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Top-Rated Tree stump removers in Winchester - Updated Nov 2026

Avatar for McDonough Tree Removal Inc
McDonough Tree Removal Inc
4.9(
61
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

In business since 1975

Free estimates

Emergency services offered

"Shaun gave us an estimate to remove 3 maples, a black cherry tree and grind one stump in our backyard. One of the trees was close to a smaller maple, which we wanted to keep and there was no damage to it after the tree removal. Shaun set up the crane on the street in front of our house. Eric and Dave drove up with the chipper equipment. Shaun and Eric worked on the tree cutting and lifted the trees right over our house, letting them down in a side street. Dave fed the large tree chunks right into the chipper. The whole operation was done in about 2 hours. They cleaned up perfectly and you could hardly tell they were here except for some sawdust. Less than 2 weeks later a truck pulled up with two guys who proceeded to grind the one stump. They also did a wonderful job. Everyone did a great job and we were very satisfied. We will hire McDonough again if we need more trees removed. We will also recommend them to all our neighbors."
Response time3 days
Recommended by100%of homeowners
Avatar for Pro Tree Service
Pro Tree Service
5.0(
26
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2019

Free estimates

Emergency services offered

"Pro tree service came and did exactly what I asked hector and his crew were excellent hector spent most of the day 40 to 60 feet high cutting and pruning over a busy main road his crew was very quick to remove the wood from the road 10 feet up the hill over and over keeping the traffic moving hector priced the job at 500 dollars cheaper than another company from Angi list the police officer was equally impressed by this company that he asked hector for his business card . I would and will recommend pro tree service to all. Thank you Angi ."
 PREVENTION IS KEY! Let's take care of the trees, shrubs, ornamental trees that surround YOUR HOME, YOUR FAMILY!

Most tree damage during severe weather events occurs due to falling trees and limbs. 

High winds and the weight of ice and snow during the winter can cause failure of branches and even entire trees.

The damage that can occur from not preparing your shrubs, ornamental trees, trees can be costly ? and permanent.

Let's set up your appointment today for your free consultation for Tre
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+7

Response time1 day
Response rate100%
Recommended by92%of homeowners
Avatar for WOOD CHUCK STUMP GRINDING
WOOD CHUCK STUMP GRINDING
4.9(
30
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

In business since 2015

Free estimates

Credit card accepted

We are a locally owned and operated company that values honesty and integrity and treats your home as if it were our own. We have many years of experience to give you confidence that we are your number one choice for your next home project. You will find us to be competitively priced with close attention to the details. We look forward to building a lasting relationship and guarantee your satisfaction!

 Stump Grind
Recommended by70%of homeowners
Avatar for K J A S Tree Services
K J A S Tree Services
4.9(
40
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2023

Free estimates

Emergency services offered

"Great job on short notice, the Thursday before Christmas. They were able to remove a tree, do some serious pruning of large branches overhanging my house, as well as a yard clean up and they did my gutters for me too. I would definitely recommend KJAY Tree Service & Landscaping."
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+34

Response time8 hrs
Response rate100%
9 neighbors recently requested a quote
Avatar for MC Tree Service and Landscape Designer
MC Tree Service and Landscape Designer
5.0(
15
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2020

Customers say: True professional

"The company owner recommended that instead of grinding the tree stump he would dig it up. I am glad for his recommendation. I can plant a new tree in the same spot. The work was done promptly and they cleaned up the area. The price was right."
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+19

23 neighbors recently requested a quote
Recommended by75%of homeowners
Pro Cut Landscape & Design
4.9(
198
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

In business since 2001

Free estimates

Credit card accepted

"Met Bob the owner for work to be done, was very sociable. Made suggestions which i agreed on. He knows his work. Showed up on time and finished. Cleaned up like he was never there. Removed existing lawn and replaced with loam ,seed, and fertilizer. Job well done 👍"
14 neighbors recently requested a quote
Recommended by72%of homeowners
Avatar for Pro Cut Landscape & Design
Pro Cut Landscape & Design
4.9(
191
)
Tree Stump - Remove

Serving Winchester, MA and surrounding areas

Approved

Super Service Award Winner

In business since 2001

Free estimates

Small jobs welcome

"Bob and team did an amazing job removing 15+ dead bushes and small trees, weeding, and mulching a yard that was long overdue for landscaping work, highly recommend!"
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+1

Response time11 hrs
41 neighbors recently requested a quote
Recommended by74%of homeowners
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FAQs for tree stump removal projects in Winchester, MA

Always transport chainsaws with the engine off and chain brake engaged. Use the protective bar cover provided by the rental company to prevent accidental contact with the cutting chain. Position the chainsaw securely in your vehicle to prevent movement during transit, ideally in a truck bed or trunk rather than the passenger compartment. 

For gas models, ensure the fuel cap is tight and position the saw to minimize potential leakage. Keep the chainsaw away from passengers and other items that could be damaged.

Proper safety equipment is essential when operating any chainsaw. At minimum, you should have eye protection (safety glasses or a face shield), hearing protection (earplugs or earmuffs), cut-resistant gloves, chainsaw chaps or pants, and sturdy boots with good traction. 

Many rental facilities offer basic safety kits alongside chainsaw rentals. If you'll be using chainsaws regularly, investing in quality personal safety gear is advisable. Never operate a chainsaw without appropriate protective equipment, regardless of the job size.

While rental companies will rent chainsaws to beginners, inexperience significantly increases safety risks. If you've never used a chainsaw before, request a demonstration from the rental staff and thoroughly review the operator's manual before starting. Begin with smaller, more manageable cutting tasks to build comfort with the tool's operation. 

For significant cutting jobs, consider either taking a chainsaw safety course first or hiring professionals instead. The learning curve for safe chainsaw operation is steep, and caution is paramount.

If mechanical problems develop during your rental, immediately cease operation and contact the rental company. Most reputable rental businesses will either provide a replacement chainsaw or repair the equipment if the breakdown resulted from normal use rather than misuse. Document the issue with photographs when possible and maintain records of when you reported the problem. 

Having your rental agreement readily available when you call will expedite the resolution process. The rental company should adjust your rental period to account for any downtime.

The Winchester, MA homeowners’ guide to tree stump removals

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