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: 222
  • Average Price: $470,759
  • 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 222 Listings
Price, High to Low

11 Bed • 7 Bath • 9,481 Sf • 20 Acres


335 Croton Dam Road, Ossining

Virtual Tour Provided: Seller Will Pay Property Taxes For 3 Years After Date Of Purchase. A Dream Estate In The Heart Of The @hudson Valley. A H...

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4 Bed • 5 Bath • 4,337 Sf • 50 Acres


249 Croton Dam Road, Ossining

Elda Castle Was Built In 1927 By David T. Abercrombie And Was Inspired By His Architect Wife S Vision. It Is Set On 49.6 Acres And This Acreage I...

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6 Bed • 6 Bath • 6,915 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 Ri...

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Reduced 5%

7 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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13 Bed • 7 Bath • 7,107 Sf • 20 Acres


116 Hawkes Avenue, Ossining

Historic Multi Family Estate Featuring 3 Homes Built In 1910, 1920 & 2001 Plus An Efficiency Studio Unit With 30 Total Rooms, 13 Bedrooms & 6.5 Bat...

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90 S Highland Avenue, Ossining

Building Package For Sale Zoned Office. Perfect For Professional Offices Or In Town Campus For Non Profits. Two Turn Of The Century Victorian...

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26-34 Main Street, Ossining

Come See This Turn-key Mixed Use Investment Building Down By The Waterfront In Beautiful Ossining. All Apartments Have Been Renovated In 2014. Al...

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33-35 Main Street, Ossining

Great Turnkey Property With Dozens Of Upgrades. 3 Out Of 5 Renovated Apartments, Brand New Siding, Stairs, Deck And Driveway, A One Bedroom, A Stu...

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6 Acres


Van Wyck Street, Ossining

Fabulous, Secluded And Private 6 Acre Parcel With Gorgeous River Views! Planned And Designed 48 Unit Community With Roof-top Lounge Area, Pool, Clu...

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8 Revolutionary Road, Ossining

6,622 S/f Of Office Currently Configured Into 19 Offices And 2530 S/f Of Storage, Half Of Which Is Heated. Current Owner Wants To Have A 3 Year Lea...

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Reduced 6%

3 Bed • 4 Bath • 4,232 Sf • 1 Acres


17 Twin Ridges Road, Ossining

Dreaming Of A Midcentury Modern Oasis That Offers A Lakeside Lifestyle And A Commutable Distance To Manhattan? Pack Up Your Paddleboard! Created Wi...

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6 Bed • 6 Bath • 3,900 Sf • 7 Acres


1145 Kitchawan Road, Ossining

Tour This Home At ,https://vimeo.com/412377194/13decd4b15 A Tranquil Oasis, Perfect For A Retreat, Country Living Or An Investment Property For Com...

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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.

© 2020 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.

Listing information last updated on May 31st, 2020 at 2:15am CDT.

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