About Ossining

Ossining, NY homes for sale are located in Westchester County bordering the Hudson River on the western side of the community and the Croton River to the north. The distance to New York City is about 40 miles, which takes about an hour via the train and about an hour and 15 minutes via car. Given the distance from New York, single-family homes are much more affordable in this area. The Ossining real estate market is the perfect place for anyone looking for a bit more space for your family and perhaps a spare room for anyone that stops by for a visit!

Real Estate Statistics

  • Total Listings: 168
  • Average Price: $518,373
  • Highest Price: $3,999,500
  • Lowest Price: $38

All Listings Under $100,000 $100,000 - $200,000
$200,000 - $300,000 $300,000 - $400,000 $400,000 - $500,000
$500,000 - $600,000 $600,000 - $700,000 $700,000 - $800,000
$800,000 - $900,000 $900,000 - $1,000,000 Over $1,000,000
1 – 12 of 168 Listings
Price, High to Low

11 Bed • 7 Bath • 9,481 Sf • 20 Acres


335 Croton Dam Road, Ossining

In The Early 1930s, Two Young Manhattan Pediatricians Built Their Dream Estate In The Heart Of The Hudson Valley. This Iconic Estate, Home To Gener...

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3 Bed • 3 Bath • 2,283 Sf • 39 Acres


16 Barnes Road, Ossining

Welcome To 16 Barnes Road, A Remarkable And Absolutely Beautiful Nearly 40 Acre Land Parcel Straddling The Town Of New Castle & Ossining. Main Hous...

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8 Bed • 7 Bath • 6,426 Sf • 18 Acres


83 Somerstown Road, Ossining

Historic Westchester Estate, Once Home To The Van Cortlandt Family,sequestered On 17.9 Acres Encompassing A Stream-fed Private Lake With Dock,olymp...

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Reduced 11%

6 Bed • 6 Bath • 8,410 Sf • 19 Acres


132 Hawkes Avenue, Ossining

Set Up At The Top Of A Gentle Hill Taking Advantage Of Captivating Hudson River Views From Maryknoll’s Iconic Tower & Stretching Up The Hudson Rive...

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5 Bed • 6 Bath • 7,732 Sf • 5 Acres


13 Tavano Road, Ossining

Grand Stone Colonial Farmhouse Set On 4.6 Tranquil Acres With Stunning Sunset Views. This Oasis Offers Manicured Lawns, Gardens, Mature Trees And A...

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32 Acres


123 Morningside (a, B, C) Drive, Ossining

An Incredible Opportunity To Own Over 30 Acres. Property Can Also Offered With Main House And Additional Land At 16 Barnes Road, Ossining. Mls: 496...

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4 Bed • 3 Bath • 3,600 Sf • 2 Acres


6 Conte Lane, Ossining

Lovely, Quiet, Tree Lined Street, This New Home Will Be Located At The End Of The Cul De Sac. Call To Arrange Appointment With Builder To Build You...

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4 Bed • 3 Bath • 3,086 Sf • 2 Acres


1848 Spring Valley Road, Ossining

Beautiful Center Hall Colonial In Cortlandt, Teatown Location & Croton Harmon Schools, Set Back On 2 Acres W/expansive Lawns And Mature Trees On Fr...

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Reduced 5%

5 Bed • 3 Bath • 5,340 Sf • 1 Acres


31 Beach Road, Ossining

Chelsea, Christened As Such By Clement Moore Of "the Night Before Christmas" Fame, Is A Historic 5300 Sq Ft Hudson River Carriage House With Winter...

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4 Bed • 4 Bath • 4,874 Sf


9 Roosa Lane, Ossining

Absolutely Stunning And Sophisticated But Cozy And Warm! Immaculate Center Hall Colonial W/hudson River Views Set Up High At Cul De Sac! Grand Entr...

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Reduced 10%

3 Bed • 3 Bath • 2,468 Sf • 3 Acres


118 Glendale Road, Ossining

Charming 1860's Farmhouse Situated On 3+ Meticulously Landscaped Acres, W/3 Car Garage & Storage/playroom Above. Two-story Pool Cabana, In-ground ...

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Reduced 3%

3,609 Sf


119 Dale Avenue, Ossining

Are You Looking For An Incredible Investment Opportunity? This Meticulously Maintained 4 Unit Duplex In Two Seperate Buildings, Is On The Market Fo...

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Discover Ossining, NY Real Estate

Ossining, NY real estate has a good selection of affordable condos along Main Street, South Highland Avenue, and Nicole Circle. First-time buyers that are looking for a maintenance-free lifestyle will be able to live in about 700 square feet, with 1 bedroom and 1 bathroom. However, if you are looking for a starter home in Ossining, then the southern end of the community is a great place to start your search. Donald Lane, Prospect Avenue, and Linden Avenue, all offer affordable starter homes with an abundance of character. These are ideal for those looking to add value to their home by restoring and updating it to a fantastic spec!

If a more luxurious home is what you are looking for, then you should explore homes along Croton Dam Road, Hawkes Avenue, and Somerstown Road. Property in this area comes in a wide variety of styles from Victorian to Cape Cod. Homes range from 4,500 square feet to just over 7,000 square feet. The amount of bedrooms range from 4-13 and the number of bathrooms range from 4-8. Many of the homes in this segment of the market have unique features and spacious interiors. Some of the more common features you may find in estates of this caliber include:

  • Chef's Kitchens
  • Commercial grade appliances
  • Spacious decks & patios
  • Outbuildings or guest houses
  • Gated entryways

Living In The Community of Ossining, NY

If you love historic buildings, arched bridges, and quaint streets to explore, then Ossining is definitely the place for you. Whether you and your family go for a walk along Old Croton Aqueduct Trail, wander through the parks and green spaces in the town, spend a day shopping for one-of-a-kind items, or picnic by the river, you'll find Ossining to have many wonderful amenities to suit your lifestyle. With affordable homes and stately properties to choose from, isn't it time you made the Ossining community your forever home?

Hudson Gateway MLS Logo The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than KELLER WILLIAMS NY REALTY are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker.

Information deemed reliable but not guaranteed.

© 2019 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.

Listing information last updated on July 21st, 2019 at 10:28am CDT.

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