$678,765Average Value$359Average Price per Sq Ft29Homes For Sale
Diverse Westchester County city with river access
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.
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Written By
Rylee Doyle
Photography Contributed By
James Leynse
Video By
Brandon Flash Craigie
Interested in learning more about homes in this area?
Reach out to
Stephen Perez,
an experienced agent in this area.
GreatSchools:
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On average, homes in Ossining, NY sell after 44 days on the market compared to the national average of 54 days. The median sale price for homes in Ossining, NY over the last 12 months is $588,000, up 6% from the median home sale price over the previous 12 months.
Spacious Contemporary Colonial tucked away on a quiet cul-de-sac in the Briarcliff Manor School District. Offering over 4,000 square feet of living space, this expansive 5-bedroom home is set on .91 beautifully landscaped acres with exceptional privacy and sweeping treetop views. A dramatic two-story entry foyer welcomes you with abundant natural light. The updated gourmet chef’s kitchen is the
Welcome to 16 Hall Rd, where the cul-de-sac is quiet enough to stroll, and the house itself feels like it's been designed just for you. You've been thinking about this move for a while now. Maybe the city apartment that once felt exciting has started to feel a little tight. Maybe you've been eyeing bigger spaces in the suburbs, but have not found the one that checks every box without needing a
Welcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. This beautifully maintained split-level ranch lives like a 4-bedroom on a private, level acre offering exceptional flexibility, indoor-outdoor flow, and room to grow. With 3 bedrooms plus two additional flexible rooms and 2 full baths, this home easily adapts to today’s evolving needs. A welcoming entry foyer leads to a
Spacious Contemporary Colonial tucked away on a quiet cul-de-sac in the Briarcliff Manor School District. Offering over 4,000 square feet of living space, this expansive 5-bedroom home is set on .91 beautifully landscaped acres with exceptional privacy and sweeping treetop views. A dramatic two-story entry foyer welcomes you with abundant natural light. The updated gourmet chef’s kitchen is the
Welcome to 16 Hall Rd, where the cul-de-sac is quiet enough to stroll, and the house itself feels like it's been designed just for you. You've been thinking about this move for a while now. Maybe the city apartment that once felt exciting has started to feel a little tight. Maybe you've been eyeing bigger spaces in the suburbs, but have not found the one that checks every box without needing a
Perched gracefully above the majestic Hudson River, this beautifully renovated one-bedroom home is ready to welcome you in. Nestled within the highly sought-after, gated Scarborough Manor community, you’ll be greeted by the gatekeeper each time you arrive—an immediate sense of comfort and care. This sun-soaked, south-facing unit feels bright and uplifting from the moment you step inside.
Legal 3-family home, located in the heart of Ossining. Excellent 1st time buyer opportunity to live in one and rent two other units and parking lot to help pay the mortgage or great investment opportunity for passive income and build equity. Prime location-close to all, easy access to transportation, downtown, and Hudson River waterfront.
First time on the market! Come enjoy a carefree lifestyle in the sought-after Rosecliff community. Beautifully built by Toll Brothers, this elegant 3-bedroom home is located at the end of a small cul-de-sac. This sun-lit home features hardwood floors throughout, 9-foot ceilings on the main level, formal living room and dining room and an open kitchen with stainless steel appliances, and breakfast
Welcome Home and discover this charming ranch-style residence nestled in one of Ossining’s most sought-after neighborhoods. Surrounded by nature and set on nearly an acre (0.85 acres) of beautifully landscaped property, this Single Family home offers comfort with 3 beds and 2 baths, lives like 2,000+ sq/ft with finished Basement, 2+ Car Garage, privacy, and timeless appeal.Enjoy a sun-filled
A great place to call home, this raised ranch–style home sits on 0.52 acres and provides inviting living spaces in Ossining, just outside the town center. Adding to its appeal, the seller recently installed a brand-new roof, providing an important recent upgrade and added value for the next owner. The foyer leads into a spacious living room with a large bay window that fills the space with
Exquisite new 5 bedroom, 4.1 bath center hall colonial to be built offering refined luxury and timeless architectural elegance in an exceptional cul-de-sac setting. Perfectly positioned on just shy of one acre and backing the serene wooded grounds of the Edith Macy Center, this residence blends privacy, prestige, and natural beauty. A rare opportunity exists to fully customize finishes,
34 Piping Rock is a stunning contemporary home that offers the perfect blend of style, functionality and comfort. Featuring 2 bedrooms but lives like 3 or more with stunning seasonal views of the Hudson River as well as a flexible floor plan ideal for a home office, den or guest space. The lower level which is completing above ground with its own private access and full bath offers endless
Approved plans for a large single family home! Vacant land opportunity located at 76 Hawkes Avenue in Ossining. This parcel offers the potential for residential development subject to municipal approvals and zoning requirements. Conveniently situated near local amenities including parks, shopping, dining, and transportation. Enjoy the benefits of being in Westchester County with access to the
Experience refined living at Trump National Golf Club, Briarcliff Manor. This 4 BR, 4.5 bath home offers effortless single-floor living with a main-level primary suite featuring his-and-hers walk-ins, whirlpool tub, enclosed shower, and double vanity. A dramatic foyer with a sweeping staircase leads to cathedral-ceilinged living spaces with hardwood floors and an elegant gas fireplace. The chef's
Located in the beautiful and quaint village of Briarcliff Manor—one of Westchester’s most desirable communities known for its award-winning Briarcliff Manor school district, charming village center, and peaceful suburban character—this exceptional, fully renovated move-in-ready ranch with a finished lower level offers an unmatched blend of modern luxury, single-level living, and
Liberty Knoll is a hidden sanctuary nestled in Ossining’s desirable Sparta neighborhood, just steps from the Hudson River. This light-filled 1-bedroom, 1.5-bath townhome offers an open, airy layout that blends contemporary comfort with warm, inviting living. The main level features a spacious living and dining area with an effortless flow for everyday living and entertaining, an updated powder
Beautifully designed 2-bedroom, 2-bath residence offers the perfect balance of modern comfort, convenience, and location. This spacious 800 sq ft apartment features modern amenities such as high efficiency heating & air conditioning with individual climate control, high end all black Samsung kitchen appliances including dishwasher, microwave, and refrigerator/freezer. Enjoy the convenience of the
Audubon Living is located in Ossining, a beautiful Rivertown in Northern Westchester. The property offers close proximity to Metro North and major highways for convenient commuting. Audubon Living is located in the residential area of Ossining, close to the High School, and a short distance from downtown, which offers many local restaurants, brewery, and the historical Aqueduct Trail. There are
Experience the ultimate in privacy and sophistication at 59 Hoags Cross Road. This stunning sanctuary is set on a lush, meticulously landscaped 1-acre lot, beginning with a stately gated driveway that offers a grand sense of arrival as it opens to welcome you home. This beautifully maintained 3-bedroom, 3-bathroom residence offers the perfect blend of modern comfort and resort-style outdoor
More than an apartment community, Cortlandt Ridge is your home. We offer affordable one, two, three, and four apartments and townhomes for rent in central Ossining, NY, near North Highland Avenue. Our homes are unique. Not only are they comfortable, they're stylish, too. Fully equipped featuring new kitchens and designer cabinetry. We have just what you need to live well in Westchester
Updated and refreshed, 2 Bedrooms, 1 bath, living room, office, renovated eat-in-kitchen with door out to private deck and water views. Minutes to shops, main road, schools and train station. A must see! Tenant pays for heat and electric.
Waterview Living, located in Ossining NY, offers beautiful views of the Hudson River, with updated apartments and wonderful amenities. The property is situated between major highways, easy access to Metro North, and a short distance from the bustling downtown area of Ossining. There is much to do and see in this historic Rivertown. With local restaurants and the Sing Sing Kill Brewery downtown,
Completely renovated in 2025, this charming second-floor two-bedroom, one-bath apartment blends modern style with village convenience. Located in the heart of Ossining, it’s just a short walk to the Metro-North train station—making your NYC commute easy and stress-free. Enjoy weekend strolls to the lively Farmers Market, local cafes, restaurants, and the scenic Hudson River waterfront. The
Altagracia Grace PatalanoBHHS River Towns Real Estate
This beautifully maintained 2017 stand-alone modern home offers privacy, space, and upscale living on just under an acre of level property. Featuring 4 bedrooms and 3 full bathrooms across 2,950 square feet, the home is thoughtfully designed with hardwood floors and an open-concept main level ideal for both everyday living and entertaining.The expansive living room flows seamlessly into a
Come see this bright, stylish 2BR Apartment in downtown Ossining! The unit is teeming with elegance and offers many great amenities, including Central Air, BIG Closets, and Hi-End Finishes. Just 48 minutes by Train to GCS, and Close to restaurants, recreation, and shopping! The apartment is on the 2nd floor and has lovely light quality and views from the bedrooms. Enjoy Hardwood Floors in
This beautifully maintained 2017 stand-alone modern home offers privacy, space, and upscale living on just under an acre of level property. Featuring 4 bedrooms and 3 full bathrooms across 2,950 square feet, the home is thoughtfully designed with hardwood floors and an open-concept main level ideal for both everyday living and entertaining.The expansive living room flows seamlessly into a
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