Ossining Homes with Oversized Parking features

Welcome to Ossining, a charming village nestled in the heart of Westchester County, New York. Known for its rich history and vibrant community, Ossining is not only a picturesque place to call home but also boasts an exceptional school district that prioritizes education and student success. The Ossining Union Free School District is committed to fostering a nurturing learning environment that empowers students to excel academically and socially. With a range of innovative programs, dedicated educators, and a strong emphasis on community involvement, parents can feel confident in the quality of education their children will receive here.

In addition to its outstanding educational offerings, Ossining is a haven for families seeking homes with oversized parking features. Imagine coming home to a spacious property that accommodates multiple vehicles, recreational toys, or even a home workshop. These oversized parking options provide both convenience and flexibility, making it easy for residents to enjoy everything Ossining has to offer—from weekend adventures to hosting family gatherings.

The combination of a top-notch school district and the practicality of homes with oversized parking makes Ossining an ideal choice for families looking to settle down in a community that values education and convenience. With its beautiful parks, scenic waterfront, and a variety of local shops and restaurants, Ossining is not just a place to live; it’s a place to thrive. Discover your dream home in Ossining today, and experience the perfect blend of comfort, community, and opportunity!

Newest Ossining Homes with Oversized Parking features

$1,085,000

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

$2,995,000

5 Beds ⋅ 7 Baths ⋅ 986239 MLS

There are homes… and then there are places that feel quietly set apart from the world around them. Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally… like a secret meant only for those who understand what true luxury feels like. This is not just a home. This is a legacy estate. Set perfectly between the Hudson River and Sleepy Hollow Country Club, the location offers the rare balance today’s buyers search for privacy, proximity, and prestige. Minutes to Metro North, fine dining, boutique shopping, and everything that defines Westchester luxury living… yet once you arrive, the outside world seems to soften. There is a stillness here. You feel it walking the grounds, where mature trees frame rolling lawns and sunlight filters through in that unmistakable golden way. There is a rhythm to the property… the kind that invites long mornings on the porch, quiet afternoons by the pool, and evenings that stretch just a little longer than planned. And somewhere within it all… life quietly thrives. Bees drift from bloom to bloom, tending to the landscape in a way that feels both timeless and grounding… a subtle reminder that this estate is not just maintained, it is alive. Inside, the home unfolds with a level of craftsmanship and scale rarely seen today. Five ensuite bedrooms offer both privacy and comfort, anchored by a truly exceptional primary suite with its own fireplace, spa like bath, expansive dressing room, and a private sleeping porch… a nod to a more romantic era of living, where fresh air and slow mornings were part of everyday life. The kitchen is designed not just for cooking, but for gathering… a chef’s workspace complemented by a generous butler’s pantry, ideal for seamless entertaining. It flows effortlessly into a formal dining room that feels pulled from the pages of a design magazine, where hand printed Zuber wallpaper and a fireplace create a setting that is both refined and deeply inviting. Every room tells a story. A wood paneled office with its own fireplace opens to the front porch, offering a work from home experience that feels anything but ordinary. The living room, wrapped in double walls of French doors, blurs the line between indoors and out, filling the space with natural light throughout the day. Nearby, the sunroom becomes its own retreat… a place to pause, unwind, and simply take in the beauty of the property. Step outside, and the estate continues to reveal itself. A gunite pool set within manicured grounds. Multiple porches designed for every mood and moment. A historic Lord and Burnham greenhouse… a rare and remarkable feature that speaks to the property’s heritage. And a four plus car garage with a private apartment above, offering flexibility for guests, extended stays, or staff. This is Westchester luxury real estate at its finest, where historic architecture meets modern lifestyle, where privacy meets convenience, and where every detail has been thoughtfully considered. Because the truth is… You can always renovate a home. But you cannot recreate land like this. You cannot replicate this setting. And you cannot manufacture the feeling this property gives you the moment you arrive. 36 Revolutionary Road is not just being listed. It is being offered.

36 Revolutionary Road, Briarcliff Manor

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