There’s a conversation that happens in Long Island kitchens every summer, and doesn’t happen just as often as it happens.
The kids are visiting. Maybe it’s a Fourth of July weekend. Maybe it’s an August week at the beach house. Maybe it’s just a normal Sunday dinner where three generations are somehow all in the same room for two hours.
Someone brings up “the house.” Not the mortgage or the property tax bill. The bigger question. What happens to it. What Mom and Dad have decided. Whether there’s a plan. Whether the will is current. Whether the estate attorney is still practicing. Whether the kids are supposed to know something or nothing.
The conversation lasts about seven minutes before someone changes the subject. Everyone is relieved.
A month later, a friend of the family has a health scare. Or a neighbor passes. Or a family across town gets into a two-year probate dispute over an inherited Long Island home. And someone in the family sends a text: We should really talk about this stuff.
Then another two years pass.
If you’re a Long Island homeowner without an updated estate plan, this newsletter is for you. In 2026, the stakes of not planning have gotten meaningfully higher.
Why This Matters More in 2026 Than It Did Even Two Years Ago
A month ago I wrote about what to do when you inherit a Long Island home — the stepped-up basis, the four paths forward, the sibling dynamics, the timeline reality. That piece was for people at the receiving end of an estate.
This one is for the other side of the conversation.
If you’re a Long Island homeowner in your 60s, 70s, or 80s — or if you’re the adult child of one — a few specific 2026 realities have raised the stakes on proactive estate planning.
Long Island home values are at records. Q1 2026 median hit $738,444 across Nassau and Suffolk (excluding the East End). Many long-tenured homeowners are sitting on $700,000 to $1.5 million of home equity. Combined with retirement accounts, life insurance, and other assets, the total estate value for a typical Long Island senior couple has crept up significantly over the past decade.
The New York estate tax cliff is now more dangerous. The NY estate tax exemption is around $7.16 million per person in 2026. Federal exemption is $15 million per person. Most families won’t trigger federal estate tax. But New York’s threshold is much lower, and the state has a “cliff” — if your estate exceeds the exemption by more than 5 percent, the entire estate becomes taxable, not just the excess. Rising home values have pushed more families toward that cliff without them realizing it.
The 5-year Medicaid lookback keeps getting more consequential. For families where long-term care in a nursing facility may become part of the future, the 5-year lookback on asset transfers matters enormously. Assets transferred within 5 years of applying for Medicaid can disqualify the applicant. This is not something that starts working when the health crisis arrives. It has to be planned five or more years earlier.
Probate delays on Long Island have not improved. Nassau and Suffolk Surrogate’s Courts remain slow. A straightforward probate takes 4-8 months on Long Island. A contested one can stretch to two years or longer. During that time, the home generally can’t be sold, decisions can’t be made, and family stress compounds.
The overall picture: bigger estates, tighter tax thresholds, longer probate delays, more complex family dynamics. The families who address this proactively — while the parents are still healthy, still making decisions with clarity, and still able to sign documents — save themselves from enormously expensive and painful problems later.
The Two Foundational Documents (and Why Most People Are Missing One)
Every serious estate plan for a Long Island homeowner starts with two foundational documents.
The first is a will. Almost everyone knows they should have one. Many people do — though sometimes the will they have is 15 or 20 years out of date and no longer reflects the family reality.
The second is a revocable living trust. Most people have heard of trusts but don’t have one. They think trusts are for wealthy people. They’re not — or at least, they’re increasingly not, given how much equity typical Long Island homeowners have built up.
Here’s the fundamental difference in practical terms.
If you die with a will and the home is in your individual name, the home goes through probate. Probate is the legal process where the Surrogate’s Court validates the will, appoints the executor, and oversees the transfer of assets. Probate is public, slow, and expensive. On Long Island specifically, probate on a straightforward estate takes 4-8 months at minimum, and any contested elements can extend it far longer.
If you die with a revocable living trust that owns your home, the home passes directly to your beneficiaries per the trust terms — without probate. No Surrogate’s Court. No public filing. No 4-8 month delay. The successor trustee (usually a spouse or adult child) can typically take title and, if the plan calls for it, sell the home within weeks rather than months or years.
Setting up a revocable living trust costs $2,500-6,000 in attorney fees typically on Long Island, depending on complexity. That’s the entire cost. The trust owns your home. You can still buy, sell, refinance, live in, or renovate the home exactly as before. You have full control while you’re alive. The only real change is what happens after you’re gone — and specifically, the fact that your family doesn’t have to go through probate.
Preserving the Stepped-Up Basis: The Tax Gift You Can’t Give Away Early
I wrote at length last month about the stepped-up basis — the IRS provision that resets the tax basis of inherited property to fair market value at the date of death. When your heirs inherit your Long Island home, they inherit it at its current market value, not at what you paid for it.
This is one of the most generous provisions in the entire tax code. And it’s easy to accidentally destroy it.
Here’s the trap. Well-meaning parents sometimes decide to “simplify things” by adding an adult child to the deed while they’re still alive. Or they gift the home outright to a child, thinking they’re avoiding probate or protecting the asset from long-term care exposure.
Both of these strategies can eliminate the stepped-up basis entirely.
When you gift a home during your lifetime, your child receives it at your cost basis — what you paid for it, plus documented improvements. Not at fair market value. If you bought the Cape Cod in Bethpage in 1985 for $150,000 and it’s worth $850,000 today, gifting it to your daughter means she inherits a $150,000 basis. When she eventually sells for $850,000, she faces $700,000 of taxable capital gain.
The general rule: assets that will appreciate should generally pass through your estate at death, not be gifted during your lifetime. This applies to your primary residence, investment properties, appreciated stocks, and other assets with built-in gains.
There are exceptions and nuances. Life estates (discussed below) can preserve stepped-up basis while accomplishing some transfer during lifetime. Irrevocable trusts have specific rules. Certain gifting strategies for assets with minimal appreciation can make sense.
But the default instinct — “let’s just put the kids on the deed to simplify things” — is often the exact wrong move. Talk to an estate attorney and a CPA before making any changes to how your home is titled.
Life Estates: An Underused Long Island Strategy
For Long Island parents in specific situations, a life estate deed can be a powerful tool worth knowing about.
Here’s how it works. You transfer ownership of your home to your children (or a trust for their benefit) but retain a “life estate” — the legal right to live in the home for the rest of your life. You still control the property while you’re alive. You can’t be evicted. You can’t be forced to sell. But upon your death, the property passes automatically to your children (the “remainder beneficiaries”) without probate.
Key advantages:
Preserves the stepped-up basis. Unlike an outright gift, a life estate transfer generally allows the property to receive a stepped-up basis at the life tenant’s (parent’s) death. The children inherit at fair market value.
Avoids probate. The transfer to the remainder beneficiaries happens automatically. No Surrogate’s Court involvement.
Starts the 5-year Medicaid lookback clock earlier. If long-term care planning is a concern, a life estate can begin the 5-year clock now, so that if the parent eventually needs Medicaid to pay for a nursing home, the home may be protected.
Life estates aren’t right for everyone. Once created, they’re generally not easily reversible — the parents can’t unilaterally change their mind and take the home back. If the parents need to sell the home to fund long-term care or move to a facility, they’ll need cooperation from all remainder beneficiaries.
The 5-Year Medicaid Lookback Reality
Every Long Island family with an aging parent should understand the 5-year lookback rule for Medicaid.
Long-term care in a Nassau or Suffolk nursing facility runs $15,000-20,000 per month. That’s $180,000-240,000 per year. Assisted living is somewhat less but still expensive. Home health aides for round-the-clock care can run $15,000+ per month.
Most families cannot self-fund this indefinitely. If the parent lives 2-3 years in memory care, that’s $500,000-700,000 out of pocket. Longer stays can consume the entire equity in a home and then some.
Medicaid can pay for nursing home care, but only after the applicant has “spent down” their assets to Medicaid limits — very low limits, typically $30,000 or less in countable assets for a single applicant.
The 5-year lookback means Medicaid reviews all asset transfers made in the 5 years before the application. Any transfers made during that window can trigger a penalty period during which Medicaid won’t pay — the applicant has to self-pay first for a certain number of months based on the value transferred.
The sooner your family addresses this, the more options you have. The families who wait until a health crisis has emerged discover that most protective strategies require the 5-year lookback that they no longer have time to complete.
For families with meaningful Medicaid concerns, an elder law attorney is worth the additional cost over a general estate attorney. Elder law attorneys specialize in the intersection of estate planning, Medicaid planning, and long-term care.
Multi-Property Considerations
Some Long Island families have more than one property to consider. A primary residence in Nassau. A summer cottage in Montauk. An investment property in Bay Shore. A parents’ condo in Florida that transferred at some point.
Each property carries its own considerations for estate planning.
Primary residence. Generally the most valuable and the most emotional. Strong candidate for a revocable living trust or life estate. Stepped-up basis is critical to preserve.
Second home / summer place. Long Island families with East End homes often have complicated dynamics — the property may have deep emotional significance across generations of the family, but different children may have different relationships to it. Some want to keep it; some want to sell their share. A well-structured plan addresses this before it becomes a source of family conflict.
Investment property. Different tax dynamics. Depreciation recapture can be an issue if the property is sold rather than passed through the estate. LLC ownership structures may be involved.
Out-of-state property. Requires “ancillary probate” in the state where the property is located, if held individually. This is another compelling reason to use a revocable living trust — properly funded trusts avoid ancillary probate.
The Sibling Fairness Question
A significant portion of estate planning conflicts on Long Island don’t come from bad planning. They come from the fairness question no one wanted to answer.
The classic scenario: three children. One lives locally and has been caring for the parents for years. Another moved out of state twenty years ago and rarely visits. A third has had a rocky relationship and hasn’t spoken to Mom or Dad in five years.
If the will divides everything equally three ways, does that feel fair to the parents? Does it feel fair to the caretaker child? Does it feel fair to the estranged child?
There’s no universal answer. But there is a universal principle: whatever the parents decide, they should decide it deliberately, communicate it clearly to the family, and document it thoroughly.
Some strategies families have used successfully:
Equal shares with explicit acknowledgment. The parents decide that despite unequal involvement, equal shares is right. They tell the family why. They put it in writing.
Adjusted shares reflecting caregiving. The caregiver child receives a larger share (or specific assets like the home) in recognition of their ongoing role. Other children receive different but comparable value in other assets.
Direct gifts during life. The parents pay for graduate school for one child but not another, and consider that “equalization” happening during life so the will can distribute what remains equally.
The letter of wishes. A non-binding letter that accompanies the will or trust, explaining the reasoning. Helps prevent siblings from misinterpreting the parents’ intent.
The single worst strategy is to leave the fairness question unresolved and hope the kids sort it out after the parents are gone. They rarely do.
Having the Conversation
None of the strategies above matter if the family doesn’t know what the plan is.
Long Island parents who have done all the right documents but never discussed them with their children put their kids in the position of learning about the plan after the parents are gone — sometimes surprised, sometimes hurt, sometimes confused about what the parents wanted or meant.
The families who navigate this best have the conversation while everyone is still healthy, still able to ask questions, and still able to have follow-up discussions over time.
The conversation doesn’t have to be a formal sit-down. It can be pieces at a time:
We updated our wills last month. Here’s what we’re thinking about the house.
We set up a living trust. When we’re gone, here’s how it will work. Any questions?
If something happens to us suddenly, here’s where our documents are and here’s who our attorney is.
Each of those conversations lasts ten minutes. Over the course of a few visits, the family can cover the whole landscape. And when the moment eventually comes, the family isn’t blindsided. They know the plan. They know the reasoning. They know what to do.
What to Do This Summer
If you’re a Long Island homeowner over 60 without a current estate plan — or with one that’s more than 5 years old — here’s the practical sequence for the next 60 days.
The parents who do this well give their children an enormous gift: the ability to focus on grieving when the time comes, instead of scrambling to figure out what Mom and Dad wanted.
The Honest Bottom Line
Long Island in 2026 is a specific place with specific dynamics. Home values are at records. The New York estate tax cliff is dangerously low relative to those values. The Medicaid lookback keeps getting more consequential. Probate takes just as long as it always has.
The families who plan proactively give their children an easier inheritance, lower taxes, faster resolution, and less conflict. The families who don’t plan create the exact opposite outcomes — often for reasons that had nothing to do with what the parents actually wanted.
The good news: the tools are all available. A good estate attorney. A well-structured trust. A thoughtful title update. A conversation with a CPA about basis and tax planning. A family conversation that starts something instead of ending it. None of these are expensive. None of them are hard.
For most Long Island parents reading this, the right time to start is now. This summer. While the family is around. While everyone is healthy. While the conversation can be had calmly, in your kitchen, with time to think.
The house you’ve built your life in becomes your family’s inheritance whether you plan or not. The question is only whether it becomes a clean inheritance or a complicated one.
Plan the clean version. Your family will thank you for generations.
If you’re thinking about the future of your Long Island home — whether that means understanding its current market value, planning your estate around it, or preparing for a potential sale down the road — get a free, no-obligation home valuation and honest conversation about your specific situation. Real numbers, thoughtful guidance, no pressure.