Reviews for Rolling Oak Tree Service

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  • March 2024

    Kerwin Tree Service was fantastic. They removed a large portion of a Bradford Pear in our front yard but did it so that you wouldn't even know a large branch is missing. Also, they removed branches from our Mimosa tree that blocked our satellite dish, but didn't destroy our tree. But the real above and beyond was replacing some shingles that we had lost during a storm. (We weren't even aware until Tom went up in the cherry picker). They were professional, courteous, respectful and just all around great young men. We wouldn't hesitate to recommend them for tree service and intend on using them in the future.

  • September 2025

    Tom and his crew are amazing and professional! They waste no time setting up. The cutting and removal of trees are carefully done and clean up is thorough! We highly recommend to anyone! All our neighbors are hooked on Rolling Oaks too! Hands down the best tree service in Southern Maryland!

  • July 2025

    Tom and his company Rolling Oak LLC is a very professional and knowledgeable company. A portion of the top of a maple tree fell on a section of my roof. It was removed safely and the clean up was excellent. I would definitely refer this company for all your tree trimming and removal needs.

  • Rolling Oak Tree Service

    44199 Medleys Neck Rd, Leonardtown

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