Customers frequently praise Winning Tree for its punctuality, clear communication, and competitive pricing across landscaping, concrete, and waste removal services. Many reviewers highlight the crew's professionalism and willingness to accommodate specific schedules or design preferences. However, recurring criticisms in low-star reviews cite unreturned calls and messages, missed service appointments, and billing for work not performed, indicating occasional lapses in responsiveness and follow-through.
Google rating: 4.8 out of 5 from 108 reviews (93% five-star).
Reviews on this page: 108 Google reviews (82 with written comments, 2 with photos).
Owner responses: the business replied to 37% of reviews.
Most recent review: October 19, 2026.
Service: Tree Service serving Jamestown, New York.
Data from Google, last updated October 25, 2026.
Photos
Customer reviews
4.8
★★★★★
108 reviews on Google
5★100
4★2
3★0
2★0
1★6
Reviews from Google, shown as published (original wording, unedited).
Debbie Gray2 reviews
★★★★★
First I want to apologize for the lengthy post/review. However, I feel it is necessary so others understand what we dealt with and do not find themselves in the same position. Secondly, this has no bearing on the laborers that did the work, as they did a good job.
In the fall of 2024 We contacted Winning Tree for a quote to plant a large section of Arborvitaes between our home and the neighbor’s home and at the same time asked if it would be possible to trim and shape a section of hemlock trees on our property. Scott from Winning Tree called with a quote and due to the cost we asked if we could wait until Spring and if the quote would still be valid. Scott advised it would and Spring would be a good time for planting the trees. My huge mistake was in trusting the phone quote and not requesting a written estimate.
Winning Tree crew brought in several yards of soil to provide a mound for the trees to be planted in. The trees were planted and the work completed over the Memorial Day weekend of 2025. May 28, 2025 I received an emailed invoice and was shocked and sickened that it was about $4,000.00 more than what we had been quoted and what we had planned for. I immediately called Scott at Winning Tree and he indicated the quote he had given me did not include the trees. However, if I could pay cash it would save about $800 and they would trim the hemlock trees for free. So we paid a very large sum of money for a mound of dirt to plant the trees in! We rearranged somethings and paid the cash to help with the cost.
6/30/25 – I texted and asked when they would be coming to trim the hemlocks. No response
7/2/25 – Sent the same text – Scott indicated the hemlocks would be the following week.
7/16/25 – Still no sign of Winning Tree – Texted and asked what the plan was. Scott indicated it was too hot to trim the trees that it would burn and kill them, but indicated they would still be here to do the work.
10/1/25 – Asked when the team would be here to trim and shape the trees – no response.
10/09/25 – Asked when they were coming to trim the trees – no response
11/4/25 - Advised weather for Thursday (when they are in our area) looked good, although cold. When were they coming? Responded they were trying to make it there, but weather has held them up and couldn’t guarantee an exact day, but may be before that Thursday. – No Show again
04/17/26 – Text asking when they were coming to shape the hemlocks. Scott indicated once it was dry enough. – No Show
6/17/26 – Asked again when they were coming – He indicated they would be here the following week either Thursday or Friday as they had a job in our area.
06/26/26 – Text that I assume they would be trimming the trees today, correct? No response
07/09/26 – Text asking if they had any intention of trimming the hemlocks as promised. Scott indicated the big hedge trimmers were getting fixed and they had two sets coming in and he would have Jose and Nate trimming going down in the dump truck and they were at Land Pro getting new blades and gears put in. – No Show
08/26/26 – Text I assume the trimmers have been repaired by now and you have received the two you ordered, but still haven’t seen anyone here. No Show, No response.
At this point after having two seasons to do what was promised, we are no longer counting on them to do the work, and we no longer would want them on our property.
I had an outstanding experience with Winning Tree in Jamestown, NY. From the very beginning, their customer service was excellent. They communicated clearly throughout the entire process, keeping me informed every step of the way and answering any questions I had promptly.
The crew was professional, courteous, and highly skilled. They arrived on time, worked efficiently, and treated my property with care. What impressed me most was how they maintained their professionalism despite dealing with neighbors who attempted to harass them while they were trying to do their job. They stayed calm, respectful, and focused on completing the work safely and efficiently.
It's refreshing to work with a company that values both quality workmanship and exceptional customer service. I highly recommend Winning Tree to anyone looking for reliable, professional services. I wouldn't hesitate to hire them again.
These guys are great. Excellent communication throughout the process very great pricing and got the job done to perfection within the timeline we agreed to! Highly recommend winning tree!
Winning Tree did a fantastic job with our landscaping project! They were extremely responsive and worked with us on design and plant selection. Best of all, they really listened to our input and designed a project to meet our exact preferences. The design is beautiful, and the crew was fantastic. They worked 11 hours straight, were professional and courteous, and cleaned everything up afterward. I can't say enough; they were exceptional, and we look forward to future projects with Winning Tree.
Honestly I can’t say enough about this team as they will drop everything to help someone in need and make your day better. Not just landscaping and concrete but, you feel like you’re being treated like a family member each time you get a quote or a job is done. True work ethic for sure mixed with impeccable timing and execution
Everything from weekly trash pickup to appliance removal. Friendly, fast and get the job done NOW... these guys do it now, do it fast and do it right! All with a smile!! Highly recommended!!
Price assessment: Great price
Positive: Responsiveness, Punctuality, Quality, Professionalism, Value
Services: Construction debris removal, Electronic waste removal & disposal, Furniture removal, House & garage cleanouts, Service not listed
I called for an estimate and I was greatly surprised at getting an estimate within the terms of my schedule. They worked around my schedule and made sure that it didn’t affect my day to day. I got my estimate and it was the best priced out of the 4 and they took time to go over step by step the process. I highly recommend winning tree and am excited to get the work done here when the weather breaks.
I called for an estimate for some concrete work that I need done. I was in need of a driveway, new patio and sidewalk. My wife and I talked it over. We knew it was going to be a big purchase but a great improvement on our property. With that being said. Scott saved us so much on this big capital improvement to our home. After getting 4 estimates they were the best priced as well as most knowledgeable. They took there time and sat and went over things with my wife and I. Vince went through all the steps that would take place. I am excited for the project to begin. If you are looking for a new driveway, patio or sidewalk I highly recommend winning tree.
