Ask any Pleasantville resident what this Northern Westchester town’s biggest draw is, and they’ll mention the strong sense of community. Saturday is the day that the Pleasantville Farmers’ Market sets up year-round, and residents from all across town gather not just to pick up farm-fresh produce, but also to socialize and enjoy the local vendors, live music, food trucks and kids’ activities with their neighbors.
Many people walk to the market, as this is definitely a walking town, an anomaly in Westchester made possible by the numerous sidewalks and 1.9 square mile size. On weekends and after school, residents can be seen strolling to the shops, restaurants, library, movie theater, and parks. There’s no school busing in Pleasantville; everyone who lives in the village gets to and from school by foot, which sets up a close-knit, neighborly dynamic.
Alethea Lynch, mother of three and Pleasantville resident since 2003, says that she’s “always surprised by how the community seems to find a way to fill any need they see for the kids.” For example, she adds, “A mountain bike team was started by a parent in town, a retired couple started the science Olympiad team at the middle school, and community members volunteer to organize and build all the scenery for the high school play.”
And there’s plenty else to do in town besides the market. You could stop for one of the staff-recommended books at the small but well-stocked Village Bookstore or catch a matinee of the latest indie flick at Jacob Burns Film Center, which also has great programming for budding filmmakers, even school-age ones (New York Times film critic Janet Maslin is the board president at JBF). The former train station depot has long been the site of a restaurant; the latest iteration is the ambitious and well-received New American brasserie Pubstreet.
For a small town, there’s a huge diversity of restaurants in Pleasantville, ranging from Bonnie Saran’s acclaimed Little Mumbai Market to gourmet pizzeria Wood & Fire to the classic Pleasantville Diner. With such an eclectic dining scene, you might even describe Pleasantville as a suburb with an urban vibe. It’s a quiet place, but with a lot going on.
Because of this blend of living styles, Pleasantville draws a mix of residents, from business people commuting to the city (50 minutes on MetroNorth) to working class folks to artists. Many local writers stop in the Black Cow Coffee Company to linger over a coffee while they work. “There’s no attitude here,” says Harriet Libov of Houlihan Lawrence, who specializes in selling homes in the area. “This is a community that’s professional, but down to earth.”
Pleasantville lacks the high pressure, high income vibe of its neighboring towns. You can get more for your money here, with the average sale price of a single-family home in 2017 recorded at $673,000 (although that includes some distressed properties at the low end of the market). The highest sale price last year was $1.2 million. In comparison, the real estate market for the surrounding areas of Armonk, Bedford and Chappaqua regularly feature homes for $2 million and up. Currently, the average price for a single-family home with 2,700 square feet in Pleasantville is $872,650. There are also some more affordable condos and co-ops in the area. “When a home that’s well maintained and on a popular street comes on the market, it goes quickly,” says Libov. “There isn’t a lot of inventory, and this is a sought-after community.”
Near the town center, the homes are older and situated on smaller parcels. As you move outwards, the lots get larger and newer, with everything from antique colonials to farmhouses built in the 1960s or more recently, and many remodeled and new construction homes. A new set of luxury townhouses called The Enclave was recently completed in the area, minutes from the train station.
As the gateway to Northern Westchester, Pleasantville features perks such as its proximity to bucolic settings like Stone Barns and the Rockefeller State Park Preserve. It’s common to drive five minutes for a hike along preservation land or a trip to the farm. In contrast, the town hosts its highly anticipated annual Pleasantville Music Festival every July in Parkway Field, which draws crowds from all over Westchester and New York City, and has featured the likes of Blues Traveler, Gin Blossoms, and The Smithereens in past years. Says Lynch, “Pleasantville’s got a traditional, small-town vibe, but it’s also close to the city.”