Ossining Homes for Sale

Welcome to Ossining, a charming town nestled in Westchester County, New York. Known for its rich history, picturesque views, and vibrant community, Ossining offers a unique blend of small-town charm and modern amenities.

As you explore homes for sale in Ossining, you'll discover a diverse range of properties to suit every lifestyle. From historic colonial-style homes with character and charm to contemporary condos with stunning river views, there's something for everyone in this sought-after area.

Whether you're looking for a cozy starter home, a spacious family residence, or a luxurious waterfront property, Ossining has it all. Enjoy the convenience of being just a short drive away from New York City while still savoring the peaceful ambiance and natural beauty that Ossining has to offer.

With top-rated schools, beautiful parks, trendy shops, and delicious dining options, Ossining has everything you need to live, work, and play. Don't miss out on the opportunity to make Ossining your new home and experience the best that Westchester County has to offer.

Contact us today to explore the latest listings of homes for sale in Ossining and start your journey towards finding your dream home in this wonderful community.

Newest Ossining Homes for Sale

$499,000

2 Beds ⋅ 3 Baths ⋅ 1064126 MLS

Welcome to 53 Hudson Watch, a 2-bedroom, 2.5-bath townhouse with an attached garage and 1,629 square feet of well-planned living space in one of Ossining’s most desirable communities. This is a wonderful opportunity to make a home your own in a setting with resort-style amenities and a true sense of community. The main level is designed for both everyday living and easy entertaining. The eat-in kitchen anchors the home, while the sunken living room with a wood-burning fireplace makes a warm and inviting place to gather on cool evenings. Step outside to your private stone patio, a serene spot for morning coffee, weekend grilling, or winding down at the end of the day. A convenient half bath and an open den/office area with a charming window seat complete the first floor, ideal for working from home, a reading nook, or a homework station. Upstairs, the bedroom level offers comfort and convenience, including laundry right where you need it. The primary suite is a true retreat, featuring an en-suite bath with a whirlpool tub and freestanding shower, a spacious walk-in closet, and a private balcony that gives you a second outdoor space of your own. A second bedroom and a second full bath complete the upper level, offering great flexibility for guests or additional workspace. A brand-new water heater and central air add peace of mind and year-round comfort, and the attached garage brings everyday convenience. Life at Hudson Watch extends well beyond your front door. Residents enjoy a community swimming pool, tennis and pickleball courts, and beautifully landscaped grounds in an elevated setting with Hudson River views from the complex. Commuters will appreciate being just 1.1 miles from the Ossining Metro-North Hudson Line station, with downtown Ossining’s waterfront, restaurants, and shops close by. Whether you’re a first-time buyer, ready to downsize, or simply looking for comfortable, convenient living with room to spread out, this home offers a great blend of space, amenities, and location. Bring your vision, add your personal touches, and make it yours.

53 Hudson Watch Drive, Ossining

$1,500,000

3 Beds ⋅ 4 Baths ⋅ 1064150 MLS

Escape to an extraordinary lakeside retreat where natural beauty, privacy, and rustic elegance come together just outside New York City. Nestled on 2.29 acres of picturesque grounds, this distinctive 3,497 square-foot residence offers a rare opportunity to enjoy waterfront living within easy reach of Manhattan. Featuring approximately 110 feet of direct frontage on 24-acre Stillwater Lake and a private dock, the property offers an exceptional connection to nature, with opportunities for kayaking, fishing, swimming, and seasonal outdoor recreation. Surrounded by mature specimen trees, beautiful gardens, a tranquil pond, and a meandering creek, the property feels like a secluded sanctuary. An expansive wraparound cedar porch invites you to relax and take in the peaceful surroundings, while multiple stone patios, landscaped seating areas, and an outdoor kitchen create wonderful settings for entertaining or quiet evenings at home. Inside, the three-bedroom, three-and-a-half-bath residence blends rustic character with generous living spaces and thoughtful architectural details. At the heart of the home, a spectacular chef's kitchen features soaring ceilings, exposed wood beams, and expansive picture windows that bring the outdoors in. A sun-filled breakfast area, formal dining room, and welcoming living spaces offer an inviting balance of comfort and functionality. The home's impressive living room features a fireplace and custom built-ins, creating a warm gathering place throughout the seasons. Upstairs, the light-filled primary suite offers the unusual convenience of two separate en-suite bathrooms, while two additional bedrooms share another full bathroom. Additional highlights include skylights, hardwood flooring in select rooms, a partial basement offering utility and storage space, and a separate workshop. The property's distinctive natural setting and indoor-outdoor living spaces make it equally appealing as a year-round residence or a peaceful weekend escape. Located in the Stillwater Lake community, the home provides a remarkable sense of privacy while remaining accessible to nearby shopping, dining, parkways, and Metro-North rail connections to Manhattan. A rare opportunity to experience the beauty and tranquility of private lakefront living without sacrificing proximity to New York City.

56 Twin Ridges Road, Ossining

$1,299,000

4 Beds ⋅ 4 Baths ⋅ 1063979 MLS

Welcome to 6 Gualtiere Lane, a pristine 4+ bedroom, 3.5-bath brick Colonial house beautifully situated on a professionally landscaped half-acre lot with mature trees, lush plantings, and stunning Hudson River views. A grand two-story entry sets the tone for the exceptional living spaces found throughout this meticulously maintained home. The impressive main level features gleaming hardwood floors, elegant crown moldings, and an ideal layout for both everyday living and entertaining. The open-concept floor plan seamlessly connects the spacious eat-in kitchen, family room, and formal dining room. The chef's kitchen is equipped with stainless steel appliances, granite countertops, a wine refrigerator, a large pantry, and abundant cabinetry. The inviting family room is anchored by a cozy wood-burning fireplace, creating the perfect gathering space. A mudroom, powder room, and convenient access to the garage complete the main level. The luxurious primary suite serves as a private retreat, offering two walk-in closets and a spa-inspired ensuite bath featuring a jetted soaking tub, dual vanities, and a separate walk-in shower. Three additional generously sized bedrooms and a full hall bathroom complete the second floor. The fully finished walk-out lower level provides exceptional versatility and additional living space, featuring a home office, guest bedroom, full bathroom, and summer kitchen with wine refrigerator and abundant cabinetry. A Sliding door leads directly to the expansive patio and private backyard, where you'll enjoy an above-ground swimming pool and ample outdoor recreation and entertaining space. Additional highlights include a two-car garage with direct mudroom access, an electric vehicle charging port, Nest smart thermostats, and fully owned 14.4 kW size solar panels that provide significant energy savings. Ideally situated on a quiet cul-de-sac in one of Ossining's most desirable neighborhoods, this exceptional home seamlessly combines luxury, comfort, and energy efficiency. Move right in and enjoy everything this remarkable Hudson River view property has to offer.

6 Gualtiere Lane, Ossining

$599,000

3 Beds ⋅ 2 Baths ⋅ 1056438 MLS

Enjoy beautiful Hudson River views from the spacious deck of this move-in-ready ranch, ideally situated on a quiet, tree-lined residential street in Ossining. Offered for sale for the first time by its original owner, this 3-bedroom, 1.5-bath home features comfortable one-level living and has just been freshly painted inside and out, with refinished hardwood floors and new carpeting throughout all carpeted areas. The updated kitchen features stone countertops and ceramic tile flooring and flows seamlessly into the dining room, where sliding glass doors open to the deck, creating the perfect setting for outdoor dining, entertaining, or simply relaxing while taking in the river views. The finished basement provides substantial additional finished space with plenty of flexibility for a family room, recreation area, home office, or a combination of uses. A doorway offers convenient access to the backyard, while the lower level also includes a half bath, laundry and utility areas, a workshop, additional storage, and access to the one-car garage. According to a CubiCasa floor plan, the home measures approximately 1,864 square feet in total, including approximately 1,128 square feet on the main level and 736 square feet on the lower level. These measurements exclude the garage, entry porch, and deck. Public records reflect 1,140 square feet of living area and separately reference a 390-square-foot recreation room. Set on a private, tree-surrounded .26-acre lot, the property also features a driveway with parking for 3–4 cars. Conveniently located just minutes from the Croton-Harmon train station, with easy access to Route 9A and the Taconic State Parkway, the home is also close to shopping, a supermarket, a gym, and Croton Point Park. A wonderful opportunity to enjoy Hudson River views, versatile living space, and the ease of ranch-style living in a convenient Ossining location!

7 Meadowbrook Drive, Ossining

$649,999

3 Beds ⋅ 2 Baths ⋅ 1060945 MLS

Located in a neighborhood rooted in local history and connected to the Native American heritage of the Hudson Valley, 24 Seneca Road is surrounded by streets whose names pay homage to various Native American tribes and communities. The historic character of the area adds another layer of distinction to the setting, connecting the neighborhood to the region’s deeper roots and the history that shaped the Hudson Valley. Immersed in approximately 1,567 square feet of living space, this property accentuates 3 bedrooms, 1 full bathroom, and 1 half bathroom. Hardwood flooring extends from the main level up the staircase and throughout the second floor, providing a warm foundation for the next owner to build upon and make their own. The detached garage adds another layer of versatility, offering numerous possibilities beyond parking. Use it for your vehicles, additional storage, a home gym, workshop, creative studio, or a dedicated space to pursue your desired hobbies. This home will give you the best of the Hudson Valley lifestyle with a residential setting that has easy access to Ossining’s vibrant downtown, Hudson River waterfront, scenic trails, Metro-North, local restaurants, and year-round community amenities. From enjoying brunch at The Tasty Table to dinner at Flames Bar and Grill, there are plenty of opportunities to enjoy the local dining scene. Golf enthusiasts can take advantage of nearby courses, including Trump National Golf Club Westchester and Hudson Hills Golf Course. Ideally located less than 7 minutes from the Ossining Metro-North Station and can be in Grand Central Terminal in under 1 hour. The home is ready for a new owner with vision and creativity to reimagine the interior and bring its full potential to life. Whether you're looking to create a personalized residence, undertake a thoughtful renovation, or transform the space to suit your own style, this property offers a great canvas for your ideas.

24 Seneca Road, Ossining

$450,000

2 Beds ⋅ 2 Baths ⋅ 1059219 MLS

Welcome to this beautiful, move-in-ready pet-friendly townhome in the desirable Liberty Knoll community! Featuring a thoughtfully designed open-concept kitchen with abundant natural light, this home offers spacious living areas, comfortable bedrooms, and a finished basement with an inviting entertainment/family room, office, or playroom. The roof and HVAC system were updated in 2021, adding comfort and peace of mind for years to come. Enjoy seamless indoor-outdoor living, tranquil surrounding grounds, and fantastic community amenities, including a swimming pool, clubhouse, and playground. Ideally located near Metro-North stations, with a weekday reimbursement program for transportation to Scarborough Station, as well as major highways, local shops, and dining. Move right in and enjoy everything this Westchester gem has to offer!

21 Knoll View, Ossining

$599,000

2 Beds ⋅ 3 Baths ⋅ 1055083 MLS

Turnkey ready, bright & fresh townhome in the Hudson Watch community. Recently renovated beautiful kitchen and baths, with an open main floor layout with hardwood floors & crisp finishes for a modern aesthetic. C of O for addition of a second bedroom with en-suite bathroom. Full, walk-out basement with new sliding glass doors to a stunning patio. Enjoy Hudson Watch's community pool, tennis/pickleball and dog park. Yes--this is a dog friendly community. Exterior maintenance--snow and landscaping, community roads & amenities all covered by the HOA fee. Close to Metro North trainline, shopping, restaurants & views of the Hudson River!

37 Hudson Watch Drive, Ossining

$565,000

3 Beds ⋅ 2 Baths ⋅ 1058195 MLS

Classic Ossining Character with Thoughtful Modern Improvements Welcome to this charming 3-bedroom, 1.5-bath home, where distinctive early-20th-century architecture meets thoughtful updates for today’s lifestyle. With its traditional Foursquare and Colonial Revival influences, the home offers the period character and craftsmanship that make Ossining’s historic homes so appealing. A wonderful window-filled enclosed front porch creates an inviting transition into the home and a delightful space for morning coffee, reading, entertaining or simply enjoying the changing seasons. Multi-pane windows, classic white trim and the distinctive sunburst detail in the front gable add to the home’s timeless appeal. The current owners have made meaningful improvements designed to enhance both comfort and efficiency, including extensive attic insulation that has resulted in significant savings on heating and cooling costs—an especially valuable upgrade in a home of this vintage. Out back, the garden has been thoughtfully enhanced with hardscape, handsome stone walls and established plantings, creating a beautifully landscaped outdoor setting with character and a sense of privacy. The combination of stonework and greenery feels particularly at home in the Hudson Valley landscape and provides a wonderful backdrop for outdoor dining, gardening and entertaining. The mud room and half bath have also been updated and create a wonderful transition from the back garden to the kitchen and dining room including a new heated floor to greet you from the outside. With three bedrooms, one full and one half bath, inviting indoor and outdoor spaces, energy-conscious improvements and architectural details worth preserving, this is a home that offers much more than vintage charm. It has been thoughtfully cared for and improved while retaining the personality that makes an older Ossining home special. The basement is clean and dry and includes a generous sized laundry area as well as space for storage. A character-filled Westchester home with history, warmth and improvements that have already been made for its next owner.

18 Linden Avenue, Ossining

$280,000

2 Beds ⋅ 1 Baths ⋅ 1057825 MLS

What an absolutely excellent opportunity! Come see this adorable cottage in the charming, unique, and AMAZING 44-home community that is Campwoods Grounds! As you walk through the property, you will notice the care that owners put into their homes...The attention to detail, the personal landscaping - in addition to the common areas, and the overall meticulousness is evident across the grounds. This two-bedroom cottage is ready for the lucky buyer(s) to add THEIR own personal touches, but plenty of wonderful features are already in place: A nice-sized eat in kitchen, beautiful hardwood floors downstairs, and a 120-square foot screened in porch are just some of these highlights. There are also two split heat/ac systems for efficiency, one up and one downstairs, as well as a gas furnace if desired for those absolutely frigid winter days/nights. The Campwoods Grounds community also boasts an extensive community garden, LARGE auditorium for neighborhood functions and other events, and a schedule of neighbohood get togethers to enjoy when you want to stay close to home. All of this, so convenient to all, and at a superb price point for the Ossining School District! Taxes with the STAR discount would be $4302/yr.

30 Campwoods Grounds, Ossining

$578,000

3 Beds ⋅ 2 Baths ⋅ 1022233 MLS

A Rare Piece of History with Original Character & Separate Barn. Own a piece of history with this truly special historic home, built circa 1888 in the town of New Castle, lovingly cared for by the same family for decades. Filled with wonderful memories and timeless character, this antique home offers a rare opportunity to enjoy original details while creating your own story for generations to come. Drenched in natural light, the home welcomes you with beautiful original wood floors, period details, and a warm wood-burning fireplace that creates an inviting gathering space in every season. The open-flow layout provides an easy connection between living spaces and is perfectly suited for entertaining family and friends. Beyond the main residence is a separate detached barn structure with a loft, offering exceptional flexibility for today's lifestyle. Imagine a private artist studio, yoga or Pilates space, creative workshop, home office, or work-from-home retreat. The additional building provides room to pursue your passions, accommodate hobbies, or simply create a peaceful escape. Set against a backdrop of rolling hills, this distinctive property combines historic charm, original craftsmanship, versatile spaces, and a sense of place that is increasingly hard to find. A special home. A remarkable history. A separate barn full of possibilities. Your chance to own a piece of the past while making it your own

115 Somerstown Road, Ossining

$1,349,500

4 Beds ⋅ 3 Baths ⋅ 1056078 MLS

Set against a backdrop of lush landscaping, rustic stone walls, panoramic golf course views, and spectacular sunsets, this exceptional one-owner Colonial offers an elevated Westchester lifestyle in sought after New Castle. Meticulously maintained and move in ready, the residence blends timeless architectural details with thoughtful modern conveniences, all just minutes from Chappaqua’s vibrant village center and Metro-North commuter service to Manhattan. Inside, beautiful craftsmanship is evident throughout, with hardwood floors accented by elegant walnut inlay, extensive custom cabinetry, crown molding, and soaring ceilings. The gracious first floor features 9 foot ceilings and a dramatic floor-to-ceiling stone fireplace framed by custom built-ins, creating a sophisticated yet inviting gathering space. Andersen windows and doors fill the home with natural light and connect the interiors beautifully to the surrounding landscape. The expansive primary suite provides a private retreat, complete with vaulted ceilings, a generous walk-in closet, and a beautifully appointed custom en-suite bath featuring a Jacuzzi tub, oversized shower, and exquisite custom tile work. Additional bathrooms are finished with the same attention to quality and detail. Thoughtfully designed for everyday living, the home includes a second-floor laundry room with sink and cabinetry, central vacuum, security system, and an oversized heated garage with side entrance and extra-high ceilings. The walk-out lower level presents exceptional possibilities, with 9-foot ceilings and ample space for a home office, gym, music studio, workshop, recreation room, or future additional living space. Outside, the private deck is the perfect vantage point to unwind, entertain, and take in sweeping golf course views and breathtaking sunsets. A rare opportunity to enjoy refined living, privacy, and exceptional craftsmanship in New Castle, with convenient access to Chappaqua, Metro-North, Manhattan, local shopping and dining, and the many recreational amenities that define the Westchester lifestyle.

115 Pinesbridge Road, Ossining

$665,000

4 Beds ⋅ 2 Baths ⋅ 1056019 MLS

Picture yourself unwinding by the fireplace, hosting summer dinners on your large deck, and gathering around the firepit under the stars. This inviting two-story Colonial on a cul-de-sac in Ossining offers 4 bedrooms, 2 bathrooms, a garage, and a basement. The backyard has room to play, entertain, and enjoy outdoor activities, with raised garden beds and a peach tree, blueberry and blackberry bush ready to inspire your green thumb. With supermarkets, schools, highway and the train close by, everyday convenience complements the comfort of home. Come see the possibilities and make this home your own!

7 Bradshaw Drive, Ossining

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

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Ossining Homes for Sale

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