Pleasantville, NY

Pleasantville, NY

Pleasantville, NY

Population: 7,055
Median home value: $556,825
Median household income: $110,368
% of the population with white collar jobs: roughly 92%
% of the adult population who are college graduates: 63%
Individuals below the poverty level: 2%
Racial Makeup / Most prominent races: 86% White, 12% Hispanic or Latino (of any race), 4% Asian, 4% Black
Residents would hang out with NYC folk from: I dunno, but not the Upper East Side and not Williamsburg.

Pleasantville, NY

Pleasantville is a village in the town of Mount Pleasant in Westchester County just north of where the Saw Mill and Taconic Parkways meet.

Metro-North train from Pleasantville to Grand Central Station: 50-59 minute train ride, depending on time of day

By car to Grand Central Station: 32 miles, or 45 minutes


Looking to buy a house in Pleasantville? A 3 bed / 2 bath isn’t too hard to find in the $480K-$600K range.


Looking for schools? Here’s what has to say:




Bedford Road School



Pleasantville Middle School



Pleasantville High School



Pleasantville did not get its name by accident. What a pleasant place with pleasant people. My husband had a shoot in Pleasantville last week, and met some of the residents, who were very pleasant and told him how pleasant Pleasantville is. Pleasantries all around. So we drove up to investigate.

Pleasantville, NY

Pleasantville is, for starters, much larger than I thought it was. I had no frame of reference for it, but it is significantly larger than all the other Westchester towns I’ve visited. It’s like Larchmont, without the beach and the money, or like Yonkers, without the racial discrimination and the poverty.

Burns Film Center

Any part of you that might want to think it’s a little “hick”-like, will be surprised to see all the cultural offerings of the town. There are dance studios, martial arts studios, and acting studios all over. And Pleasantville houses the very chic movie art house, the Burns Film Center.

Pleasantville, NY


They have a number of mom n’ pop businesses, including the fantastic and adorable toy store, Try & Buy. But Pleasantville is big enough to warrant some of the big guns too: Starbucks, McDonald’s, and a VW dealership. It’s small enough that you’ll run into all your friends at the post office, but you can still get a 99-cent Filet o’ Fish any time a day.


It’s so cozy of a town that we even ran into the same woman who my husband met on his shoot. She told me about the other “moms” in the town. She said you can have as many playdates as you want, as the mom community is very active. Everyone’s up for playgroups and playdates. And a number of your neighbors will watch your kids when you’re in a bind. It’s just that kind of place. She said a lot of the mothers work, but a lot stay home too. “Barely any nannies”. I asked her the kinds of jobs people in town have, and she said every kind. Blue collar mixed with “a guy from the New Yorker” and “a trainer from the Mets teaches at the high school part time” (or something like that… don’t quote my quotes, please.)

All in all, I liked it. As it’s bigger than other Westchester towns, it’s nice to know that there’s a movie theater right nearby. But the larger size also attracts some anonymous tomfoolery, like when some guys in a car hooted and hollered at me as they drove by (good for my ego, bad for my desire to be in a cozy, friendly town.)

May I introduce to you… Pleasantville!


2 thoughts on “Pleasantville, NY

  1. My husband and I moved to Pleasantville from Brooklyn in 2011 and we can’t say enough positive things about our little village. In our short time here we’ve seen subtle changes that continue to make it better and better. There is definitely an influx of other city folks moving in who are contributing to a growth in culture and sophistication, but honestly, part of Pleasantville’s charm is in its passé attitude towards “cool”. And this is so refreshing after witnessing the changes in our former Brooklyn stopping grounds. (Holy crap crap, Williamsburg, my dear old friend.)

    There are so many other highlights you may not have had the opportunity to experience while stopping through… For example, the year-round farmers market. On Saturday mornings mid-May through October, locals gather in the quintessential town square to buy fresh food, sit at cafe tables to have a coffee or falafel sandwich, listen to live music or the children’s entertainment, and just chat with neighbors. Once we became parents, we discovered the amazing playgrounds in town with sandboxes over flowing with trucks and other toys that just stay there for all to enjoy. There is the last-of-its-kind independent bookstore, the village pool, amazing library programming, excellent schools (and yes, with it come high taxes), and miles upon miles of gorgeous Rockefeller State Park trails right at our doorstep. My husband has become an avid fly fisherman since moving here. He can travel no more than 20 miles to have access to beautiful streams and reservoirs and still be home by noon. Peasantville is also known as a walking town with most of the village homes located within walking distance to the metro-north station. This alone is a major selling point for former city dwellers.

    My husband and I were pushed out of our truly lovely Prospect Heights apartment over 4 years ago when the owner decided to sell. It ended up being the final push we needed to stop drinking the NYC flavored Kool-Aid. We spent many happy, exciting, adventurous years apart and then together in the LES, Greenpoint, Williamsburg, Park Slope, and lastly, Prospect Heights. There were also plenty of difficult, infuriating, insanely expensive, stinky, and annoying times. Our love affair with the city began to dwindle after we bought a ’93 Pathfinder for $1500 on eBay. The “Finder” took us out of the city on weekends surfing, hiking, and fishing. We realized there is life outside of brunch, shopping, and sitting in a crowded park with thousands of strangers on weekends. Also, there comes a time in your adult life when you’re just not willing to settle for spending 40% (or more) of your monthly income on a place without “luxury” ammenities like a washer and dryer. Once you’ve experienced the amazingness of an in-apartment dishwasher and W/D, you simply can’t go back. When we realized we were priced out of Brooklyn and might be forced to move to – gasp – Queens for what we wanted (sorry), we apprehensively drove to Westchester and began our rental search in Dobbs. We eventually landed with real estate agent, Penny, from Tarrytown’s Hudson Homes. After seeing about 1200 rentals and then homes for sale, we stumbled upon our little casa in Pleasantville. The stars aligned and we bought our 1040 sq ft fixer-upper. Pleasantville may not be hip enough for everyone, but we sure love it.

    • I love what you’ve written here! Thank you for your comment. We adored Pleasantville. I think it has probably the best downtown area of any place we visited. And I couldn’t agree with you more about the NYC Kool-Aid and knowing how little you’re getting for the amount you’re spending. And yes, I can’t go to Brooklyn without feeling completely out of style and uncool. 😀

      All the best to you and your family!

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