they were never there. I will be hiring them again to do the rest of the painting in my home." - Rachel H., Google Review
Every painter listed on this page has been evaluated using the Chooz multi-step quality process. We combine data analysis with human review to identify companies that consistently deliver strong results for property owners in Annapolis, MD.
The Chooz Score is a 100-point rating built on platform reviews, review quality and engagement, website and digital presence, and business authority and operations. We use the same scoring framework nationwide while evaluating each contractor's performance specifically within Annapolis, MD.