How to Choose a Caretaker for Your Nantucket Home

Start with how the relationship will work

A good caretaker relationship gives you a clear picture of your home while you are away. Before comparing proposals, define the support you need: routine oversight, seasonal preparation, vendor coordination, arrival readiness, or a more comprehensive concierge experience. Ask each prospective team to describe what a normal week of care would look like for your property.

Ask to see the reporting

Request a sample report with identifying details removed. Look for dated observations, useful photographs, changes since the previous visit, and recommendations that distinguish an urgent issue from planned maintenance. A message saying “all looks good” tells you little about what was checked or what could not be accessed.

Make responsiveness specific

Ask who your primary contact will be, how routine questions are handled, and what happens when that person is unavailable. Agree on communication expectations and an escalation process for urgent concerns. Responsiveness is easier to assess when both sides know which channel to use and what follow-up to expect.

Understand authority and accountability

Discuss spending limits, vendor selection, access arrangements, and approval requirements before work begins. Ask how estimates, invoices, and completion details are recorded. Confirm the team’s relevant insurance and any licenses required for the work it will actually perform; do not assume coordinating a trade means performing that trade.

Questions to take to your first meeting

• What does each visit cover, and how are exceptions reported?
• How will you learn and record the home’s systems?
• Who follows up when a vendor’s work is incomplete?
• What is included, and what requires a separate fee or approval?
• How are keys, access information, and homeowner preferences handled?

The Harborward approach

We bring a homeowner’s perspective to these questions. Our concierge approach combines responsive communication, systems documentation, detailed reporting, and proactive coordination. The goal is a relationship in which you understand what is happening at your home without having to chase every detail.