Welcome to Ossining, NY – a charming community nestled in the heart of Westchester County, where education meets opportunity. Ossining School District is renowned for its commitment to academic excellence and holistic development, making it an ideal choice for families seeking a nurturing environment for their children. With a diverse range of programs, including advanced placement courses and a focus on the arts, Ossining schools strive to empower students to reach their full potential.
The district prides itself on fostering a strong sense of community and inclusivity, providing students with not only a solid academic foundation but also the skills they need to thrive in an increasingly complex world. From dedicated teachers to engaging extracurricular activities, Ossining School District ensures that every child is supported in their educational journey.
In addition to its exceptional schools, Ossining offers a variety of homes that cater to families looking for space and comfort. Many properties in this picturesque town feature spacious backyards, perfect for children to play, pets to roam, or for hosting summer barbecues with friends and family. Imagine sipping your morning coffee on a sun-drenched patio or enjoying a peaceful evening under the stars in your private outdoor oasis.
With its blend of educational excellence and charming homes with backyard lots, Ossining is more than just a place to live; it’s a community where families can grow, thrive, and create lasting memories. Explore the possibilities of making Ossining your home, and discover the perfect setting for your family's future.
A charming split-level home set on land that was once part of the historic Waldheim Estate of James and Ellin Speyer. Tucked into a peaceful setting just minutes from the...
Listing courtesy of Listing Agent: Jan Pierre Chavez (jp.chavez@compass.com) from Listing Office: Compass Greater NY, LLC.
This adorable Ossining Schools gem awaits new owners to provide personal touches and TLC. It boast a welcoming entry leading to living room with charming details includin...
Listing courtesy of Listing Agent: Teresa C. Keys (GetYourNewKeys@gmail.com) from Listing Office: Keller Williams Realty Group.
Charm meets flexibility in this rare Ossining find! A legal mother-daughter bungalow ranch that feels like a secret waiting to be discovered! Tucked back from the road am...
Listing courtesy of Listing Agent: Heather A. Bouza (heather.bouza@compass.com) from Listing Office: Compass Greater NY, LLC.
This lovingly maintained, one level home offers the ideal location- so convenient to all and a beautiful level backyard....You will be impressed with the very private out...
Listing courtesy of Listing Agent: Maureen Connolly (maureen.connolly@cbmoves.com) from Listing Office: Coldwell Banker Realty.
Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Fra...
Listing courtesy of Listing Agent: Diana Polack (diana@upstatecurious.com) from Listing Office: Compass Greater NY, LLC.
Some homes ask you to imagine what they could be. This one is already there and waiting for you. This classic colonial has been lovingly updated and impeccably maintaine...
Listing courtesy of Listing Agent: Hillary A. Landau (hillary.landau@compass.com) from Listing Office: Compass Greater NY, LLC.
FULLY AVAILABLE as of 7-7-2026. Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and offering a strong combination of space, convenien...
Listing courtesy of Listing Agent: Tana M. McGuire (Tana.McGuire@exprealty.com) from Listing Office: eXp Realty.
Full of warmth, character, and timeless appeal, this charming colonial home offers a wonderful blend of classic details, comfortable living spaces, and an exceptional loc...
Listing courtesy of Listing Agent: Amanda Saraceno (ASaraceno@KW.com) from Listing Office: Keller Williams Realty Group.
Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Position...
Listing courtesy of Listing Agent: Derek J. Greene (office@thegreenerealtygroup.com) from Listing Office: Greene Realty Group.
Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded a...
Listing courtesy of Listing Agent: Helena Macintyre (helena.macintyre@sothebysrealty.com) from Listing Office: North Country Sothebys Int Rlt.