How Do You Know When It’s Time to Move?

3 Smart Things to Consider Before Your Next Chapter

For many homeowners—especially those 50 and over—the question “Should we move?” isn’t just about real estate. It’s about lifestyle, financial confidence, health, and staying connected to the people and activities that matter most.

There’s rarely one single moment that makes the answer obvious. Instead, clarity usually comes from stepping back and looking at the bigger picture. If you’re beginning to wonder whether your current home still fits your life, these three considerations can help guide your decision.

1. Your Finances: Affordability, Equity, and Cash Flow

Housing is often the largest expense in midlife and retirement. Evaluating how your home impacts your finances today—and tomorrow—is a powerful starting point.

Can You Afford to Stay, or Do You Need the Equity?

Many homeowners find themselves house-rich but cash-poor. While their home has appreciated significantly, a large portion of their net worth is tied up in equity rather than accessible cash. The key question becomes:
Is your home supporting your retirement goals—or limiting them?

Cost of Living: Taxes, Utilities, and Insurance

Where you live matters more than ever.

  • Are you in a high-tax state with elevated income, property, or sales taxes?
  • Would relocating to a state with lower taxes or senior property tax exemptions improve your monthly cash flow?
  • Utilities and insurance also vary widely, especially in areas prone to extreme weather.

A move can significantly reduce ongoing expenses and create more financial breathing room.

Maintenance vs. Downsizing

Larger homes often come with:

  • Higher repair and maintenance costs
  • Yard work and upkeep
  • Increased utility bills

Downsizing to a smaller, newer, or low-maintenance home can free up equity while reducing stress and monthly expenses.

Mortgage Status

Still carrying a mortgage? Eliminating or dramatically reducing this debt through downsizing can be one of the most impactful financial moves in your 50s and 60s—often improving peace of mind as much as cash flow.

2. Health & Accessibility: Planning Ahead, Not Reacting Later

One of the biggest mistakes people make is waiting for a health event to force a move. Planning proactively allows for thoughtful decisions rather than rushed ones.

Instead of thinking decades ahead, consider your needs in 3–5 year increments.

Home Functionality

Ask yourself:

  • Will stairs, narrow hallways, or multi-level living become obstacles?
  • Is yard work or ongoing maintenance already feeling burdensome?

Moving now gives you the opportunity to choose:

  • A single-level home
  • A maintenance-free community
  • A property designed with accessibility in mind

Access to Healthcare

As health needs evolve, proximity to:

  • Quality hospitals
  • Medical specialists
  • Reliable healthcare networks

becomes essential—not optional. Location matters.

Mobility & Transportation

If driving becomes limited in the future, will you still be able to:

  • Get groceries
  • Visit doctors
  • Stay socially connected

Walkable neighborhoods, public transportation, and senior-focused transit options can help preserve independence and quality of life.

3. Social & Emotional Well-Being: Community, Connection, and Purpose

Midlife and beyond often bring major life shifts—retirement, children moving away, or changes in social circles. Where you live plays a huge role in how connected and fulfilled you feel.

Proximity to Family

One of the most common reasons people choose to move is to be closer to:

  • Adult children
  • Grandchildren
  • Trusted support systems

Being nearby can strengthen relationships and provide peace of mind for everyone involved.

Community and Social Network

Has your local circle changed over time?
Moving can be an opportunity to:

  • Join an active adult or lifestyle-focused community
  • Live in an area centered around shared interests like arts, wellness, or outdoor recreation
  • Build new friendships and routines that align with your current chapter

Lifestyle and Purpose

Ask yourself:

  • Do you want a slower pace—or a new adventure?
  • Are you envisioning more travel, volunteering, or hobbies?

A move can help align your physical surroundings with your post-career goals—whether that means ocean views, mountain air, or simply a home that feels easier to live in.

Bringing It All Together

Knowing when it’s time to move isn’t about urgency—it’s about alignment.

By thoughtfully weighing:

  • Financial feasibility
  • Future health and accessibility needs
  • Social connection and lifestyle goals

you can determine not just if a move makes sense, but when and where it will best support your next chapter.

If you’re starting to ask these questions, the most important step is having an informed conversation. With the right planning, a move doesn’t have to feel overwhelming—it can feel empowering.

The Keit Team specializes in helping homeowners navigate these transitions with clarity, confidence, and care.
When you’re ready to explore your options, we’re here to help you plan your next move—on your terms.