Older couple standing in front of their massive home

The housing market feels frozen for a reason. Homes exist, demand exists, but movement does not. Large family houses stay occupied by one or two people while buyers with kids search endlessly for space. Prices climb, listings stay scarce, and frustration grows.

This is not about blaming older homeowners. It is about understanding why the system rewards staying put and discourages reasonable moves. By 2026, those incentives line up in a way that keeps many oversized homes off the market longer than people expect.

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Tax rules make selling financially unattractive

One of the biggest reasons empty nesters hesitate to sell is the tax treatment of home equity. Federal capital gains rules allow homeowners to exclude a fixed amount of profit when selling a primary residence, but that exclusion has not changed in decades. In many markets, home values have grown far beyond it.

For long-time owners, selling can trigger a large tax bill. Many realize they are financially better off holding the home until death, when heirs receive a stepped-up tax basis that wipes out capital gains, a dynamic explained in reporting on how current tax law incentivizes homeowners to keep property rather than sell it.

Large homes are concentrated among older owners

This tax dynamic matters because of who owns the housing stock. Older Americans hold a disproportionate share of large single-family homes, including many three- and four-bedroom properties built for families.

Housing data shows that older Americans control a large share of family-sized homes. Redfin found that empty-nest baby boomers own nearly 3 in 10 large U.S. homes, about twice the share owned by millennials with kids.

Downsizing often costs more month to month

Retired couple moving and unpacking boxes
Image Credit: Feverpitch via Deposit Photos.

On paper, downsizing sounds practical. In reality, it often raises monthly expenses. Smaller homes in desirable areas can cost nearly as much as larger ones. New mortgages come with higher interest rates than older loans. Property taxes and insurance often reset after a sale.

For many older homeowners, staying in a larger house remains the cheapest option, even if much of the space goes unused. That decision is rational on an individual level, but it limits turnover in the part of the market under the most pressure.

Limited movement creates a chain reaction

When larger homes do not come up for sale, pressure spreads across the market. Families stay in starter homes longer because there is nowhere to move next. Renters remain renters because fewer homes open up. Buyers compete harder for the same limited listings.

This gridlock pushes prices higher across multiple tiers. The problem is not only how many homes exist, but how rarely they change hands.

Why 2026 matters

By 2026, a large share of the baby boomer generation will be well into their seventies. Maintenance becomes harder. Health needs increase. Yet the financial incentives still reward staying put.

This does not mean older homeowners should be forced out of their homes. It means the system penalizes reasonable moves and rewards inaction. Until those incentives change, many family-sized homes will remain off the market, even when they no longer fit the household living in them.

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