Ossining Homes with Driveway Parking features

Welcome to Ossining, New York – a charming riverside town nestled in the heart of Westchester County. Known for its rich history and vibrant community, Ossining offers the perfect blend of suburban tranquility and urban convenience. With the beautiful Hudson River as your backdrop, residents enjoy picturesque views, lush parks, and a myriad of recreational activities. The town is well-connected to New York City via the Metro-North Railroad, making it an ideal location for commuters seeking a peaceful retreat after a bustling day in the city.

Ossining boasts a diverse range of homes, each with unique character and charm. One of the standout features of many properties in this area is the convenience of driveway parking. Imagine coming home to a spacious driveway, providing easy access to your vehicle without the hassle of street parking. This feature not only adds to the overall appeal of a home but also enhances the quality of life for families and individuals alike.

Whether you’re looking for a cozy single-family home, a modern townhouse, or a historic gem, Ossining has something to fit every lifestyle and budget. The community is known for its friendly atmosphere, excellent schools, and a variety of local shops and restaurants that cater to all tastes. With its stunning natural beauty, rich cultural heritage, and the practicality of driveway parking, Ossining is not just a place to live – it’s a place to thrive. Discover your dream home in this enchanting town today!

Newest Ossining Homes with Driveway Parking features

$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

$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

$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

$599,000

3 Beds ⋅ 1 Baths ⋅ 1025170 MLS

This lovingly maintained, one level home offers the ideal location- so convenient to all and a beautiful level backyard....You will be impressed with the very private outdoor space ready for entertaining and warm weather enjoyment -a country neighborhood feel yet only 10 minutes to Metro North station- a 50 min express commute to Grand Central and 2-3 miles to Rt 9/ Taconic Parkway....A warm and welcoming ranch in the wonderful Rivertown of Ossining where comfort, charm, convenience and community come together....This cozy retreat offers spacious living and a dining area that seamlessly connects to the kitchen creating the perfect setting for everyday living and entertaining. Conveniently located first floor bedrooms provide added accessibility and ease. Step outside to a welcoming patio perfect for outdoor living, gardening or simply enjoying your own private oasis. Known for its rich history, vibrant downtown, beautiful river views and breathtaking sunsets, Ossining offers the charm of riverfront living with waterfront parks, scenic walking neighborhoods and vibrant dining and shopping. Nature lovers will appreciate nearby hiking trails, Teatown Nature Preserve, Veterans Park and the Ossining Farmers Market. If you you are looking for a move in condition home, tranquility, the ideal commuter location or a lifestyle that comes with Rivertown living, this home with gas heat/ cooking, town water & sewer could be just what you are looking for!

23 Gates Avenue, Ossining

$1,700,000

2 Beds ⋅ 2 Baths ⋅ 1023302 MLS

Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes. Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles of organic architecture, where walls of glass, natural materials, and thoughtful siting dissolve the boundaries between indoors and out. Built from Philippine mahogany, stone, slate, and glass, every detail was carefully considered to create harmony with the surrounding landscape. The result is a 2 bedroom 2 bathroom home that feels remarkably current nearly seventy years later. Inside, soaring glass walls frame the changing seasons while a dramatic stone fireplace anchors the main living space. Original built-ins, slate floors, rich mahogany, and a signature wraparound deck celebrate Henken's vision, while the thoughtfully updated kitchen and recent improvements allow the home to function beautifully for modern living. Designed using passive solar principles decades before sustainability became mainstream, the home captures the low winter sun for natural warmth while deep roof overhangs provide cooling shade throughout the summer additionally geothermal heating, solar, and other thoughtful updates bring modern all-electric comfort to the home. Complementing the main residence is a beautifully reimagined 1,200 square foot studio that expands the property's possibilities. Completely renovated, the space now offers a bedroom, full bath, living area, kitchenette, and a stunning spa-inspired sauna suite finished with terrazzo tile, warm Aspen wood, and premium contemporary materials throughout. Whether used as a guest retreat, artist's studio, wellness space, home office, or income-producing guest accommodation, it offers the same thoughtful design and craftsmanship found in the main home. Recent improvements, including a newly constructed carport, estate-style gravel driveway, high-performance siding, Energy Star windows, updated insulation, and new mechanical connections to the studio, ensure the property is ready for years of effortless enjoyment. The setting is every bit as extraordinary as the architecture. Wander your own seventeen-acre landscape, listen to the year-round stream, or spend the afternoon exploring nearby Teatown Lake Reservation. Just beyond, you'll find some of the Hudson Valley's most celebrated destinations, including Blue Hill at Stone Barns and The Farmer & The Fish. Nearby towns of Ridgefield, Pound Ridge, Katonah and Bedford, offer exceptional dining, galleries, farmers markets, and hiking. Metro-North provides easy access to New York City, making this an extraordinary full-time residence or one of the region's most remarkable weekend escapes. Architecturally significant homes of this caliber rarely become available. This is more than a residence—it's an opportunity to own a living piece of mid-century design history, thoughtfully preserved for the next generation.

1306 Grants Lane, Ossining

$525,000

3 Beds ⋅ 2 Baths ⋅ 1024303 MLS

A true brick home in the Village of Ossining, offering beautiful sunset and river views, tremendous character, low taxes, and a location that’s hard to beat — just minutes to the train station, riverfront dining, and Teatown Nature Preserve. This 3-bedroom, 2-bath home features 1,240 sq ft across the main floors, plus a 340 sq ft walk-out lower level and a walk-up attic ideal for an artist loft, studio, or storage. Inside, original exposed beam ceilings and a striking stone-and-brick fireplace with a Jotul wood stove sets an unmistakable tone. Outside, enjoy a rare three-tiered outdoor living setup: a brick patio off the lower level, a large deck off the kitchen, and an upper balcony with year-round views of the Mario Cuomo Bridge and Croton Point Park — expanding to a full 180-degree Hudson River panorama in winter. The lower level includes a convenient kitchenette for guests or extended living. Classic brick architecture, arched window lintels, mature trees, a large rear yard, and a storage shed complete this home with genuine architectural soul.

33 Cedar Lane, Ossining

$1,045,000

4 Beds ⋅ 3 Baths ⋅ 1023043 MLS

Welcome to this beautifully renovated Dutch Colonial, where timeless charm meets modern comfort and breathtaking Hudson River views create an unforgettable setting. Thoughtfully redesigned, the sun-filled chef's kitchen is the heart of the home, featuring crisp white cabinetry, expansive quartz countertops, abundant storage, and a seamless flow into the dining and living areas, perfect for everyday living and effortless entertaining. The spacious living room is warm and inviting, highlighted by a beautiful fireplace and elegant French doors that open to a covered patio, creating an ideal space to gather with family and friends. Just beyond, the expansive west-facing deck showcases spectacular Hudson River vistas and provides the perfect place to unwind while taking in stunning sunsets. A private office or study with sliding glass doors to the deck allows you to work while enjoying the scenic surroundings, and a beautifully renovated full bath completes the main level. Upstairs, the primary suite is a true retreat, offering a generous walk-in dressing area and a spa-inspired bath with a soaking tub, separate shower, and picturesque views. Three additional spacious bedrooms and another beautifully updated full bath provide ample room for family and guests. Additional highlights include a built-in speaker system throughout much of the home, an expansive yard, abundant parking, an oversized two-car garage, and a full basement, offering endless possibilities for storage, recreation, or future living space. Combining exceptional renovations, generous living spaces, and captivating vistas, this is a home you'll want to experience in person.

27 Ryder Road, Ossining

$950,000

4 Beds ⋅ 3 Baths ⋅ 1019889 MLS

Welcome to one of Ossining's most captivating homes, where breathtaking panoramic Hudson River views take center stage. Perfectly positioned on a quiet cul-de-sac in the sought-after Sparta neighborhood, this beautifully updated 4-bedroom, 2.5-bath residence offers an exceptional blend of style, comfort, and unforgettable scenery. From the moment you enter, you're greeted by abundant natural light and spectacular water views from nearly every level. The thoughtfully renovated kitchen flows seamlessly into the main living and dining spaces, while hardwood floors, two fireplaces, and oversized windows create a warm yet sophisticated atmosphere. Wake up to stunning river vistas from the bedrooms, then unwind each evening as the sun sets over the Hudson from your expansive wraparound patio. Designed for both entertaining and everyday living, the outdoor space features a private backyard with a stone fire pit—perfect for gathering with family and friends while enjoying the ever-changing beauty of the river. Located just moments from Sparta Park, the Ossining waterfront, restaurants, shopping, and the Scarborough Metro-North station, this home offers the perfect balance of tranquility and convenience. If you've been searching for a home with truly spectacular water views, timeless charm, and an unbeatable location, this is an opportunity you won't want to miss.

12 Riverview Court, Ossining

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