Finding the Right Next Chapter in Pleasantville

How Suburban Jungle helped this Riverdale family make the move to Westchester

After 15 years in NYC, moving from NYC to Westchester wasn’t something Kelsey and her husband Dean had seriously considered. The family loved their life in Riverdale – they could walk their kids to school, grab coffee nearby, head to soccer, spend time at the park, and would almost always run into someone they knew. Kelsey and a friend used to joke that it felt like Sesame Street – you couldn’t leave the apartment without seeing a familiar face. 

“We had no real desire to leave the city,” Kelsey says. 

But after welcoming their second child, life began to feel a little different. Their two-bedroom apartment was getting tighter. Their son and daughter were happily sharing a room, but Kelsey knew that wouldn’t work forever. And after a particularly tough winter spent largely indoors, more space began to feel less like a nice-to-have and more like a must-have. 

At the same time, with their daughter approaching kindergarten, Kelsey and Dean were thinking more seriously about school and what they wanted the next chapter of life to look like. Hoping to stay in the neighborhood they loved, Kelsey and Dean found a larger apartment in Riverdale and made an offer. It was accepted, but when the seller unexpectedly backed out, they began to reconsider their plans. Rather than starting another apartment search, they took the opportunity to think more seriously about what they wanted for their family’s future.  

“We were so ready to double down on staying in Riverdale,” Kelsey says. “But we decided maybe it was time to zoom out a little and reconsider.” 

Figuring Out What Came Next 

Once they opened themselves up to the idea of the suburbs, Kelsey and Dean quickly encountered a new problem: they had no idea where to start. Kelsey had grown up on Long Island, but wanted to explore her options. New Jersey would put them farther from her mother, who was central to her family’s day-to-day life. And while Westchester seemed like it could make sense, they knew very little about its communities. That’s when Kelsey remembered hearing about Suburban Jungle.

“I remember my mother-in-law telling me that one of her friend’s sons moved to New Jersey and used a service, but she couldn’t remember the name. I started looking into it and right away found Suburban Jungle,” she says. 

She initially assumed there had to be a catch and a price tag. When she discovered the service was free, she figured they had nothing to lose. She and Dean booked a call with Alli Levine, their Suburban Jungle Strategist, and what followed was a conversation that lasted about an hour and a half.

“Alli asked us everything,” Kelsey says. “It wasn’t just things about where we wanted to live, it was more about what we do for fun, what’s important to us. We went to an arts college, and we love theater, we love movies, we love the art scene. We really wanted a town that was smaller and more tight-knit, too.” Most importantly, she says, they wanted to preserve the sense of community they had loved so much in Riverdale. 

Turning Priorities Into a Search 

With a clearer picture of what Kelsey and Dean wanted, Alli helped narrow the possibilities to a handful of Westchester communities that aligned with their priorities, including Pleasantville, a town that hadn’t really been on the radar. 

From there, they spent the fall getting to know the area, digging into Suburban Jungle’s detailed town information, learning about everything from schools, camps, and after-school programs to the local restaurant scene and overall feel of each community. Then they headed out on town tours, where they could see firsthand what everyday life might actually look like. Those visits helped fill in the details that were difficult to understand through online research alone: where kids spend time, how neighbors connect, how school boundaries work, and where families meet up. They also gave Kelsey and Dean the chance to experience the communities for themselves. 

The more they explored, the more Pleasantville stood out. The town offered the close-knit community, arts and culture, family activities, schools, and space they were looking for. The commute was slightly longer than they had initially envisioned, but Dean agreed the tradeoff was worth it for the lifestyle they could have there. 

Staying Focused When the Search Got Hard

By winter, Kelsey and Dean were ready to move from exploring towns to seriously looking for a home. They hoped to relocate before kindergarten began in the fall, putting them squarely in a competitive market – but the process tested their patience. 

Pleasantville remained their first choice, but limited inventory made the search challenging. As the months went on, Kelsey and Dean expanded their house hunt to other towns and put in several offers that didn’t work out. After one unsuccessful offer on a home that Kelsey admits never felt quite right, she began to wonder whether the frustration of the search was pushing them to compromise simply for the sake of finding something. 

That’s when Alli checked in. Kelsey and Dean told her they were discouraged. They even asked whether they should widen their search just to improve their chances of finding something. But Alli encouraged them not to lose sight of everything they had already learned about themselves and the communities that fit them best. “You’re doing all the right things,” Kelsey remembers her telling them. So rather than starting over, they stayed focused. 

Then a house in Pleasantville came on the market. 

It needed work and cost more than they once imagined spending, but Kelsey could see what it could become. More importantly, they already knew how they felt about the town. They made an offer, and this time, they got the house. 

More Than Finding the Right Town 

For Kelsey, one of the things that stands out most about her experience with Suburban Jungle is that the support didn’t end once they knew where they wanted to live. 

Alli stayed connected throughout the house hunt, checking in when the process got discouraging and offering reassurance along the way. For Kelsey, having someone who understood what they were looking for, and was there to help them navigate the ups and downs, made a stressful process feel much more manageable. 

The support continued even after their offer was accepted. Alli celebrated the news with them, checked in after they closed, and continued sharing ideas and activities to help the family settle into their new community. 

“It just felt so supportive,” Kelsey says. “We really had our hand held from the very beginning.” That meant even more as they navigated the move with two young children. Their five-year-old daughter was leaving behind friends and teachers she had known since she was a toddler, and Kelsey knew that a bigger house and backyard couldn’t replace those relationships overnight. Having someone continue to share ways to explore their new community and get the kids excited about where they lived made the transition feel a little easier and gave Kelsey one less thing to think about during an already busy move. 

Finding Community Again

Today, the things Kelsey loves most about Pleasantville sound remarkably similar to the things she once loved about Riverdale. Not because the two places are the same, but because both offer the sense of connection that her family values.

Their daughter has found a warm school community, where a summer program helped her make friends before kindergarten even began. Their cul-de-sac has plenty of children, and afternoons often mean kids riding bikes, knocking on doors, or ending up in Kelsey and Dean’s backyard. The family is discovering local movie nights, arts programming, theatre, and town events. 

And then there’s the farmers market. Almost every weekend, the family heads there for bagels, lemonade, coffee, and music. They make a lap, pick up what they need, and still get home in time for their son’s nap. “It’s the perfect Saturday,” Kelsey says. It’s a small ritual, but one that captures what they were searching for all along: more space without sacrificing connection, and a community where everyday life feels full. 

Kelsey’s Advice: Start With the Town

For families considering a move, Kelsey recommends starting before the pressure to buy takes over. Because she and Dean began exploring months before they needed a house, they had time to tour communities, go out to dinner, grab lunch, and experience different towns without evaluating every visit through the lens of a listing. 

That ultimately helped them separate two very different decisions: 1) Where do we want to live? and 2) Which house do we want to buy? 

“I can’t even quantify how much that was worth to us and how that helped us,” Kelsey says of working with Suburban Jungle. “Pleasantville was not on our radar at all.” 

Kelsey and Dean didn’t leave Riverdale because they stopped loving their life there. Their family was simply ready for something different. And with Alli and the Suburban Jungle team helping them define what mattered, explore their options, and stay focused through a challenging search, they found a place they hadn’t expected. And ultimately, a place that feels like home.  

For more client stories, visit Suburban Jungle’s blog page on our website.

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