Best Places to Live: The Old Village, Pleasantville

Best for families, empty nesters, and commuters alike.

Blueprint: Settled in 1695, Pleasantville was a prosperous farming community and later became home to several industries. With the arrival of commuter train service to New York City, the area gradually evolved into a suburban destination prized for its central location and easy access to Manhattan.

Façade: Still somewhat affordable compared with neighboring Chappaqua, with a more laid-back, slightly artsier vibe, the 1.8-square-mile village of Pleasantville has what many residents consider an ideal location, almost smack-dab in the center of the county. This walkable village, just 30 miles from Manhattan, has a pretty shopping-and-dining corridor, the Jacob Burns Film Center and its Media Arts Lab film school, and lots of lovely architecture, all just a 15-minute drive or less from White Plains to the south, Mount Kisco to the north, and the Rivertowns to the west.

Foundation: The Old Village, near the train station and the Burns Center, is a big draw for homebuyers looking for coveted Colonials and Victorians just a stone’s throw from the equally coveted public schools, as well as cafés like The Black Cow Coffee Co., shops including Glass Onion and the Village Bookstore, and restaurants like Mediterraneo. There are co-ops, condos, and apartments close to town, and the Saturday farmer’s market is one of the county’s most popular.

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Recent Reno: N/A

Trending: Most single-family homes are priced from $600,000 to $1M.

Selling Points: vibrant village center; cultural amenities; great schools (there’s one elementary school, middle school, and high school, all a short walk from each other, town, and the library); good mix of town and country living; convenient location; great accessibility; easy commute to Manhattan; family-centered community; laid-back vibe.

Trade-off: Pleasantville does not provide school busing.

Starting Point: $395,000

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Topping Out: $1,695,000. Three-bedroom detached single-family homes start at approximately $450,000.

Best For: families, empty nesters, commuters 

Need to Know: Though part of Mount Pleasant, Pleasantville has its own police force, parks-and-rec department, pool, etc.’

Best Thing About Living Here: “We wanted a place where we didn’t have to drive everywhere. My husband and I grew up in small towns, so it’s like going back to our roots. We have parks and the Rivertowns nearby. It’s a great place to raise our kids.” —Suzanne Cunningham, recent transplant

Fast Fact: Pleasantville is home to Usonia, a Frank Lloyd Wright-designed enclave. Outdoor enthusiasts can hike the nearby Rockefeller Preserve, mountain bike at Graham Hills Park, or cycle on the 20-plus miles of the North County Trailway.

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Assessment: easygoing, family-oriented yet slightly artsy vibe; small-town charm without being “Anytown USA”; convenient to all of Westchester’s shops and attractions


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