Westchester Tax Planning Attorney

Estate planning is not only about who receives your assets—it’s also about how much of your estate is preserved after taxes. Without proactive strategies in place, a large portion of your wealth may be lost to estate, gift, or income taxes. At Cavallo & Cavallo, our Westchester tax planning attorneys help individuals, families, and business owners minimize tax exposure and create efficient plans that support both short- and long-term financial goals.

What Is Estate and Tax Planning?

Estate and tax planning involves structuring your assets and wealth transfers in a way that reduces potential tax liabilities. With changing state and federal laws, it’s essential to regularly evaluate your plan to ensure it remains optimized.

Effective tax planning can help:

• Lower or eliminate estate taxes
• Minimize gift and generation-skipping transfer (GST) taxes
• Reduce capital gains taxes for heirs
• Coordinate charitable giving for tax benefit
• Keep more wealth in the hands of your beneficiaries

Our approach balances tax efficiency with personal goals—so your legacy is both protected and impactful.

Understanding Estate Taxes in New York

New York is one of a handful of states that still imposes a separate estate tax. If your estate exceeds the exemption limit, your family could face significant tax bills.

As of 2025, key thresholds include:

• Federal estate tax exemption: Scheduled to reduce to around $6 million per individual
• New York estate tax exemption: Slightly over $6 million per individual, with a “cliff” that causes the full estate to be taxable if you exceed the exemption by just 5%

This “cliff” makes detailed tax planning critical for Westchester residents with even moderately large estates.

Strategies to Reduce Estate and Gift Taxes

There are many legal tools available to minimize estate and gift tax liability. At Cavallo & Cavallo, we craft personalized strategies that may include:

• Credit Shelter Trusts (Bypass Trusts): Preserve both spouses’ estate tax exemptions
• Spousal Lifetime Access Trusts (SLATs): Move assets out of your estate while providing financial access through a spouse
• Irrevocable Life Insurance Trusts (ILITs): Keep large insurance payouts outside your estate
• Annual gifting: Use the yearly gift exclusion (currently $18,000 per recipient) to transfer wealth tax-free
• Charitable trusts: Reduce your taxable estate while supporting causes you care about
• Family Limited Partnerships (FLPs): Transfer business interests with valuation discounts

These techniques help protect family wealth and ensure a smoother transfer to future generations.

Income and Capital Gains Tax Considerations

Estate planning isn’t just about estate taxes. Income and capital gains taxes also play a role in your overall financial picture—especially when transferring appreciated assets.

Our tax-conscious planning considers:

• Step-up in basis: Ensuring your heirs receive a new tax basis to avoid large capital gains
• Roth IRA conversions: Shifting taxable assets into tax-free accounts during retirement
• Timing of asset sales: Coordinating when to sell certain investments to minimize gains
• Trust income tax brackets: Structuring trusts to avoid compressed tax rates

With proper guidance, you can reduce your lifetime tax burden and increase what your beneficiaries actually receive.

Lifetime Gifting Strategies

Gifting is one of the simplest and most effective ways to reduce the size of your taxable estate. We help Westchester clients take advantage of:

• Annual gift exclusion: Give up to $18,000 per person, per year, without affecting your lifetime exemption
• 529 plan contributions: Front-load up to five years’ worth of education gifts
• Medical and tuition payments: Pay these directly to institutions to avoid gift tax rules
• Irrevocable trust gifts: Transfer appreciating assets into trusts to “freeze” their future value

Gifting not only reduces future taxes—it allows you to witness your legacy in action.

Planning for Married Couples

Married couples in Westchester can significantly reduce estate tax liability with proper planning. Strategies include:

• Using both spouses’ estate tax exemptions
• Creating credit shelter or marital trusts
• Ensuring proper ownership titling of real estate and accounts
• Coordinating lifetime gifts and beneficiary designations

We build coordinated plans that protect both spouses and preserve flexibility for the survivor.

Charitable Giving and Tax Efficiency

For philanthropic families, charitable giving is not only a way to make a difference—it’s also a powerful tax tool. You can use:

• Charitable Remainder Trusts (CRTs) to generate lifetime income and defer capital gains
• Charitable Lead Trusts (CLTs) to support charities now while leaving assets to heirs later
• Private foundations for long-term giving and control
• Outright bequests through your Will or trust

We work to align your giving with both your values and your financial objectives.

Frequently Asked Questions About Tax Planning

Do I need tax planning if I’m not ultra-wealthy?
Yes. Many Westchester families may be affected by New York’s estate tax or capital gains on appreciated property. Smart planning can save your heirs money regardless of your wealth level.

Can I avoid taxes by giving money to my kids now?
In part. Gifting during your lifetime can reduce the size of your estate, but large gifts may still apply against your lifetime exemption. We help you balance your goals with tax rules.

What’s the difference between a gift tax and estate tax?
Gift taxes apply during your lifetime, while estate taxes apply after death. Both are tied to the same exemption amount and tracked together.

Are life insurance proceeds taxed?
Not as income—but they may be included in your taxable estate unless held in an ILIT.

What happens to appreciated assets when I pass away?
In most cases, your heirs receive a step-up in basis, meaning they inherit the asset at its current market value, reducing capital gains if they sell it.

Serving Throughout Westchester, NY

• Scarsdale
• Bronxville
• Larchmont
• Rye
• Chappaqua
• Pelham
• Armonk
• Mamaroneck
• Dobbs Ferry
• Tarrytown

How Cavallo & Cavallo Can Help

Cavallo & Cavallo has been helping Westchester individuals and families minimize tax burdens and preserve wealth for over 30 years. We provide practical guidance backed by deep experience and a thorough understanding of both state and federal tax laws.

Our tax planning services include:

• Estate and gift tax minimization strategies
• Trust-based tax planning
• Lifetime gifting and exemption planning
• Charitable and foundation planning
• Coordination with financial and tax professionals

We make your estate plan work smarter—so you can focus on what matters most.

Speak With a Westchester Estate and Tax Planning Attorney Today

The right plan can make a major difference in how your estate is preserved and passed on. Contact Cavallo & Cavallo today to speak with an experienced Westchester estate and tax planning attorney and start building a strategy that protects your wealth, your goals, and your family’s future.