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Ossining, NY Multifamily Homes & Duplexes for Sale

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  • /50

    $650,000

    • 5 Beds
    • 2 Baths
    • 1,800 Sq Ft

    23 Ann St, Ossining, NY 10562

    100% renovation. Quality materials and workmanship. First level has 2 Br, second floor has 2 large Br and one small one. The attic is a big walk up finished storage area. Newer boiler and oil tank. Short walk to everything that makes Ossining a great place to live. Coffee Shops, Farmers Market, restaurants', Fairs, Festivals, River Front Parks, Concerts, Nature trails and parks with athletic

    Eric Schatz Schatz Realty Group

    23 Ann St, Ossining, NY 10562
  • /24

    $699,000

    • 5 Beds
    • 3 Baths
    • 2,000 Sq Ft

    33 Ann St, Ossining, NY 10562

    Two-Family Home!! Here is a wonderful opportunity for a picturesque Colonial home near the Hudson River in desirable Ossining. Originally built in 1902, the charming clapboard property with its cute green shutters has since been expanded and is currently configured as a two-family residence. The possibilities are endless!The home presents beautifully with its postcard-perfect fenced front yard

    Matthew Bizzarro Bizzarro Agency, LLC

    33 Ann St, Ossining, NY 10562
  • /27

    $599,001

    • 5 Beds
    • 2 Baths
    • 2,500 Sq Ft

    141 N Highland Ave, Ossining, NY 10562

    Great Opportunity in Ossining! This versatile 2-family home is ideal for a first-time buyer looking to offset their mortgage or an investor seeking solid rental income. The first-floor unit features 2 spacious bedrooms, a full bathroom, and a comfortable living room. The second unit offers 2 bedrooms, a large living room, a full bathroom, and a good-sized kitchen. Upstairs, you'll find an

    Cynthia Leite ERA Insite Realty Services

    141 N Highland Ave, Ossining, NY 10562
  • /26

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,408 Sq Ft

    58 Yale Ave, Ossining, NY 10562

    Exceptional Two-Family Opportunity in Ossining, NY! This versatile property offers a fantastic chance for first-time buyers or investors to maximize their investment. With one unit freshly vacated, move right in and rent out the second to help cover your mortgage. The home features an attached two-car garage, providing ample parking and storage space. What truly sets this property apart is the

    Chaim Lebrecht eRealty Advisors, Inc

    58 Yale Ave, Ossining, NY 10562
  • /36

    $799,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3 Baths
    • 2,840 Sq Ft

    37 Secor Rd, Ossining, NY 10562

    A Multi Family and Single family being sold as a package. Left side is a 2 Bedroom, One Bath Single family (one level - like an apartment) home with a garage below and basement. Multi family is a 1Bedroom over 1 Bedroom w/ access to basement. Basement extends full length of both homes and is unfinished. Above ground Oil tank. One furnace, 3 Meters. Garage parking for 1 to 2 cars. Unobstructed

    Monica Cooper THD Homes LLC

    37 Secor Rd, Ossining, NY 10562
  • /38

    $875,000

    • 8 Beds
    • 4 Baths
    • 2,380 Sq Ft

    39 Terrace Ave, Ossining, NY 10562

    Welcome to 39 Terrace Avenue, a well-maintained and versatile three-family property nestled on a 0.20-acre lot in the vibrant Village of Ossining. With a total of 2,380 square feet across three distinct residential units—including a detached rear cottage—this offering is perfect for primary residency AND investors seeking strong income potential and long-term upside.**Unit 1 – First Floor

    James Schunk Schunk Realty Group

    39 Terrace Ave, Ossining, NY 10562
  • /2

    $398,200

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    4 William St, Ossining, NY 10562

    The property is occupied so all potential buyers are asked to check with city and tax records to determine actual bedroom, bathroom counts and all details on this property listed above to their satisfaction. This is an AS-IS foreclosed/REO property. Do not disturb occupants or walk on property. Buyers’ premium paid at closing by buyer. *** Seller makes no guarantees about property’s condition,

    Christopher Rose REALHome Services & Solutions

    4 William St, Ossining, NY 10562
  • /8

    $679,000 Pre-Foreclosure

    • 3 Beds
    • 3.5 Baths
    • 2,820 Sq Ft

    37 Washington Ave, Ossining, NY 10562

    Large 2 family Great location older victorian style 9 ft ceilings Across street from scenic park

    Louis Zazzarino ZAZZARINO LOUIS

    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

Housing Trends

Median Sale Price
$597,500
Median Single Family Sale Price
$700,000
Median Townhouse Sale Price
$605,000
Median 2 Bedroom Sale Price
$435,000
Median 1 Bedroom Sale Price
$364,000
Average Price Per Sq Ft
$349
Number of Homes for Sale
57
Last 12 months Home Sales
246
Months of Supply
2.80
Median List Price
$595,000
Median Change From 1st List Price
-3%
Median Home Sale Price YoY Change
8%
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