$681,724Average Value$358Average Price per Sq Ft35Homes 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
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GreatSchools:
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On average, homes in Ossining, NY sell after 46 days on the market compared to the national average of 55 days. The median sale price for homes in Ossining, NY over the last 12 months is $598,185, up 7% from the median home sale price over the previous 12 months.
Welcome to 128 South Highland Avenue — a beautifully maintained home that perfectly blends comfort, character, and convenience in the heart of Ossining. From the moment you arrive, you’ll appreciate the inviting curb appeal and thoughtfully cared-for exterior. Inside, the home offers a bright and functional layout with generous living spaces designed for both everyday living and effortless
Welcome to this spacious and versatile 2-bedroom, 3-bathroom townhouse that lives like a 3-bedroom, offering flexibility to suit a variety of lifestyles.As you enter, the main level welcomes you with a grand living room featuring its own fireplace and sliding doors that lead to your deck—perfect for both everyday living and entertaining. The galley kitchen includes a cozy eat-in nook,
PLEASE NOTE: Home is occupied, appointment required for access to the property. Do not trespass! Welcome home to this beautifully updated and maintained American Foursquare full of original charm and tasteful modern upgrades. A picturesque and centrally located home in the Village of Ossining, just an hour north of NYC. A large, private front porch and entry welcomes you into the main floor of
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.
Welcome to 128 South Highland Avenue — a beautifully maintained home that perfectly blends comfort, character, and convenience in the heart of Ossining. From the moment you arrive, you’ll appreciate the inviting curb appeal and thoughtfully cared-for exterior. Inside, the home offers a bright and functional layout with generous living spaces designed for both everyday living and effortless
Income-producing duplex in a desirable location! Has 5 bedrooms and two baths total. 3 bedrooms 1 bath in one unit, 2 bedrooms 1 bath in second unit. This well-maintained property offers two units with strong rental history and consistent cash flow. Ideal for investors or owner-occupants looking to offset their mortgage. Features include separate utilities, spacious layouts, and convenient access
Bright, sun-drenched, and move-in ready! This top-floor co-op unit offers peaceful living with a host of recent upgrades. The spacious layout features new living room carpeting (2021) and stylish new vinyl wood flooring leading to the bedroom and bath areas (2021). The kitchen is equipped with a new refrigerator and microwave (both 2022). Enjoy the elevated views and natural light that only a
Welcome to this spacious and versatile 2-bedroom, 3-bathroom townhouse that lives like a 3-bedroom, offering flexibility to suit a variety of lifestyles.As you enter, the main level welcomes you with a grand living room featuring its own fireplace and sliding doors that lead to your deck—perfect for both everyday living and entertaining. The galley kitchen includes a cozy eat-in nook,
PLEASE NOTE: Home is occupied, appointment required for access to the property. Do not trespass! Welcome home to this beautifully updated and maintained American Foursquare full of original charm and tasteful modern upgrades. A picturesque and centrally located home in the Village of Ossining, just an hour north of NYC. A large, private front porch and entry welcomes you into the main floor of
Welcome to Briar Hill, one of Briarcliff Manor’s most charming garden-style co-op communities. This classic brick Colonial complex is set amid tranquil, park-like grounds, yet is just minutes from the village center, dining, and everyday conveniences.This pristine first-floor residence offers two comfortable bedrooms, a beautifully renovated gourmet kitchen featuring granite countertops and a
Welcome to 35 Havell St, a legal two family home with a great oppottunity for owner occupied & rental income for the other unit. Unit 1 has 3 bedrooms, 1 full bath, living room, large eat in kitchen with access to backyard patio area. Full basement with plenty of storage, laundry area, mechanicals & 1 car garage. Unit 2 which is tenant occupied, has 2 bedrooms, 1 full bath, living room, large eat
You can’t ask for a more turn-key home! Everything inside has been updated tastefully in the last few years, and the shy 1/2 acre is beautifully landscaped and perfect for entertaining, with a large deck plus back patio and privacy fence in the rear. If you’re looking for a mother-daughter home, or a home office with a separate entrance, this ranch with a walk-out lower level would be perfect for
Welcome home to this stately brick center-hall colonial that takes your breath away! This beautiful home is set on a professionally landscaped & fenced shy acre of level property at the end of a cul-de-sac in Briarcliff Manor. This expansive and thoughtfully designed residence blends timeless elegance with modern comfort. A grand entry foyer welcomes you into a home filled with refined
This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning
Rare and expansive 1-bedroom triplex offering approximately 1,450 square feet of living space, featuring a large bonus room ideal for a home office, den, or entertaining space. This sun-filled residence enjoys beautiful natural light throughout, with morning sun in the kitchen and warm sunset light in the living room. The multi-level layout provides a unique sense of space and separation rarely
Beautiful 4-bedroom, 3.5-bath single-family home located in a quiet residential neighborhood offering great space and flexibility. The main level features a bright living room filled with natural light and highlighted by a bay window, an open kitchen with nice countertops, and a dining room perfect for everyday living. A cozy den provides additional space for a home office or sitting
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
Come see this bright, stylish 3BR/2BA 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
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
Step into a spacious, fully renovated, turn-key lifestyle with this extraordinary first-floor apartment in the heart of historic Town of Ossining. This extra-large 2-bedroom residence has been meticulously transformed with high-end finishes, ready for immediate occupancy. Brand-new, Contemporary Kitchen: A chef's delight featuring sleek countertops, new cabinetry, and a full suite of brand-new,
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,
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
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
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
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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