Ossining

There are about 25,000 people in the Village of Ossining. It’s located the Town of Ossining, at the widest part of the Hudson River. Like Peekskill, in Putnam County, it has much more of a diverse population than its surrounding areas, with a mix of races, religions, and cultures.

The Village’s downtown shopping area has a variety of stores, shops, banks, and restaurants. Westchester Magazine just named Ossining as the “Best Place to Live for Architecture,” and many of its Village buildings are listed on the National Register of Historic Places. There are buildings from every era – Victorian, Gothic Revival, Federal-style, Italianate, Art Deco, American Craftsman - even a Sears Roebuck kit house from the 1920s. The Ossining Public Library, a nearly-$16 million renovation completed in 2007, is a dazzling 48,000-square foot building which uses a geothermal system for heat and cooling. It has over 50 public Internet terminals, a 250-seat theater, an art gallery, and a café. The main reading room is named for long-time Ossining resident John Cheever.

Ossining has two school districts. The Briarcliff Manor School District has one elementary school, and a combined middle and high school; it’s a smaller district, and thanks to the pricey real estate in Briarcliff Manor, has better facilities and higher test scores. However, the Ossining Union Free School, which has 3 elementary schools, one middle, and one high school, does very well itself; the high school offers AP classes, as well as SAT and ACT prep courses, and has a far more diverse student body. The Maryknoll headquarters is located in Ossining, so there is a strong Catholic presence here: private schools include St. August, St. Anne, and St. Theresa.

Westchester Community College has a satellite campus in the Village, Pace University has one in Briarcliff, and SUNY Purchase is a short commute.

Metro-North stops at Ossining as well as nearby Croton-Harmon. There is a Bee-line Bus System, and a ferry between Ossining and Haverstraw (in Rockland County.)

There are two town parks, with one located on the waterfront, and a new aquatic facility at the Community Center which sports a competition-sized pool. There is a yearly Village Fair, and a weekly summer Farmer’s Market on the corner of Main and Spring Streets Saturdays from 8:30 until 1. Ossining has a Food Pantry for those in need, and even delivers to those who cannot travel.

The Phelps Memorial Hospital Center is located in nearby Sleepy Hollow.

Like Buchanan, the quaint little Putnam County village whose main drawback is that it is the home of Entergy, the nuclear power plant, Ossining is a nice, more-affordable-than-most Westchester town whose main drawback is that it is the home of Sing Sing, a maximum security prison housing over 2,000 inmates. As with Entergy, the threat of what could go wrong with Sing Sing is far worse than the odds of it actually happening.

Ossining has not yet been completely gentrified, which is why it’s still possible to live there on a budget. There is a range of real estate, from the million-dollar neighborhoods of Briarcliff Manor to the more run-down apartment and townhouse areas of Ossining. An artist friend recently told me how excited he was to have located a fixer-upper for a great price, only to find that in that specific area, street crime was still an issue. However, he liked the town so much that he’s still looking.

Ossining is 15 square miles, includes the Village of Ossining and Briarcliff Manor, and its western boundary is the Hudson River. There is a Metro-North stop right in Ossining, making it an easy commute to New York City. It is more racially diverse than many of its neighboring towns, making it a far more culturally interesting place to live.

Westchester Magazine just named Ossining as the “Best Place to Live for Architecture,” and large areas of it have been placed on the National Register of Historic Places. The village of Ossining is home to buildings from every era – Victorian, Gothic Revival, Federal-style, Italianate, Art Deco, American Craftsman - even a Sears Roebuck kit house from the 1920s. The Ossining Public Library, a nearly-$16 million renovation completed in 2007, is a dazzling 48,000-square foot building which uses a geothermal system for heat and cooling. It has over 50 public Internet terminals, a 250-seat theater, an art gallery, and a café.

Ossining has two school districts. The Briarcliff Manor School District has one elementary school, and a combined middle and high school; it’s a smaller district, and thanks to the pricey real estate in Briarcliff Manor, has better facilities and higher test scores. However, the Ossining Union Free School, which has 3 elementary schools, one middle, and one high school, does very well itself; the high school offers AP classes, as well as SAT and ACT prep courses, and has a far more diverse student body. The Maryknoll headquarters is located in Ossining, so there is a strong Catholic presence here: private schools include St. August, St. Anne, and St. Theresa.

Westchester Community College has a campus in Ossining, Pace University has one in Briarcliff, and SUNY Purchase is a short commute.

There are two town parks, with one located on the waterfront, and a new aquatic facility at the Community Center which sports a competition-sized pool. There is a yearly Village Fair, and a weekly summer Farmer’s Market on the corner of Main and Spring Streets Saturdays from 8:30 until 1. Ossining has a Food Pantry for those in need, and even delivers to those who cannot travel.

The Phelps Memorial Hospital Center is located in nearby Sleepy Hollow.

The Town of Ossining includes the village by the same name, and the village of Briarcliff Manor. Both areas share part of the Hudson River’s waterfront, with an easy commute to Manhattan.

Both towns originated as part of the manor of Frederick Philipse, who emigrated from the Netherlands and owned vast quantities of land in the Bronx and Westchester during the late 1600s. During the Revolutionary War, his descendents stood with England and King George III and ultimately lost the lands when America won the war.

Ossining has the distinction of being Westchester’s first incorporated village. In 1813 the area was incorporated and called Sing Sing, but the name was later changed to distinguish it from the prison. Much of modern-day Briarcliff Manor was once farmland, and was incorporated as a village in 1902. Both villages have active historical societies focused on sharing and preserving the stories of the area.

On paper the Briarcliff Manor schools have a clear edge over Ossining; it’s a smaller district and gets outstanding results on state exams in all grade levels and subjects. However, Ossining’s schools have received their share of honors; the high school has been recognized for its outstanding science program. Students in Ossining’s schools hail from 53 countries and speak 39 languages, and many parents appreciate the way the school mirrors the real world.

The differences between the school districts mean homes in Ossining are less expensive than Briarcliff Manor. There are also more apartments and multifamily homes in Ossining, and more homes priced above the million-dollar mark in Briarcliff Manor.

Recreation departments in the two villages function independently of each other; both areas have good programs, parks and activities. With two courses, Briarcliff Manor is known as a great golf destination. Both villages have excellent dining and shopping options, and aren’t too far from White Plains and the additional shopping, dining and cultural activities it offers.

Ossining offers great variety in housing choices, schools, and recreation. Many have found, and will continue to find, exactly what they’re seeking in a place to live.

Westchester County has its share of picturesque river towns, and Ossining is no exception. Occupying three square miles of Hudson waterfront, it has a population of 24,000 residents. It’s a diverse community with a busy village, an interesting history and good shopping and dining.

Ossining’s wealth of history tends to be overshadowed by its neighbor Sleepy Hollow and the presence of the notorious Sing Sing Prison. The Downtown Ossining Historic District features commercial buildings from the late 19th and early 20th century, with the First Baptist Church of Ossining and the Old Croton Aqueduct as its cornerstones. In 1813, the village, under the name Sing Sing, was the first in Westchester to be chartered as an incorporated village. As the nearby prison developed a violent reputation, the village changed its name to Ossining in 1901 in an effort to disassociate itself.

In addition to its historic treasures, Ossining has some great dining and retail options. The Arcadian Shopping Center has a large grocery store and hosts a satellite campus of Westchester Community College. A farmers’ market, active since 1991, operates seasonally during the warmer months. The Traveler’s Rest and the Goldfish Oyster Bar and Restaurant are two eaters popular with both locals and visitors.

The Ossining UFSD has 4,500 students and greatly values its diversity. There are six schools, including an early childhood center. Schools are organized by grade level, not neighborhood, which allows children to remain together as a group for their entire school career. Though the district earns respectable results on state exams, it was identified this year as being in need of improvement in English Language Arts on the middle and secondary level. However, the high school is currently one of three finalists in the prestigious Intel Schools of Distinction science competition. The district was also recently recognized for its wellness programs, which focused on exercise and nutrition and their role in better health for children.

Travel to New York City via the Metro-North Hudson line takes about fifty minutes. Route 9 is the main road through the town, providing access to towns north and south. The nearest highway is the Taconic, though car commuters likely find it’s not very convenient.

Home prices in Ossining are well below the median for Westchester County, making the village an affordable choice. There are a handful of properties with million dollar price tags, and lots of options for those interested in condominiums.

Ossining village is a slow n steady work-in-progress. It has come a long way in recent years by way of gentrification and urban renewal and is a popular choice for students, artists and young starter families in particular. There are lovely old homes of modest to large size as well as many apartment complexes and in-house apartment rentals in the area, all of which are still quite affordable especially in light of being in very affluent Westchester County. Ossining retains an old town by the docks feel and doesn’t feel as harried and hurried, which to some, is a huge draw to living there.

There are quite a few decent restaurants in the area including family-friendly Wobble café known for its outstanding waffles, the tiny storefront Lonnie’s Fish and Chips place where the owner is almost always present behind the counter with a warm, welcoming smile on his face, Goldfish Oyster Bar & Restaurant, Los Abuelos, a tiny joint with authentic Mexican food, Ossining Pizzeria and Restaurant, Okinawa Hibachi Steak House, Karma Lounge , Brasserie Swiss with excellent bratwurst and yodeling music in the background, and the Boat House, which offers fine food and cocktails with a sea-faring décor, lovely river views and a bar that is often called “Cheers on the Hudson.”

The village itself is very quaint and plays host to a hodgepodge of delis, coffee houses and a more upscale dollar store. Minutes from downtown, within walking distance, is the recently renovated Ossining Library which has a great collection and quality programming.

For shopping there is the nearby Arcadian Shopping Center which has a McDonalds, a GNC, a card store/gift shop, a Subway, an impressively outfitted Dollar World, the Purple Monkey Ice Cream Store, a pet store, a dry cleaners and an optician. There is a C-Town and a Stop and Shop for all one's grocery needs.

For those who want to learn about the darker side of Ossining, there is the Sing-Sing Museum located in the Caputo Community Center which talks of the infamous prison's history and has two actual cells displayed as well as some weaponry. It definitely makes for an interesting afternoon and a unique history lesson.

Ossining has an extensive Parks and Rec Department and a good summer day camp for children. There are several nice parks near the village including Louis B. Engel Waterfront Park which is adjacent to the train station parking lot. It has a beach, fishing areas, picnic tables, a playground and restrooms. Nelson Park has athletic courts but one must first obtain a permit. And lastly there is Snowden Avenue Park.

Ossining recently became home to a satellite branch of the highly regarded Westchester Community College.

Ossining is mostly safe with some pockets of crime. It is best to avoid certain areas by night and certainly use the buddy system when you can.

The Ossining Union Free School District is fairly good and the median SAT score is reported to be 1512. Ossining High School has made the list of the best 250 schools in the nation in the past.

Ossining is approximately 78% White, 12% Hispanic, 6% Asian and 3% Black.

The median household income is $70,468. The median home value is $295,464 and the median rental rate for an apartment is $1,253.00

The village population is approximately 24,010 people with the median age being 35 years of age.

The only thing I knew about Ossining before I moved to the Westchester area was the passing references to Sing Sing in ‘Law & Order.’ Now that I live in the neighborhood, I haven’t heard anything about it! I think it’s a case of one thing taking over the identity of the town for outsiders, while those who live around here know too much about the good things there to give too much importance to the penitentiary.
So, what are those good things? Nice homes and relatively affordable prices and good schools – the perfect suburban package! Ossining has a diverse population in terms of income and race and this is reflected in the range of housing options here. You can get single family homes, condos and apartments for rent. There is more racial diversity in Ossining than is typical of Westchester and some people see this as illegal immigrants problem and other celebrate it as a dose of multi-culturalism.
Ossining feels less village-like and more spread out because of the way the town is laid out. Route 9 is the busy road in Ossining and it does draw a lot of traffic. It can be a little trying sometimes to navigate in peak commute traffic. There is the train station which allows for a direct connection to Grand Central.
Los Abuelos, Goldfish Oyster Bar and Traveler’s Rest are some of Ossining’s good dining options. There is not much that I would mention by way of shopping.
The key with Ossining is to understand that it is a town of variety. Most residents rave about the fact that it’s a great place to raise kids.

Ossining is meant for the middle class population who want a quaint river view. There's some shops along the main road, including a coffee shop and a 7-11. Right before you hit the main stretch, there's the Arcadian Shopping Plaza which hosts a Starbucks, some clothing stores, a fried chicken restaurant, a pet store, an ice-cream shop and a McDonald's. It's very easy to get to local towns from Rt. 9, so it makes for an easy commute to local areas. The schools are large and after they leave school, lots kids walk home unsupervised. Rt. 9 is a busy road so I would warn against having your child walk home if you want to raise your kid here. There's a heavy white population in Ossining but it's culturally mixed, with a heavy Hispanic population as well, so it's interesting how diverse it is. You have an excellent view of the Hudson River all along the main road and beyond. Ossining is also along the Metro-North train route, which takes you to NYC. (It's about 30 mns. away.)  There’s also many elegant churches. (A friend of mine hosts her artwork in one of the churches in town, so it shows you how friendly people can be here.
While you’re here, don’t forget to visit the Ossining Historical Museum, which will tell you about the role that Ossining played in the Revolutionary War, and you can see many artifacts from around the area. There’s also a day camp that your kids can take part in during the summer, and you can find out more by looking up Ossining Summer Day Camps on Google. Brining your kids to Ossining might not give them a lot to do, but they’ll get a top-notch education; for, in the year 2000 the High School was one of 250 best American schools.

A couple of serious drawbacks is that Ossining deals with a lot of traffic via Rt. 9 as well as violence (including gangs).

All in all, it’s like a lot of other towns in Westchester, a mix of good and bad.

Bordered by the Hudson River in Westchester County, Ossining is a quaint and colorful village that is very safe and relatively affordable. The area covers just a little more than three square miles, and has a pretty diverse population with a pretty large percentage of Hispanic residents. This is a relatively low income area (when you compare it to the rest of Westchester County). As a result, the stores and restaurants in Ossining are fairly diverse too. Housing is somewhat diverse; there are co-ops and condos, as well as great classical private houses, but it may not be for you if you're into new constructions or contemporary designs. As the previous reviewer mentioned, a big issue for some people is the fact that the state penitentiary is located here in Ossining. However, it doesn't seem to be a very big deal unless you live so close that you can actually see the watch tower or hear the alarms. Also, it is good to note that the town has a lower crime rate than towns that don't house a prison. The town also offers a good deal of community events and programs for kids. There are some nice local parks here as well, but the schools leave much to be desired, so it's not the best place to raise your kids.