Why Some Retirees Are Upsizing Instead of Downsizing

by Jason Burke

For years, the traditional retirement housing plan was pretty simple: Sell the big house, move into something smaller, and use the leftover equity to reduce expenses or boost retirement savings.

But that script is starting to change.

A recent Realtor.com article highlights an interesting shift among some retirees who are finding that downsizing doesn’t always produce the financial benefit they expected. In some cases, they’re actually choosing to upsize instead, often with a long-term family strategy in mind.

Here’s what’s driving that change.

Why Downsizing Isn’t Always a Financial Win

On paper, downsizing should free up equity. But in today’s market, that gap is often smaller than expected.

Many retirees are running into:

Higher prices for smaller, newer homes
HOA fees in low-maintenance communities
Renovation or relocation costs that eat into equity gains
Limited inventory in the most desirable “right-size” homes

In some cases, after selling and buying again, the net financial benefit is not as large as it used to be.

That’s causing some homeowners to rethink whether moving down in size actually improves their financial picture.

The Upsizing Strategy: A Different Way to Think About Equity

Instead of downsizing, some retirees are choosing to move into larger or more flexible homes.

The motivation isn’t lifestyle inflation. It’s planning.

These buyers are:

Purchasing homes that can accommodate adult children or extended family
Choosing properties that can eventually be passed down as an inheritance
Using existing equity to purchase homes that better fit multi-generational living

In other words, the home is becoming less about reducing expenses and more about strategic wealth transfer and long-term family planning.

Why This Shift Is Happening Now

A few broader market forces are influencing this trend:

Higher housing costs across all price points: Even smaller homes and condos have become significantly more expensive in many markets.
Strong home equity gains: Many long-term homeowners have accumulated substantial equity, especially those who purchased before the pandemic housing surge.
Limited inventory: The “perfect downsizing home” is often harder to find than expected.
Changing family dynamics: More families are considering multigenerational living or financial support for adult children in high-cost markets.

What This Looks Like in Markets Like Richmond

Here in the Greater Richmond area, I’m seeing similar conversations play out.

Many longtime homeowners in Chesterfield, Henrico, Hanover, and surrounding areas are sitting on significant equity after years of appreciation, exploring options beyond traditional downsizing, and/or weighing whether moving even makes sense financially once taxes, insurance, and new purchase prices are factored in.

Further, new construction communities and larger homes in suburban areas are still attracting buyers who want flexibility for family, guests, or long-term planning.

The key difference today is that there is no one-size-fits-all retirement move anymore.

How I Can Help

If you’re thinking about whether to stay put, downsize, or even consider a different type of move, I’m happy to walk through the numbers with you.

Every situation is different, and the right decision often comes down to:

Your current equity position
Local market conditions
Your long-term goals

I can also connect you with trusted local lenders to help you understand what your options look like in today’s market.

Every move starts with a conversation

Jason Burke headshot Let's talk! I’ve proudly served the Greater Richmond area as a full-time Realtor for more than 19 years, and I’ve called Virginia home for over 25.