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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

4 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
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Tree Service FAQs, answered by experts

Stump grinding consists of removing the visible part of the stump, but the roots remain intact. Depending on the tree and root system, the roots may still grow after stump grinding. If you are concerned about root growth and damage, you may want to consider having a stump removed completely.

You can shape a cherry tree by trimming vertical branches, dense branches, and intersecting branches. Your personal aesthetic comes into play, as well. If you want to simply thin and shape the tree, you can get away with trimming the aforementioned parts of your cherry tree. If you want to shorten branches, however, consider thinning cuts, which alter the length of the branches while encouraging light penetration, new buds and shoots, and a structurally-sound shape.

Generally, you should prune around 20% of an apple tree’s growth—and never more than 30%. This means that if you have a severely overgrown tree, it can take a few seasons to prune it back enough to produce the healthiest fruit. 

If you’re dealing with a newly planted or juvenile tree, hold off on pruning beyond the initial shaping. Wait at least a couple of seasons into fruit production since pruning can increase the number of water sprouts and unproductive foliage.

Ideally, you should wait to prune until trees have gone dormant in late fall to early winter. The worst times to prune trees are early fall and late summer, as pruning them so close to dormancy makes it difficult for the tree recover before it goes dormant for the season.

Generally, you’ll want to avoid pruning more than 25% of the tree’s canopy at one time. While pruning your tree is important, it’s possible to do it too often or to go too far. Again, this is why hiring a tree trimming pro to do the work is wise. However, if you do decide to DIY, going slow and trimming gradually is the name of the game.

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.