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Your information about Ossining schools is incorrect. I live just outside ossining and the schools are very good and nationally recognized. However, having moved to Ossining 5 years ago from NYC there are a few MAJOR DOWNSIDES. In exchange for reasonably more living space you get to live in a boring area with absolutely no good restaurants or places to eat. If your used to ordering in, you might as well forget about it. The commute to Manhattan is reasonably tolerable (still well over an hour) but you will probably end up using the Croton train station due to its better train schedule. However, Croton is notorious for flooding so you have to be on your toes when it rains or your car might be destroyed. Ossining real estate prices have also started to drop but are still slightly higher than a few years ago. One can only hope that prices in Ossining do not continue to decline. Town budget is reasonable although I believe the average tax increase was about 10% higher than last year. Is it worth it? If I had to do it again I would say no. It's a boring place to live filled with a growing underclass of unenthusiastic NYC transplants priced out of NYC. Aside from growing numbers of immigrants, most new residents will confide to you that they are not living here by choice. However, given the fact that we can not afford to live in NYC we have no real choice in the matter with two kids.
In a followup to the previous post, I don't want to give the impression that Ossining is all bad. Although there are major downsides real estate prices are comparatively affordable. For example, you should be able to get a nice home in a townhouse development (appx. 1500-2000 sf) for anywhere between $350,000 to $425,000 depending on condition and location. Prices, have already declined (expect prices to fall some more) but are still higher than a few years ago. A similar apartment in New York City could easily cost you 4-5 times that amount (think premier UES, UWS, Chelsea) and you will still end up paying significant taxes and common charges on top of any mortgage you might hold. If you can handle the boring lifestyle and don't miss living in New York or some other larger city, reasonable (still not cheap) real estate prices and excellent schools might make Ossining a good place for you to live. However, you might wan't to wait while home prices continue to correct. I've been told (privately) that anywhere from 10-30% is highly possible. Larger and single family homes will most likely retain more of their value then town houses. Ultimately, Ossinings proximity to NYC transportation routes still make it attractive to people who are willing to handle the commute. Also, although you may appreciate the "country" lifestyle, do not forget that it does get colder then NYC and you have to be prepared for dealing with a cold and snowy commute thats not always fun. If you check out the area in the warmer months, before you move you should know that things are very dreary in Janaury/Feb/March March.
I live 20ish miles west/north of Albany and 350-400k would buy you a 2500+ sq foot house with 5 acres (quality new construction) with all of the bells and whistles.
This isn't a poor area really ..median household income is over 70K....
But maybe it is because of our winters and the fact that we get 85 inches of snow a year versus Ossining's 35 inches per year! I love winter recreation though so I'm not complaining.
You probably have more decent restaurants within 20 miles of Ossining than we do within 100 miles. Not to put down our culinary delights up here. (we have some good restaurants) but just to add perspective.
Ossining may pale compared to Manhattan though....
I posted this in the other Ossining post, but I am copying it here:
Familyman Joe, I live in the general area and I must disagree with you on a number of points: Restaurants: 2 restaurants in Ossining have recently gotten good reviewin in the NY Times. And there are a large number of excellent places very nearby. Croton has three 4 star restaurants and a number off other good ones. Peekskill has 6 or 7 excellent restaurants. Stone Barns, a 5 star restaurant, is about 15 minutes away. Yorktown Heights has Peter Pratt's Inn, another 5 star restaurant, as well as about 10 good-quality restaturants. And Mt Kisco, all of 15 minutes away, has a huge number of excellent restauransts. There are also good restaurants in Tarrytown, all of 5 minutes south of Ossining. Boring Place: Well, compared to Manhattan perhaps. But there is a lot of art and music around the area on a regualr basis, so I hardly think I'd call it boring. There's an excellent art museum in Peekskill as well as a number of great galelries. There are lots of restaurants, coffee houses, and other places that have live music regularly. There are art shows and poetry readings almost every week at area libraries. There are a huge number of parks and nature preserves which regualry have workshops and events for kidd and grownups. We're 15 minutes from 2 other excellent museums (the Aldrich and the Neuberger) as well as Caramor, a fabulous music recital palce that has regualr concerts. In the summer there are outdoor concerrts every weekend as well as outdoor movies. Boring People: Almost everyone I know in the area (I live in Yorktown Heights) is a graphic designer, artist, editor, architect, web-site something, or some other "creative professional." Most are from Brooklyn or the Upper West Side and came here for both financial and lifestyle reasons.
ossining is not bad. hs is in the top 10 of nys. (it is next to croton, briarcliff, and mt.kisco) people just say that because there are hispanic and african americans .
When are they going to build that Sing Sing Museum? I drove through that area over 20 years ago and the whole Hudson River Valley made a lasting impression. I'm close enough to do a day trip by bus but all they offer here are trips to the Vanderbuilt mansion once a year. I'd really like to see the Old Dutch Church and North Tarrytown( Sleepy Hollow) and Washington's Irving home but again that trip is rarely offered. The Sing Sing prison Museum sounds cool since Alacatraz is an awesome day trip from the looks of it.
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Not to put down our culinary delights up here. (we have some good restaurants) but just to add perspective. 
