Excavation Contractor backed by 2026+ years of local experience

Chris Stupak Enterprises grew from a one-truck operation into a seven-truck crew built on honest work and reliable results across Connecticut. We handle drainage, excavation, site work, hardscape, and more, so you get one dependable team from start to finish. This is who we are and how we got here.

2026+

Years Serving

5

Service Areas

20+

Services Offered

2026+

Years Serving

Started with a truck,
built for the long haul

Chris Stupak Enterprises started with a mower and a truck. Six years later, we run a fleet of seven trucks and a full spread of equipment that lets us take on serious work across Connecticut. That growth did not happen by accident. It happened because we show up, do the job right, and move on to the next one.

We are a local excavation, drainage, and property maintenance company serving Oxford, Middlebury, Southbury, Newtown, Watertown, and surrounding towns in Connecticut. Our crew handles everything from small landscape installs to full site work, so property owners do not have to call five different contractors to get one project done.

Drainage is one of our core strengths. Whether you have standing water in your yard, a failing catch basin, or a basement that takes on water after every rain, we dig in and fix the problem at the source. We also handle water line and sewer line plumbing services, so underground utility work stays under one roof.

On the site work and hardscape side, we pour concrete, build retaining walls, set Belgium block, and lay small patios and walkways. We grade and topsoil yards, install gravel driveways, and clear light brush when a property needs a fresh start. If a project needs foundation work, trenching, or underground utility installation, we have the equipment and the experience to handle it.

Our dump truck service keeps jobs moving. Debris, fill, and material hauling are part of how we support both our own projects and other contractors in the area.

We answer our phone and we give straight answers. If you are in our service area and need a crew that treats your property like it matters, give us a call. Visit chrisstupakpropertymaintenance.com to see all the towns we serve, then reach out for your free estimate.

What you can count on

Real Equipment, Real Capacity

We run a full fleet of trucks and machines, so your project does not sit waiting on a backlog. From trenching to grading, we show up ready to work.

Licensed Plumbing Work

Water line and sewer line work is handled with proper licensing, keeping your project code-compliant and your property protected.

Drainage Done Right

Yard drainage, catch basins, and basement drainage are designed to move water away from your property, not just patch the symptom.

Site Work Experience

We handle foundations, trenching, and underground utilities with the equipment and field knowledge to get it done cleanly the first time.

Clean, Finished Results

Whether it is a Belgium block border, a retaining wall, or a gravel driveway, we leave the site looking finished, not just functional.

Always Reachable

We keep our lines open because property problems do not follow a schedule. Reach us any time and we will get back to you promptly.

What homeowners say.

5.0
36 Google reviews

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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 Google review · May 2023

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 Google review · May 2024

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 Google review · June 2024

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 Google review · April 2025

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 Google review · August 2024

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Hours

Free, No-Obligation Estimate

Ready to get your project off the ground?

We serve Oxford, Middlebury, Southbury, Newtown, Watertown, and more. Call (203) 706-0743 or visit chrisstupakpropertymaintenance.com to request your free estimate today.

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