Fall Maintenance Checklist for Homeowners & Associations

As the summer heat gives way to cooler autumn days, September is the perfect time for homeowners and associations to prepare their properties for the colder months ahead. Taking care of some simpler maintenance items now can help avoid costly repairs in the future, improve safety, and keep your home, rental property or Association community looking its best throughout the season. Ongoing maintenance is one of the most important things one can do to preserve property values.

Here’s a practical fall maintenance checklist for self-managed landlords, homeowners and HOA Associations to follow:

Homeowners and Landlords

1. HVAC System Service

Maintenance and spot-checks help ensure heat will function properly in the coming winter months. For landlords, scheduling an inspection can eliminate a costly and inconvenient maintenance call from a tenant.

• Consider scheduling a professional inspection of your systems.

• Change your HVAC filter(s).

• Perform basic maintenance on a boiler

• Perform a visual check on water heater.

2. Gutters & Downspouts, Grading

Standing water and the freeze-thaw cycle in Northern climates can wreak havoc on a property if not properly directed away from the structure.

• Clean leaves and debris before fall rains and winter snow cause clogs.

• Check that downspouts direct water away from the foundation.

• Check for any low spots near the foundation where water can collect and add dirt. Bags of dirt are usually on sale at the local hardware store as they clear out inventory from the outdoor landscaping area.

3. Windows & Doors

Windows and doors that don't seal properly are typically the biggest culprit for loss of heat.

• Seal gaps with weatherstripping or caulk to improve energy efficiency.

• Consider storm windows if your home is prone to drafts.

• Use plastic film on windows where appropriate.

4. Outdoor Landscaping

Fall is a great time to over-seed. The cooler weather helps with outdoor work. Look for areas that collect water. Any standing water will freeze and expand.

• Trim trees and bushes to prevent branches from breaking under snow. See our prior blog on What HOA Associations Should Consider Regarding Trees for more information.

• Consider aerating and over-seeding lawns for healthy growth in spring.

• If you placed dirt in low-grade areas near the foundation, now is the perfect time to put grass seed.

5. Safety Check

Having a good understanding of what to do in an emergency is never a bad thing. Be prepared!

• Test smoke and carbon monoxide detectors in the home. Replace with 10-year alarms which come in smoke only, or both smoke and carbon monoxide.

• Review your fire escape plan with family members.

For Associations (Community Owners, HOA & Condo Boards)

1. Common Area Inspections

Remember, Associations are typically not-for-profit communities and run by volunteers so everyone can participate to offer insight and a bit of "elbow grease" to help make the Association look nice. Perhaps plan a community fall picnic or BBQ and ask HOA members to volunteer an afternoon to help do light tasks?

• Walk the property to check sidewalks, parking lots, lighting, fences and signage.

• Schedule any absolutely necessary repairs before winter weather worsens conditions.

• Be familiar with troublesome areas for snow plows, etc. Make sure they are marked accordingly.

• Make sure garden hoses are collected, drained and stored indoors and out of sight.

2. Seasonal Vendor Contracts

Winter brings freezing temperatures and any areas with water are susceptible to the freeze-thaw cycle. Prepare any areas to minimize or eliminate damage. Make sure gutters are clean, etc.

• Confirm contracts for snow removal, landscaping, and seasonal clean-up.

• Confirm contracts for pond pumps, pool equipment, and any winter-sensitive areas.

• Ensure vendors are properly insured and ready to go.

3. Roof & Building Maintenance

How many years has the existing roof been protecting the structure?

• Visually inspect roofs, gutters, and siding for signs of wear and tear.

• Plan repairs proactively to avoid leaks and emergency calls later.

• Schedule a spring inspection if shingles, flashing areas are needing attention.

• Check for tripping hazards due to lifted concrete, etc. With snow and ice coverings, these hazards could pose additional problems.

4. Budget & Reserves

The reserve study is a living document. Planning should be adjusted with changes to inflation and any reserve expenditures that may have been experienced. When was the last time the Board has reviewed reserve budgeting?

• Fall is an ideal time to review your association’s financial health.

• Evaluate next year’s budget needs and set aside reserves for big projects.

5. Community Communication

A timely reminder or checklist for residents can be helpful. HOA boards should ask for feedback periodically.

• Send a seasonal reminder email or newsletter to residents.

• Highlight important rules, safety tips, and upcoming fall events.

The Bottom Line

Whether you’re maintaining your personal home, rental property or overseeing a community, the fall season in the Chicago area is the time to be proactive. Taking these steps in September helps ensure a smooth, stress-free transition into winter and protects both property values, resident satisfaction and peace of mind.

By tackling maintenance early, homeowners, tenants and HOA Associations alike can save money, reduce risks, and keep their communities safe and welcoming year-round.