Get matched with top tree service pros in Winchester, MA
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TRUSTED BY WINCHESTER, MA HOMEOWNERS
4.7 Average homeowner rating
462 Verified tree services reviews
Verified Reviews for Tree Service pros in Winchester, MA
*The Angi rating for Tree Service companies in Winchester, MA 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 Winchester, MA 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 15, 2025
Find Tree service pros in Winchester
Roberto's Affordable Landscaping
Roberto's Affordable Landscaping
Customers say: Super punctual
573 local quotes requested
18 years of experience
Roberto Affordable Landscaping proudly serves Waltham, MA. Are you tired of spending time and money trying to keep your grass green to no avail? Let us give it a try! We specialize in providing quality, beautiful landscapes for your home or business. In every job, we strive for 100% customer satisfaction. Our staff will take the time to listen to you and then create a landscape that is designed to meet your individual needs and desires. Meeting and exceeding customer expectations is how “Roberto Affordable Landscaping” has grown to one of the region’s most respected landscaping service firms. Our focus on customer service gives you confidence that your property will be designed, installed, and maintained to industry standards and beyond. With 12 years of experience we know how to get it done right. Please Email or Text us today to schedule an appointment!
"Roberto and his crew did an outstanding job! We usually do all of our hedge abs shrub trimming ourselves, but with a few other projects going on we hadn’t gotten them all season long and they were seriously overgrown. Since we COULD do it ourselves, we had a limit on what we were willing to pay, so we were getting several quotes … most of which were higher than we had hoped. Roberto worked with us on the pricing, which was good news because now it was off of our plate! His crew was there the early next day … fast, friendly, courteous, conscientious and neat! We are now looking to have Roberto and his crew back to take a few more projects off of our plate too! If you want a great job, at great price, by a great crew … we highly recommend Roberto’s Affordable Lands aping!"
James L on September 2025
Roberto Affordable Landscaping proudly serves Waltham, MA. Are you tired of spending time and money trying to keep your grass green to no avail? Let us give it a try! We specialize in providing quality, beautiful landscapes for your home or business. In every job, we strive for 100% customer satisfaction. Our staff will take the time to listen to you and then create a landscape that is designed to meet your individual needs and desires. Meeting and exceeding customer expectations is how “Roberto Affordable Landscaping” has grown to one of the region’s most respected landscaping service firms. Our focus on customer service gives you confidence that your property will be designed, installed, and maintained to industry standards and beyond. With 12 years of experience we know how to get it done right. Please Email or Text us today to schedule an appointment!
"Roberto and his crew did an outstanding job! We usually do all of our hedge abs shrub trimming ourselves, but with a few other projects going on we hadn’t gotten them all season long and they were seriously overgrown. Since we COULD do it ourselves, we had a limit on what we were willing to pay, so we were getting several quotes … most of which were higher than we had hoped. Roberto worked with us on the pricing, which was good news because now it was off of our plate! His crew was there the early next day … fast, friendly, courteous, conscientious and neat! We are now looking to have Roberto and his crew back to take a few more projects off of our plate too! If you want a great job, at great price, by a great crew … we highly recommend Roberto’s Affordable Lands aping!"
James L on September 2025
Ruiz Landscaping
Ruiz Landscaping
Customers say: Super punctual
314 local quotes requested
8 years of experience
We are a professional landscaping service covering the Boston metropolitan area. Our services include: Landscaping, Lawn & Yard Work, Tree Services, Lawn Clean-Ups, Gutter Cleanings, General Lawn Maintenance and much more! Please call us today to schedule an appointment!
"I am a regular customer of this company. The do my spring cleanup, fall cleanup, trim, mulching, and lawn maintenance. I am always amazed at how great the yard looks after they are done. They keep the edges sharp and provide the little extras that other companies do not. They show up on time, are professional and thorough. If you want a great looking yard for a reasonable price, hire this company. Their work is excellent."
Alease B on March 2025
We are a professional landscaping service covering the Boston metropolitan area. Our services include: Landscaping, Lawn & Yard Work, Tree Services, Lawn Clean-Ups, Gutter Cleanings, General Lawn Maintenance and much more! Please call us today to schedule an appointment!
"I am a regular customer of this company. The do my spring cleanup, fall cleanup, trim, mulching, and lawn maintenance. I am always amazed at how great the yard looks after they are done. They keep the edges sharp and provide the little extras that other companies do not. They show up on time, are professional and thorough. If you want a great looking yard for a reasonable price, hire this company. Their work is excellent."
Alease B on March 2025
RGS Tree Service
RGS Tree Service
Customers say: Quick response
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
68 local quotes requested
RGS Tree Service in Boston is your go-to for all your tree service needs. Our full-service tree removal sets us apart from the competition. Contact us today for expert assistance with your home projects.
"Awesome job, the crew was very professional. They completed the job as planned and in a timely manner. The cost was very reasonable. The tree was removed w/o any issues and everything was cleaned up before leaving. I would highly recommend them for tree removal and landscaping needs."
Sheila K on March 2018
RGS Tree Service in Boston is your go-to for all your tree service needs. Our full-service tree removal sets us apart from the competition. Contact us today for expert assistance with your home projects.
"Awesome job, the crew was very professional. They completed the job as planned and in a timely manner. The cost was very reasonable. The tree was removed w/o any issues and everything was cleaned up before leaving. I would highly recommend them for tree removal and landscaping needs."
Sheila K on March 2018
Eddie's Tree Service
Eddie's Tree Service
Customers say: Quick response
Recommended by 100% of Angi customers
Recommended by 100% of HomeAdvisor customers
15 years of experience
Eddie's Tree Service Inc is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business. Eddiestree.com $50 Estimate Fee. 20 years of experience.
"Cory and Toby pruned dry branches and tree limbs out of our 60-year old sugar maple on our property. It required climbing well into the canopy of the tree; it was impressive to watch their agility. Both gentlemen were exceptionally professional, proactive, and last but not least very pleasant to interact with. They also tidied up well after their work. The work was done for a fair price and as scheduled. I can recommend them based on their performance with us, and would use them again for future work."
Bernie H on September 2023
Eddie's Tree Service Inc is committed to excellence in every aspect of our business. We uphold a standard of integrity bound by fairness, honesty, and personal responsibility. Our distinction is the quality of service we bring to our customers. Accurate knowledge of our trade combined with ability is what makes us true professionals. Above all, we are watchful of our customers' interests, and make their concerns the basis of our business. Eddiestree.com $50 Estimate Fee. 20 years of experience.
"Cory and Toby pruned dry branches and tree limbs out of our 60-year old sugar maple on our property. It required climbing well into the canopy of the tree; it was impressive to watch their agility. Both gentlemen were exceptionally professional, proactive, and last but not least very pleasant to interact with. They also tidied up well after their work. The work was done for a fair price and as scheduled. I can recommend them based on their performance with us, and would use them again for future work."
Bernie H on September 2023
Pro Cut Landscape & Design
Pro Cut Landscape & Design
Customers say: Super punctual
16 local quotes requested
24 years of experience
We here at Pro Cut Landscape & Design, proudly serve Watertown and surrounding areas. We pride ourselves on our ability to take on any project large or small, residential or commercial. We make sure when completing each project that our customer's needs and wants are fully in mind and we aim to exceed their expectations to ensure a lifelong customer. We complete each project cleanly, on time, and done right the first time. Contact us for a fair and accurate estimate of your project. We look forward to adding you to our long and growing list of happy customers.
"Great communication and easy transaction "
James G on October 2025
We here at Pro Cut Landscape & Design, proudly serve Watertown and surrounding areas. We pride ourselves on our ability to take on any project large or small, residential or commercial. We make sure when completing each project that our customer's needs and wants are fully in mind and we aim to exceed their expectations to ensure a lifelong customer. We complete each project cleanly, on time, and done right the first time. Contact us for a fair and accurate estimate of your project. We look forward to adding you to our long and growing list of happy customers.
"Great communication and easy transaction "
James G on October 2025
Junior's Landscaping
Junior's Landscaping
Super Service Award
Customers say: True professional
16 local quotes requested
7 years of experience
Welcome to Junior Landscaping! We are excited to exceed your expectations. As experts, we will handle your needs with the high-quality expertise that your home deserves. We offer competitive prices and customer satisfaction is our number one priority. Call us now!
"They did a beautiful job with a lawn that looked more like a jungle! Friendly, honest and reasonably priced. Thanks 😊 "
DIANA F on August 2025
Welcome to Junior Landscaping! We are excited to exceed your expectations. As experts, we will handle your needs with the high-quality expertise that your home deserves. We offer competitive prices and customer satisfaction is our number one priority. Call us now!
"They did a beautiful job with a lawn that looked more like a jungle! Friendly, honest and reasonably priced. Thanks 😊 "
DIANA F on August 2025
The Beavers S&N Landscaping Tree Services, Inc.
The Beavers S&N Landscaping Tree Services, Inc.
Customers say: True professional
Recommended by 92% of Angi customers
Recommended by 92% of HomeAdvisor customers
95 local quotes requested
Here at company , we pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects no matter how big or small. We are experts in our trade and will always keep you educated on your particular task or project. We look forward to earning your business!
"Yes, they worked all day, in intense heat"
Anne K on August 2025
Here at company , we pride our company on reliability, great communication, integrity, and quality work. We strongly believe in giving our absolute best in all of our projects no matter how big or small. We are experts in our trade and will always keep you educated on your particular task or project. We look forward to earning your business!
"Yes, they worked all day, in intense heat"
Anne K on August 2025
"Ever called and set up a time to meet and check out my property. We discussed what I needed and he made recommendations which I happily accepted. We agreed on a price and work started. His workers were efficient, professional and hard workers. They were done in no time. My property looks amazing and I look forward to using his services again/"
Kathleen P on August 2025
tbd
"Ever called and set up a time to meet and check out my property. We discussed what I needed and he made recommendations which I happily accepted. We agreed on a price and work started. His workers were efficient, professional and hard workers. They were done in no time. My property looks amazing and I look forward to using his services again/"
Kathleen P on August 2025
Alex's Landscaping
Alex's Landscaping
8 years of experience
Free onsite estimate
Alex's Landscaping is a locally owned and operated company that values honesty and integrity in all aspects of our business. Our dedicated team of professionals have years of hands on experience, to provide innovative ideas and suggestions tailored to your projects. Our services are customized to your individual needs, paying close attention to the details of each project that we are involved with. Please feel free to contact us today!
Alex's Landscaping is a locally owned and operated company that values honesty and integrity in all aspects of our business. Our dedicated team of professionals have years of hands on experience, to provide innovative ideas and suggestions tailored to your projects. Our services are customized to your individual needs, paying close attention to the details of each project that we are involved with. Please feel free to contact us today!
GT Optimo Landscape and Construction, Inc.
GT Optimo Landscape and Construction, Inc.
Customers say: True professional
Recommended by 95% of Angi customers
Recommended by 95% of HomeAdvisor customers
59 local quotes requested
When it comes to taking care of your property, choose someone you can trust. Here at GT Optimo Landscape and Construction, Inc., we believe in a job done right the first time, every time. We specialize in tree removal, lawn care and property clean up. Give us a call today and let us make you our next satisfied customer.
"Did a good job"
Philip S on July 2025
When it comes to taking care of your property, choose someone you can trust. Here at GT Optimo Landscape and Construction, Inc., we believe in a job done right the first time, every time. We specialize in tree removal, lawn care and property clean up. Give us a call today and let us make you our next satisfied customer.
"Did a good job"
Philip S on July 2025
Tree Service questions, answered by experts
The Winchester, MA homeowners’ guide to tree services
From average costs to expert advice, get all the answers you need to get your job done.
It’s important to remove troublesome stumps: Here’s everything you can expect from stump grinding costs for your next landscaping project.
•Discover the average tree maintenance cost, key price factors, and tips to save. Get expert insights to plan your tree care budget with confidence.
•Get a clear estimate of palm tree maintenance cost, including trimming, fertilization, and pest control, so you can keep your palms healthy and your budget on track.
If you’re searching for people who cut down trees, look for arborists and tree cutters. Our guide will show you who to hire for tree cutting.
Learn what the tree removal process entails and find out what qualities to look for in professional tree removal services in this guide
What do elm trees look like? Learn how to identify elm tree leaves, bark, and the different types of this picturesque tree with this informational guide.
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