Pleasantville, N.Y.: A Walkable Village That Checks ‘All the Boxes’

Before discovering Pleasantville, N.Y., several years ago, Erin Williams lived with her husband and elementary-school-age daughter in a succession of Westchester communities. They bought a house in Ossining, N.Y., but found the commute to Manhattan too time-consuming. And getting around town wasn’t any easier. After selling their house and renting in Manhattan for a while, they moved into a rental in Tarrytown, N.Y., while searching for their next stop.

That’s when they hit upon Pleasantville, a village in the Westchester town of Mount Pleasant. There, the family found a three-bedroom 1880s colonial house for $600,000, in a close-knit neighborhood with residents of various cultures, near the village center.

“It checked all the boxes,” said Ms. Williams, 40, a graphic novelist, who likes the area’s walkability, the school system and the community. “We love our neighbors. One snow-blows our driveway without asking and another, a Korean lady, brings us cucumbers from her garden.”

Another draw was the arts scene. At the center of the village is the Jacob Burns Film Center, which has been attracting moviegoers from Westchester and beyond for more than 20 years. Three of the five screening rooms were recently revamped and there are plans to install a wine bar, said Denise Treco, the center’s director of marketing and communications.

The film center “put Pleasantville on the map,” said Hillary Landau, an associate real estate broker with Compass, attracting a “very eclectic” mix of residents, including “creative types, entrepreneurs, doctors, lawyers.”

Her clients from New York City and elsewhere in Westchester, she added, “want to walk into town, to the train and to the farmers’ market.”

That should be even easier come fall, when a state-sponsored project to widen downtown sidewalks and add more pedestrian-friendly streets is expected to be completed, said Eric Morrissey, the village administrator. And a 79-unit rental building currently under construction downtown will yield more housing — both market-rate and affordable apartments — a short walk from the train station. (Other planned development includes a handful of single-family homes on a 1.2-acre site outside the village center that once was owned by the Girl Scouts Heart of the Hudson.)

Loretta Chiavetta, an agent with Coldwell Banker, wanted the same small-town experience for her family that she had as a child in Hastings-on-Hudson, N.Y., when she and her husband moved out of a Manhattan co-op 30 years ago. With prices too high in Hastings, she said, they visited Pleasantville at the suggestion of a relative. There, Ms. Chiavetta saw “kids in the street and bikes on the lawn,” and was hooked.

Her family settled into an 1890 three-bedroom colonial house on Washington Avenue, in the downtown area, within walking distance of restaurants, shops and the Metro-North station. Ms. Chiavetta still lives there with her husband and college-age daughter, and now has many clients seeking the same experience.

“There are so many from Brooklyn,” she said. “And I can see why — the charm of the houses, the walkability of the village and the closeness of the city.”

What You’ll Find

Pleasantville occupies less than two square miles in the town of Mount Pleasant, in Westchester County, about 30 miles north of Manhattan. According to 2021 census figures, the village has around 7,400 residents, about 84 percent of whom identify as white, 14 percent as Hispanic, 4 percent as Black, 4 percent as Asian and 3 percent as multiracial.The median household income was $165,987.

The village is best known for its colonial-style houses downtown, but the inventory also includes ranches, split-levels and Cape Cod-style homes on lots of a third of an acre or less. While larger houses on bigger lots can be found farther from the village center, “you don’t come to Pleasantville to get an acre and a pool,” Ms. Landau said.

Attached townhouses are available at Club Court, a development bordering a nine-hole golf course operated by the Pleasantville Country Club, and at the Enclave at Pleasantville, a high-end Toll Brothers development. Foxwood offers condominiums in a multi-building complex, and there are garden-style condominiums at Greenwood and Pleasantville Gardens. As for co-ops, options include the Commons, Pleasant Manor and Ledgerock Gardens. Apartment rentals include lofts along Washington Avenue and one- and two-bedroom units at the Atwood, on Vanderbilt Avenue.

What You’ll Pay

With low inventory, high demand and rising mortgage rates, this is a “very competitive time for buyers,” said Ms. Chiavetta, who co-hosts “The Real Estate Connection,” a local cable show about real estate.

According to a Coldwell Banker analysis of data from the OneKey Multiple Listing Service, the median sales price of a single-family home dropped to $652,500 in April, from $784,000 a year earlier. This was due, in part, to fewer sales at the high end — and fewer sales overall — than during the previous year, Ms. Chiavetta said.

In April, there were 16 single-family homes on the market in the Pleasantville postal zone, including a three-bedroom, one-bath raised ranch listed for $599,000, and a five-bedroom, four-and-a-half-bath home listed for $3.999 million. Also listed were two three-bedroom townhouses (for $1.99 million and $1.050 million) and several condominiums ranging from $240,000 to $429,900.

Monthly apartment rentals can run $4,800 for a loft on Washington Avenue or slightly less than $3,000 for a one-bedroom at the Atwood, on Vanderbilt Avenue.

The Vibe

On nice days, students in middle school and high school stroll from their nearby campus to Frank & Joe’s Deli and the Black Cow Coffee Company on Wheeler Avenue, in the village center. Diners fill the outdoor tables at Pubstreet and Fatt Root, an Asian food shop recently featured in Westchester Magazine, while brown-baggers eat lunch on benches along Memorial Plaza. Cheese lovers praise Second Mouse Cheese on Manville Road. For casual dining, there is the Pleasantville Diner, on Memorial Plaza.

On Saturday mornings, the Pleasantville Farmers Market — considered by some the best in Westchester — draws crowds to Memorial Plaza. Popular annual events include the Pleasantville Music Festival, which will be held this year on July 8 at Parkway Field, and Pleasantville Day, a celebration of the village’s food, goods and services held in May at Memorial Plaza.

Favorite spots for young families include the playing fields at Roselle Park and Soldiers & Sailors Park, as well as the pool at Nannahagan Park. Mountain bikers enjoy five miles of trails in Graham Hills Park, off Route 117. Indoor activities are held at the Mount Pleasant Public Library, on Bedford Road, and the Recreation Center, on Marble Avenue. Older residents gather at the Senior Center on Clinton Street. For Ping-Pong fans, there is the Westchester Table Tennis Center, on Tompkins Avenue.

The Schools

The Pleasantville Union Free School District has an enrollment of about 1,635 at three schools. Bedford Road School serves students in kindergarten through fourth grade; Pleasantville Middle School and Pleasantville High School share a campus on Romer Avenue, serving students in fifth through 12th grade. Some high school students are from nearby Pocantico Hills, which does not have a high school.

“The school is the hub here,” said Tina DeSa, the superintendent of schools. “We care about the kids, and that’s why everyone wants to live in Pleasantville.”

According to New York State Education Department data from 2021-22, Pleasantville High School had a 97 percent graduation rate and the student body was 73 percent white, 15 percent Hispanic, 6 percent Asian, 2 percent Black and 4 percent multiracial. Average SAT scores for the class of 2022 reported by the district were 618 in evidence-based reading and writing and 622 in math, compared with statewide averages of 534 and 533. The high school was named a National Blue Ribbon School in 2021.

A 200-acre branch of Pace University is also in Pleasantville.

The Commute

The trip to Grand Central Terminal in Manhattan on the Harlem Line of the Metro-North Railroad takes a little less than an hour. A one-way ticket bought in advance is $14.75; a monthly pass is $322.

Annual parking passes are available for $600 to village residents and business owners only. For nonresidents, there are 12-hour and hourly parking spaces.

The History

In the 18th century, Pleasantville was an agricultural area known as the Manor of Philipseburgh. Early inhabitants included members of the Sint Sincks and Rechgawawanks Native American tribes, as well as Dutch settlers and Quakers.

In the mid-1800s, the village was known as Clark’s Corners. During the Civil War, it was a stop on the Underground Railroad. Past residents include the writers Lillian Hellman and Dashiell Hammett, and the actor Sidney Poitier. Reader’s Digest magazine was co-founded by a former resident, DeWitt Wallace, and was headquartered in the village before it moved to neighboring Chappaqua and, later, to Manhattan. The Usonia Historic District, a planned community designed by Frank Lloyd Wright in the 1940s, is listed on the National Register of Historic Places.

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