Ossining Homes with Private Parking features

Welcome to Ossining, a vibrant community nestled in Westchester County, New York, where scenic beauty meets a rich cultural tapestry. Known for its historical significance and picturesque views along the Hudson River, Ossining is not just a place to live; it's a lifestyle. One of the standout features of this charming town is its highly regarded school district, which is committed to fostering academic excellence and providing a well-rounded education. Ossining School District offers a diverse curriculum, dedicated educators, and a variety of extracurricular activities that nurture students' talents and interests. Families can feel confident that their children are receiving a top-notch education in a supportive environment.

In addition to its educational offerings, Ossining boasts an array of homes that cater to modern living, including properties with the coveted feature of private parking. Imagine the convenience of having your own dedicated space, free from the hassle of street parking. Many homes in this area come with private driveways or garages, ensuring that your vehicle is safe and easily accessible. Whether you're seeking a charming single-family home or a contemporary townhouse, Ossining's real estate market has options that suit every lifestyle.

Living in Ossining means enjoying the best of both worlds: a peaceful suburban atmosphere while being just a short commute from the bustling city of New York. With its excellent schools, beautiful homes with private parking, and a tight-knit community, Ossining is the perfect place to plant your roots and watch your family flourish. Come discover the charm of Ossining—your new home awaits!

Newest Ossining Homes with Private Parking features

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 1021711 MLS

"Living at Beechwood has been a truly special experience. The beauty, serenity, and wonderful sense of community make it a place that feels like home from the moment you arrive. Some of my favorite memories have been simply sitting on the balcony, watching breathtaking sunsets paint the sky, greeting the peaceful sunrise with a cup of coffee, and enjoying the quiet glow of the moonlight in the evenings. The natural beauty that surrounds the home changes with every season, creating a tranquil retreat that is both inspiring and relaxing. Combined with the warmth and kindness of the lovely neighbors, Beechwood offers a rare lifestyle where every day feels peaceful, welcoming, and connected to nature." (Seller's words) 32 Beechwood Way is part of an 80-acre private parkland. Beechwood was designed by Frederick Law Olmsted (who also designed Central Park in NYC and Prospect Park in Brooklyn). Its expansive lawns, grove of large beech trees, imported trees, and Italianate Garden with an alcove, fountain, and small pool with wisteria-covered gazebo have been well-preserved. Serene, tranquil, alluring is at the essence of Beechwood. Natural light abounds from large windows in living room and sky lights in entrance foyer. The primary bedroom has en-suite bath, double walk-in closet (it is a room all its own!), walk-in-shower for ease in entry/exit, & private terrace with seasonal Hudson River views. Scarborough Station/Metro North is less than a mile away (.9 miles). Working remotely? Two additional bedrooms on main & lower level easily accommodate your lifestyle. Efficient & responsive resident property manager. Entire house painted within the year. Floors refinished and stained in the last 2 years. Whole-house water filtration system installed less than a year ago. Roof less than 3 years old. Residents at Beechwood may avail themselves of the Olympic-size pool, library, & elegant formal ballroom to celebrate life events in style.

32 Beechwood Way, Briarcliff Manor

$1,750,000

9 Beds ⋅ 8 Baths ⋅ 1005133 MLS

Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining

$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

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