Ossining Condos for Sale

Ossining Condos for Sale

Welcome to Ossining, a picturesque village nestled along the Hudson River in Westchester County, New York. This charming community is known for its rich history, vibrant culture, and stunning natural beauty, making it one of the most sought-after places to call home in the region. With its scenic waterfront, lush parks, and a delightful mix of historic architecture and modern conveniences, Ossining offers a unique blend of small-town charm and urban accessibility.

As you explore the village, you'll find a variety of local shops, restaurants, and cafes that reflect the diverse culture of its residents. The Ossining Farmers Market is a must-visit, showcasing fresh produce and artisan goods, while the scenic trails along the river provide the perfect backdrop for outdoor activities. With excellent schools, community events, and a strong sense of belonging, Ossining is ideal for families, young professionals, and retirees alike.

For those considering a move to this enchanting village, there are beautiful condos for sale that perfectly capture the essence of Ossining living. These modern residences offer a blend of comfort and convenience, featuring spacious layouts, contemporary amenities, and stunning views of the Hudson River. Many condos are located within walking distance of the vibrant downtown area, providing easy access to shops, dining, and public transportation.

Whether you're looking to downsize, invest, or find your first home, Ossining's condos present an incredible opportunity to enjoy a relaxed lifestyle in a thriving community. Come discover the charm of Ossining and find your perfect home today!

Newest Ossining Condos for Sale

$469,900
2 Beds ⋅ 2 Baths ⋅ 1049340 MLS
Welcome to this chic, beautifully renovated 2-bedroom, 2-bathroom condominium in Ossining's iconic 1820 schoolhouse conversion. Originally built as a schoolhouse and thoughtfully converted in 2007 into an intimate 12-unit condominium, this one-of-a-kind residence seamlessly blends a Soho-inspired aesthetic with the warmth, character and charm of the Hudson Valley. Step inside to a spacious, open-concept interior featuring soaring ceilings and a huge sun-filled living room. The elevated kitchen offers granite countertops and new stainless steel appliances (2025). The open-layout allows the kitchen, dining and living areas to flow effortlessly together, creating a sophisticated yet comfortable sense of space. The private bedroom area offers two beautiful bedrooms, including a large primary ensuite designed as a serene retreat. The primary bedroom is filled with natural light through large windows, complemented by automated window treatments for effortless comfort and privacy. A fews steps down lead to tastefully renovated primary bathroom, featuring a sophisticated, modern design complete with radiant heated floors. A walk-in custom organized closet completes this exceptional primary suite. The generously sized second bedroom is ideal for guests or a home office. Just beyond is the distinctive, updated second bathroom that adds another layer of style and sophistication to this home. The unit also comes with an assigned parking spot(#11) and private laundry. Fabulous location with easy access to the scenic Croton Aqueduct trail and all that Ossining has to offer. This vibrant, welcoming community has a cool vibe, with a Recreation Center offering something for everyone, from adult basketball to children's programs, as well as a stunning riverfront and close proximity to the Metro North Train station. Enjoy delicious local restaurants, an amazing famers market, lively street fairs, outdoor summer concerts and so much more-all adding to the energy that makes Ossining such a special place to call home.

88 Broadway Unit #2B, Ossining
$590,000
2 Beds ⋅ 3 Baths ⋅ 1039859 MLS
Love the NYC loft lifestyle, but not the NYC-sized floor plan—or price tag? Welcome to The Penthouse. Set within a reimagined historic 1820s schoolhouse, this dramatic tri-level penthouse loft delivers the attitude of a downtown loft with the space, light and breathing room Manhattan forgot to include. The result? Something seriously cool—and anything but ordinary. The Entertaining Level sets the tone with soaring volume, exposed brick elements, original wood beams, exposed copper piping, hardwood floors and distinctive low-set windows that help fill the space with natural light. An elevated kitchen with granite counters and stainless-steel appliances overlooks the expansive open-concept living and dining area, creating one incredible backdrop for entertaining or simply hanging out at home. A powder room completes the level. Then there’s The Loft—perched above and overlooking the entertaining space below. Skylights bring in even more natural light, while the open design gives you a completely different perspective on the architecture of The Penthouse. Home office, studio, lounge, reading retreat or creative escape—it’s the kind of flexible space that makes loft living so much fun. The Private Level changes gears completely. Two generously sized bedrooms each enjoy their own private en-suite bath. The oversized primary suite features a huge walk-in closet and spacious bath with double sinks and a jetted whirlpool tub. The second bedroom has its own beautifully refreshed en-suite bath with brand-new tile. In-unit laundry is conveniently tucked into this level as well. And here’s something you won’t see in the photos: some of the most impressive improvements in The Penthouse are hidden behind the finished walls. Extensive sound-control upgrades were incorporated into select walls and ceilings using additional framing and separation, ROCKWOOL mineral-wool insulation, spray foam and heavier 5/8-inch drywall. The primary-bedroom ceiling received its own extensive insulated assembly, all designed with acoustic comfort and reduced sound transmission in mind. Drenched in natural light? Absolutely. Drenched in noise? This renovation took that on from the inside out. And then there’s Ossining. Hudson River waterfront parks, marinas, downtown shops and cafes, the Old Croton Aqueduct Trail and Metro-North are all nearby—giving you the space and character of Hudson Valley living without giving up your connection to NYC. And when Manhattan calls? Metro-North express service can have you at Grand Central in under 50 minutes. Two assigned parking spaces and dedicated private storage round it all out—two more things Manhattan generally forgets to include. Historic character. Downtown attitude. Suburban breathing room. Three incredible levels. Serious sound-control improvements. This isn’t another suburban condo. This is The Penthouse—and that’s exactly the point.

88 Broadway Unit #PH4, 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
$895,000
2 Beds ⋅ 3 Baths ⋅ 1045247 MLS
There is something very special about Mystic Pointe, you feel it as soon as you enter through the gates. 33 Mystic Drive is a tri-level, end unit, Biscayne model home in the heart of Mystic, overlooking the Nature Trail. It offers a traditional layout with an eat-in kitchen, living and dining areas with sliding glass doors to one of the decks, a powder room, and access to the two-car garage all on the main level. The upper level has two generous bedrooms, two full baths, and a den/office room. The lower level is a wonderful all-around everything room, with sliding glass doors to the oversized deck, a generous walk-in storage closet, a laundry room, plus an additional storage room and utility room. One of the few homes with double decks for double entertaining! And Mystic Pointe has so much to offer: two pools, one adult and one for children; a clubhouse with a full kitchen and gym; a tennis/pickleball court; and a warm, welcoming community with weekly bridge nights, book club, and so much more. And since you don't have to mow the lawn, shovel the snow, or repair the exterior of your home, you will have plenty of time to enjoy it all.

33 Mystic Drive, Ossining
$202,500
1 Beds ⋅ 1 Baths ⋅ 1032192 MLS
Exciting 1-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. Walk to train, restaurants, stores, farmers' market, festivals, waterfront park, community recreation center, library, and more. Cats and dogs friendly (limit 2 per unit)! As an owner, you can obtain a parking permit for both the village and train station. This property is a part of "fair and affordable" housing. Per affordability restrictions under the HOME program, the potential new owner(s) income may not exceed 80% of the Westchester County area median income (As of August 1, 2025, those limits are: 1 person - $95,000, 2 persons - $108,600, 3 persons - $122,150, with maximum occupancy of the persons in the unit). Income limits are subject to change. MUST be occupied as a primary residence (no investors). The affordable sale price is $214,682 (your offer price may not exceed that amount). The Westchester County subsidy of $30,000 is available for this unit. It stays at the full amount for 20 years, then it terminates. ***AGENTS – MUST see confidential remarks and all MLS listing attachments for additional instructions***

135 Main Street Unit #201, Ossining
$229,222
2 Beds ⋅ 1 Baths ⋅ 1032252 MLS
Move right into this beautifully updated 2-bedroom unit featuring stylish finishes and modern upgrades throughout. New luxury waterproof vinyl flooring, new interior doors and hardware, and a renovated kitchen and bath create a fresh, contemporary feel. The updated kitchen boasts new cabinetry, butcher block countertops, a subway tile backsplash, and stainless steel appliances, including a built-in microwave and gas range. The open-concept living and dining area is filled with natural light and opens to a private balcony—perfect for relaxing and enjoying beautiful sunset views. The renovated bathroom features classic subway tile, a bathtub with a rainfall showerhead, and an updated vanity. Ceiling fans in both bedrooms and the living room provide added comfort, while the large picture window and generous closet space enhance the bright, spacious layout. Residents enjoy excellent amenities, including an outdoor pool, fitness center, on-site laundry, assigned parking, secure building entry with a security camera system, and an on-site superintendent for added convenience. Ideally located near parks, schools, the village, shopping, dining, and public transportation, this exceptionally well-maintained home offers comfort, style, and convenience in one desirable package. There are no audio recording devices inside this property.

119 S Highland Avenue Unit #5E, Ossining
$150,000
1 Beds ⋅ 1 Baths ⋅ 1024369 MLS
Welcome to this beautifully maintained, pet-friendly 1-bedroom co-op in desirable Ossining, offering the perfect blend of comfort, convenience, and a rare private patio. A spacious foyer welcomes you inside and leads to a thoughtfully designed layout featuring an updated bathroom, a functional kitchen with ample cabinet space, and a generously sized bedroom. The expansive living and dining area provides an ideal setting for both everyday living and entertaining, with a private back door opening directly to your patio, creating a seamless indoor-outdoor lifestyle. Nestled within a well-maintained garden-style community, residents enjoy exceptional amenities including an in-ground swimming pool, basketball court, scenic walking trails, beautifully landscaped grounds, plentiful guest parking, and an assigned parking space conveniently located just steps from the building. Ideally situated just minutes from Metro-North, the Taconic State Parkway, shopping, dining, parks, and the vibrant Ossining waterfront, this home offers the perfect balance of tranquility and accessibility. Whether you're purchasing your first home, downsizing, or searching for a commuter-friendly residence with sought-after outdoor space, this move-in-ready opportunity is one you won't want to miss.

129-3 S Highland Avenue Unit #A2, Ossining
$234,500
2 Beds ⋅ 1 Baths ⋅ 987888 MLS
Spacious two bedroom light & airy updated END-unit in heart of town offers easy affordable living in a quiet, pet-friendly community. Common charges include taxes, heat, water, buildings/grounds and pool maintenance, insurance & parking. This low-maintenance one-level unit is located on the first floor. Features include an updated Kitchen with quartz countertops, white cabinetry, natural gas cooking stove; high-hat lighting and wiring for Verizon Fios/Spectrum/Cablevision. Multiple ceiling fans and windows in every room; multiple a/c units included. Corner location offers more windows and privacy than most and lets in more natural sunlight. Lovely landscaping, basketball/sports court, outdoor in-ground pool & common-use patios with BBQ set ups, along with well-maintained outdoor seating areas. Ossining's award-winning Schools are known for having the most Intel Science winners year after year along with great Robotics & STEM Programs. This is one of a very limited number of co-op complexes that is pet friendly (2 pet limit). Walk to the Arcadian Shopping Center's stores, banks and restaurants (i.e., McDonald's, Verizon, Starbucks, Capri Pizza, Valley Bank, Stop & Shop Supermarket +) all for your dining & shopping pleasure. If you work in the City, or want to head up north to Bear Mountain and beyond, Highland Terrace Co-ops has easy access to all main thoroughfares. You're only minutes from Metro-North's Hudson train line with less than an hour's commute to Manhattan. Nelson Park is just a block away. Scenic Aqueduct walking trails are nearby; and only seconds from riverfront options to fish or sail on the Hudson! Who needs anything more? Why not say "Welcome Home" to Unit #B3 today.

127-1 South Highland Avenue Unit #B3, Ossining
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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.