Top 3 Outdoor Upgrades Before Winter Hits

When the temperature starts to drop, most homeowners focus on indoor maintenance and forget that outdoor spaces need attention too. The months leading up to winter are crucial for protecting your property from harsh weather. Frozen soil, moisture buildup, and heavy snow can cause serious damage if decks, fences, and landscapes aren’t ready for the cold.
Investing in outdoor upgrades before winter is all about long-term value and safety. With proper care and the right improvements, you can save on spring repairs, prevent structural wear, and enhance your property’s curb appeal year-round.
Related Article: The Benefits of Building a Deck
1. Restore and Protect Your Deck
Your deck faces constant exposure to the elements. Sun, rain, and falling temperatures all affect its structure and finish. By the time autumn arrives, small cracks or fading stains are signs that your deck needs attention. Early maintenance prevents water damage, rot, and costly repairs later on.
A complete deck restoration includes cleaning, sanding, staining, and sealing. Power washing removes debris and mildew, while sanding smooths out rough areas. A high-quality stain enhances the wood’s natural tone and provides a waterproof barrier. Sealing keeps moisture out and protects against snow and ice.
If your deck shows loose boards or shifting posts, it might be time to upgrade rather than patch. Green Side Up Contracting’s team can assess the structure and recommend improvements in deck design and installation to meet both style and safety needs. Our people can also reinforce framing or replace outdated materials with modern, durable options like composite decking, which handles extreme temperatures with ease.
Pro tip: Schedule deck work in early fall, when temperatures are cool but not freezing. This allows finishes to dry properly and gives you time to enjoy the space before winter fully sets in.
A well-maintained deck means it stays ready for next year’s patio season without warping, cracking, or fading.
Related Article: Preparing Your Deck for Winter: Checklist

2. Reinforce and Repair Fences
A sturdy fence does more than mark boundaries; it shields your property from strong winds and drifting snow. However, worn-out posts or damaged panels can collapse under pressure when winter storms arrive. Inspecting and repairing your fence now saves you from dealing with costly replacements in the spring.
Begin by walking your fence line and checking for rotted posts, cracked panels, and rusted hardware. Tighten or replace loose screws, and if any sections lean or sag, have them reset before frost settles in. For fences that show widespread wear, this is the ideal season for a complete fence installation using materials that can withstand Toronto’s freezing conditions.
Top options to consider:
- Vinyl fencing: Resistant to moisture and cracking, making it ideal for snowy and rainy months.
- Composite fencing: Combines the look of natural wood with the durability of engineered materials, offering minimal upkeep.
- Pressure-treated wood fencing: Affordable, classic, and easy to customize with stains or paints for added weather protection.
- Aluminum fencing: Lightweight yet exceptionally strong, it resists rust and corrosion—perfect for homeowners who want a sleek, modern appearance with long-lasting performance.
Green Side Up Contracting can also design custom fencing that complements your home’s style, from tall privacy panels and lattice tops to contemporary horizontal slats.
Pro tip: Apply a fresh coat of paint or weather-resistant sealant before winter. It not only enhances appearance but also creates a strong barrier against moisture and UV exposure.
Related Article: How Long Does an Aluminum Fence Last

3. Refresh Your Landscaping and Drainage
Landscaping might be the last thing on your mind before winter, but this is when preparation matters most. Proper landscape maintenance keeps your outdoor space tidy, healthy, and ready to bounce back in spring.
Start with a thorough cleanup. Rake fallen leaves, remove debris, and aerate the soil to prevent waterlogging. Trim shrubs and trees to reduce the risk of broken branches under snow weight. Mulching garden beds helps regulate soil temperature and protect plant roots from frost.
If your yard has drainage issues, fall is the time to fix them. Standing water or improper slope can lead to ice buildup, soil erosion, and damage to walkways. Installing a landscape and hardscape solution—like stone borders, permeable pavers, or retaining walls—can redirect runoff while improving the property’s appearance.
Pro tip: Shut down your irrigation system before the first freeze. Emptying pipes and valves prevents cracks caused by expanding ice, saving you from spring plumbing repairs.
Well-planned landscaping is more than just visual appeal; it’s a defence system against winter wear. When done right, it keeps your property looking cared for even under a blanket of snow.

Pre-Winter Planning Checklist
Before the first snowfall, take a few hours to inspect and prepare your outdoor features:
- Check decks for loose nails, soft spots, or exposed wood.
- Clean and seal wooden surfaces for weatherproofing.
- Inspect fences for rot or shifting posts.
- Trim branches that could snap under snow.
- Add mulch to flower beds for insulation.
- Clear gutters and direct downspouts away from your foundation.
These small tasks can make a major difference in your property’s resilience through winter.
Related Article: 10 Ideas for Increasing Your Property’s Curb Appeal in Toronto
Why Early Upgrades Matter
Delaying outdoor maintenance can lead to expensive spring repairs. Freezing temperatures cause materials to contract, leading to cracks and splits. Moisture seeps into untreated wood and concrete, creating long-term damage. Completing outdoor upgrades before winter ensures every structure can withstand seasonal stress.
More importantly, these projects enhance your property’s year-round value. Whether you plan to stay for years or sell in the future, well-maintained exteriors leave a lasting impression on potential buyers.
Partner With Green Side Up Contracting
Green Side Up Contracting is a trusted name for deck restoration, fence installation, and landscape services across the Greater Toronto Area and York Region. Our professionals deliver craftsmanship that blends quality, style, and long-term durability.
We provide free consultations to help homeowners prioritize upgrades based on condition, budget, and seasonal timing. Whether you’re repairing a deck, rebuilding a fence, or preparing your landscape for the frost, we ensure every project adds value and protection.
Get your outdoor space ready before the snow arrives. Book your consultation with Green Side Up Contracting today and enjoy peace of mind all winter long.
Frequently Asked Questions
1. What month should I start outdoor upgrades before winter?
Late September to early November is ideal in the GTA. The weather at this time is still mild enough for construction and sealing materials to set properly.
2. How do I know if my deck needs restoration or replacement?
If you notice sagging, deep cracks, or structural instability, it’s best to consult a professional for a full inspection. Minor surface wear can often be restored.
3. Are composite decks better for winter durability?
Yes. Composite materials resist moisture, don’t splinter, and maintain colour despite snow and ice exposure, making them a smart investment.
4. Can new fences be installed in cold weather?
Light frost is manageable, but frozen ground makes installation difficult. Scheduling before consistent freezing ensures stable post placement.
5. How does landscaping help with winter protection?
Proper drainage, mulching, and pruning prevent plant death, soil erosion, and ice buildup, ensuring your landscape stays healthy until spring.
6. Do outdoor upgrades increase property resale value?
Absolutely. Well-maintained decks, fences, and landscapes enhance curb appeal, signalling quality upkeep and boosting market value.
7. Does Green Side Up Contracting offer winter maintenance?We provide year-round services, including commercial snow removal, deck care, and landscape maintenance for residential and commercial clients.