Ossining Homes with Driveway Parking features

Welcome to Ossining, New York – a charming village nestled in the picturesque Westchester County, where community spirit and educational excellence thrive. Known for its rich history and vibrant culture, Ossining offers residents a unique blend of suburban tranquility and easy access to the bustling life of New York City.

One of the standout features of Ossining is its highly regarded school district. The Ossining Union Free School District is dedicated to providing a top-notch education, with a strong emphasis on academic achievement, creativity, and character development. Families can take pride in knowing their children will benefit from a diverse curriculum, experienced educators, and a variety of extracurricular activities that foster personal growth and community involvement. The district’s commitment to excellence has earned it recognition, making it a desirable location for families seeking quality education.

When it comes to housing, Ossining offers a variety of charming homes, many of which feature convenient driveway parking. This desirable amenity not only enhances accessibility but also adds to the overall appeal of the properties. Imagine coming home after a long day and effortlessly parking your car right outside your door, ready to unwind in your cozy abode. Whether you’re looking for a quaint cottage or a spacious family home, Ossining’s real estate options cater to various lifestyles and preferences.

In Ossining, you’ll find not just a home, but a community that values education, convenience, and a rich quality of life. Come explore the possibilities and discover why Ossining is the perfect place to call home!

Newest Ossining Homes with Driveway Parking features

$849,999

4 Beds ⋅ 2 Baths ⋅ 1033351 MLS

Offered for the first time in over 60 years and a rare opportunity to own a piece of history! This historic mid-nineteenth century farmhouse sits on 1.3 private acres bordering the protected land of Ryder Park, ensuring permanent privacy and an undisturbed natural setting. This stunning four bedroom, one and a half bathroom home has charm and character everywhere you look. Exposed beams, wood flooring, original wanescoting, barnwood, stonework, two fireplaces and more. The front porch is used as a three season room and is the perfect place to watch the birds and drink your morning coffee. Oversized two car garage can easily an double as a work shop. All of this set on 1.3 acres with 3/4 acre zoning, offering future potential to split and create an additional building lot (buyer to verify with the town). The property features mature trees, historic stone walls and rolling hills surrounded by natural woodlands. Walk out your back door and onto the Ryder Park Walking Trail enjoy all of the features Ryder Park has to offer including baseball fields, tennis courts, summer camp, pavilion and more! Do not miss this unique opportunity to own a piece of history!

97 Morningside Drive, Ossining

$675,000

2 Beds ⋅ 3 Baths ⋅ 939652 MLS

Welcome to this well maintained 2-bedroom 2.5 bathroom end-unit townhouse in the Woods where comfort, space and easy-living come together. Freshly painted throughout and featuring brand new carpeting, this home offers a clean, move in ready interior with a bright and welcoming atmosphere. Discover the added privacy and abundance of natural light that comes with an end-unit location. Recent updates include a new central air conditioner, water heater, and washer and dryer all replaced within the last year, as well as a new boiler installed within the last few years. Step inside to a two-story entry with a soaring ceiling that creates an immediate sense of openness. The light-filled eat-in kitchen features granite countertops, ample cabinetry and plenty of space for casual dining. Just beyond, the spacious living and dining room are ideal both for everyday living and entertaining. Sliding glass doors from the dining room open to a private patio, providing a perfect spot to relax or dine outdoors. Completing the main level is a convenient powder room, access to the garage and a bonus room which may be used as an office, sitting room or guest space. The second level features a spacious primary bedroom with an ensuite bathroom, a large dressing area and access to a private balcony. A versatile loft provides flexible space for home office, den or sitting area. A well sized second bedroom, full bathroom, and a conveniently located second floor laundry complete the upper level. Residents of the Woods enjoy a variety of community amenities including a fabulous pool, tennis/pickleball courts, scenic walking paths, a tranquil pond, and professionally maintained grounds offering a relaxed, low-maintenance lifestyle. Ideally located just minutes from the Croton-Harmon Metro North train station, major parkways, an abundance of delicious dining options, wonderful shops and the scenic Hudson River waterfront. Enjoy easy access to the many amenities of nearby Croton on Hudson and Briarcliff Manor.

56 Pond View Court, Ossining

$539,999

1 Beds ⋅ 2 Baths ⋅ 1030990 MLS

Discover your dream home at 93 Bridle Path Road, nestled within the highly sought after Fox Hill Condominiums in Ossining, NY. This charming 2 level townhouse features a spacious 1 bedroom and a versatile loft, perfect for an office or study area. The first level boasts a modern galley kitchen with stainless steel appliances, a cozy living room with a wood burning fireplace, and a dining area that opens to a tranquil deck ideal for relaxing or entertaining. Enjoy the benefits of hardwood floors throughout, recessed lighting, and recently renovated kitchen and bathrooms. With a one car garage and additional driveway space, this property offers both convenience and comfort. Embrace the pet-friendly lifestyle and the serene, park-like setting of Fox Hill, which spans 45 wooded acres and includes amenities such as a pool, tennis court, basketball court, and playground. Located just 30 miles from New York City, with easy access to the Metro North rail line making your commute approximately 55 minutes, this home perfectly balances suburban tranquility with urban convenience. Don't miss the opportunity to make this peaceful retreat your own!

93 Bridle Path Road, Ossining

$700,000

2 Beds ⋅ 3 Baths ⋅ 1030619 MLS

Welcome to effortless living in the highly desirable Scarborough Glen community. Beautifully updated and impeccably maintained, this move-in ready home offers the perfect combination of spacious living and a private natural setting. Step inside to discover hardwood floors throughout the main living areas, complemented by brand new carpeting in the bedrooms, loft, and finished lower level. The kitchen has been refreshed with brand new appliances, while a brand new roof and brand new skylights with remote-controlled shades provide both peace of mind and an abundance of natural light. The impressive primary suite is a true retreat, featuring soaring cathedral ceilings, a spacious walk-in closet, and an expansive loft that is perfect for a home office, reading nook, fitness area, or additional living space. The finished lower level offers exceptional flexibility for a recreation room, media room, home gym, or guest space. Sliding glass doors provide seamless access to a private stone patio, creating the perfect indoor-outdoor living space for relaxing, entertaining, or enjoying your morning coffee. Perfectly positioned within the community, the home enjoys one of Scarborough Glen's most desirable settings. Visitor parking is conveniently located directly across from the home, making it easy for family and friends to visit. Rather than looking into neighboring homes, your front view overlooks a tranquil brook and lush greenery, providing a rare sense of privacy and a peaceful natural backdrop. With extensive updates, a versatile floor plan, and a premium location, this exceptional home offers the comfort, convenience, and serene lifestyle that today's buyers have been searching for. Enjoy the ease of maintenance-free living while being just minutes from the village, shopping, restaurants, parks, and Metro-North for an easy commute to New York City.

34 Briarbrook Drive, Briarcliff Manor

$899,000

4 Beds ⋅ 3 Baths ⋅ 1024630 MLS

A charming split-level home set on land that was once part of the historic Waldheim Estate of James and Ellin Speyer. Tucked into a peaceful setting just minutes from the heart of Briarcliff Manor, this inviting property reflects the area's rich history while offering the comfort of everyday living. Offering 4 bedrooms and 3 bathrooms, the home is filled with warmth, character, and a wonderful connection between indoor and outdoor living. From the moment you arrive, the tranquil surroundings make a lasting impression. Mature trees, established gardens, and natural landscaping provide exceptional privacy and create a beautiful backdrop that changes with the seasons—from colorful spring blooms to vibrant autumn foliage. Thoughtfully maintained over the years, the gardens offer a peaceful retreat that's as beautiful as it is easy to enjoy. Inside, soaring ceilings and abundant natural light enhance the home's welcoming atmosphere. The main living area is centered around a beautiful fireplace, creating a cozy gathering place, while large windows bring the beauty of the outdoors inside. The comfortable layout flows effortlessly to the outdoor living spaces, making everyday living and entertaining equally enjoyable. Step outside to the flagstone patio, where you can enjoy outdoor dining, entertain family and friends, or simply relax while taking in the peaceful surroundings. The in-ground cement pool complements the backyard, providing the perfect setting for warm summer days. Whether hosting gatherings or enjoying a quiet morning coffee surrounded by nature, the outdoor spaces offer endless opportunities to relax and unwind. Lovingly cared for over the years, the home presents an opportunity for its next owner to bring their own vision while enjoying its timeless charm, generous living space, and exceptional setting. Located just minutes from the many amenities of Briarcliff Manor, you'll enjoy access to Briarcliff Manor Recreation, nearby parks, scenic hiking trails, top-tier golf courses, charming shops, and local restaurants. The nearby Scarborough Train Station provides a convenient Hudson River commute to New York City, making this peaceful retreat as practical as it is picturesque. 54 Holbrook Road is more than a home—it's a place where nature, comfort, and community come together in one of Westchester's most desirable locations.

54 Holbrook Road, Briarcliff Manor

$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

$899,000

4 Beds ⋅ 3 Baths ⋅ 1027151 MLS

Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless character with modern updates. The main level offers an updated kitchen with granite countertops, stainless steel appliances, a gas Viking stove, laundry, and access to a private backyard. The oversized primary bedroom features elegant arch and tray ceilings. The walk out basement includes a finished recreation room and plenty of storage. The second floor apartment features an updated kitchen, three bedrooms, two full bathrooms, and access to a finished attic with a wainscoted ceiling, providing excellent income potential or additional living space. Conveniently located just 0.5 miles from the Ossining train station and close to downtown restaurants, shops, the farmers market, parks, schools, and major highways. A fantastic opportunity for homeowners and investors alike!

20 Waller Avenue, Ossining

$425,000

2 Beds ⋅ 2 Baths ⋅ 1006040 MLS

This adorable Ossining Schools gem awaits new owners to provide personal touches and TLC. It boast a welcoming entry leading to living room with charming details including arched doorway, built in shelving, and fireplace. Bright airy dining/flex room, 1st floor half bath, eat in kitchen with breakfast nook/ dining area and sliding door to patio. Climb the stairs to enjoy two sunny bedrooms each with double closets, and large full skylit bath including laundry hook up. With so much to offer it’s hard to determine but the best detail of this home may be the expansive private yard ready to become the entertainment center for its new owners. Don't sleep on this amazingly convenient location…less than 1 mile to two train stations (Scarborough and Ossining), 35 min to NYC, walking distance to market, and Ossining village shops. Near to bus, schools and more! This might just be the best deal in town. Apx. $1500 STAR tax saving available. Make your appointment today.

42 Revolutionary Road, Ossining

$625,000

4 Beds ⋅ 3 Baths ⋅ 1027201 MLS

Legal two-family Colonial tucked away on large cul-de-sac adjacent to Ossining's historic Sparta community. Originally built as a two-family (not a conversion), the home offers a practical layout with separate living spaces. The first floor apartment features 1 bedroom and 1 full bath, while the upper apartment spans the 2nd and 3rd floors with 3 bedrooms and 1.5 baths. The upper apartment can be accessed by either: 1) A private exterior staircase. 2) A shared enclosed stairwell with its own exterior entrance and separate lockable doors to each apartment. Whether you're looking for an owner-occupied property with rental income or a solid investment opportunity, this home offers flexibility and strong potential. Conveniently located just around the corner from Sparta Park, .5 miles from the Arcadian Shopping Center and .8 miles from the Scarborough Train Station for an easy commute to Manhattan.

20 Riverview Court, Ossining

$639,500

4 Beds ⋅ 2 Baths ⋅ 1021344 MLS

Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle. The private backyard offers a peaceful retreat with a patio ideal for outdoor dining, entertaining, or simply relaxing. Experience the best of Hudson Valley living with convenient access to the scenic Hudson River waterfront, parks, hiking and biking trails, local restaurants, shopping, and year-round community events. Whether you're commuting, exploring the outdoors, or enjoying the vibrant Rivertown lifestyle, this home offers the perfect balance of tranquility and convenience. Don't miss this opportunity to own a beautiful home in one of the Hudson Valley's most sought-after communities.

42 Pershing Avenue, Ossining

$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

$698,000

4 Beds ⋅ 3 Baths ⋅ 1023097 MLS

Charm meets flexibility in this rare Ossining find! A legal mother-daughter bungalow ranch that feels like a secret waiting to be discovered! Tucked back from the road amid mature plantings and lush landscaping, this home delivers a bright, cheerful, private pocket of comfort. Step inside to a sun-drenched three-season room with recessed lighting, then through French doors into a warm kitchen with abundant cabinets and granite countertops. A dining area with oversized windows keeps the light flowing all day, opening into a family room with a fireplace, large bay window, and a door to the back deck. The first-floor primary bedroom features an en-suite bath and is joined by two additional bedrooms and a hall bath, with hardwood floors throughout the main level. A standout feature is the legal mother-daughter suite, complete with its own private entrance, summer kitchen, bedroom, full bath, and living/dining area. Ideal for multigenerational living, guests, or extra income potential. Out back, a fenced-in yard feels like your own private retreat - leafy, tucked away, and made for slow mornings and long summer nights. Fire up the grill on the spacious deck, linger under the stars, or lose an afternoon in the gardens. Ideally located close to the Croton train station (and the villages of both Croton-on-Hudson and Ossining, with plenty of amenities, shopping, and eateries nearby. Well-priced and move-in ready, this one won’t sit on the market long. Schedule your showing today.

7 Ogden Road, Ossining

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