Logo of Rolling Oak Tree Service

Rolling Oak Tree Service

  • 44199 Medleys Neck Rd, Leonardtown, MD 20650
  • Commercial Roofing
  • Industrial Roofing
  • Licensed & Insured
  • Locally Owned & Operated
  • Warranties Offered
Hours
Mon7:30 AM - 9:00 PM
Tue7:30 AM - 9:00 PM
Wed7:30 AM - 9:00 PM
Thu7:30 AM - 9:00 PM
Fri7:30 AM - 9:00 PM
Sat7:30 AM - 9:00 PM
Sun7:30 AM - 9:00 PM

About the Business

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What people say about “Rolling Oak Tree Service”?

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Recommended Reviews

Overall Company Rating
Excellent 4.9
Out of 32 reviews
5 stars
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Ray Coston
Jul 24, 2025

Tom and his company Rolling Oak LLC is a very professional and knowledgeable company. A portion of the top of a maple tree fell on a section of my roof. It was removed safely and the clean up was excellent. I would definitely refer this company for all your tree trimming and removal needs.

Maureen
Jul 23, 2025

Excellent service!! I highly recommend Rolling Oak Tree Service! Tom and his crew were hard-working, professional, and friendly! Very reasonable prices too! Tom was patient and knowledgeable - he answered all my questions - very responsive communications! Great job removing a damaged tree/grinding the stump and trimming a tall willow & pear tree. Will definitely use them again!

Darryl Robinite
Sep 5, 2024

Lifelong customers from Kerwin to now Rolling Oak. Tom is doing great business here in St. Mary's County - latest job was a 25ft dead tree in the middle of my backyard. Great price, quick execution, and the crew left the yard spotless. Pictures are after the job... Last two jobs were major undertakings and they always had stellar results.

Vincent Fisher
Oct 10, 2023

the Kerwin guys were great and did a wonderful job, getting rid of a huge pine tree and having to use the crane and bucket truck to remover the tree. They also trimmed a bunch of oak and maple trees. Always polite and and professional.

Tony Allen
Jun 27, 2023

Very fair price, job was done in less than 2 hours, removed and cleaned up all branches and leaves, very friendly, hard working, would recommend them to anyone.

Debi Justice
Jun 16, 2023

They are so professional. On time. Quality work. Cleaned up that you can't tell a tree was taken down. The price was right. I highly recommend them.

Barbara
Apr 21, 2023

Kerwin Tree Service removed a large Maple tree for me that was messing up my foundation and furnace under my crawl space. They were able to do the removal within days of calling them. They were punctual, courteous, affordable, and very professional. They also did a great clean up job! I highly recommend them.

Lindsey Noffsinger
Mar 30, 2023

We had 7 trees removed and two large trees trimmed/pruned. The Kerwin team was amazing from receiveing the quote to the end of the service. They are extremely professional, helpful and all around wonderful to work with. We will recommend them to our family and friends and continue to use their services.

Lakeesha Mcknight
Mar 24, 2023

Kerwin Tree Service did an excellent job on removing and trimming trees around my house. I highly recommend this company.

Stacy Shaver-Titus
Feb 22, 2023

We had a number of large dead and/or rotting trees that needed to be taken down and removed (one of which had already partially fallen and was wedged high up in another tree). We also had stumps that needed grinding and wood from other large trees that were cut down by the power company and needed to be removed. We obtained assessments and estimates from three top-rated companies. Kerwin's estimate was highly competitive with the other two and captured the full scope of the job. The team was very responsive and communicative with respect to addressing our questions and making sure that we understood how the job would be completed as well as the cost of the job. At no additional charge, they were able to assemble the team two days after we accepted the estimate to work on a holiday when we could both be on site. They handled a complicated job efficiently and took great care to maintain the safety of the crew as well as to limit the impact of the equipment and dismantled trees on the surrounding trees, bushes, and plants. They cleaned up the area and went above and beyond in performing some extra, much appreciated tasks with no additional charge. They made sure that we were completely satisfied before accepting payment. The price quoted was the price of the job. We noted on the estimate that there was an additional charge non cash payment (due to charges that the company would have to incur) so we opted to pay in cash. It is obvious that they care about and take pride about what they do. I would not hesitate to recommend them to others or use them again in the future.

Joseph Davis
Jan 17, 2023

What a fantastic group! Very professional and timely. I would highly recommend them to ANYONE in the St Mary’s area!!

Steve Baker
Aug 9, 2022

Tom and his crew did an amazing job. Professional all the way. The yard looks beautiful.. They left it looking better then it did when they arrived. I've used Kerwins trees several times and know I'll never use anyone else. I highly, highly recommend. Thanks Kerwin Tree, I couldn't be more pleased. Anne Baker

Jessica Franceschini
Jul 14, 2022

The team was so great to work with. They were ahead of schedule and ready to get the job. I would suggest them to anyone look for affordable, professional work.

Meagan B
Apr 26, 2022

We were so impressed by Bill, Tom, and the rest of the crew. They were extremely responsive and prompt in getting out to get us an estimate on several troublesome trees and they were out the next day to take care of the work for us. They were extremely prompt, friendly, thorough, professional, and clean, and it is evident they take great pride in their work. We couldn't have asked for a better experience and will certainly be using them for our future tree removal and trimming needs.

Zach
Jan 4, 2022

They’ve earned a lifelong customer. I was so impressed with every aspect of their work. Customer service, quality of work, pricing. All around great and our new go to.

brian taylor
Aug 19, 2021

Wow!
We had a tree fall down in a storm on a Friday night which highlighted several troublesome trees on our property. Bill was there on Saturday morning between jobs to give us an estimate. He sized up the job and emailed us a detailed estimate. Two days later he and his crew were there and did an amazing job removing the troublesome trees and trimming some large branches back from our house. They have the right equipment and are very thoughtful and methodical about how they operate. They cleaned up all the sticks and mess before they left. We couldn’t have been happier with their service; super responsive, they respected our property and they were super friendly. We will certainly be using them in the future.

Tricia Kocka
Jul 29, 2021

Outstanding job done by Bill, Tom, and the crew. I had 4 huge pines and a large oak tree removed, along with trim work on over 10 trees along with wood line near my house. The yard looks great now! I received a quote right away, and work was able to begin soon afterwards. The crew hauled away all the trees and debris and now people can see my house from the road. I couldn’t be happier with the service I received and I will definitely contact Mr. Kerwin again in the future.

Wade Robinite
Jun 9, 2021

This was our second time using this company. They do an amazing job, and work super fast to get it done the right way. We use Bill and his team because they are the best and insured. Our property shares a driveway with the neighbors so we had to block them in, but because of Bills excellent communication skills and time management the neighbors had no issue. He even offered a discount on a tree that they wanted down for letting him use there driveway.
If you need to have some trees removed I highly recommend you calling Bill. He will get to you as fast as he can with great prices.
Also the cleanup work that him and his team did was awesome. I didn’t see one leaf left behind. They truly are the best. We will be using Bill and his team for any other projects we may run into.
Thanks again Bill!!!!

Darryl Robinite
Jun 8, 2021

Bill and his crew are the best around. First, there was an outstanding turn around on the initial visit for the quote and the price was great. They brought a squad and all the necessary equipment to quickly and efficiently take down a dozen trees within 5 hours. Cleanup was superb and aside from the stumps we decided to keep you wouldn’t be able to tell we had trees taken down.

This is our second job we’ve hired Kerwin Tree Service for and we’ll be sure to call him for all our future jobs. If you need a tree handled, give Bill and his team a call!

Jenna Hamlet
Apr 20, 2021

Couldn’t have had a better experience with Bill and his team. They did it safely and in a timely manner. They also allowed my kids to ask a gazillion questions throughout the entire day! Thanks again for giving us more room to play in the yard ! Definitely recommend these guys !!!

Michael Mycek
Apr 6, 2021

Scheduling: I just wanted a dead tree fell in between my neighbor and my yard. I could have done it, but it was dangerously leaning towards our house. I asked for a quote on a Thursday and they were able to get back to me on Friday with a very reasonable quote. I emailed saying I'm available all week just let me know your schedule and they were able to come out Monday afternoon!

Workmanship: I just asked them to fell the tree for me and I would cut it up and remove it, but they went far beyond just felling the tree. They were able to cut up the tree into smaller pieces and limbing it leaving me only a few things to cut and going above the actual work order all within 1 hr!

Bottom line: I will be using Kerwin tree's for all my tree needs in the future. Nice people and a breeze to work with, thank you.

Paul Croisetiere
May 22, 2020

Bill and his team removed a large tree from our property. His price was very competitive, and everything about our experience with him and his team was great. He has, arguably, some of the most modern equipment available in the industry, which helps ensure the work is done efficiently and safely. We enthusiastically recommend Kerwin Tree Service!

Brad Wright
Mar 6, 2020

Best tree service in Southern Maryland! The owner Bill and his crew took down a large dead oak that was endangering my home as well as 3 large pine trees that were "widow makers". It took them about 4 hours, they had all of the right equipment including a large crane and a spider lift. They hauled everything away, ground the stumps a left my yard in better condition than when they arrived. Super happy with the results and at a price that I thought was very reasonable, and they are fully insured which gave me the piece of mind that if anything went wrong my property was covered. I would recommend Kerwin Tree Service to anyone!

Brad knipmeyer
Dec 28, 2019

Pleasure doing business with Mr Kerwin, he returned my initial call promptly and did a great job pruning the trees on my property.

Jim Brown
Jul 31, 2019

Bill and his crew showed up and in a few short hours removed one very large oak tree and a few smaller trees. Every member of the crew was very professional and took steps to treat my property with respect. Once complete, they cleaned up and it did not look like they had ever been there with the exception of a few trees gone! Highly recommend their services!!!!!

Linda Chaney
Jun 6, 2019

While they did a good job of removing the tree branches a $35.00 finch feeder of mine turned up missing after the crew left. Unsure of what happened to it I texted twice to have crew leader ask workers if they knew anything regarding this. Consequently the texts were not answered.
Bad way to run a business

Sojourner 23
Nov 27, 2018

We’re very pleased with the job done by Bill and his crew of Kerwin Tree Service in removing several trees from our inaccessible sloping backyard. Prompt, affordable, professional, knowledgeable are just a few of the many positive adjectives to describe this man and the way he runs his business. Bill and his crew are an impressive team and their systematic approach to work is brilliant. Bill’s leadership definitely is reflected by his crew who are equally dedicated to doing a great job in the safest way possible. We would definitely use Kerwin Tree Service for any future needs and highly recommend them!

Steven Mekus
Nov 18, 2018

Kerwin and crew did an outstanding job. They were professional and courteous throughout the entire process of removing six large trees. They left the place nicer than it was prior to starting the job. GREAT JOB!!! I would highly recommend them to anyone.

Amber Wood
Oct 18, 2018

I called Mr. Kerwin first thing this morning to rescue my cat from 30 feet up a tree and he was there within an hour. The cat had actually found her way down (after being up there for 36 hrs) while he was en route which annoyed me but Mr. Kerwin was very understanding and super nice about it. Bottom line...I will not hesitate to call Mr. Kerwin for tree services in the future and highly recommend him as he made an unpleasant predicament much easier to deal with!!! Thank you so much!!!

Liz Passarelli
Oct 12, 2018

Awesome service! After last night's storm I lost a massive Bradford pear in the front yard. They were here this morning and removed everything including the remainder of the tree trunks and branches. Also ground the stumps. Cleanup was great. I would not hesitate to call upon them in the future. Made a bad experience much better by their quick response and attentiveness.

Liz Passarelli

Ron Throneberry
Aug 31, 2018

So impressed with how professional and transparent Kerwin Tree Service is about the whole process from assessing the situation to cleanup when all the work is done.

Hank Davison
Mar 3, 2018

We called Kerwin Tree Service this morning following the big winds of 2018 Within an hour he called us back and within 30 minutes he was here and scoped out the large tree that had fallen against our house Two hours later his trucks arrived and an hour later the problem was totally gone! I had worried it might take a couple weeks before this could be resolved because of all the trees down in the county His crew was fast, efficient, couldn't have been nicer Two large machines (one a 60 foot crane) rolled across our lawn and there was NO damage done to the lawn! The crew knew exactly what to do and within an hour the tree was down, the wood and debris piled out of the way and the lawn cleaned up They more then met our hopes and I wish I could give them more than 5 stars!

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137 locals recently requested a quote
  • 44199 Medleys Neck Rd, Leonardtown, MD 20650
  • Commercial Roofing
  • Industrial Roofing
  • Licensed & Insured
  • Locally Owned & Operated
  • Warranties Offered
Hours
Mon7:30 AM - 9:00 PM
Tue7:30 AM - 9:00 PM
Wed7:30 AM - 9:00 PM
Thu7:30 AM - 9:00 PM
Fri7:30 AM - 9:00 PM
Sat7:30 AM - 9:00 PM
Sun7:30 AM - 9:00 PM

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