The Off-Season Caretaker's Walkthrough Checklist for Nantucket Properties

The off-season on Nantucket is the part of the year nobody sees. The owners are in Boca Raton or Manhattan or Aspen. The summer rentals are dark. The fence-line beach roses have lost their leaves. And the only people walking through these eight-bedroom shingle-style houses are the caretakers, the plumbers we call when something goes wrong, and the contractor whose crew is trying to finish the addition before Memorial Day.

If you're the caretaker, the visit you make on a Tuesday in February is the only thing standing between a $40,000 frozen-pipe insurance claim and a normal opening week in May. The owner cannot see what you saw. They can only read what you wrote. So write something worth reading.

This is a field-tested off-season walkthrough checklist, organized the way an experienced caretaker actually walks a house — not the way a software product wants you to fill in a form. Use it as a reference. Adapt it to the specific property. Most importantly: record what you find as you find it.

Before you walk in: the exterior pass

Before you even unlock the door, walk the perimeter. Half the issues you'll find on an off-season visit are visible from outside.

• Roof line. Lifted shingles. Missing tabs. Ice dams forming in the valleys. Anything that wasn't there last week is something to flag.
• Gutters. Clogged with the last of November's leaves, with ice backing up behind the clog. East-facing gutters fill faster on Nantucket because of the salt air carrying grit.
• Downspouts. Are they actually clearing the foundation, or is the discharge pooling against the basement wall? Frozen pooling is how basement leaks start.
• Dryer vent and gas vent terminations. Birds, squirrels, ice. Walk past them with the back of your hand near the louver to confirm air movement.
• Window wells, bulkheads, foundation vents. Snow drifts blocking foundation vents are a humidity problem you will not see from inside.
• Exterior wood — sills, trim, sheathing. Anything that's gone soft or grown moss since the last visit gets photographed.

Houses near the water — Quidnet, Pocomo, the Cliff — get a salt-spray pass too. A quick rinse of brass and bronze door hardware in early spring saves a fortune in replacement.

The mechanical room

This is the room where the bad things happen. Walk it slowly.

• Heating system. Confirm the system is running. Listen for short cycling. Look at the oil tank level if it's an oil-fired system; many island houses are on propane and the gauge tells you whether to call for a fill.
• Boiler / furnace area. Soot streaks on a boiler face are a flue-draft issue, not a routine cleaning issue. Photograph it and call the heating contractor.
• Hot water tank. Look for any moisture at the base. Tanks fail slowly, then suddenly. A pencil-thick rust trail on the side is a warning, not just cosmetic.
• Water main and shutoff. Confirm the main is on if the house is heated, off if it's drained. Mistaking one for the other is how you get a flooded ground floor.
• Pressure tank (well systems). Tap the side. The bottom third should sound dull (water-filled), the top hollow (air-charged). All hollow means a waterlogged tank or a failed bladder. All solid means the air charge is gone.
• Pressure regulator (PRV). A drip from the relief valve is a sign of pressure creep. Water pressure on island municipal supply tends to run high; PRVs fail.
• Sump pump. Lift the float by hand. Listen for the pump to cycle. A pump that ran every 90 seconds during November storms and is now silent could be fine — or could have a stuck float.
• Backup battery / generator. Generator transfer-switch test on a schedule. Battery voltage check. Note the run hours.

If the house is winterized — drained and antifreezed — you're looking for a different pattern: any sign that the system has been re-energized, any moisture where there shouldn't be, any rodent activity in pipe penetrations.

The kitchen

• Faucets — hot and cold, both lines. Run each for 30 seconds. Listen for pressure drop or air. Check under the sink for slow drips.
• Refrigerator. Confirm temperature. Listen for the compressor cycling normally. Check the icemaker line if it's plumbed; the saddle valves on icemaker lines are notorious failure points.
• Dishwasher. Run a short cycle quarterly. Confirm fill, drain, and that the door gasket hasn't dried out and cracked.
• Disposal. Run for 5 seconds with water to keep the seals wet.
• Range and oven. Confirm pilots are lit on gas ranges, or that electric elements heat. Check the hood vent.

The reason for running things on a schedule isn't because the appliance needs the exercise — it's because the seals dry out. A dishwasher that has not seen water in five months will leak when the owners run it the first weekend back.

The bathrooms

• Every faucet and shower. Hot and cold for 30 seconds. Check for drips at handles and spouts.
• Toilets. Flush each one. Listen for the fill cycle to terminate. A toilet that runs continuously is the most common silent water-bill issue on a closed-up house.
• Drain traps. Pour a cup of water down each rarely-used drain. Dry traps are where sewer gas comes from.
• Shower pans and tile grout. Look for any cracking that wasn't there before.
• Exhaust fans. Run each for a minute. Listen for bearing noise.

The bedrooms and living spaces

This pass is more about cataloging than fixing.

• Smoke and CO detectors. Test each. Replace any that chirp. Photograph the test result.
• Windows. Walk every room and verify each window is closed and locked. The owner's housekeeper opens them in October. Sometimes one stays open all winter.
• Curtains and blinds. Note any UV damage on the south-facing rooms.
• Walls and ceilings. Look up. Water stains are easy to miss because nobody looks up. The first sign of a roof leak is usually a faint amber stain on a bedroom ceiling, fingernail-sized.

The attic and basement

• Attic. Smell it. Mold has a smell before it has a visible footprint. Look at the underside of the roof sheathing — dark streaking is a moisture problem. Check for daylight through the soffits or ridge.
• Insulation. Walked-on insulation is compressed insulation. Note any rodent runs.
• Basement. Look at the floor for any moisture trail. Smell the air. Check the dehumidifier — empty the reservoir or confirm the condensate drain is clear. A frozen condensate line means the dehumidifier is running but doing nothing.

Pest activity

• Mouse stations. Check each. Replace bait or rotate snap traps. Photograph any catches.
• Carpenter ants. Look at sill plates and the underside of any exterior wood for sawdust-like frass. Carpenter ants do not stop in winter; they slow down.
• Bats. Listen, especially in attics. Bat guano accumulating on insulation is a serious problem and an immediate call to a wildlife specialist.

What to record on every visit

Here is the part most caretakers shortchange: writing it up. The walkthrough is the easy part. The recording is what makes you trustworthy in March, when the owner's lawyer asks why a leak from January wasn't flagged.

A good off-season visit record contains:

• Date and time of the visit
• Weather at the time of the visit (matters for storm context)
• Heat status — set point, actual, any deviation
• Water status — on/off, pressure, any leaks
• Issues found — categorized as urgent, monitor, or cosmetic
• Maintenance performed — what you actually did
• Photos — at minimum: the thermostat reading, the boiler, the basement, any issue
• Recommendations — anything the owner needs to authorize or the next vendor needs to address

This is also where Vocalog fits, candidly. Most caretakers who use it record their walkthrough as a voice memo and Vocalog produces a structured visit report — categorized, photographed, dated — that they forward to the owner before they're back in the truck. It's faster than typing on a phone and produces a more thorough record than handwritten notes.

But the format matters more than the tool. A handwritten log book that you actually fill in beats a slick app that you skip. The point is consistency.

A note on storm visits

Off-season Nantucket means nor'easters. Storm visits are a different category from routine visits and need their own framing:

• Pre-storm: outdoor furniture stowed, anything loose secured, generator fueled, water main verified, owner notified.
• During storm: drive-by if conditions allow, photograph any visible damage, monitor for power outages.
• Post-storm: full walkthrough within 24 hours of conditions clearing, with explicit attention to roof, gutters, exterior trim, downed limbs, water intrusion, basement, generator hours run, fuel level after the run.

Storm visits are also when you discover the issues that the routine visits don't catch — flashings that pulled away under wind load, shingles that lifted, a single dormer that took the brunt of an east-northeast direction.

The season in March

The point of the off-season walkthrough is not the walkthrough itself. The point is what the owner gets to read in March, when they're deciding whether to keep working with you for another year. A house that opens up cleanly in May, with a documented record of every issue caught and addressed during the winter, is the proof that you're worth the retainer.

Write it up. Photograph it. Send it. Do that every visit, every week, every month — and the owner will trust you the way the best Nantucket caretakers have always been trusted: not because they say the right things, but because they have the record.