The Dream List: September in Westchester | Fall Events, Real Estate & More

THE DREAM LIST

September 2026 | Westchester Edition

September has that fresh start feeling.

Summer is winding down, routines are returning, and fall is starting to make its way into Westchester.

But there’s also a lot happening behind the scenes in real estate — and if you thought the market cooled down this summer, you might be surprised.

So I pulled together what’s worth knowing, doing and dreaming about in Westchester this month.

Here’s your September Dream List. ✨

 

01 | THE MARKET

Think Westchester Real Estate Cooled Down This Summer?

If you stepped away from the market this summer expecting things to cool down, the latest numbers tell a different story.

In July, the median price of a single-family home in Westchester was $1.26 million — up 9.4% from last year.

And buyers were still making moves. Across the OneKey MLS market, pending home sales were up 6% from last year. 

 

Simply put: Prices went up, and buyers kept buying.

Stephanie’s Take

Buying? Don’t let the numbers make the decision for you. There are different homes, towns and price points throughout Westchester. The opportunity is finding where your budget works best.

Selling? Buyers are still out there — but pricing and positioning your home correctly still matters.

Thinking about making a move this fall? Let’s talk strategy.

 

02 | THE FALL LIST

Ready for Fall Yet? 🍂

September is giving us the first taste of fall in Westchester — and I’ve already found a few things worth adding to your calendar.

🎶 Bedford Music Festival | September 6
Live music, beautiful grounds and an afternoon at Caramoor in Katonah.

🎡 Yorktown Grange Fair | September 11–13
A classic hometown fair with that first-of-fall feeling. Bring the family and make a day of it.

🍂 The Great Jack O’Lantern Blaze | Begins September 18
One of Westchester’s most iconic fall traditions is back in Croton-on-Hudson. Thousands of hand-carved pumpkins, glowing displays and peak fall atmosphere.

Save this list — September weekends are filling up.

 

03 | BACK TO THE HOUSE HUNT

Put Your Home Search on Pause This Summer?

Vacations, summer plans, busy schedules — sometimes the house hunt simply takes a back seat.

But if buying a home is still on your list, September is a good time to get back in the game.

Before you start scrolling listings again, do these 3 things:

1. Refresh your budget.
Know what monthly payment feels comfortable for you today.

2. Update your pre-approval.
If yours is a few months old, check in with your lender so you know exactly where you stand.

3. Revisit your wish list.
What are your must-haves — and what are you willing to compromise on for the right home?

Stephanie’s Take

Don’t restart your search by looking at more homes.

Restart with a better strategy.

The clearer you are about your budget, location and priorities, the easier it becomes to recognize the right opportunity when it shows up.

Ready to start looking again? Let’s build your fall home search strategy.

 

04 | THE DREAM HOME

Wait Until You See What’s Coming to Katonah… 👀

29 Upper Hook Road in Katonah recently caught my eye — and this one deserved a spot on The Dream List.

Offered at $7.95 million, the estate features 10 bedrooms, 15 bathrooms, a pool, four fireplaces and beautiful grounds.

But with a home like this, the numbers only tell part of the story.

Stephanie’s Take

Luxury isn’t just about the price tag.

What makes a home memorable is often what you can’t capture on a property sheet — the setting, the architectural details, the lifestyle and those unexpected features that give a home its character.

And this one? You’ll want to see inside. 👀

29 Upper Hook Road, Katonah, NY | Offered at $7,950,000 | Listed by Mary Dowdle, Ginnel Real Estate

 

Until Next Month ✨

That’s your September Dream List — a little real estate, a little Westchester, and a little something to dream about.

If a move has been on your mind — now or somewhere down the road — sometimes the best moves begin with a simple conversation.

Stephanie Smith
Real Estate Dream Girl®
Coldwell Banker Realty