Water is a property's biggest enemy. A blocked gutter can go unnoticed through a dry September, and then a few weeks of rain can turn it into a damp patch on an upstairs wall. Winter tends to expose small faults, especially in a property that has been empty between tenancies. October is a sensible time to walk round your home, test the heating and arrange any jobs that need a professional before the weather makes them urgent.
At Squires Estates, we've worked across Finchley, Hendon and Mill Hill since 2004. We're an independent agency with a dedicated property management team, and our Mill Hill office is a 2025–2026 British Property Awards Gold Winner for lettings in NW7. Our local knowledge and property management experience help landlords look after their properties throughout the year, including the maintenance jobs that winter brings.
Start with the roof and guttering
A top down check of the property is a good place to start. Look for slipped tiles from ground level and gutters that are overflowing or have come away from the wall. Water staining beneath the roofline needs attention even if the room inside still feels dry. The Met Office’s winter property advice recommends checking the roof and clearing guttering, as fallen leaves can cause water to back up.
Book a suitable contractor for any work at height. In a converted house or block of flats, work out who is responsible for the roof and communal drainage before arranging repairs. The freeholder or managing agent may need to deal with them. Take photographs of anything concerning so you can explain the problem clearly and see whether it changes after the next spell of heavy rain.
Give the heating a proper check
Run the heating before you really need it. Check whether rooms warm up as expected and whether the controls are straightforward to use. If the boiler is due for a service, arrange it with a suitably qualified engineer; you can check a gas engineer’s registration. A boiler service and a landlord's gas safety check are different, so make sure you know which appointment you are booking.
Tenants should know how to use the heating and who to contact if it fails. A brief set of instructions next to the controls can prevent confusion when a new tenant moves in. Report repeated pressure loss, leaks or unusual noises to the engineer rather than repeatedly resetting the appliance and hoping the fault disappears.
Protect pipes
Find the internal stopcock and make sure it is accessible. Knowing where to turn off the water is useful if a leak starts.
Check exposed pipework in unheated spaces, including the loft and garage, and ask a plumber about suitable insulation where it is missing.
If the property will be empty for any period, check the insurer's conditions before deciding what to do with the heating or water supply. Requirements can vary depending on how long the property will be empty.
Agree suitable frost protection with your plumber or heating engineer, and arrange checks during cold weather. Keep a record of visits and any work carried out.
Investigate damp rather than covering it up
English Housing Survey’s housing quality findings found damp problems in 10% of private rented homes in England in 2024. That national figure is a reminder to investigate problems early. While it is not a measure of conditions in Finchley or Hendon, a persistent musty smell, peeling wallpaper or a stain that returns after rain needs more than another coat of paint.
Ask a damp specialist to take a look. Condensation, a plumbing leak and water entering through the building will need different fixes. Check that extractor fans work and that ventilation openings are clear. If tenants report mould, arrange an assessment quickly and keep them updated. Treating it as a decorating issue, or assuming their habits are responsible without investigating, can leave the underlying fault unresolved.
Check the outside spaces too
Loose fence panels, an unsecured shed door or a slippery path can become a problem once the wind and rain arrive. Secure garden furniture, clear leaves from paths and check that outdoor lighting works. Have damaged trees assessed by a qualified arborist, particularly where branches overhang the building or a neighbour's property.
If the property is a flat, check the shared access routes and report any defects to the responsible party. Photograph the condition of the garden and boundaries as well. If the property is occupied, make sure you agree on access with the tenants in advance.
Make reporting repairs easy
Give your tenants an easy way to report issues and explain what to do outside office hours. Ask for photographs, but make sure urgent problems receive a prompt response.
Government guidance on landlord responsibilities says rented homes should be kept safe and free from health hazards. Routine winter preparation supports those responsibilities, but it does not replace required safety checks.
Keep a maintenance record, including the date a problem was reported, the person instructed to resolve the issue and the outcome. This will make follow up easier and helps you spot recurring issues. If a repair needs another visit, tell the tenant what is happening rather than leaving them to chase for an update.
Get your property ready for the colder months
A little planning in October gives you time to get quotes and arrange access before a problem disrupts someone's home. Our property management service supports landlords across Finchley, Hendon and Mill Hill with maintenance and day-to-day tenancy matters. If you would like help looking after your rental this winter, speak to our lettings teamabout your property and the support you need.
Share this article
Sign up for our newsletter
Subscribe to receive the latest property market information to your inbox, full of market knowledge and tips for your home.
You may unsubscribe at any time. See our Privacy Policy.

