July 24, 2025
A Day, Three Homes and a Lot of Tennis Spirit
Not every visit goes as smoothly as planned, especially with the kind of summer weather we’ve had this year. Rainy days made us postpone more than once. But when the skies finally cleared, we knew it was the right moment to hit the road.
In one packed day, we left the city behind to explore three very different tennis homes. Each one reminding us why this search is never just about the sport. It’s about character, setting, the way a place makes you feel.
Our first stop was in the Hamptons, where we met Kyle Barisich from CeeJackTeam at Compass. He welcomed us with a full tour and shared the story behind a one-of-a-kind 1980s home. Skylights everywhere, a layout designed for entertaining, and a pavilion right next to the court with a bar and space to change before or after a match. This home hasn’t been retrofitted, but you can feel how well it’s been maintained. There’s room for even more, yet what’s already there is rare. The architecture has soul.
We then met Deborah Pirro from Sotheby’s over coffee, a perfect chance to connect before heading to our next stops. Deborah introduced us to two listings: one we passed by in Remsenburg (very charming, and we’ll be sharing more visuals soon), and the other, “The Point” in Bellport Village, where we explored on our own.
That last one was something else.
Perched right at the edge of the bay, with expansive views and a setting that unfolds like a story, this property beyond being a tennis home offers a full landscape experience. A sculptural garden, a swimming pool, benches made for contemplation, a small beach and a private pier. And the tennis court? Depending on where you stand, the water becomes your backdrop. You don’t get that kind of court presence often.
Why This Trip Mattered
As much as we love showcasing properties with photos and videos, nothing compares to actually walking through a space. Feeling the light, the air, the way sound travels. That’s where the real magic is, and it’s what makes a tennis home so much more than just a place to play.
Meeting brokers in person also makes all the difference. We walked away from this day not just with footage and ideas, but with stronger relationships. Kyle and Deborah are pros, deeply knowledgeable and clearly passionate about what they do. We’re grateful to count them as part of our growing Tennis Homes network.
Tennis Homes Outside New York City
A Tennis Lifestyle Within Reach
Driving back to the city, we couldn’t help but reflect on how close these places actually are. A couple of hours out, and suddenly you’re in a completely different rhythm. For those who want a weekend escape, or even a full lifestyle shift, these homes make it feel possible. The city’s always nearby if you need it.
We visited them all in one day. It was a stretch, but completely worth it.
We’ll be sharing more from the day soon, including some of our favorite moments on and off the court. Stay tuned.
Until the next match,
Tennis Homes Team
