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Does the Five-Year Medicaid Look-Back Apply to Home Ownership Transfers?

July 21, 2026 //  by John McCann, Estate Planning Attorney

Medicaid five-year look-back, image of a nice homeProtecting the family home is a top priority for Connecticut seniors. A home represents decades of hard work and memories. Naturally, families want to pass this legacy down to their children. However, the rising costs of long-term care frequently threaten that security.

As families explore ways to safeguard their property, a critical question arises. Does the five-year Medicaid look-back period apply to home ownership transfers?

The short answer is yes. The look-back period absolutely applies to real estate and primary residences. However, Connecticut regulations are highly nuanced. The rules contain both hidden traps and powerful exceptions.

To understand the impact on your estate, we must first clear up a major misconception about senior healthcare.

The Structural Gap: Why Medicare Won’t Cover Long-Term Care

Many families mistakenly assume that Medicare pays for nursing home stays. This is an understandable mistake.

Seniors pay into the system throughout their working lives. Furthermore, Medicare works excellently as health insurance for acute medical conditions, surgeries, and prescriptions.

Unfortunately, Medicare is not fundamentally designed to cover long-term “custodial care.” This term refers to non-medical assistance with daily living, such as bathing, dressing, and eating.

Medicare Limitations

Medicare only covers rehabilitative care in a skilled nursing facility for a limited time. The absolute maximum coverage is 100 days per illness.

Even then, Medicare only pays the full cost for the first 20 days. From days 21 through 100, patients face a hefty daily co-insurance payment. Past day 100, coverage drops to zero.

Private long-term care insurance is often prohibitively expensive. Many seniors cannot qualify due to pre-existing conditions. Consequently, many Connecticut residents ultimately rely on Connecticut Medicaid (administered through HUSKY Health) to help finance long-term care.

Medicare is an entitlement program available to anyone over 65. Conversely, Medicaid is a strictly needs-based, means-tested program.

Understanding the Five-Year Look-Back and Asset Limits

To qualify for long-term Medicaid in Connecticut, applicants must meet rigid financial limits. Currently, an individual applicant can keep only $1,600 in countable assets.

Historically, some people tried to bypass these limits by giving away assets just before applying. To prevent this loophole, the federal government established the five-year look-back period.

When you apply for Medicaid, the Connecticut Department of Social Services (DSS) reviews your past finances. They audit all transactions, bank accounts, and property deeds going back exactly 60 months.

Did you transfer, gift, or sell an asset below fair market value during those five years? If so, the DSS will impose a penalty period.

During the penalty period, Medicaid refuses to pay for your nursing home care. This applies even if you are otherwise financially eligible.

The state calculates the penalty length by dividing the gifted asset’s value by the average monthly cost of private care. In Connecticut, that regional rate is currently between $15,000 and $18,000 per month, and they are higher in Westport and Glastonbury where we practice.

Applying the Rules to Your Home: The Transfer Trap

Your home receives unique treatment while you reside in it. For a single applicant, a primary residence is generally considered an “exempt” asset.

However, the home equity must stay below the state-defined threshold, which is currently capped at $1,130,000. The applicant must also intend to return home.

The trap springs the moment you sign a deed transferring ownership. Gifting the home to your children for $1 creates an uncompensated transfer.

If this happens within the five-year look-back window, severe penalties apply. The DSS uses the home’s full fair market value to calculate a multi-year penalty period.

Its duration is based on the amount of long-term care the home sale proceeds could have covered. For example, if the money could have paid for three years of nursing home care, your Medicaid eligibility would be delayed for three years.

Crucial Exceptions: The Caregiver Child Provision

Fortunately, Medicaid rules recognize that family dynamics deserve flexibility. Connecticut provides critical exemptions for home transfers within the five-year window. You can transfer a home penalty-free to:

  • Your spouse.
  • Minor child under 21, or a disabled child of any age.
  • A sibling who has equity in the home and lived there for at least one year before you entered a facility.

Beyond these rules, the Caregiver Child Provision is an incredibly powerful tool.

Under this exception, you can legally transfer your primary residence to an adult child without penalty. To qualify, the child must have lived in the home with you for at least two years immediately before your nursing home admission.

Additionally, they must have provided care that actively delayed your institutionalization.

But here’s a warning on documentation: Connecticut DSS caseworkers heavily scrutinize caregiver child claims. You cannot simply assert that your child provided care; you must prove it with extensive medical documentation. This includes physician letters and detailed care logs showing the care was clinically necessary.

Proactive Planning vs. Crisis Navigation

Advance planning allows you to use the five-year look-back period to your advantage. An elder law attorney can help you transfer property into an irrevocable Medicaid asset protection trust.

If you outlive the five-year look-back period, a properly structured Medicaid Asset Protection Trust can help protect your home from being counted for Medicaid eligibility and may also help preserve it for your heirs by reducing the risk of Medicaid estate recovery.

What if your family is currently facing a crisis? If a loved one needs immediate care and a recent transfer caused a penalty, hope remains.

Elder law attorneys utilize several strategic tools to mitigate penalties. These include undue hardship waivers, “partial cures” through returned assets, or converting funds into Medicaid-compliant immediate annuities.

Schedule A Consultation Today!

Advance planning is the key to effective nursing home asset protection, and there is no time like the present. We have a Westport, CT elder law office, and another location in Glastonbury, and you can call us at 860-548-1000 to schedule a consultation at either office.

Plus, if you are interested in learning more before you take that step, join us at one of our complimentary monthly seminars.

  • Author
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John McCann, Estate Planning Attorney
John McCann, Estate Planning Attorney
Estate Planning Attorney at Nirenstein, Horowitz & Associates PC
John McCann is a partner with the law firm of Nirenstein, Horowitz & Associates, P.C. He received his bachelor of arts degree in economics from the University of Virginia and his master of arts degree in economics from Trinity College in Hartford. He received his law degree from the University of Connecticut School of Law. Mr. McCann is licensed to practice before the courts of the State of Connecticut. He is a member of the American Academy of Estate Planning Attorneys...Read More!
John McCann, Estate Planning Attorney
Latest posts by John McCann, Estate Planning Attorney (see all)
  • Medicaid Planning vs. Crisis Planning: What’s the Difference? - August 6, 2026
  • Does the Five-Year Medicaid Look-Back Apply to Home Ownership Transfers? - July 21, 2026
  • What Is Estate Tax Exclusion Portability? - June 25, 2026
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