Retiring in Westchester County, NY: Your Questions Answered
By Todd Stankiewicz | CIO, SYKON Capital | Portfolio Manager, Free Markets ETF (FMKT)
There is a lot of noise out there about whether retiring in Westchester County is actually realistic, and we hear the question constantly. SYKON Capital is a national firm with offices in both Westchester County, NY and Jupiter, Florida, and we work with pre-retirees and retirees navigating this exact question every day. Below are 3 of the questions we field most often, with the kind of straight, experience-based answers we share with our clients.
The Financial Reality of Retiring in Westchester County
Q1: Is it actually realistic to retire in Westchester County, NY, or is it just too expensive?
Yes and no. I am not going to sugarcoat it: Westchester County is one of the most expensive places to retire in the country. Property taxes are among the highest in the nation, the cost of living is elevated, and for years the federal tax code was adding insult to injury with the $10,000 SALT deduction cap that essentially penalized you for owning a home in a high-tax state. But here is what I have watched play out for clients in Harrison, Rye, Rye Brook, Scarsdale, and Bronxville over and over again: retirement income looks very different than working income, and that difference opens doors. Programs that were out of reach when your income was high (like Enhanced STAR property tax relief, certain senior tax deductions, and New York State income exclusions) can suddenly become available once you are thoughtfully managing distributions in retirement. The SALT deduction cap has also been raised significantly to $40,000 under the One Big Beautiful Bill Act of 2025, which can be a genuine improvement for Westchester homeowners. We are a national firm with offices in both Westchester County, NY and Jupiter, Florida, and we work with pre-retirees and retirees in this region constantly. In our experience, retiring in Westchester is achievable for the right retirees: it just requires a coordinated, proactive plan, not a generic one.
Q2: How does the new $40,000 SALT deduction cap change things for Westchester County retirees?
This one matters a lot, and I think it is not getting enough attention yet. From 2017 through 2024, homeowners in Westchester were essentially capped at a $10,000 federal deduction for state and local taxes combined. If your property taxes alone were $25,000 or $30,000 a year (and in towns like Harrison, Rye, and Scarsdale, that number is very real), you were only deducting $10,000 of it federally. The rest simply evaporated.
Under the One Big Beautiful Bill Act signed into law in 2025, the SALT deduction cap has been raised to $40,000 for tax years 2025 through 2029. That is a meaningful change for Westchester homeowners. If you are paying $30,000 or more per year in property taxes, the combination of your property taxes, mortgage interest, and charitable contributions could potentially get you back to genuinely benefiting from itemizing, something that was off the table for nearly a decade.
I want to be clear-eyed here: the $40,000 cap phases out for taxpayers above $500,000 in income, so for very high earners, the benefit diminishes. But for retiring Westchester homeowners managing incomes between roughly $100,000 and $500,000, this change is genuinely significant. It is one of the reasons we believe the retirement affordability story in Westchester is improving, not getting worse.
Q3: What is New York's Enhanced STAR program, and how can Westchester seniors take advantage of it?
STAR stands for School Tax Assessment Relief, and it is New York State's program to provide direct property tax relief to homeowners, specifically on the school tax portion of your bill, which is typically the single largest piece of what you pay. There are two tiers: Basic STAR and Enhanced STAR.
Enhanced STAR is designed for seniors age 65 and older and provides a greater benefit than Basic STAR. The income limit for Enhanced STAR is $110,750 or less in combined household income. Here is an important update starting in 2026: only one homeowner in the household needs to be age 65, which matters a great deal for couples where one spouse is younger.
Here is where income planning becomes absolutely central to this conversation. Qualifying for Enhanced STAR depends on your reportable income. While you were working, your income likely put you well above the eligibility threshold. In retirement, if you manage your IRA distributions and other income sources thoughtfully, you may find yourself eligible for programs you never qualified for during your working years. Many Westchester municipalities also layer on an additional local Senior Citizens Exemption on top of STAR, which can provide further property tax reductions.
This is exactly why we emphasize coordination across your entire financial picture. Managing your taxable income in retirement is not just about paying less in taxes today: it can open up eligibility for ongoing programs that add up to real, meaningful savings over the life of your retirement.
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About Author
Todd Stankiewicz | Chief Investment Officer, SYKON Capital
Todd Stankiewicz is the Chief Investment Officer of SYKON Capital, a fee-based registered investment advisor with offices in Westchester County, NY and Jupiter, FL. He is a recurring guest on Fox Business and the Schwab Network, where he discusses markets, portfolio strategy, and investor behavior. Todd is also the portfolio manager of the Free Markets ETF (FMKT).
Learn more at www.sykoncapital.com
Investment advisory services offered through SYKON Capital, LLC, a Registered Investment Advisor with the U.S. Securities and Exchange Commission.
This material is intended for informational purposes only. It should not be construed as legal or tax advice and is not intended to replace the advice of a qualified attorney or tax advisor. This information is not an offer or a solicitation to buy or sell securities. The information contained may have been compiled from third party sources and is believed to be reliable. Please note that contacting us does not establish a client-advisor relationship, and we may receive compensation for advisory services. Personalized advice should be obtained before making financial decisions. Our advice is based on our experience and relationships in both markets. Investment advisory services are offered through SYKON Capital, LLC, a Registered Investment Advisor. Contact us for personalized advice.'
Disclaimer: This content is for educational purposes only and does not constitute tax, legal, or financial advice. The information presented is based on general tax rules as of the 2026 tax year and may not reflect your individual circumstances. Please consult a qualified tax professional or enrolled agent regarding your specific situation before taking any action. All figures cited are for the 2026 tax year and are subject to change.
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