Ossining, NY Multifamily Homes & Duplexes for Sale
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$599,001
- 5 Beds
- 2 Baths
- 2,500 Sq Ft
141 N Highland Ave, Ossining, NY 10562
141 N Highland Ave, Ossining, NY 10562 -
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$799,000 Open Sat 12PM - 2PM
- 5 Beds
- 3 Baths
- 2,840 Sq Ft
37 Secor Rd, Ossining, NY 10562
37 Secor Rd, Ossining, NY 10562 -
$875,000
- 8 Beds
- 4 Baths
- 2,380 Sq Ft
39 Terrace Ave, Ossining, NY 10562
39 Terrace Ave, Ossining, NY 10562 -
$398,200
- 3 Beds
- 2 Baths
- 1,160 Sq Ft
4 William St, Ossining, NY 10562
4 William St, Ossining, NY 10562 -
$679,000 Pre-Foreclosure
- 3 Beds
- 3.5 Baths
- 2,820 Sq Ft
37 Washington Ave, Ossining, NY 10562
37 Washington Ave, Ossining, NY 10562
Why Live in Ossining



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 wi ...
Home Trends in Ossining, NY
On average, homes in Ossining, NY sell after 43 days on the market compared to the national average of 50 days. The median sale price for homes in Ossining, NY over the last 12 months is $597,500, up 8% from the median home sale price over the previous 12 months.
Housing Trends
In Ossining, there are currently 8 multi-family homes for sale, providing an appealing investment opportunity for buyers. With multi-family homes priced between $398,200 to $875,000, there's a range to accomodate every budget. As of June, 2025 the median home price in Ossining is $595,000, while the average sale price is $646,006, offering insights into the local housing market. On average, multi-family homes spend 43 days listed before being sold. Multi-family homes include a variety of property types, from duplexes, triplexes, and fourplexes, to apartment complexes, all within a single building divided to accommodate multiple families living separately. These multi-family properties for sale offer investors the chance to generate rental income. Whether you're considering a duplex for a beginner investment or an apartment complex for a more substantial venture, there are investment properties available to meet your requirements. Explore the range of multi-family homes for sale in Ossining, NY.
Ossining Types of Homes for Sale
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