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Yes, you can install a trench drain if you already have concrete in your yard or garden. While it can complicate some aspects of the job and slightly run up the cost, it is doable. Residential trench drains can be easily retrofitted to outdoor areas with concrete without having to remove excessive amounts of your patio, pool area, or decorative walkways.

You can dig 60 to 80 linear feet by hand per day depending on the depth. Digging a 100-foot trench by hand will take you two work days, but it can take longer if you have heavy or rocky soil. If you’re digging a deep trench or one that’s over 100 feet, consider renting a mechanical trencher, such as a walk-behind or ride-on, or calling a pro for help. 

Yes, most services include site leveling and foundation work. Confirm with your contractor for specifics.

To drill a shallow well, you may be able to use a drive well point. This is a tapered point that is driven into the ground. A drill bit at the end of PVC pipe may be another option to consider. A lot of the cost depends on what tools are available near you.