FAQ - Frequently Asked Questions

1. What’s the best time of year to sell a home in Westchester County?

Westchester’s market is active year-round, but homes often attract the strongest interest between March and June.
If you’re planning a move to Florida, listing before summer allows time to coordinate both ends of your transition.
Through my New York referral network, I connect clients with experienced local REALTORS® who handle the listing process, while I stay involved as a planning resource to help coordinate timing and next-steps for your Florida move.

2. How can I prepare my home for sale if my parents are downsizing or relocating to Florida?

Start with organization and trusted guidance.
Through my network of New York agents, senior-move specialists, and estate professionals, I can connect families with the right local help to prepare a property for sale.
As a Seniors Real Estate Specialist® (SRES®), I remain a consultative resource — helping you plan, coordinate introductions, and ensure the process aligns with your family’s needs on both ends of the move.

3. What should Gen X homeowners consider before selling a longtime family home?

Many Gen X clients are balancing retirement goals with supporting an aging parent.
It’s important to evaluate capital-gains timing, estate planning, and where you’ll live next.
I work collaboratively with trusted New York agents and Florida advisors so your sale, purchase, and financial strategy are aligned — while licensed REALTORS® in each state handle the local transactions.

4. Can you help coordinate the sale of a New York home and the purchase of a Florida property?

Yes — that’s my specialty.
I’m licensed in both New York and Florida, and I help clients bridge the two states seamlessly.
In Florida, I personally represent buyers and sellers through Realty ONE Group MVP.
In New York, I connect clients with carefully selected REALTORS® from my referral network who handle the listing side locally.
I stay involved as an advisor to help coordinate timing, logistics, and overall strategy.

5. What are common pitfalls when selling an estate or inherited property?

Families often underestimate probate timelines, tax implications, and emotional considerations.
I can refer you to experienced estate attorneys, financial advisors, and trusted REALTORS® in my New York network to guide the process.
My role is to help ensure your transition plan remains organized, transparent, and aligned with your family’s goals.

6. What resources do you offer for seniors or adult children managing a transition?

I collaborate with a team of professionals across both states, including elder-law attorneys, financial planners, senior-move specialists, and real-estate partners.
Together, we help families make confident, well-timed decisions about selling, relocating, or right-sizing — with me coordinating introductions and providing continuity from start to finish.

7. How do property taxes compare between New York and Florida?

Westchester County typically has some of the highest property taxes in the nation, while Florida offers no state income tax and generally lower annual property taxes.
Understanding this difference helps many clients decide when to sell, retire, or establish Florida residency.
I can connect you with local professionals in both states to review specific tax or residency questions.

8. How do I start the process of emptying my parents’ home?

Begin early and plan with compassion. Sorting through decades of belongings can be overwhelming, so start by dividing tasks into manageable phases: keep, donate, sell, or archive.
I can connect you with trusted senior-move managers, estate clean-out services, and donation resources in the Hudson Valley who specialize in helping families respectfully transition a longtime residence.
As an SRES®, I also provide advice on what improvements or contents can add resale value before listing.

9. How can I avoid family conflicts when selling an inherited or family home?

The most common pitfall is making assumptions.
Establish open communication among siblings early, decide on one spokesperson or executor, and keep all decisions transparent.
Through my referral partners, I can connect you with experienced estate attorneys and financial planners who help families structure agreements clearly and reduce tension before the sale begins.

10. What should we do if a parent can no longer manage the property?

If upkeep has become too difficult or unsafe, it may be time to evaluate rightsizing or assisted-living options.
A local REALTOR® from my referral network can assess the home’s market potential while I guide you on planning and timing — especially if the next step involves relocation to Florida or another warm-weather community.

11. Are there financial or tax surprises when selling a longtime family home?

Yes — long-term ownership can trigger capital gains, estate, or inheritance considerations.
Before listing, always consult a CPA or tax professional familiar with both New York and Florida laws.
I can introduce you to vetted professionals who help families understand net proceeds, cost basis, and potential exemptions, especially when proceeds are being used to purchase in another state.

12. What are common mistakes families make when preparing an older home for sale?

• Over-renovating beyond market value
  
  

• Ignoring deferred maintenance
  
  

• Disposing of items with sentimental or historical value too quickly
  
  

• Attempting to “go it alone” without local expertise
  
  

Through my referral network, I connect clients with trusted REALTORS®, inspectors, and staging experts who can recommend cost-effective updates and ensure the property is positioned competitively.

13. How can we protect our parents from real-estate or contractor scams?

Unfortunately, seniors are often targeted by misleading offers or inflated repair quotes.
Always verify licensing, check references, and have a trusted advocate review any documents before signing.
I can refer families to licensed, reputable professionals in New York and Florida, and help coordinate communication between your family and verified vendors.

14. What emotional pitfalls should families expect when selling a longtime home?

It’s normal for parents or adult children to feel grief or guilt about leaving a family home.
Acknowledging those emotions early helps everyone stay realistic about timing and expectations.
My role is to provide objective, compassionate guidance while connecting families with local professionals who specialize in senior transition coaching and estate organization.

15. What happens if a parent passes before the home is sold?

If ownership transfers to heirs, the estate will typically go through probate before the property can be listed.
I can help families connect with probate-experienced REALTORS® and attorneys in New York who streamline the process and protect the estate’s value.

16. How do I plan my own next step while helping my parent?

That’s one of the most common Gen X realities — balancing caregiving with your own retirement goals.
I can help you map out a dual-timeline strategy that aligns both transitions, ensuring your parent’s move and your next home purchase (in Florida or elsewhere) work together financially and logistically.

Have more questions?

Contact John S. Pontillo, REALTOR® | SRES® for one-on-one guidance about selling, downsizing, or planning your transition from New York to Florida.
Phone: 845-220-6179 Email: jpontillorealtor@gmail.com