Living in Pleasantville, NY—A unique town with a quaint vibe and creative spirit.
There’s a reason so many city dwellers want to call Pleasantville, New York “home.” With a population of approximately 7,000, Pleasantville offers a close-knit community feel and a range of amenities. From A+ schools to amazing eats, culture, activities, and a strong sense of community, this Westchester County suburb is a great place to be – here’s what we love about this dynamic suburb.
#1. A+ Schools
Getting an education in Pleasantville means attending an elementary school, middle school, and high school that have all been recognized as “Schools of Excellence” nationally, as well as in New York State. All three schools prioritize STEAM (Science, Technology, Engineering, Arts, and Mathematics) as well as theater arts in their curriculum.
Pleasantville Middle School offers a comprehensive four-year program designed to facilitate students’ transition from elementary to secondary education. This includes block scheduling and a diverse range of academic and extracurricular opportunities.
Pleasantville High School earned a Platinum Rating from U.S. News & World Report in 2024, with call-outs to its powerhouse academics, including 20 AP courses available. The school offers a distinctive three-year science and humanities research program and senior internship opportunities, fostering hands-on learning experiences.
Beyond academics, students can engage in college-preparatory coursework while also delving into various extracurricular avenues such as art, athletics, and community service, preparing them holistically for future career and academic pursuits.
#2. A Quick, Convenient Commute
With a train station downtown, many residents can get to the train within minutes – even on foot. Once onboard, the commute to NYC is a breeze on Metro-North: trains to Harlem 125th Street are just 41 minutes and to Grand Central Station in 56 minutes during rush hour. Residents who don’t want to walk to the station can apply for a parking pass online, but there is usually a waitlist.
#3. A Culinary Melting Pot
Pleasantville’s vibrant downtown is a go-to for culture, charm, and plenty of amazing food. While you’re here check out Frank & Joe’s Deli (AKA “Your Neighborhood Italian Deli”), Dai Sushi, Southern Table Kitchen & Bar, Jean-Jacques’ Culinary Creations, Black Cow Coffee Company, and The Raconteur Bar & Kitchen, known for seasonally-inspired dishes and drinks.
Other popular restaurants in town include Fatt Root (Asian Street Food), Miyabi Asian Bistro (Japanese & South East Asian cuisine), Falafel Taco, Root2RiseNY (Vegan), Vela Kitchen (New American), and Second Mouse Cheese, a cheese shop that has a daily sandwich and soup menu.
For locals seeking homegrown delights, the weekly Farmers Market Stands out as a top destination in the area. Pleasantville hosts one of the region’s largest markets, boasting over 50 vendors, lively weekly music performances, and engaging activities like the Market Sprouts program for children, culinary demonstrations, and initiatives focused on health and sustainability.
#4. An Always-Active Community
Pleasantville is a nature lover’s paradise with easy year-round access to Graham Hills Park and its 431 acres of mountain biking and hiking trails. Dogs are welcome on leashes. Rockefeller State Park Preserve is another popular spot, with miles of carriage roads and trails to explore. The town’s parks and green spaces facilitate outdoor activities such as hiking, biking, and picnicking, contributing significantly to its family-friendly atmosphere and overall livability.
When temperatures rise, check out the community pool at Nannahagan Park. Here, you’ll find a pool, playground, walking trail, fishing pond and basketball courts. Roselle Park and Soldiers & Sailors Park also have playgrounds and sports fields, as does Parkway Field, which hosts the town’s annual musical festival.
Pleasantville is also a perfect spot for fitness enthusiasts. Whether you’re looking for a traditional gym or boutique classes, locals can choose between Anytime Fitness, PFX Fitness, Immortal Fitness, The Partners Gym (Thornwood), Equinox (Armonk), Breathe Pilates and Yoga (Chappaqua), F45 Training (Mt. Kisco) and Orangetheory Fitness (Mt. Kisco).
#5. Arts & Culture are Off the Charts
Jacob Burns Film Center is a nonprofit five-screen cinema and education center in downtown Pleasantville. Touted as one of the most successful suburban art houses in the country, the theater celebrates film as a vehicle for entertainment, education, and inspiration. Housing a state-of-the-art theater complex, a 27,000-square-foot Media Arts Lab, and a residence for international filmmakers provides opportunities for people of all ages to discover, explore and learn through the power of film, media, and 21st-century technology. Pleasantville is an artistic hub that features a vibrant and diverse art scene, including local galleries and cultural institutions. Bibliophiles flock to The Village Bookstore and Mount Pleasant Public Library, both hosting reading events for the community.
Choosing the right town to call “home” is the most important decision you’ll ever make—why go it alone?, and our expert Suburbs Strategists will help you navigate the ‘burbs and find the right town to call “home.”
