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25 September 2026

Can a dying homeowner avoid a $100,000 capital gains hit by selling?

A terminally ill friend weighs selling a rental condo, facing a sizable capital gains tax and a son eager to move out. The article breaks down tax rules and family‑focused alternatives.

Can a dying homeowner avoid a $100,000 capital gains hit by selling?

When a property owner receives a terminal diagnosis, the urgency to simplify assets can clash with the complexity of tax law. In this case, a rental condo that generated a $100,000 capital gain on sale sits at the center of the dilemma. The younger son currently occupies the unit but plans to relocate with friends, adding a familial layer to the financial decision.

Understanding the $100,000 capital gains tax burden

The capital gains tax applies to the difference between the sale price and the adjusted basis of the property. For a rental condo, the basis typically reflects the original purchase price plus improvements, minus depreciation claimed over the years. If the net gain reaches $100,000, the owner could owe between 15% and 20% of that amount, depending on her marginal income tax bracket. In practice, this translates to a liability of roughly $15,000 to $20,000.

Two specific provisions can ease the load. First, the exclusion for primary residences—up to $250,000 for single filers—does not apply because the unit has been used as an investment property. Second, the step-up in basis rule, which automatically resets the cost basis of inherited assets to fair market value at the date of death, only benefits heirs after the owner’s passing. Since the sale is contemplated now, the step-up cannot be leveraged.

Family considerations and alternative strategies

The son’s desire to move out creates an opportunity to restructure ownership without immediate liquidation. One option is to transfer the condo to him via a gift or a sale at fair market value. A gift would trigger a gift tax unless it stays within the annual exclusion ($17,000 per recipient in ). A fair-market sale, on the other hand, would generate a capital gain for the mother but could eliminate future rental income and management responsibilities.

If the mother chooses to keep the property until her death, the heirs would inherit it with the stepped-up basis, potentially erasing the $100,000 gain altogether. This approach preserves the asset for the son while shielding the estate from immediate tax. However, it also means continuing to collect rental income, covering maintenance, and managing tenant turnover—tasks that may be burdensome given the health situation.

Another practical route is to lease the condo to a third party for a short term, thereby generating cash flow without the need for a full sale. The rental income would be taxable, but it could offset living expenses and medical costs. Once the mother’s condition stabilizes or the son decides to move, the property can be sold at a later date when the market environment might be more favorable.

Key financial checkpoints before deciding

Before taking action, it is essential to run a simple cost-benefit analysis:

  • Calculate the exact adjusted basis of the condo, including all depreciation taken.
  • Project the capital gains tax liability based on current marginal rates.
  • Estimate the medical and living expenses that could be covered by the sale proceeds.
  • Assess the son’s willingness and ability to assume ownership or manage a rental.

Consulting a qualified tax professional or estate planner is highly recommended. They can model scenarios, advise on potential 1031 exchanges (like-kind swaps for investment property), and ensure compliance with both federal and state regulations.

Retaining the property offers a future step-up benefit for heirs but requires ongoing management. The optimal path hinges on the balance between short-term cash needs, the son’s housing plans, and the desire to preserve wealth for the family’s long-term stability.