The Calendar Group

Hiring guide

Property Caretaker

Eyes and hands on a property you're not always at — systems checked, grounds kept, and the house ready whenever you are.

Begin a search for this role(877) 404-5290

Compensation

$65,000–$110,000 base

Typical base compensation, major U.S. markets, 2026. Scope, travel, and household complexity move the range.

We advise on offer structure — schedule, housing, benefits, bonus — before every search. The right package is how great people stay.

A property caretaker watches over a home that isn't lived in year-round. They walk the house weekly or daily, run the water, test the systems, clear the storm debris, and meet every trade at the door. When a pipe weeps behind a wall in February, it is found in February — not in June, three inches into the floorboards.

The role is the difference between owning a second home and worrying about one. Caretakers handle the unglamorous essentials — gutters, generators, pest control, snow — and prepare the property so your arrival is an arrival, not a project: heat up, fridge stocked, boat in the water, beds made.

Some caretakers live on site in separate quarters; others live nearby and keep a schedule of visits. The right structure depends on the property's remoteness, its systems, and how often you come. Either way, you are hiring vigilance and honesty — someone who reports the small problem while it is still small.

What the role owns

  • Conduct regular property inspections and systems checks
  • Maintain grounds, landscaping, and seasonal exterior work
  • Handle minor repairs and supervise trades on site
  • Open and close the property for seasons and family visits
  • Monitor security, alarms, and weather events
  • Manage pools, docks, boats, or equipment as the property requires
  • Keep vehicles serviced, fueled, and ready
  • Report conditions and expenses to the principal or estate manager

What great looks like

A great caretaker inspects on a written route — same rooms, same valves, same roofline — so nothing is skipped because nothing seemed wrong.

They photograph and log what they find, and their monthly report reads like the property's medical chart.

They know the house's systems cold: where every shutoff is, what the generator needs, which breaker trips in a storm.

They are honest about small failures, including their own — the caretaker who reports the scratch they made is the one you keep for a decade.

Before your arrival, they think like a guest: not just is it working, but is it welcoming.

Interview questions worth asking

  1. 01

    Walk me through your inspection routine at your last property — what did you check, and how often?

  2. 02

    Tell me about a problem you caught early. What tipped you off?

  3. 03

    A nor'easter is forecast to hit the property in thirty-six hours and the family is abroad. What do you do?

  4. 04

    What can you fix yourself — plumbing, electrical, small engines — and what do you call in?

  5. 05

    How do you keep the principal informed without flooding them? Show me how you reported at your last post.

Questions

Hiring a property caretaker, answered.

How is a caretaker different from a house manager?
Occupancy. A house manager runs a home the family lives in — daily service, errands, the rhythm of an occupied residence. A caretaker stewards a property that sits empty for stretches, with a bias toward systems, grounds, and vigilance. The skills overlap, but the temperament differs: caretaking rewards self-directed people who work well in solitude and take an empty house seriously.
Live-in or live-out?
Remote properties, working land, and homes with vulnerable systems argue for live-in, usually in a cottage or apartment with its own entrance — presence deters trouble and shortens response time. Properties near town with good monitoring can be well served by a caretaker who lives locally and visits on schedule. Housing changes the compensation conversation, so settle the structure before the search.
Can one caretaker handle a large or complex property alone?
For inspection, minor repair, and coordination — yes, and that is the job. For specialized work — tree crews, roofing, marine mechanics — a good caretaker acts as your general contractor, hiring and supervising trades rather than improvising. Be wary of the candidate who claims to do everything personally; the honest ones know exactly where their competence ends.
What about a couple instead of a single caretaker?
If the property also needs interior care — housekeeping, cooking during visits, a house that feels kept rather than merely maintained — a domestic couple often fits better, with one partner inside and one out. A single caretaker suits properties where the work is chiefly exterior and mechanical. The property's needs, listed honestly, usually make the choice for you.

Begin

Looking for a property caretaker?

Tell us about the household and the role. A senior advisor — not a coordinator — will come back to you within one business day.

Held in confidence. No obligation.