Ossining Homes with Garage Door Opener Parking features

Welcome to Ossining, New York—a charming village nestled in the heart of Westchester County, where the beauty of the Hudson River meets the rich tapestry of history and community. Known for its picturesque landscapes and vibrant downtown, Ossining offers a unique blend of suburban tranquility and urban convenience. With its tree-lined streets, historic architecture, and a warm, welcoming atmosphere, this is a place where families thrive and friendships flourish.

Ossining is not just about scenic beauty; it boasts an array of amenities, including excellent schools, diverse dining options, and easy access to parks and recreational activities. The village is well-connected by public transportation, making it a commuter's dream for those working in New York City. Residents can enjoy a leisurely stroll along the waterfront or explore the local shops and cafes that add to the village's charm.

When it comes to homes in Ossining, you'll find a variety of options that cater to different lifestyles. Many properties feature convenient garage door opener parking, ensuring easy access and added security for your vehicles. Imagine coming home after a long day to a cozy abode, where you can park effortlessly and unwind in your own sanctuary. These homes not only provide the practicality of modern living but also the comfort and style that make Ossining a sought-after destination for homebuyers.

Experience the best of both worlds in Ossining—where community spirit meets contemporary living. Come discover your dream home in this delightful village!

Newest Ossining Homes with Garage Door Opener Parking features

$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

$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

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