CS Property Maintenance

Chris Stupak Property Maintenance services in Middlebury, CT and surrounding areas. Drainage, Excavation, Lawn Installation, and Grading are just a few of the services we offer. Reach out today to learn how we can help!

Locally Owned

Insured

CS Property Maintenance team in Middlebury, CT - people or person

About Us

Chris Stupak Property Maintenance is a full-service drainage and excavation company that is owner-operated provides quality services to residential and commercial clients in Middlebury, CT, and around. We offer a wide range of services that include drainage, excavation, lawn installation, snow removal, grading and more. We are committed to providing our clients with exceptional service and outstanding results.

What we are best at

Our Services

Ready to get started? Book an appointment today.

Get a quote

Receiving a quote is easy and only takes three simple steps

Send us a text

Chat on the phone

Receive a quote

Send us a text

We'll respond quickly to find a time that works for you to chat.

See why our customers love us

Our Best Work

See more photos

Testimonials & Reviews

Don't just take our word for it

Leave us a review on Google

Leave us a review on Facebook

Leave us a review

out of 5 stars

Chris Stupak Property Maintenance is responsible for mowing my lawn and doing Spring & Fall Clean-Up. Mowing services include weed-wacking, blowing the patios and edging garden beds. Thanks to Chris my lawn looked great all season. He is reliable and trustworthy.

Sam Watts Roxbury, CT

Google
out of 5 stars

Chris and his crew were fantastic to work with- thorough, detailed, and professional. Excellent communication. Already thinking about my next project for him...

Stephanie Pocius Greaves Roxbury, CT

Facebook
out of 5 stars

We highly recommend Chris! I called him for an estimate and he was willing to come out on a Saturday to give me one. He was very confident that he could complete a very large job. We had very overgrown weeds from my grandparent's gardens and the tenant who lived there after, never took care of them so they were as big as the house. He said he’d come the following Monday and he did. He took out the weeds and dead trees and planted some grass in the area and put down some mulch in the front. It took him two days and my yard is now useable and gorgeous!! We even hired him to cut our lawn every two weeks!

Tina Marie Roxbury, CT

Facebook
out of 5 stars

Chris and his crew were fantastic to work with- thorough, detailed, professional. Excellent communication. Already thinking about my next project for him...

Roxbury, CT

Facebook
out of 5 stars

I am happy with this service.

Home Owner

Facebook
out of 5 stars

Chris did an amazing job on my pool land excavation/regrading that included area regrading, drain pipes, retaining wall, and stone/general cleanup. Very professional, prompt and courteous. Price very fair for this quality work. Highly recommend.

William Lynn Home Owner

Google
out of 5 stars

We use Chris’s service for landscaping, and snow removal, he also installed drainage piping from back yard to front. All work is done in a timely and professional manner and the prices are reasonable

Ed G Roxbury, CT

Google
out of 5 stars

Chris and his team are professional, smart and hard working. They're easy to do business with and do a great job. They provide our lawn service and snow plowing. You never wait too long for the snow clearing and they do a pretty thorough job.

Charlie Callahan Roxbury, CT

Google
out of 5 stars

When I first spoke with Chris to figure out what we should do with our landscaping project, it was very clear that Chris knew what he was doing. When he came on site to give us a quote, he listened carefully to what we wanted to do, made some great suggestions based on his vision and experience, and then went on to do a phenomenal job. We couldn't be happier. Chris and his team were extremely professional, meticulous and thorough. Also, communication on timelines, questions or any issues that came up were handled immediately, which was refreshing. Also, Chris, being a drainage expert, noticed a cracked pipe drain issue that could have developed into a major problem if not handled right away. Chris, was honest, straightforward and helpful with the price since he was already on site. After seeing the work he and his team did on the backyard, I knew I could trust him and quite frankly, I didn't want anyone else to do the job. If you want it done right, call Chris.

Jason Webster Home Owner

Google
out of 5 stars

Chris and his crew are the best! I have asked Chris to do all kinds of special projects from removing overgrown bushes, to mortaring steps. He even did extra work at my daughter’s house-which was pretty far out of his way- and he drove his excavator all the way up within the week and did a great job. I am so happy with his professionalism- fabulous work ethic.

Lisa Osur Home Owner

Google
out of 5 stars

Snowplowing and salting driveway

Tom A Roxbury, CT

Google
out of 5 stars

I can’t say enough good about Chris and the work he & his employees did in my yard to fix a drainage problem. He was prompt, responsive, thorough & fair. He fixed the issue and left my property in good condition after the job. I highly recommended him for your drainage issues.

Kathleen McManamy Home Owner

Google
out of 5 stars

Chris did an amazing job! Thanks

Erich Home Owner

Google
out of 5 stars

I cannot say enough great things about Chris, his crew and the work they did on literally every aspect of our yard. From the routine mows and annual cleanup and now removing bushes and trees all around our property and regrading/filling in our gravel drive. Everything was clearly communicated and my expectations exceeded. Everything was cleared out, work done and even little things like moving a large rock out of care my kids might trip over. So thoughtful. Expert work. Great crew. Highly highly recommend Chris for any work you may need.

Home Owner

Facebook
out of 5 stars

Very responsive, did great job leveling my backyard

Jason Arcuri Home Owner

Google
out of 5 stars

Chris cleared a large area in my yard and it looks fantastic. Returns texts in a timely manner, on time for the job, reasonably priced. Scheduled fall cleanups with him.

Lori Ciocca Home Owner

Google

out of 5 stars

I just had Chris and his crew come out for a fall cleanup and was very happy with everything. The yard looks great. I will be using him for all yard work going forward because his communication is wonderful and the work matches.

Roxbury, CT

Facebook
out of 5 stars

I would highly recommend Chris and his team.....

Jason White Home Owner

Google
out of 5 stars

I’ve worked with Chris for quite a while now and he’s always done a great job on my lawn and accommodating my requests.

Andrew Heavens Roxbury, CT

Google
out of 5 stars

Chris and team did a great job repairing our driveway after the Augst 2024 storms in Southbury. He adjusted his schedule to both the temporary and permanent fixes asap.

Paul Carella Home Owner

Google
out of 5 stars

Chris and his crew did a great job of installing a new lawn in my backyard. They also installed decorative stone all around my patio, fence and rock garden. They built a shed pad for me as well. Chris and his crew went above and beyond what was expected. Everything was done on time and at a great price. Chris was easy to work with and made excellent suggestions throughout the process. I recommend Chris 100%.

tom paola Home Owner

Google
out of 5 stars

Chris stupak is very reliable for all the services he has done for me on all my properties from landscaping to snow removal also very flexible on his pricing. Seeram James

Seeram James Home Owner

Google
out of 5 stars

Chris is wise beyond his years and knows how to run a business properly. He’s personable and will talk you through any services you may need with transparent pricing. Clearly cares about his clients and I’m looking forward to using him for years to come.

Max Cunha Home Owner

Google
out of 5 stars

Chris and his crew were reliable. The job was done quickly and efficiently. I would highly recommend Chris Stupak.

Diane K Home Owner

Google
out of 5 stars

I had initially connected with Chris on Facebook with the intention of simply asking him about topsoil installation. However, as our conversation progressed, Chris went above and beyond by recommending not only topsoil but also hydroseeding. Throughout the entire process, Chris and his team were incredibly informative, answering all my questions and guiding me through the steps. The staff was friendly, and they completed the job on time. I wholeheartedly recommend Chris and his team for their exceptional service and professionalism.

Dat Kien Ly Home Owner

Google
out of 5 stars

Chris is great to work with. He does commercial snow plowing for me and will likely be doing lawn care in the spring at my commercial plaza. Always on top of things, excellent communication. Would recommend to anyone considering working with him!

Mike Guastaferri Roxbury, CT

Google
out of 5 stars

I have worked with Chris Stupak Property Maintenance on a few excavation projects and had them do some work for us on some of our own projects. Chris has a high attention to detail and a good work ethic. Highly recommended!

Dominic Brown Roxbury, CT

Google
out of 5 stars

Chris and his team do an awesome. Wouldn't want to go with anyone else. They were super professional and treated my home with care. Will be using them again

Christian (CJ) Febles Roxbury, CT

Google
out of 5 stars

Chris did an amazing job on my pool land excavation/regrading that included area regrading, drain pipes, retaining wall, and stone/general cleanup. Very professional, prompt and courteous. Price very fair for this quality work. Highly recommend.

Matt Lynn Home Owner

Google
out of 5 stars

Alway's on time, personable, professional and thorough. Definitely recommend using Chris and his team for all your property maintenance needs.

jay m Roxbury, CT

Google
out of 5 stars

They helped our family solve a drainage issue that no one else could solve!! Finally have the right solution and can enjoy our beautiful home after almost 3 years of stressful water situations! thanks to these guys! HIGHLY RECOMMEND!

Home Owner

Facebook
out of 5 stars

We highly recommend Chris! I called him for an estimate and he was willing to come out on a Saturday to give me one. He was very confident that he could complete the very large job. We had very over grown weeds from my grandparents gardens and the tenant who lived there after, never took care of them so they were as big as the house. He said he’d come the following Monday and he did. He took out the weeds and dead trees and planted some grass in the area and put down some mulch in the front. It took him two days and my yard is now useable and gorgeous!! We even hired him to cut our lawn every two weeks!

Roxbury, CT

Facebook

out of 5 stars

Chris and his team are excellent, they got right on an emergency Sewer main repair job and handled everything perfectly. Highly recommend!

Scott Sans Home Owner

Google
out of 5 stars

Highly recommend Chris and his crew. Very reliable and my yard looks amazing!

Home Owner

Facebook
out of 5 stars

Hope to do business with you

kerrie ford Home Owner

Google
out of 5 stars

We have used Chris's services for Spring and Fall cleanup, weekly lawn services and have added snow removal. We could not be happier with his service.

Curtis Bosco Roxbury, CT

Google
out of 5 stars

Chris and Austin are a great team. They came in and executed the plan to perfection and were extremely helpful in keeping us in the loop, advising on the project timeline as we went, and just all around great communication. Both are excellent operators, generally great people to do business with, and my wife and I are extremely happy with the pretty complex and in depth excavation and drainage project they completed for us. I would highly recommend CS to anyone looking for high end work done with solid value. Thank you guys, great job. - A happy property owner in Southbury.

Ken Sargavakian Home Owner

Google
out of 5 stars

Chris has been a blessing to my family very professional well mannered. Top notch service he has a great team and he keeps my yard looking impeccable.

Joseph Palmer Roxbury, CT

Google
out of 5 stars

Chris & his team were professional & were able to do everything in a timely manner. Will be using again

Kyle Pashley Roxbury, CT

Google
out of 5 stars

Great work and great service, 10/10. Would recommend for anything to do with property maintenance.

Austin Herb Roxbury, CT

Google
out of 5 stars

Snowplowing and salting driveway

Tom Home Owner

Google
out of 5 stars

These guys are amazing! Super professional and true experts. I was very impressed with the work and will be a customer for life!

Shakour Jarrett Home Owner

Google
out of 5 stars

Excellent machine work and the opening of our washed out driveway was a blessing. Work was completed and a great clean up. This was a very stressful time for all. Many people still with no access to roads from their properties, Chris is a great person and his word and a handshake was all it took to start our recovery. Highly recommend Chris.

Francis Bresson Home Owner

Google
out of 5 stars

Phil Dawson Home Owner

Google
out of 5 stars

Bonnie & Geoff May Home Owner

Google
out of 5 stars

Patricia Kissane Home Owner

Google
out of 5 stars

Dave Behlman Home Owner

Google
out of 5 stars

David Webster Home Owner

Google

See more reviews

FAQs

: Give us a call or send us a text at (203) 706-0743. Thanks!
: Yes, we'll always estimate the job for free. Just give us a call to get started.
: We're a customer-first company that will do whatever it takes to make sure the job is well done.
: We offer a variety of services including Drainage, Excavation, Lawn Installation, Grading, and more!

Service Areas

Proudly Serving Middlebury, Southbury, Woodbury, Watertown, Litchfield, Bethlehem, Roxbury & Surrounding Areas

CS Property Maintenance

TODO: Our properties

About Us

Our Services

Ready to get started? Book an appointment today.

Get a quote

Contact us

Our Best Work

Testimonials & Reviews

FAQs

Service Areas

Ready to get started? Book an appointment today.