4.8 
52 *The Angi rating for Tree Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Tree Service needs.
*The HomeAdvisor rating for Tree Service companies in Chestertown, MD is a rating based on verified reviews from our community of homeowners who have used these pros to meet their Tree Service needs.
Last update on November 21, 2025
Serving Chestertown, MD and surrounding areas
Approved
In business since 1997
Free estimates
Emergency services offered
"The job went very well. Hometown Tree Experts did what they said they would do. Good cleanup after removal of tree. Reasonable pricing."
+2
Serving Chestertown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2019
Free estimates
Emergency services offered
"jmc employees expert in ability to perform tree service. very helpful and efficient."
+2
Serving Chestertown, MD and surrounding areas
Approved
In business since 2015
Free estimates
Offers commercial services
"Prompt response for estimate and prompt service when hired. Rate was very reasonable and he (the owner) conveyed an air of responsibility and honesty. Worksite was well cleaned when he finished. I watched the tree removal; he clearly knew what he was doing. Would recommend with full confidence."
Serving Chestertown, MD and surrounding areas
Approved
In business since 2016
Free estimates
Credit card accepted
"I was very impressed by Fernando Reyes and his entire team. They cleared 4 poplar trees and trimmed my 3 crepe mertyl. Their price was good, and their work was excellent. I was most impressed at the finished product and clean up. My yard looked great. I will be using them again for future tree work."
Serving Chestertown, MD and surrounding areas
Approved
In business since 2002
Free estimates
Customers say: Quick response
"On time, efficient, quick, personable and removed our tree stump seamlessly with a minimum of mess. Highly recommend!"
+7
Serving Chestertown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2025
Free estimates
Customers say: Quick response
"Excellent service, punctual and very professional. I give this company stars."
Serving Chestertown, MD and surrounding areas
Approved
In business since 2005
Free estimates
Credit card accepted
At _____Grass Roots Landscaping LLC_______, our company is based on the belief that our customers' needs are of the utmost importance. Our team is committed to meeting those needs. We welcome the opportunity to earn your trust and deliver you the best service. No job is too big or too small for our experienced team. Call today for a quote!
Serving Chestertown, MD and surrounding areas
Approved
In business since 2021
Free estimates
We are a locally owned and operated company. We value honesty and integrity in all aspects of our business. We offer a variety of home improvement services that are customized to each individual project. We pride ourselves on the quality of our work, as well as our commitment to outstanding results. We look forward to building lasting relationships with our clients and guarantee your satisfaction!
+12
Serving Chestertown, MD and surrounding areas
In business since 2017
Free estimates
Emergency services offered
"This company provides superior service. They removed 6 trees from my property at a very reasonable price. The workers were pleasant and respectful to me and my property. They also removed trees from my neighbors property after my neighbors saw what a good job they did at mine. It was truly amazing to watch them work as they removed my trees which were enormous."
Serving Chestertown, MD and surrounding areas
In business since 2002
Free estimates
Emergency services offered
"KB Tree and Landscaping Service did an outstanding job removing a tree in my yard, and I truly can’t recommend them enough. From start to finish, they were professional, patient, and extremely skilled. What really impressed me was how calmly and respectfully they handled a challenging situation with difficult neighbors. They communicated clearly, took extra precautions, and still completed the job efficiently and safely without any damage to surrounding property. The crew was punctual, knowledgeable, and left my yard clean when they were done. It’s rare to find a company that combines expert workmanship with great customer service, but KB Tree and Landscaping absolutely does. If you need tree work done and want a team you can trust, this is the company to call. I would hire them again without hesitation."
+17
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