Top-rated tree service pros.

Best tree service pros near Chestertown, NY

Enter your zip and get matched with up to 5 pros

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

Select your specific project to find the pro for you.

TRUSTED BY CHESTERTOWN, NY HOMEOWNERS

  • Average homeowner rating star icon4.6
    Average homeowner rating
  • Verified reviews icon46
    Verified tree services reviews

Top-Rated Tree service pros in Chestertown - Updated Nov 2026

Avatar for Capital Flips Property Management
Capital Flips Property Management
5.0(
3
)
Tree RemovalTree Stump - RemoveTree Trimming

Serving Chestertown, NY and surrounding areas

Approved

Free estimates

Small jobs welcome

"I had only planned to have my lawn mowed once but Joshua was excellent so I hired him to mow and trim my yard bi- weekly. Very reliable, great work and excellent clean up. Price was reasonable and very professional."
Small Front Lawn
High Brush
Brunch Cut
Weed & Mulch
Weed & Mulch

+1

7 neighbors recently requested a quote
Avatar for Gravity property solutions
Gravity property solutions
5.0(
2
)
Tree RemovalTree Stump - RemoveTree Trimming

Serving Chestertown, NY and surrounding areas

Approved

Free estimates

Emergency services offered

Warranties offered

At Gravity Property Solutions LLC, we make property maintenance simple, convenient, and dependable for homeowners and businesses\. We provide professional landscaping, lawn care, leaf removal, snow plowing, junk removal, and general property maintenance services designed to keep your property clean, safe, and looking its best\.\n\nYou can count on us for reliable service, clear communication, attention to detail, and quality results\. Whether you need seasonal cleanup, unwanted items removed, snow cleared, or ongoing property maintenance, we handle the work efficiently so you can save time and enjoy peace of mind\.\n\nWe proudly serve our local community and surrounding areas with a commitment to convenience, fair pricing, and customer satisfaction\. Our goal is to make every service experience easy and stress\-free while delivering results you can rely on\.\n\n**Contact us today for a quote\!**

Lawn mowing
Lawn mowing
Lawn mowing
Tree removal
Tree removal

+21

Avatar for Riffle Lawn Care & More
Riffle Lawn Care & More
5.0(
1
)
Tree Trimming

Serving Chestertown, NY and surrounding areas

Approved

Free estimates

Emergency services offered

Small jobs welcome

"Absolutely fabulous! I had an overgrown lawn about 3ft high and they didn’t even blink! Just said no problem! They were also the only people I called that actually answered their phone.& I didn’t have to leave a msg with a computer prompt that kept cutting me off. They even came to ck out the job first. It was a huge job and they are miracle workers. I will be utilizing their services for years to come. 10 stars! Definitely recommend them."
Ballston Spa
Ballston Spa
4 neighbors recently requested a quote
H&J Landscaping
New to Angi
Tree TrimmingTree Trimming - For Business

Serving Chestertown, NY and surrounding areas

Approved

In business since 2022

Free estimates

Offers commercial services

With 15 years of experience, we take great pride in our experience, expertise, quality, and customer service that we provide to meet the consumer need. It is our mission to provide excellent workmanship and complete customer satisfaction from start to completion of a project. In order to understand the needs and expectations of our customers, we take great care to work and communicate with every customer in a professional manner. Our reputation is based on service, safety, and quality, regardless of how large or small the job.

Mulching
Planting
Planting
Planting
Pruning

+4

3 neighbors recently requested a quote
Avatar for Mark's Tree Removal
Mark's Tree Removal
4.1(
15
)
Tree RemovalTree Stump - RemoveTree Trimming

Serving Chestertown, NY and surrounding areas

In business since 2008

Free estimates

Emergency services offered

"With all the rain that we have had this summer, he did a great job taking down two very old and tall pine trees and grinding the stumps. Definitely going to hire him again to top a few trees."
Our Work
Our Work
Our Work
Our Work
Our Work

+5

Response time2 days
Recommended by85%of homeowners
...
Showing 1-10 of 52
Tree Service FAQs, answered by experts

Most jobs take 2-8 hours, but extensive trimming may take multiple days.

The best time to transplant a tree is when it is dormant. For many trees, this means either in the fall after the leaves have dropped (around October or November) or in early spring before new growth begins (around March). The ideal timing can depend on the type of tree. Deciduous trees do well when moved in early spring or fall, while evergreens are best transplanted in early spring or late summer. For example, pine trees are best moved in early fall, but maples prefer late fall. Avoid transplanting in winter, as the frozen or hard, cold soil poses a significant risk to the roots and prevents the tree from acclimating properly.

Generally, homeowners do not need permission to cut down a tree on their own private property, but there are several exceptions where a permit may be required. You might need a permit if the tree is particularly large, old, or a protected species, such as a heritage tree. Trees located near public property or power lines can also be subject to special rules. Additionally, many local governments and homeowners associations (HOAs) have regulations controlling which trees can be removed to manage an area's appearance or prevent the spread of invasive species. To avoid hefty fines, it is crucial to check with your local government and HOA to determine if a permit is needed before you begin.

There are several methods to hollow out a tree stump, and the best one depends on your tools, experience, and priorities. Common methods include using a chisel and hammer, a chainsaw, or burning.

  • Chisel and Hammer: This is often considered the easiest approach for those with limited tools or experience, though it is the most time-consuming.

  • Chainsaw: Using a chainsaw is the fastest method, but it comes with significant safety risks, especially for inexperienced users.

  • Burning: This can be an effective method, but it is not recommended unless you can first drill holes into the stump. Without holes, the stump will be difficult to light and may not burn completely through.

A power drill with at least a ⅜-inch diameter bit can make the job quicker and easier, regardless of the primary method. While you can use a chisel or chainsaw without a drill, it will require more time and effort. Always wear protective goggles and thick gloves, as splinters are an inevitable risk.

Carefully pruning small roots no thicker than three inches in diameter won’t harm the tree. However, cutting larger roots may impact the tree's stability and nutrient absorption. It's advisable to consult an arborist or tree care professional to evaluate the root's size, the tree's health, and the potential impact of cutting. Proper tree pruning techniques and timing can minimize damage, but larger root removal may necessitate expert guidance to avoid compromising the tree's overall health and stability.

The Chestertown, NY homeowners’ guide to tree services

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