09/26/2026
10 Mistakes Property Owners Make When Preparing for Winter
Winter preparation is one of those jobs that is easy to put off until the temperature drops, the leaves are gone, and the first real snowfall is already on the way.
By then, some of the easiest preventative jobs become harder, more expensive, or simply impossible to do properly until spring.
Here are 10 common mistakes property owners make when getting ready for winter — and what to do instead.
1. Waiting Until the First Snowfall
One of the biggest mistakes is waiting until winter actually arrives before thinking about winter maintenance.
Snow-removal routes can fill up, outdoor repairs become harder in cold weather, and fall cleanup jobs are much easier before the ground freezes.
The better approach is to start preparing in early fall and have your winter service arrangements in place well before the first major storm.
2. Leaving Leaves and Debris on the Lawn
A heavy layer of wet leaves can trap moisture against the grass and create problems underneath the snow.
Leaves can also clog drains, collect around foundations, and make walkways slippery.
A proper fall cleanup should include removing excess leaves, branches, and other yard debris before winter sets in.
3. Skipping the Final Lawn Cut
Many property owners simply stop cutting the lawn when temperatures cool down.
Giving the lawn a final cut before winter helps leave the property neat and reduces long, matted grass sitting under snow for several months.
The goal isn’t to scalp the lawn — just leave it properly maintained before dormancy.
4. Forgetting About Garden Beds
Garden beds often get ignored once summer flowers have finished.
Dead annuals, fallen leaves, weeds, and damaged plant material can build up quickly.
A fall garden cleanup is a good opportunity to remove debris, tidy beds, prune where appropriate, and prepare the property for spring.
5. Not Checking Gutters and Drainage
Water needs somewhere to go during fall rain, winter thaws, and spring melt.
Clogged gutters, blocked downspouts, or poor drainage can cause water to collect where you don’t want it.
Before winter, check that gutters and drainage areas are clear and that water is being directed away from the home wherever possible.
6. Leaving Outdoor Items in Snow-Clearing Areas
Garden decorations, extension cords, toys, hoses, planters, edging, landscape lights, and other objects can disappear completely after a heavy snowfall.
That creates a problem for both the homeowner and the snow-removal contractor.
Remove what you can and clearly mark permanent objects that may become hidden once snow begins accumulating.
7. Not Planning Where Snow Will Go
Snow takes up a lot of space over the course of a Canadian winter.
A pile that looks small in December can become a major obstacle by February.
Think ahead about where snow can safely be stored without blocking visibility, drainage, walkways, entrances, or neighbouring properties.
8. Ignoring Small Property Repairs
A loose step, damaged walkway, broken fence section, uneven paving stone, or deteriorating asphalt may become much harder to see once covered by snow.
Small problems can also get worse through repeated freezing and thawing.
Fall is a good time to identify obvious hazards and repair what can reasonably be handled before winter.
9. Assuming Snow Removal Includes Everything
Not every winter contract covers the same areas.
Some agreements may cover only the driveway, while walkways, stairs, porches, entrances, windrows, or ice management may be separate.
Read your contract carefully and make sure the areas you expect to be serviced are actually listed.
Clear expectations before winter help avoid misunderstandings during the first storm.
10. Choosing a Contractor Without Doing Your Homework
Price matters, but it shouldn’t be the only consideration.
Before hiring a property maintenance or snow-removal company, ask about insurance, written contracts, service areas, communication, equipment, and what happens during major storms.
A professional contractor should be able to clearly explain what you are paying for and what you can expect throughout the season.
A Little Fall Preparation Goes a Long Way
Preparing your property for winter doesn’t have to happen all at once.
A few preventative jobs in the fall can make the property safer, cleaner, and easier to maintain once snow and freezing temperatures arrive.
At A&J Property Service, we help homeowners throughout Georgina prepare their properties for the changing seasons with fall cleanups, lawn and garden maintenance, and seasonal snow removal.
If there’s something on your winter-prep list you’d rather not tackle yourself, give us a call or send us a message.
A&J Property Service
We Care For Your Property Like It’s Our Own.
Call or Text: 289-763-6112
Cell/Text: 289-763-8370
Email: [email protected]
Website: ajpropertyservice.com
