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Annual Home Maintenance Checklist to Keep Your Property Value Up

Jerry Goodwin December 12, 2025


When you own a home, staying ahead of maintenance makes a huge difference in how your property performs over time. I talk with clients across Chicago who want simple ways to protect their investment without feeling overwhelmed. Whether you’re caring for a condo in Streeterville or a classic bungalow in Portage Park, following a consistent home maintenance checklist helps you avoid costly surprises. I’m sharing the steps I personally recommend to keep your home running smoothly year after year.

Key Takeaways

  • A structured home maintenance checklist helps preserve long-term value.
  • Seasonal care prevents issues that become expensive repairs.
  • Small updates throughout the year make your home more enjoyable to live in.
  • Consistent upkeep improves resale appeal in competitive Chicago neighborhoods.

Start With an Annual Whole-Home Review

I always suggest beginning each year with a full check of your property’s systems and surfaces. This helps you understand what needs attention before small issues start affecting value.

Why This Review Matters

  • It helps you catch early signs of wear or damage.
  • It gives you a clear understanding of your home’s current condition.
  • It helps you plan your yearly maintenance budget.

What I Recommend Checking First

  • Walk the exterior and look for cracks, aging trim, or loose materials.
  • Review interior surfaces for moisture spots or uneven flooring.
  • Test outlets, switches, and essential appliances.
  • Note anything that may need a contractor’s opinion.

Winter: Protecting Your Home From Chicago’s Cold

Chicago winters can be tough on your home. I remind clients that cold weather is when preventative steps matter most.

Why Winter Prep Helps

  • Protects your home from freeze-related issues.
  • Keeps heating costs manageable.
  • Reduces strain on your home’s major systems.

Key Tasks I Suggest Each Winter

  • Change furnace filters to improve airflow and efficiency.
  • Check windows for drafts and reseal if needed.
  • Inspect attic insulation to maintain stable indoor temperatures.
  • Test smoke and carbon monoxide detectors and replace batteries.

Spring: Refresh and Repair After the Freeze

Spring is the perfect time to reset after winter. I often walk clients through simple steps that prepare their home for warmer weather.

Why Spring Tasks Matter

  • Helps you address any damage from snow and ice.
  • Prepares outdoor spaces for full use.
  • Supports overall property value as the selling season begins.

Your Spring Home Maintenance Checklist

  • Clean gutters to improve water flow during spring rains.
  • Look for damage along the roofline, especially on older Chicago homes.
  • Power wash exterior surfaces to remove winter buildup.
  • Inspect decks, patios, and balconies for loose boards or wear.

Summer: Focus on Outdoor Living and Energy Efficiency

Summer makes it easier to identify improvements that benefit both comfort and property value. I help homeowners focus on updates that make their space more enjoyable.

How Summer Care Supports Value

  • Enhances your home’s curb appeal.
  • Improves energy efficiency during peak temperatures.
  • Creates long-term savings through preventative updates.

Smart Summer Tasks to Include

  • Service your air conditioning unit before peak use.
  • Refresh landscaping to enhance first impressions.
  • Inspect fences, railings, and exterior stairs for stability.
  • Touch up paint to protect siding and trim from sun exposure.

Fall: Prepare Your Home for the Coming Cold

Fall is one of the best times to handle tasks that protect your home through winter. I often help clients prioritize seasonal updates that make the colder months easier.

Why Fall Preparation Is Important

  • Reduces the impact of harsh winter temperatures.
  • Prevents damage from snow and ice buildup.
  • Keeps your home comfortable and efficient.

Essential Fall Home Maintenance Checklist Items

  • Clean and store outdoor furniture.
  • Inspect the roof for loose shingles or worn flashing.
  • Drain and store garden hoses to prevent cracking.
  • Schedule heating system maintenance before temperatures drop.

Indoor Maintenance That Helps Year-Round

Beyond seasonal updates, ongoing indoor care keeps your home feeling fresh and increases long-term value. I suggest reviewing these tasks periodically throughout the year.

Why Year-Round Indoor Care Helps

  • Keeps your home functioning smoothly.
  • Supports a clean, comfortable living environment.
  • Reduces the need for large repairs later.

Ongoing Tasks Worth Prioritizing

  • Clean dryer vents to improve airflow and reduce wear.
  • Deep clean high-use areas like kitchens and bathrooms.
  • Check plumbing fixtures for slow drips or buildup.
  • Replace older lighting with efficient LED options.

Exterior Care That Protects Value Over Time

Chicago homes benefit from consistent exterior maintenance, especially in neighborhoods with older architecture. I guide clients through outdoor care that keeps their property looking its best.

Why Exterior Care Matters

  • Enhances curb appeal in competitive markets.
  • Extends the life of your home’s exterior materials.
  • Helps you identify issues early before they escalate.

Tasks to Prioritize Outside

  • Trim overgrown shrubs and trees.
  • Inspect siding for damage or wear.
  • Check porch steps and railings for movement.
  • Keep walkways clean and clear of buildup.

FAQs

How often should I complete a full home maintenance checklist?

I recommend reviewing everything once a year and revisiting seasonal tasks every few months. This keeps you ahead of issues and protects your long-term property value.

Which tasks add the most value long-term?

I usually see the biggest impact from HVAC maintenance, exterior care, and keeping your home’s systems updated. These areas affect both daily comfort and resale appeal.

Can I handle most maintenance myself?

Many tasks are homeowner-friendly, but some — like roof evaluations or major system servicing — benefit from a professional. I’m always happy to connect clients with trusted local experts.

Contact Jerry Goodwin Today

If you want a personalized plan for your home, I’d be glad to help you understand which tasks matter most based on your property and your long-term goals. I work with homeowners across Chicago who want to protect their investment with clarity and confidence.

Reach out to me at Jerry Goodwin, and I’ll help you build a maintenance strategy that keeps your home running smoothly, boosts long-term value, and supports your lifestyle year after year. Whether you’re caring for a condo, a single-family home, or an investment property, I’m here to make maintenance feel manageable and worthwhile.



Work With Jerry

Jerry helps his clients consider the financial goals and implications of investment ownership. Being able to show clients how real estate can build their wealth is among his greatest joys, and it is a thrill giving them keys at the end of the day.