Tell me about the different towns of Westchester county.
June 24, 2020 12:48 PM   Subscribe

After braving COVID-19 in our Manhattan apartment with no childcare, full-time jobs, and 16-month-old twins, Mr. Millipede and I are looking to sell said apartment and decamp to an enormously big house with outdoor space and nature and a spare room so next time there's a global pandemic, family can come quarantine with us and help. We are city people, but we appreciate a quaint town. We know this will be a big change. We have some questions.

We're looking at Westchester county for a variety of reasons, and this is settled. Please don't suggest Long Island or New Jersey or Connecticut.

We're most familiar with the river towns, and originally were only considering them--mostly around the Tarrytown/Irvington area. We realized we should consider everything, though.

We're looking for a good school district in a town that feels more like a town than a terrible suburb rife with strip malls and giant roads (I hate a terrible suburb with strip malls and giant roads). Ideally, we could live in our Big House and then take a walk to the town and the train station. It doesn't need to be a five minute walk. It can be a 20 minute walk. It can be a 25 minute walk. But we don't want to live in the absolute middle of nowhere, where it's a 20 minute drive to the town and the station. We understand about driving and having a car and we can do this. But we do like the idea of being able to walk to do some things, too. City people.

We'd like to be no more than 40 minutes from Grand Central. We DO need to be on a train line. This is not negotiable.

Which charming towns fit this criteria? Pretend price is not an object for Operation Big House. It is, but I'll eliminate based on that later.
posted by millipede to Travel & Transportation around New York (23 answers total) 6 users marked this as a favorite
Underrated, but probably only close-in Westchester town I'd move to: Pelham
posted by sandmanwv at 12:55 PM on June 24, 2020 [1 favorite]

40 minutes to Grand Central--is that Express or Local? That'll affect your range.
posted by mollymayhem at 12:57 PM on June 24, 2020

Response by poster: Either. And it's a fairly loose guideline.
posted by millipede at 12:59 PM on June 24, 2020

Best answer: West: Hastings-on-Hudson, Dobbs Ferry, Irvington
East: Bronxville (Bronxville school district), Scarsdale, Rye, Mamaroneck, Larchmont

Loosening criteria:
(school system) Eastchester, Tuckahoe, White Plains
(time to GCT) Chappaqua
(distance from station) Ardsley, Rye Brook

... just my opinion. YMMV.
posted by cgs06 at 1:27 PM on June 24, 2020 [2 favorites]

Best answer: Hi, millipede! Remember me, from our Brooklyn days? 'Sup?!

I grew up in Rye, which ticks all your boxes, but is quite an expensive place to live. Port Chester/Rye Brook, which are sister towns and are right next door to Rye, are surely up-and-coming. Mamaroneck fits your bill, as does Harrison; so do some parts of New Rochelle (which might be an easier transition for you City Folk, as it's somewhat more urban, but with strongly suburban elements).

Though I haven't lived in Westchester for decades, the only strip-mall-less town of the ones I've listed is ... my hometown, Rye. Definitely the quaintest of the lot.

I have friends who live in Hastings (and work in midtown) and LOVE it. Tarrytown might also work but I'm not sure of the commute times.
posted by Dr. Wu at 1:35 PM on June 24, 2020 [2 favorites]

Oh, and I think Dobbs Ferry might be a good option, too, though I think trains are less frequent there.
posted by Dr. Wu at 1:43 PM on June 24, 2020

We have friends who just moved to Bronxville, which absolutely is a charming walkable little enclave, but holy cow it's VERY VERY MUCH an enclave. Wonderful public school, by all accounts, but looking there may stress your "pretend price is no object" rule.
posted by uberchet at 1:52 PM on June 24, 2020 [1 favorite]

I think cost is actually going to be your main constraint-- yes any house is bigger than an apartment, but local taxes in some of the places mentioned are astronomical and go to support the truly high-end schools. are you ready to drop 2-3m on a house in Bronxville, and then an additional 20k in taxes each year? if not, you need to re-calibrate your price range. (obviously you can go cheaper, but it's always eyeopening to review the prices)

Don't discount Riverdale in the Bronx; you can buy a lovely home there (if you have the money) and either take an express bus into NYC, or metro-north. Also consider that living in the Bronx means your kids can apply for NYC's highschools.

(I grew up in Southern Yonkers- I can take a bus-> 4 subway and be in union sq in under an hour from my parent's house if you time it right. Although I don't necessarily recommend HS in Yonkers, I had a great time in elementary/middle schools with a very diverse group of kids. Westchester towns trend towards fairly monolithic rich white bedroom communities, with a more aggressive parenting set. The term Helicopter parent fairly accurately described every single parent of my HS friends- we were all over-scheduled, over-achieving, extremely anxious and knew no other way of being. )

posted by larthegreat at 2:03 PM on June 24, 2020 [7 favorites]

This is 13 years old now, but still mostly accurate and super packed with information: NY Times commute time infographic

For the river towns I'd go as far north as Croton (where I live, and would recommend) without relaxing too many of your constraints - it's about a 43 minute express to GCT from there, and there are many express trains.
posted by true at 2:08 PM on June 24, 2020 [2 favorites]

Response by poster: Gentle reminders: 1) we are pretending price isn’t a constraint. I said it and everyone is not following that at all! I really meant I didn’t want to hear about price in this initial review of towns. I’m more interested in literally everything else about them. It may or may not be a constraint, depending on how much we get for our apartment.

2) Commute time is less important than its coming across. I don’t expect I will ever have to go into an office every single day ever again. Husband mostly works from home.

3) we definitely prefer tiny town quaintness over anything suburban in character. I originally wanted to go much further away, if that provides context. The 40 minutes is less important than other aspects and can definitely be stretched.
posted by millipede at 2:30 PM on June 24, 2020 [1 favorite]

posted by mlis at 2:41 PM on June 24, 2020 [2 favorites]

I think Schools/Walkability/Price are going to be the constraints you operate within. Walkable neighborhoods near enough a train with good schools are going to be some of the traditional towns we've mentioned- Scarsdale, Bronxville, Pelham, Tarrytown, Mammaroneck ,Rye, Larchmont. It very quickly gets suburban once you are farther from the traditional train/commuter towns.

If the commute time is less of an issue, then there are several towns above White Plains that might work for you- Katonah is nice, as is Croton.

There's a lot of nice towns in westchester that are perfectly walkable- the key will be finding what other factors are really important to you- with 16m twins, schools are probably pretty high on the list- so going through the schools and their programs would be useful to you, followed by what shops actually are on their main street, and if the town's vibe is one you like.

(you gave us commute time and walkability as factors... property taxes in these communities are really, really high- Bronxville's average annual property tax is about 35k.)
posted by larthegreat at 3:08 PM on June 24, 2020 [1 favorite]

Best answer: I grew up in the New York suburbs and just really, really hate them—any place that feels too suburban now makes my skin crawl. However, there is one single town in Westchester that I genuinely like, and that town is Hastings-on-Hudson. To me, it really feels like a small town, one with art and culture and a history of its own. In your position, that's where I would look first.
posted by Mender at 4:04 PM on June 24, 2020 [3 favorites]

There's a 3 bedroom, 3 bath home for sale in my neighborhood for 1.2 million (taxes around $8500/year). Excellent public schools and lots of choices for private. Walk to the train (3 minute walk, 55 minute train ride). Walk to the elementary school, library, waterfront park, butcher, fish shop, cheese shop, coffee/chocolate shop, smoothie shop (2), pizza (2), Indian, ice cream, tea/antique shop, CVS, banks, post office, playground, field, tennis. 10 minute drive to the beach or hiking trails, three other libraries, small museum, movie theaters.

Oh, but it's Connecticut! Sorry - doesn't meet your criteria.

To me, the biggest difference between CT and Westchester is that CT is all wood that's painted white and Westchester is all brick. (And Westchester's taxes are insane.)

We spend a lot of time in Rye because my kid takes some after school classes there (definitely charming, walkable downtown, library, beach, art center, nature centers, amusement park) but couldn't afford to live there.

We go to Tarrytown a few times a year to see things at their theater or for the occasional unique class like circus. As a town it reads as depressed to me. I keep expecting it to spruce up but it hasn't in all my years of commuting from this area.

We go to Mamaroneck about once a month for their theater or library. Their downtown has lots of options for food and interesting shops. On the down side, it feels like Mamaroneck is two main retail streets, surrounded by strip malls.

Pleasantville is similar to Mamaroneck (but no beach) in that it has the cute intersection downtown of two streets with an outer rim of bigger things with more parking. It has a bit of a charm around the Jacob Burns film center and its events.

I always thought Dobbs Ferry was sweet and had a nice small town energy, but I haven't been there in years.
posted by xo at 5:17 PM on June 24, 2020 [2 favorites]

Based on your elevation of tiny town quaintness over commute time and all of the other considerations, I would suggest Katonah. It's farther than most folks would choose to commute to NYC pre-pandemic when commuting frequency was set at daily (although many do it), but now it seems to me like a stroke of genius to have chosen to live there. I don't know about schools, etc., but always really was attracted to it (reminded me enough of Vermont, where I grew up, that I was nostalgic). I suspect there are other recommended towns in the thread that would equally fit your bill, but Katonah's the one I have direct experience with and I was kind of smitten.
posted by clownschool at 9:33 PM on June 24, 2020 [1 favorite]

I would recommend checking out Edgemont, which is located in the town of Greenburg. Top tier schools and beautiful neighborhoods, with an easy commute to Manhattan on the Metro North train line.
posted by catywampus at 3:49 AM on June 25, 2020 [1 favorite]

Just the other day, I met a nurse who, with her husband and twins, moved from NYC to Stamford, CT for just the reasons you describe. Zoning north of the Merritt Parkway is 3, or maybe 5, acres per home.

When we moved to Stamford in '76, houses were cheaper in Westchester, but real estate taxes were higher, so it came out just about even. Greenwich, in the middle, is more expensive because Greenwich.

A friend just sold his house near where I live. It didn't get much interest until Covid-19 when lots of people have the same idea you do. Buying now is going to be pretty much top of the market anywhere far enough from NYC to be leafy.
posted by SemiSalt at 6:11 AM on June 25, 2020

Hi, I grew up in Ardsley (which doesn't fit your criteria). Some towns that have the kind of walkable downtown that I think you're looking for are Dobbs Ferry, Irvington, Scarsdale, Bronxville, and Hastings. All of them also have a more suburban side, so it depends a little bit on which part of the town you live in. Bronxville is also kinda a college town, with Sarah Lawrence, if that appeals.
posted by Ragged Richard at 6:21 AM on June 25, 2020

My brother lives in Mount Kisco, on the side of town that's in the Chappaqua school district. It's apparently a good one, and the town of Mount Kisco itself is charming and walkable, although their house (and anywhere else in the town limits which is in the Chappaqua school district) is about a mile on foot from the near edge of the town's main street (and train station). It's also considerably further out the Harlem line than your 40-minute limit.
posted by jackbishop at 6:46 AM on June 25, 2020

Response by poster: Last update and then I am done updating! I realize I should have been narrower in my question, and wasn’t because I wanted to hear every option. Originally I wanted to move to Cold Spring. We go hiking there and like it and always walk a bit away from the town and look at the houses and imagine living in one. It’s too far from the city for husband to be comfortable. We like the quaintness and natural beauty and unsuburban feel. Is there anything approximating any of this that also comes close to my criteria? That should have been the question. And I need to remain in NYS for my job.
posted by millipede at 8:07 AM on June 25, 2020

Parts of Croton (which I mentioned above) are quite rural. The town is small but pleasant, split into two sections. There's a small-ish intersection of places that feel like you're in the middle of the woods and are also easily walkable to the town, but they do exist. Places that are walkable to the train AND the town AND have a rural feel will be much harder to come by. Schools (one elementary, middle, and high) are good enough, depending on what you're looking for.
posted by true at 9:17 AM on June 25, 2020

I think Cold Spring is unique. Putnam County really has a quite different feel to Westchester, because of the proximity to the mountains/hills. The whole topography is different. Westchester is criss-crossed by several highways and arteries, is much flatter, has lower buildings in the downtowns, is denser, has more apartment buildings. I firmly believe that in Westchester there is nothing that feels like Cold Spring.

I think the compromise is going to have to be either on distance (go ahead and live in Cold Spring), or the Westchester version of charm, which limits you to Bronxville, Pleasantville, Katonah, Mount Kisco, Dobbs Ferry, Tarrytown, and Rye.
posted by xo at 9:21 AM on June 25, 2020

I like Cold Spring very much, but it's gotten crazy popular in the last ten years or so. It's incredibly busy on the weekends, which you may or may not appreciate if you're trying to go out for a walk or run errands. Also I think there's only one grocery store in town and I'm not sure how far it is to the nearest town with better shopping infrastructure (Fishkill and Beacon).

Good luck with your search!
posted by computech_apolloniajames at 6:20 AM on June 27, 2020

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