Pleasantville Charms With Arts, Culture, and a Stellar Food Scene

In Westchester County, Pleasantville attracts homeowners with two school districts and robust dining options.

Known for its walkable downtown, robust cultural scene, and excellent schools, the Westchester village of Pleasantville has long been a coveted place to call home. Judy Exton, director of development at the Jacob Burns Film Center (JBFC), made the move back in 1996, citing the schools and the village’s charm as major selling points. “It’s vibrant and culturally engaging with great, diverse restaurants—a popular destination with a welcoming, small-town atmosphere.”

Pleasantville is part of the town of Mount Pleasant, which also encompasses Sleepy Hollow, Hawthorne, Thornwood, Valhalla, and Pocantico Hills. Although the town was formally incorporated in 1788, Pleasantville was settled nearly a century earlier in 1695 (and known as Clark’s Corners). Throughout its existence, Pleasantville has served as an agricultural hub, a stop on the Underground Railroad, and an attractive draw for visitors.

Family Life

Pleasantville is served by two public school districts: The Pleasantville Union Free School District, which has an enrollment of 1,629 students across three schools, and the Mount Pleasant CSD, which services 1,938 students in four schools. Both districts are rated highly on Niche, with an A grade and an A-, respectively.

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The Jacob Burns Film Center and the annual Pleasantville Music Festival are cultural anchors of the village.
The Jacob Burns Film Center (above) and the annual Pleasantville Music Festival are cultural anchors of the village. Photo by Vladimir Kolesnikov.

With a busy, well-populated downtown area, it’s no surprise that the village is teeming with things to do. Enroll the kids in dance classes at Addie-tude Cultural Arts Center, Breaking Ground Dance Center, or Shake It Off studio, which offers movement classes for toddlers. There’s also the Pleasantville Academy of Music for guitar, piano, and vocal lessons, and Arc Stages, which puts on live shows and runs theater classes for all ages. The JBFC also hosts afterschool sessions for kids interested in the behind-the-scenes world of film.

And, we’d be remiss if we didn’t mention the annual Pleasantville Music Festival: The one-day backyard-style jam returns on July 12 with local artists and nationally acclaimed musicians, food and drink vendors, merchant tents, and fun and games for kids and families.

On the Town

Since Exton arrived in Pleasantville some 30 years ago, the downtown has boomed with new businesses. “There were a number of empty storefronts when we first moved here. Now, it’s rare to see a vacant building,” she says. Eateries are diverse with Fatt Root, an Asian-fusion spot; Crawdaddy’s Creole Kitchen; Falafel Taco; Pubstreet for elevated pub fare; the locally loved Pleasantville Diner; Take 3 Wine Bar & Café at the JBFC; the new-ish Lulu’s Kitchenette; and many more.

The shopping scene is just as hopping. Peruse clothing and accessories at Rhoda, Chloe USA Inc., and Twin Jewelers of Pleasantville. Homewares, gifts, and more await at Kimberly House. Foodies will find treats at Second Mouse Cheese and the Lil’ Chocolate Shoppe. If you’re in town on a Saturday, stop by the Pleasantville Farmers’ Market in the Metro-North station parking lot—it’s the largest in the county and operates year-round.

Get out There

Another big draw of Pleasantville? Its arts and culture. In addition to the aforementioned classes, the JBFC—housed in a 100-year-old building—hosts movie screenings, events, and more. Per Exton, “It transformed Pleasantville in many ways and continues to provide a wide range of cultural programs and experiences.” Photography enthusiasts will also appreciate a trip to the Gordon Parks Foundation, a gallery that preserves and showcases the works of the famous artist.

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As far as natural attractions, residents flock to the nearby 1,771-acre Rockefeller State Park Preserve for walking, bird watching, fishing, horseback riding, and more.

Above all, Pleasantville is just that—a very pleasant place to live. Per village government, “Its name is synonymous with neighborliness and tranquility, attributes that are embraced by all who live or work here.”

On the fence about moving to the area? Exton offers one piece of advice: “Do it!”

To find a real estate agent in Pleasantville or any Hudson Valley town check out near-me.hvmag.com/realtors.

Neighborhood Stats

Area
1.9 sq. mi.

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Population
7,430

Median value of owner-occupied homes
$773,800

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