Ossining Homes under $500,000

Nestled along the picturesque banks of the Hudson River, Ossining, New York, is a charming town that effortlessly blends rich history with modern living. Located in Westchester County, Ossining is known for its vibrant community, stunning natural landscapes, and a strong sense of local pride. With its proximity to New York City—just a short train ride away—Ossining offers the perfect balance of suburban tranquility and urban accessibility.

One of the most appealing aspects of Ossining is its diverse range of homes available for under $500,000. Whether you’re a first-time buyer, looking to downsize, or searching for a cozy retreat, Ossining has something for everyone. From charming historic homes with unique architectural details to contemporary townhouses and condos, the real estate market here caters to a variety of tastes and budgets.

Residents enjoy the convenience of local amenities, including delightful shops, restaurants, and parks. The scenic waterfront and nearby hiking trails provide ample opportunities for outdoor recreation, while the community's rich cultural heritage can be explored through local events and festivals. Families will also appreciate the highly regarded schools and safe neighborhoods that Ossining offers.

In Ossining, you can find a welcoming community that feels like home, all while staying within an affordable budget. Discover the charm of this beautiful town and explore the incredible homes waiting for you under $500,000—your dream home in Ossining is just a visit away!

Newest Ossining Homes under $500,000

$280,000

2 Beds ⋅ 1 Baths ⋅ 1057825 MLS

What an absolutely excellent opportunity! Come see this adorable cottage in the charming, unique, and AMAZING 44-home community that is Campwoods Grounds! As you walk through the property, you will notice the care that owners put into their homes...The attention to detail, the personal landscaping - in addition to the common areas, and the overall meticulousness is evident across the grounds. This two-bedroom cottage is ready for the lucky buyer(s) to add THEIR own personal touches, but plenty of wonderful features are already in place: A nice-sized eat in kitchen, beautiful hardwood floors downstairs, and a 120-square foot screened in porch are just some of these highlights. There are also two split heat/ac systems for efficiency, one up and one downstairs, as well as a gas furnace if desired for those absolutely frigid winter days/nights. The Campwoods Grounds community also boasts an extensive community garden, LARGE auditorium for neighborhood functions and other events, and a schedule of neighbohood get togethers to enjoy when you want to stay close to home. All of this, so convenient to all, and at a superb price point for the Ossining School District! Taxes with the STAR discount would be $4302/yr.

30 Campwoods Grounds, Ossining

$465,000

2 Beds ⋅ 2 Baths ⋅ 1051559 MLS

Welcome to this updated top-floor, end-unit condo offering privacy, light, and effortless living. A private balcony provides the perfect spot to enjoy your morning coffee or unwind at the end of the day. The inviting living room features a fireplace, skylight, and direct access to the balcony, creating a bright and welcoming gathering space. The newly renovated eat-in kitchen offers stylish updates and functionality, while two spacious bedrooms each feature their own walk-in closet. Two beautifully updated baths add to the comfort and convenience. A washer and dryer are located within the unit. Additional highlights include assigned parking plus ample visitor parking. Enjoy an array of community amenities including a swimming pool, clubhouse, and sports court. A complimentary shuttle provides convenient access to the Croton-Harmon Metro-North Railroad Station, making commuting a breeze. A wonderful opportunity to enjoy turnkey condominium living in a well-appointed community.

10 Briarcliff Drive S Unit #5, Ossining

$225,000

2 Beds ⋅ 1 Baths ⋅ 1041072 MLS

Opportunity awaits at this 2-bedroom, 1-bath bi-level co-op in the High Meadow Cooperative! This home offers comfortable, functional living that has been lovingly lived-in and ready for your personal touch, it's a great chance to build equity and make it your own. The monthly maintenance covers heat, hot water, sewer, trash, and grounds — a simple, low-hassle way to own. Commuters will love the location: about 1 mile to the Scarborough Metro-North station for an easy 45-minute ride to Grand Central, plus shopping and restaurants nearby. Don't miss this value-priced opportunity in a convenient location! Make your appointment today!

4 Charter Circle Unit #4, Ossining

$455,000

2 Beds ⋅ 2 Baths ⋅ 1053845 MLS

Tucked away above the Hudson River in the private Liberty Knoll community, this two bedroom renovated end-unit townhouse offers approximately 1,452 square feet across three levels. Dual exposures bring abundant natural light throughout, while the main level features a renovated kitchen, bright living and dining areas, a powder room and a rear deck. Upstairs, a spacious primary bedroom is joined by a renovated full bathroom and an additional bedroom offering flexible living space. An attached one-car garage opens directly into the finished basement, adding everyday convenience and additional space for a rec room or office. Liberty Knoll residents enjoy a community pool and clubhouse, plus a weekday reimbursement program for transportation to the nearby Scarborough Metro-North station. Close to shopping, the Hudson River and the Rivertowns, 13 Knoll View offers the ease of townhouse living with the space, flexibility and updates that make it an exceptional find.

13 Knoll View, Ossining

127-1 S Highland Avenue Unit #B5, Ossining

$228,000

2 Beds ⋅ 1 Baths ⋅ 1051780 MLS

Bring your furniture and move right into this beautiful top-floor co-op in Highland Terrace! From the moment you enter, you will appreciate the spacious foyer with hardwood floors, suitable as a entryway drop zone, office space, or breakfast nook. Just beyond is the open galley-style kitchen, featuring granite countertops, a tile backsplash, and a double-basin sink with an under-sink water filtration system. The kitchen opens seamlessly to the living and dining area, complete with a breakfast bar that’s perfect for casual meals or entertaining. The living space features BRAND NEW carpeting, which continues into both bedrooms, and the entire unit has been freshly painted. Down the hallway, you will find a tiled bathroom with a BRAND NEW vanity, toilet, medicine cabinet, and light fixture, plus a bathtub that has just been reglazed. The primary bedroom offers ample closet space, and the second bedroom can function as a guest room, home office, or additional living space. Outside, enjoy the beautifully landscaped grounds, complete with a swimming pool and direct access to the Old Croton Aqueduct Trail. Bring your four-legged companions, as Highland Terrace is a pet-friendly community. Enjoy the best of both convenience and surroundings with this ideally situated home, just under two miles from the Ossining Metro-North station and close to the many attractions, recreation, and natural beauty of the Hudson River area. Come see it today!

127-1 S Highland Avenue Unit #B5, Ossining

$399,000

1 Beds ⋅ 1 Baths ⋅ 1051520 MLS

Welcome to Hudson View Hills community in Ossining, NY! This adorable 1-bedroom, 1-bath unit offers approximately 832 square feet of comfortable, open-concept living. The inviting layout features a spacious living room, dining area, and kitchen, along with the convenience of in-unit laundry. Enjoy plenty of natural light throughout and step out onto your private, freshly painted unit, deck—perfect for relaxing or enjoying your morning coffee. Additional features include an updated bathroom, ample storage located beneath the unit that is shared, and a private outdoor carport included with the home. The pet-friendly community also offers a pool for residents to enjoy. Conveniently located near Metro-North, the historic Hudson River waterfront, shopping, restaurants, and more. With low common charges and a self-managed HOA, this is a wonderful opportunity to own instead of rent. Come see for yourself why this charming unit is a must-see! Great location for commuting with train within close proximity, restaurants, shopping and tons of Ossining community events through out the year.

58 Hudson View Hill, Ossining

$150,000

1 Beds ⋅ 1 Baths ⋅ 1050807 MLS

ATTENTION BUILDERS & FLIPPERS. Almost a blank canvas to create your masterpiece in a "ONE OF A KIND" community. One bedroom, one bath, cozy cottage. With some work you can bring back all the charm of days gone by for yourself or as an investment. Ownership includes two parking spaces (one assigned, one unassigned). Community social hall, and community garden. Don't just talk about being neighborly, be neighborly in a community that values the word neighbor. Location, location, location, close to transportation, shops, and downtown. CASH DEALS ONLY. Interior viewing by appointment with release form.

54 Campwoods Ground, Ossining

$340,000

1 Beds ⋅ 1 Baths ⋅ 1052224 MLS

Welcome to the highly sought-after Orchid Condominiums! This spacious one-bedroom, one-bathroom corner unit is located at the end of the building with no neighbors above. The bright, open-concept floor plan features 9-foot ceilings, abundant windows and beautiful modern finishes throughout. The large bedroom includes a generous walk-in closet, while the spacious bathroom offers a walk-in glass shower and a relaxing spa tub. The washer and dryer within the unit provide added convenience. The Orchid is an elevator building featuring 26 luxury condominium residences, a modern entry system, a fitness center, and private parking. Located less than one mile from Metro-North for an easy commute to New York City and close to shopping, dining, the waterfront and more!

73 Spring Street Unit #3D, Ossining

$349,900

1 Beds ⋅ 1 Baths ⋅ 1047497 MLS

Sunlight spills across the hardwood floors, the fireplace sets the mood, and that spiral staircase gives this first-floor end unit serious personality. Step out to your private deck, head up to the loft, or pull into your own garage and call it a day. Pet-friendly, plant-lover approved, and filled with sun-soaked corners where your greenery can thrive. Just minutes from Ossining’s Hudson River waterfront, parks, dining, shops, and Metro-North. First floor. End unit. Garage. Loft. Big energy. This one just hits different.

10 Nicole Circle Unit #9, Ossining

$349,900

1 Beds ⋅ 1 Baths ⋅ 1047960 MLS

Set among the mature landscaping and beautifully maintained grounds of Briarcliff Woods, this one-bedroom condo offers a peaceful setting for easy Hudson Valley living. The comfortable one-level layout features a spacious living room centered around a wood-burning fireplace, with sliding glass doors opening to a private balcony — a wonderful extension of the living space for relaxing outdoors. A dedicated dining area, separate kitchen, in-unit laundry, and excellent storage, including a generously sized walk-in closet, add everyday functionality, while the bedroom offers plenty of room to create a comfortable private retreat. One reserved parking space completes the package. Beyond the front door, Briarcliff Woods feels more like a landscaped retreat than a typical condo community, with a beautiful in-ground pool, tennis courts, clubhouse, an on-site superintendent, and well-cared-for grounds to enjoy throughout the seasons. Commuters will appreciate the convenient proximity to Croton-Harmon, with weekday jitney service from Briarcliff Woods to the station, express Metro-North service to Grand Central Terminal and Amtrak service to Penn Station, while the Ossining Metro-North station is also nearby. And when it’s time to stay closer to home, some of the best of the Hudson River Valley is just minutes away — waterfront parks, scenic walking and hiking trails, restaurants, shopping, seasonal events and the vibrant riverfront communities of Ossining and Croton-on-Hudson. It’s a wonderful combination of comfortable condo living, outdoor space, community amenities and easy access to everything that makes this corner of Westchester so appealing.

1 Briarcliff Drive S Unit #4, Ossining

$425,000

1 Beds ⋅ 2 Baths ⋅ 1041117 MLS

Welcome to LIBERTY KNOLL. . . This attractive 1 BEDROOM, 1.5 BATHS Tri-level townhouse is ready for its next owner! The Eat-in-Kitchen has ceramic tile flooring, a Frigidaire gas oven/range/microwave & dishwasher. The large Living Room leads to an inviting Deck that overlooks the rear yard. You'll find the Powder Room as well. The upper level showcases a generous size Bedroom that offers a walk-in closet and second closet. The clothes Washer/Dryer are located in the adjacent hall closet and next to the full Bathroom that offers a much appreciated double sink vanity. The Lower Level offers unfinished storage and potential living space at some point. Driveway parking along with an assigned space diagonally across the driveway is yours as well. Professionally maintained grounds, community pool, clubhouse and playground area amenities included. The Arcadian Shopping Center is across the way from the complex. And, the Scarborough Train Station is a stones throw (.6 miles) away providing timely access to GSC. Historic Sparta homes and Hudson River views are around the corner too.

17 Davids Lane, Ossining

129-1 S Highland Avenue Unit #B3, Ossining

$230,000

2 Beds ⋅ 1 Baths ⋅ 1036334 MLS

Welcome to this spacious and sun-filled two bedroom co-op in the beautiful Highland Terrace! Step into a welcoming foyer, currently arranged as a home office but easily adaptable as a dining area or flexible bonus space. The generously sized kitchen offers abundant cabinet storage and stainless-steel appliances. Just beyond, the bright and airy living room features large windows that fill the space with natural light. Down the hallway, you will find a spacious primary bedroom with ample closet space, along with a second bedroom that functions as a guest room, home office, or additional living space. The tiled bathroom is complete with a full bathtub. Outdoor enthusiasts will especially love the direct access to the historic Old Croton Aqueduct Trail from the property. This community is pet friendly, so your four-legged companion can enjoy the surroundings with you. Enjoy scenic and peaceful time in nature without having to get in the car. Return home and cool off in the beautiful swimming pool. Located less than two miles from the Ossining Metro-North station, this unit offers convenient access to transportation while keeping you close to the natural beauty and vibrant energy of the Hudson River area. Spacious, well located, and pet friendly, this co-op is an exciting opportunity you will not want to miss!

129-1 S Highland Avenue Unit #B3, Ossining

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