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
"Brian and his team were just awesome. We had 4 projects going at once. He was knowledgeable about the best way to achieve the tree removal that was causing our problem. Just good old fashion great service."
Serving Chestertown, MD and surrounding areas
Approved
In business since 2016
Free estimates
Credit card accepted
"I contracted White Oak Tree Experts to remove some trees, grind stomps, and perform light pruning at my single family home. Right from the start, from the free estimate where Fernando Reyes walked my property line with me while listening to my concerns and goals while offering helpful suggestions, to the day he brought his crew and equipment, I knew I was in good hands. I highly recommend Fernando and White Oak Tree Experts since they are professional, hard working, very efficient, affordable, and committed to their customers needs. They exceeded my expectations!"
Serving Chestertown, MD and surrounding areas
Approved
In business since 2002
Free estimates
Customers say: Quick response
"They completed the job very fast. It was 3 tree stumps. He was great and very professional"
+7
Serving Chestertown, MD and surrounding areas
Approved
Super Service Award Winner
In business since 2025
Free estimates
Customers say: Quick response
"I received same day service!!"
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
Approved
Free estimates
Small jobs welcome
Why choose me: Reliable, careful with your items, and looking to support my family that's growing from just us two up to three next month by making a few extra $ on my spare time.
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."
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