Ossining Homes with Parking Lot Parking features

Ossining Homes with Parking Lot Parking features

Welcome to Ossining, New York, a vibrant community nestled in the heart of Westchester County. Known for its rich history, scenic views, and a strong sense of community, Ossining is not only an ideal place to call home but also boasts an exceptional school district that prioritizes educational excellence and student well-being.

The Ossining Union Free School District serves a diverse population and is dedicated to fostering a nurturing environment where students can thrive academically and socially. With a variety of innovative programs, dedicated educators, and modern facilities, the district is committed to preparing students for success in an ever-evolving world. Parents can take comfort in knowing that their children will receive a top-notch education, with schools that emphasize not just academic achievement, but also the importance of arts, athletics, and community involvement.

When it comes to finding your perfect home in Ossining, you’ll discover a range of charming properties that cater to various lifestyles. Many homes in this picturesque area feature convenient parking lot parking, ensuring that you and your guests will always have a space to park. Imagine coming home to a cozy abode after a long day, knowing that your vehicle is just steps away, ready for your next adventure.

Whether you're drawn to Ossining for its outstanding schools, beautiful parks, or the welcoming community spirit, this town has something for everyone. Come explore Ossining—where education meets comfort and community!

Newest Ossining Homes with Parking Lot Parking features

$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

$1,079,000
4 Beds 3 Baths 1002953 MLS
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. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping, dining, and everyday essentials. The Croton-Harmon Train Station is even closer, while convenient access to Route 9A and the Taconic State Parkway makes commuting throughout Westchester and beyond easily accessible. Thoughtfully redesigned and extensively reconstructed under architectural plans, the home features spacious light-filled living areas, a dramatic vaulted great room ceiling, and an architect-designed wall of glass that brings natural light and the surrounding landscape into the heart of the home. Multiple Marvin door systems were designed to create seamless indoor-outdoor flow and future deck integration. The home was designed with a similar footprint across both levels, resulting in an exceptionally large lower level that dramatically expands the usable space of the home and offers substantial flexibility for workshop space, storage, recreation, future finishing, home business use, gym space, or other expanded uses rarely found in the area. The kitchen and main living spaces were rebuilt from the foundation up during the 2008 reconstruction and create a true chef’s kitchen experience, featuring radiant heated flooring beneath large-format tile, custom-built cabinetry, an oversized 5’ x 7’ island, a large built-in KitchenAid refrigerator, KitchenAid dishwasher, and a Thermador professional oven. The kitchen was intentionally designed with exceptional spacing and flow for cooking, entertaining, and everyday living, creating an openness rarely found in homes of this style. A large high-ceiling lower level was also added during the reconstruction, offering excellent flexibility as a workshop, workspace, storage area, gym, hobby space, or potential future finished area. The lower level also includes a second laundry setup with an additional washer and dryer. The spacious primary suite addition includes a large ensuite bath with jacuzzi tub, oversized shower, and private water closet. A second primary-style bedroom offers its own ensuite bathroom with shower and direct access to the backyard, creating excellent flexibility for guests, extended family, multigenerational living, or private workspace use. A second primary bathroom was also fully renovated in 2025. The rare 4-car tandem garage configuration, expansive multi-driveway parking setup with space for approximately 20 vehicles, and oversized lower level create exceptional flexibility for car enthusiasts, collectors, hobbyists, workshop use, home business needs, or anyone seeking substantial additional storage and utility space rarely found in northern Westchester. Additional highlights include a central vacuum system with multiple in-wall outlets and kitchen kick-plate crumb sweeper, fireplace-ready buildout with propane option, generator-ready electrical infrastructure, alarm system, updated water systems, and numerous structural and mechanical improvements completed over the years. A unique opportunity to enjoy peaceful acreage, architectural character, exceptional utility space, commuter convenience, and a level of flexibility rarely found in one property.

54 Allapartus Road, 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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