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.
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.
Proudly Based in ,
Stop by, call, or book online — we're always nearby when you need us.
Phone
+12037060743Hours
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.