Ossining Real Estate

Welcome to Ossining, New York – a charming village nestled along the picturesque banks of the Hudson River in Westchester County. With its rich history, vibrant community, and stunning natural landscapes, Ossining offers a unique blend of suburban tranquility and urban convenience.

Ossining boasts a diverse community, where residents enjoy a welcoming atmosphere and a strong sense of belonging. The village is steeped in history, with roots dating back to the early 1600s. Today, you can explore its historic architecture, including the iconic Sing Sing Correctional Facility, which has played a significant role in the area’s past.

Nature enthusiasts will find plenty to love in Ossining, with numerous parks, hiking trails, and waterfront activities. The scenic Croton Aqueduct Trail offers miles of picturesque paths perfect for walking, jogging, or biking. The Hudson River waterfront is ideal for leisurely strolls, picnics, or simply soaking in the breathtaking views of the river and the distant Palisades.

Ossining is also known for its vibrant arts scene, with local galleries, theaters, and cultural events that showcase the talents of its residents. The community hosts various festivals throughout the year, fostering a sense of unity and celebration.

For families, Ossining is home to highly rated schools and a plethora of recreational activities for children of all ages. With convenient access to New York City via Metro-North Railroad, commuting is a breeze, making Ossining an ideal choice for those seeking the perfect balance between suburban living and urban accessibility.

Discover the charm of Ossining, where history, community, and nature come together to create a truly exceptional place to call home.

Newest Listings in Ossining

$124,900

1 Baths ⋅ 1031793 MLS

Welcome to The Parkview! This large studio at 117 South Highland Avenue lives like a one-bedroom, with a separate room comfortably fitting a full-size bed. The kitchen was fully renovated with stainless steel appliances, custom cabinetry, a large island, and quartz countertops. Oversized windows fill the space with natural light and frame wonderful Hudson River views year-round. The bathroom has also been remodeled, with a custom-built glass shower door, and hardwood floors run throughout. This unit comes with a guaranteed assigned parking spot. Building amenities include an in-ground pool, on-site fitness center, and a recently renovated lobby laundry room and main entrance. Located close to the train, shopping, and restaurants. Come see why Parkview residents love calling this home!

117 Highland Unit #4F, Ossining

$539,999

1 Beds ⋅ 2 Baths ⋅ 1030990 MLS

Discover your dream home at 93 Bridle Path Road, nestled within the highly sought after Fox Hill Condominiums in Ossining, NY. This charming 2 level townhouse features a spacious 1 bedroom and a versatile loft, perfect for an office or study area. The first level boasts a modern galley kitchen with stainless steel appliances, a cozy living room with a wood burning fireplace, and a dining area that opens to a tranquil deck ideal for relaxing or entertaining. Enjoy the benefits of hardwood floors throughout, recessed lighting, and recently renovated kitchen and bathrooms. With a one car garage and additional driveway space, this property offers both convenience and comfort. Embrace the pet-friendly lifestyle and the serene, park-like setting of Fox Hill, which spans 45 wooded acres and includes amenities such as a pool, tennis court, basketball court, and playground. Located just 30 miles from New York City, with easy access to the Metro North rail line making your commute approximately 55 minutes, this home perfectly balances suburban tranquility with urban convenience. Don't miss the opportunity to make this peaceful retreat your own!

93 Bridle Path Road, Ossining

$950,000

4 Beds ⋅ 3 Baths ⋅ 1023457 MLS

Welcome to 61 Underhill! Expanded in approximately 2008, this spacious home offers far more space than first meets the eye. The substantial rear addition nearly doubled the size of the home, creating a layout that blends the character of the original residence with a newer, expansive living area featuring generous room sizes and an open feel. While the original portion of the home is ready for updating, the addition provides comfortable living today, offering buyers the opportunity to modernize over time while building equity. The thoughtfully designed layout creates two distinct living areas within the home, offering exceptional flexibility for extended family, long-term guests or those simply looking for additional space and privacy. The full unfinished basement offers excellent ceiling height and abundant square footage, presenting outstanding potential for future finished living space, recreation, storage or a workshop. Outside, the terraced backyard features multiple levels, a storage shed and a charming playhouse, offering plenty of outdoor space to restore and personalize. Conveniently located near shopping, restaurants, parks and major commuting routes, this is an excellent opportunity for buyers with vision to unlock the full potential of a home with exceptional space and versatility.

61 Underhill Road, Ossining

$624,000

1029679 MLS

Freshly refurbished and move-in ready, individually owned, Professional Condo! This prime first-floor two unit professional suite, formerly two separate adjacent medical offices, offers a versatile layout perfect for healthcare, therapy, or high-end administrative use. The space features two individual welcoming reception and administrative areas, private offices, a break room, and ample storage. Designed for efficiency, the units include ten office rooms, several equipped with its own sanitary station and two separate reception/waiting rooms for maximum privacy. Use one and lease out the other or bring your entire practice to this new professional location. Situated in a prestigious, high-visibility location, your business will benefit from maximum exposure with signage opportunities directly on busy Route 9. Don’t miss this opportunity to position your practice in one of Ossining’s most accessible and sought-after professional corridors.

100 S Highland, Ossining

$4,500,000

1029548 MLS

An exceptional investment opportunity at 37 Old Albany Post Road in Ossining, New York, featuring three industrial buildings situated on a spacious 1.9416-acre lot. The property comprises approximately 11,600 square feet of building space and is currently configured with five income-producing units, providing a diversified tenant base and multiple revenue streams. Additional income is generated through on-site parking, including a separate parking area with 16 spaces. The property currently produces approximately $30,455 in combined monthly building and parking income, totaling approximately $365,460 annually, with scheduled rent increases offering further income-growth potential. Current annual operating expenses are estimated at approximately $61,109, resulting in a projected net operating income of approximately $304,351. With substantial land, multiple buildings, strong existing cash flow, parking income and future upside, this property presents a compelling opportunity for investors seeking a well-located commercial asset in Westchester County. Bring an offer.

37 Old Albany Post Road, Ossining

$125,000

1 Beds ⋅ 1 Baths ⋅ 1027696 MLS

It's oh so quiet. This High Meadows top floor one bedroom, one bath is fresh and ready to go. Hard wood floors throughout, A sun filled living room with dining nook, new stove and refrigerator, lot's of closet space. A small hall leads to extra closets and the bedroom. High Meadows Cooperative features a common laundry and storage space around the back. 2 playgrounds and a basketball court are available as well. Reserved spot number 5 is a short walk to the door, street parking with permit. This gem is tucked away, off route 9, with easy access and close proximity to shopping, fitness center, trails, public transport, and highways, just 2 miles to the train station. The best of both worlds. Peaceful oasis, and convenient to the business district.

50 Charter Circle Unit #C, Ossining

$899,000

4 Beds ⋅ 3 Baths ⋅ 1027151 MLS

Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless character with modern updates. The main level offers an updated kitchen with granite countertops, stainless steel appliances, a gas Viking stove, laundry, and access to a private backyard. The oversized primary bedroom features elegant arch and tray ceilings. The walk out basement includes a finished recreation room and plenty of storage. The second floor apartment features an updated kitchen, three bedrooms, two full bathrooms, and access to a finished attic with a wainscoted ceiling, providing excellent income potential or additional living space. Conveniently located just 0.5 miles from the Ossining train station and close to downtown restaurants, shops, the farmers market, parks, schools, and major highways. A fantastic opportunity for homeowners and investors alike!

20 Waller Avenue, Ossining

$425,000

2 Beds ⋅ 2 Baths ⋅ 1006040 MLS

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 including arched doorway, built in shelving, and fireplace. Bright airy dining/flex room, 1st floor half bath, eat in kitchen with breakfast nook/ dining area and sliding door to patio. Climb the stairs to enjoy two sunny bedrooms each with double closets, and large full skylit bath including laundry hook up. With so much to offer it’s hard to determine but the best detail of this home may be the expansive private yard ready to become the entertainment center for its new owners. Don't sleep on this amazingly convenient location…less than 1 mile to two train stations (Scarborough and Ossining), 35 min to NYC, walking distance to market, and Ossining village shops. Near to bus, schools and more! This might just be the best deal in town. Apx. $1500 STAR tax saving available. Make your appointment today.

42 Revolutionary Road, Ossining

$625,000

4 Beds ⋅ 3 Baths ⋅ 1027201 MLS

Legal two-family Colonial tucked away on large cul-de-sac adjacent to Ossining's historic Sparta community. Originally built as a two-family (not a conversion), the home offers a practical layout with separate living spaces. The first floor apartment features 1 bedroom and 1 full bath, while the upper apartment spans the 2nd and 3rd floors with 3 bedrooms and 1.5 baths. The upper apartment can be accessed by either: 1) A private exterior staircase. 2) A shared enclosed stairwell with its own exterior entrance and separate lockable doors to each apartment. Whether you're looking for an owner-occupied property with rental income or a solid investment opportunity, this home offers flexibility and strong potential. Conveniently located just around the corner from Sparta Park, .5 miles from the Arcadian Shopping Center and .8 miles from the Scarborough Train Station for an easy commute to Manhattan.

20 Riverview Court, Ossining

$639,500

4 Beds ⋅ 2 Baths ⋅ 1021344 MLS

Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle. The private backyard offers a peaceful retreat with a patio ideal for outdoor dining, entertaining, or simply relaxing. Experience the best of Hudson Valley living with convenient access to the scenic Hudson River waterfront, parks, hiking and biking trails, local restaurants, shopping, and year-round community events. Whether you're commuting, exploring the outdoors, or enjoying the vibrant Rivertown lifestyle, this home offers the perfect balance of tranquility and convenience. Don't miss this opportunity to own a beautiful home in one of the Hudson Valley's most sought-after communities.

42 Pershing Avenue, Ossining

$698,000

4 Beds ⋅ 3 Baths ⋅ 1023097 MLS

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 amid mature plantings and lush landscaping, this home delivers a bright, cheerful, private pocket of comfort. Step inside to a sun-drenched three-season room with recessed lighting, then through French doors into a warm kitchen with abundant cabinets and granite countertops. A dining area with oversized windows keeps the light flowing all day, opening into a family room with a fireplace, large bay window, and a door to the back deck. The first-floor primary bedroom features an en-suite bath and is joined by two additional bedrooms and a hall bath, with hardwood floors throughout the main level. A standout feature is the legal mother-daughter suite, complete with its own private entrance, summer kitchen, bedroom, full bath, and living/dining area. Ideal for multigenerational living, guests, or extra income potential. Out back, a fenced-in yard feels like your own private retreat - leafy, tucked away, and made for slow mornings and long summer nights. Fire up the grill on the spacious deck, linger under the stars, or lose an afternoon in the gardens. Ideally located close to the Croton train station (and the villages of both Croton-on-Hudson and Ossining, with plenty of amenities, shopping, and eateries nearby. Well-priced and move-in ready, this one won’t sit on the market long. Schedule your showing today.

7 Ogden Road, Ossining

$599,000

3 Beds ⋅ 1 Baths ⋅ 1025170 MLS

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 outdoor space ready for entertaining and warm weather enjoyment -a country neighborhood feel yet only 10 minutes to Metro North station- a 50 min express commute to Grand Central and 2-3 miles to Rt 9/ Taconic Parkway....A warm and welcoming ranch in the wonderful Rivertown of Ossining where comfort, charm, convenience and community come together....This cozy retreat offers spacious living and a dining area that seamlessly connects to the kitchen creating the perfect setting for everyday living and entertaining. Conveniently located first floor bedrooms provide added accessibility and ease. Step outside to a welcoming patio perfect for outdoor living, gardening or simply enjoying your own private oasis. Known for its rich history, vibrant downtown, beautiful river views and breathtaking sunsets, Ossining offers the charm of riverfront living with waterfront parks, scenic walking neighborhoods and vibrant dining and shopping. Nature lovers will appreciate nearby hiking trails, Teatown Nature Preserve, Veterans Park and the Ossining Farmers Market. If you you are looking for a move in condition home, tranquility, the ideal commuter location or a lifestyle that comes with Rivertown living, this home with gas heat/ cooking, town water & sewer could be just what you are looking for!

23 Gates Avenue, Ossining

Start Your Search

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.