Ossining is a town in Westchester County with two villages, the Hudson River along the western edge and a growing downtown scene. The Sintsink Native American tribe lived in the area first, leading to the village’s first name — “Sing Sing.” The Sing Sing Prison caused controversy in the 20th century, so the town name was changed to Ossining in 1901 to separate the town from the prison’s reputation and avoid public confusion.
Greg Young has been an Ossining resident since 2020 and owns Ossining Riverworks, a local coworking community. “My wife and I were city people. We lived in Brooklyn, and I grew up in Queens. I had never lived in the suburbs, so it was a new life for me, and I wasn’t ready to say yes, initially. Then COVID happened, and the walls started closing in a little. We decided it was the right time to get a little more space. Ossining was one of the only towns I said yes to in Westchester County. The reason was Ossining’s diversity and commitment as a community to its diversity. They also had an amazing up-and-coming small business community, so it was the right place at the right time.”
Historic buildings are in abundance in downtown Ossining.
Ossining Riverworks co-working space is one of many new business incubators in town.
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Living in town, villages or historic homes
The Town of Ossining encompasses the Villages of Ossining and Briarcliff Manor. Living in either village comes with paying village and town taxes. Crotonville and Scarborough are residential areas within the town. “Young families are moving into the community,” Young says. “There’s a huge up-and-coming perspective in Ossining, and I think we’re absolutely going to see more young families moving in from New York City and other more urban areas. I’m a real estate attorney, and I represent quite a few young families moving into the area.”
Homes in Briarcliff Manor are often more expensive than those in Ossining, ranging between $800,000 and $2 million. Ossining and Crotonville feature split-levels, Colonial Revivals and Cape Cods that usually start in the $400,000s and reach into the $800,000s. Scarborough’s historic mansions can sell for up to $2 million. Condos with river views fall in the $300,000 to $500,000 range. Ossining’s median home price is $675,000, higher than the $418,700 national median reported by the National Association of Realtors.
Colonials in Ossining usually start in the $400,000s and reach into the $800,000s.
A new colonial in Briarcliff Manor where prices range from $800,000 and $2 million.
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A downtown on the cusp of a business boom
Around 40,000 people live in the Town of Ossining, many of whom work in health care, construction or education. The Sing Sing Correctional Facility still operates today and has about 900 employees.
The Village of Ossining holds most of the town’s restaurants and boutiques, which primarily line Main Street and Spring Street. “Downtown Ossining is ripe for major changes, especially with a huge amount of grant funding coming in these last few years,” Young says. “You definitely see more new and modern businesses that are future-forward. I think that will continue to change as the grant-funded projects commence in 2025.”
Many of the businesses fill ground-floor spaces with condos in the levels above. Market Square is the venue for The Ossining Down to Earth Farmers Market every Saturday, where local farmers sell fresh produce and vendors sell homemade goods. Briarcliff Manor has a smaller collection of shops and stores along Pleasantville Road and shopping centers along Briarcliffe-Peekskill Parkway.
The Sing Sing Correctional Facility still operates today and has about 900 employees.
Melita's Home on Main Street is stocked with locally sourced art and home furnishings.
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Constant events held by the town and nonprofits
Young says the town’s packed event schedule is one of the major draws for the area. “There are amazing things every week, whether it’s municipally organized or from one of our nonprofit arts groups,” Young says. “When it comes to spring and summer in Ossining, you really have to pick and choose what you’re doing on any given weekend because there could be eight to 10 events going on. With our diverse community, you also get a big multicultural aspect to events. Whether it’s the annual Portuguese Day Festival or amazing new Ecuadorian restaurants opening up.”
The Ossining Police Department organizes the beloved Candy Cane Run every December. The Ossining Fire Department drives Santa throughout the Village and Town of Ossining in one of their fire trucks, making stops along the way so Santa can hand out candy canes and take pictures with kids.
The Town of Ossining doesn’t have a police force or fire department, so the town contracts with the Village of Ossining and Briarcliff Manor. According to FBI data, both villages had lower reported crime rates than state and national averages in 2023.
People come from all over Westchester to watch Blues at the Up the River Blues Festival.
Families interact with animals at Green Ossining's Earth Day Festival in Ossining.
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Playing along the Hudson River
Living along the Hudson River means having beautiful water views and easy access to fishing and boating spots. Louis Engel Waterfront Park features a playground, fishing piers, a walking trail along the river and a stage where the RiverJam summer concert series is held every year. “I think what makes Ossining unique is that it's one of the prime river towns in the northern Westchester area,” Young says. “The Town of Ossining puts on an incredible concert series, RiverJam, which grows every year. You might have Latin music one night and hip-hop the next. There were fireworks last year, and I’ve never seen so many people in downtown Ossining.” In 2024, the town received a $125,000 grant from the state that will go toward renovating the park, and residents have a chance to voice their opinions on what should be updated.
Young highlights the Bethany Art Community, which holds art classes, community events and artist residencies in a renovated convent. Croton Point Park in the north part of town has over 500 acres of land, with campgrounds, a nature center and historic landmarks throughout the peninsula. Briarcliff Manor features the Trump National Golf Club Winchester and the Sleepy Hollow Country Club.
Louis Engle Park is the place to be in Ossining on a hot day.
Croton Point Park in the north part of town has over 500 acres of land.
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Trains, highways and buses to Manhattan
Anyone who commutes to Manhattan has multiple ways of traveling the roughly 35-mile distance south. The Metro-North Rail Road’s Hudson line runs by the Ossining and Scarborough train stations. Using the train takes about an hour to reach Manhattan. Heavy rain can cause flooding in Ossining, but the flooding usually affects the nearby train station parking lots.
Westchester County’s Bee-Line buses run along major thoroughfares, like U.S. Route 9 and the Briarcliff-Peekskill Parkway. When it comes to shopping and dining, many residents in the Village of Ossining walk along paved sidewalks to reach destinations on Main Street. Ossining has an urgent care center off Route 9, but the nearest hospital is Phelps Hospital in Archville, 5 miles south of the town by car.
Briarcliff Manor has a more rural setting, with thick patches of tall trees, so owning a car on this side of town is ideal for getting around. The city is still planning for a future bike trail network that will loop into nearby New Castle and Yorktown.
Two highly rated school districts in one town
The Ossining Union Free School District serves most of the town and receives an A-minus from Niche. Westchester County residents voted for a $210 million bond for new school facilities and renovations. The southeastern side of the town is in the Briarcliff Manor Union Free School District, which gets an A-plus and is ranked as the third-best district in Westchester County.
Most places of worship in town are churches. St. Augustine Roman Catholic Church runs St. Augustine School, a private middle school that is currently unrated by Niche.
Ossining High School is a comprehensive public high school located in Ossining, New York.
Todd Elementary School provides a safe and academic environment in Briarcliff Manor.
Kenneth Moran believes that a home is not defined by its physical attributes but by the emotions it evokes and the vision it inspires for one's life. As a real estate professional at Keller Williams Realty, Kenneth embraces a unique approach focused on personal connections, mutually beneficial transactions, and delivering positive outcomes.
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