Downsizing in the Driftless: A Different Kind of Move

For many homeowners in La Crosse and the surrounding Driftless Region, downsizing isn’t just a real estate decision — it’s an emotional one. You may have raised a family in your home, celebrated milestones there, and put years of care into maintaining it.

Whether you’re thinking about reducing upkeep, preparing for retirement, moving closer to family, or transitioning to a condo or assisted living community, downsizing requires a different mindset than a traditional sale.

Before you list the family home, here are 10 essential questions to ask — ones that can help you avoid surprises and feel confident about your next chapter.

1. Why Am I Downsizing Now?

Start with clarity. Are you motivated by:

• Maintenance becoming overwhelming?

• Rising property taxes or utility costs?

• A desire to travel or simplify?

• Health, mobility, or lifestyle changes?

There’s no “right” reason — but understanding why now helps guide decisions about timing, pricing, and your next move.

2. Where Do I Want to Go Next?

Downsizing isn’t just about selling — it’s about what comes after.

Common next-step options in the Driftless include:

• Smaller single-family homes

• Condos or townhomes

• Senior or 55+ communities

• Assisted or independent living

• Moving closer to children or grandchildren

Knowing whether you plan to buy, rent, or transition to a facility will shape your entire selling strategy.

3. How Much Space Do I Actually Need?

Many longtime homeowners are surprised by how much unused space they’ve accumulated.

Ask yourself:

• Which rooms are rarely used?

• How much storage do I realistically need?

• Could I live comfortably with fewer bedrooms or bathrooms?

This question helps prevent downsizing into a home that still feels “too big” — or too small.

4. What Will I Do With a Lifetime of Belongings?

This is often the hardest part.

Downsizing means deciding what to:

• Keep

• Gift to family

• Donate

• Sell

• Discard

Starting this process before listing reduces stress and makes your home easier to show. Many sellers find it helpful to work room-by-room, months ahead of time.

5. Is My Current Home Ready for the Market?

Homes that have been lovingly lived in for decades may need:

• Minor repairs

• Updates for safety or accessibility

• Decluttering and deep cleaning

The good news? Not everything needs to be fixed. A thoughtful plan focuses on what matters most to today’s buyers — without unnecessary expense.

6. How Will Downsizing Affect My Finances?

Downsizing can free up equity, but it also comes with costs:

• Moving expenses

• Taxes or fees

• HOA dues (for condos or communities)

• Healthcare or assisted living costs

Understanding the net impact — not just the sale price — is key to making a confident decision.

7. What Is the Right Timing in the La Crosse Market?

Market conditions matter, but so does your personal timeline.

Some sellers benefit from:

• Selling first, then buying

• Buying first, then selling

• Coordinating a move with a facility opening or family availability

A local strategy — especially in Driftless Region communities — can help reduce stress and avoid rushed decisions.

8. Will I Need Temporary Housing?

Depending on timing, you may need:

• Short-term rentals

• Month-to-month housing

• Staying with family briefly

Planning for this early prevents last-minute scrambling and allows for smoother transitions.

9. Who Can Help Me Through the Process?

Downsizing often involves more than a real estate agent. You may also need:

• Movers or senior-move specialists

• Estate sale or donation coordinators

• Contractors for small repairs

• Financial or legal advisors

Having a trusted local resource network can make the experience far less overwhelming.

10. Do I Want a Transaction — or a Plan?

Downsizing isn’t a quick sale. It’s a transition.

The most successful downsizers work with someone who:

• Understands emotional and logistical complexity

• Helps coordinate timing, prep, and next steps

• Communicates clearly and patiently

• Acts as a guide, not just a salesperson

Downsizing Done Thoughtfully

Downsizing in La Crosse and the Driftless Region is less about “giving things up” and more about creating space for what’s next — whether that’s freedom, flexibility, or peace of mind.

The right questions, asked early, can turn a stressful idea into a confident plan.  Julie has over a decade of experience helping people make the right choices with their homes and their biggest investments, contact her today to make a plan.