Top-rated tree service pros.

Get matched with top tree service pros in Chestertown, MD

Enter your zip and get matched with up to 5 pros

Need a pro for your tree service project in Chestertown, MD?

Select your specific project to find the pro for you.

TRUSTED BY CHESTERTOWN, MD HOMEOWNERS

  • Average homeowner rating star icon4.8
    Average homeowner rating
  • Verified reviews icon52
    Verified tree services reviews

Verified Reviews for Tree Service pros in Chestertown, MD

*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

Find Tree service pros in Chestertown

Avatar for Hometown Tree Experts
Hometown Tree Experts
4.6(
388
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 1997

Free estimates

Emergency services offered

"Hometown Tree Experts provided a first class service from start to finish. They removed several large trees on our properties for a great price and did an excellent job. All tree limbs, trunks, branches (etc) were dropped with precision (very talented crew). We would hire them again and we plan to provide referrals to our neighbors."
Additional Photos
Additional Photos
Additional Photos
Additional Photos
Additional Photos

+2

Response time7 hrs
Response rate100%
9 neighbors recently requested a quote
Request Quote
Avatar for JMC Tree Service, LLC
JMC Tree Service, LLC
4.8(
72
)

Serving Chestertown, MD and surrounding areas

Approved

Super Service Award Winner

In business since 2019

Free estimates

Emergency services offered

"The best. Kind, courteous, considerate and very careful with property. I will only use this tree service in the future. Excellent job.!"
Trimmings
Trimmings
Stump Grinding
Removals!
Removal

+2

Response time6 hrs
Response rate88%
42 neighbors recently requested a quote
Request Quote
Avatar for White Oak Tree Experts
White Oak Tree Experts
4.8(
14
)

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."
Tree removed
Response time5 hrs
Response rate91%
Recommended by76%of homeowners
Request Quote
Avatar for Alfaro Construction
Alfaro Construction
4.8(
690
)

Serving Chestertown, MD and surrounding areas

Approved

In business since 2002

Free estimates

Customers say: Quick response

"They returned my phone call immediately and scheduled an appointment for the same day they arrived probably completed the work in a timely and professional way at a reasonable cost I would definitely recommend them to anyone looking To have tree services provided"
OUR WORK
OUR WORK
OUR WORK
OUR WORK
OUR WORK

+7

Response time5 hrs
91 neighbors recently requested a quote
Recommended by97%of homeowners
Request Quote
Avatar for Reynaldo Perez Landscaping, LLC
Reynaldo Perez Landscaping, LLC
4.5(
8
)

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."
Response time6 hrs
Response rate85%
3 neighbors recently requested a quote
Request Quote
Avatar for Grass Roots Landscaping
Grass Roots Landscaping
New to Angi

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!

Gallery
14 neighbors recently requested a quote
Request Quote
Avatar for Pmb renovations
Pmb renovations
5.0(
1
)

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!

Asphalt repair
Asphalt repair
Asphalt repair
Asphalt repair
Asphalt repair

+12

1 neighbors recently requested a quote
Request Quote
Avatar for KB Tree & Landscaping Services
KB Tree & Landscaping Services
4.6(
37
)

Serving Chestertown, MD and surrounding areas

In business since 2002

Free estimates

Emergency services offered

"I’ve been using KB Landscaping and trees for 7 years now and they have always provided timely and quality work. They are willing and able to complete any task I have brought to them. Highly recommend"
Paver 2
Paver 3
Paver 4
Paver 5
Paver 7

+17

Recommended by85%of homeowners
Request Quote
...
Showing 1-10 of 76
Tree Service questions, answered by experts

Service costs depend on several factors, including the system's age, type, and size, as well as the complexity of the repair. Labor costs and whether replacement parts are necessary also play a significant role.

If you’re planning on keeping the tree, unless the roots are invasive, there’s no need to remove them, as doing so can cause damage to the tree. If the tree has been cut down and the stump and roots are left, grinding and removing the stump can cause root decay for some species. For other species, the stump and roots will need to be removed to prevent pests, disease, and possible tree regrowth.

In most cases, your neighbor is responsible for roots from their tree that cause damage to your property. If your pavement, the foundation of your home, or a fence is damaged by roots from a neighbor’s tree, you likely will have legal recourse for financial relief. While it’s better to notify your neighbor of any problems you notice as soon as they arise to avoid costly damage, there are some instances where filing a civil suit is your only recourse. Your homeowner’s insurance company might wish to do so on your behalf if you file a claim.

Palm tree stumps can take as long as seven to ten years to rot naturally. Whereas some tree stumps rot within a year, palm trees tend to last longer due to their deep root networks. Chemical rotting (described above) can help speed the process up so your palm tree stumps rot in under two months.

If tree branches cross well into your property line, in many cases, these branches become part of your property, and you can trim them up until your neighbor’s property line. However, this issue will vary based on local ordinances, so you should do your research before making any decisions. Better yet, speak with your neighbor about how to handle any tree issues. 

If you don’t mind the branches, you can leave them be, but if they’re becoming a hazard, it’s definitely worth having a conversation.

The Chestertown, MD homeowners’ guide to tree services

From average costs to expert advice, get all the answers you need to get your job done.

See all articles