Ossining Homes under $800,000

Welcome to Ossining, New York, a charming community nestled in the heart of Westchester County. Known for its picturesque landscapes and vibrant culture, Ossining is not just a lovely place to live; it’s also home to an excellent school district that prioritizes education and student development.

The Ossining Union Free School District is renowned for its commitment to academic excellence and holistic student growth. With a diverse range of programs and a dedicated faculty, the district serves students from pre-kindergarten through high school, ensuring a well-rounded education that prepares them for future success. Parents can feel confident knowing that their children are receiving top-notch education in a supportive environment, with access to advanced placement courses, arts programs, and extracurricular activities that foster creativity and leadership.

For those looking to call Ossining home, there are fantastic housing options available under $800,000. Whether you’re searching for a cozy single-family home, a charming townhouse, or a spacious condo, the real estate market in Ossining offers a variety of choices to suit different lifestyles and budgets. Many of these homes boast beautiful outdoor spaces, modern amenities, and easy access to local parks, shops, and restaurants, making it a perfect spot for families and individuals alike.

Living in Ossining means enjoying a tight-knit community with a rich history, beautiful riverfront views, and a strong sense of belonging. With its excellent schools and affordable housing options, Ossining is truly a hidden gem in Westchester County, waiting for you to discover its many delights!

Newest Ossining Homes under $800,000

$599,000

2 Beds ⋅ 2 Baths ⋅ 1061081 MLS

Welcome to 125 Whitetail Circle, a beautifully renovated 2-bedroom, 1.5-bath townhouse offering the perfect blend of modern updates, comfort, and convenience. Thoughtfully refreshed and move-in ready, this inviting home features a stylish interior and a functional layout designed for easy everyday living and effortless entertaining. The spacious living area provides a welcoming place to relax, while the updated kitchen offers a fresh, modern feel. Upstairs, two comfortable bedrooms provide peaceful retreats, complemented by a full bath, with an additional half bath on the main level adding convenience for guests. Enjoy a low-maintenance lifestyle in a desirable Ossining community, conveniently located near shopping, dining, parks, and transportation. Whether you're a first-time buyer, downsizing, or looking for a turnkey home, this renovated townhouse is an opportunity you won't want to miss!

125 Whitetail Circle, Ossining

$675,000

1 Beds ⋅ 3 Baths ⋅ 1059886 MLS

This is an absolute gem: Welcome to 113 Woods Brooke Circle, a beautifully designed contemporary townhouse at sought-after "The Woods" development in the Hudson Valley, Westchester County. This rare "A" unit with Lower Level is surrounded by tranquility with both a DR balcony deck and patio (with gardens) for easy enjoyment of the outdoors. Recently painted, you will adore the cheery vibe, open concept and spaciousness that spans across three living levels. This bright, fabulous home has been impeccably maintained and lives like a 2 Bedroom with the additional rooms and guest spaces on both the second floor and lower level totaling about 1750 square feet. Kitchen and all bathrooms have been thoughtfully updated with high-end materials. And when temps start to fall, the pretty, custom-designed LR fireplace will keep you warm and happy. Upstairs has a lovely Primary Bedroom en-suite with gorgeous spa-like bathroom that includes subway tiles, shower/jetted tub, porcelain sink, crafted beadboard and tiled flooring. Bedroom closets are fitted with shelves for easy organizing. A bright additional room can be used as an office, exercise room or nursery. Plus another large closet is fantastic for storage. There are pretty touches everywhere! A French Door from the first floor leads to the roomy lower level - Guest room, large playroom/office area with fitted closet. And with the Full Bathroom that features a tiled shower and colorful whimsical porcelain sink, this level is a happy option for guests, in-laws, visiting friends or relatives. Sliders lead outside to a private Patio. Other highlights: Garage includes 2 "Monster Racks" custom shelving to hold 300 and 500 pounds each. LG Stainless Refrigerator replaced 2024; Touch faucet and filtered water in kitchen. Quartz Kitchen counters. Recessed lighting. Separate Pantry. "The Woods" amenities include Pool, Tennis/pickleball and is pet-friendly. Tucked away but close enough to highway and train station to get to your destination quickly. Nearby Croton Train Station is just a 50 minute ride along the gorgeous Hudson River to Grand Central/NYC. Close to the Hudson for boating/water sports, championship golf, shopping, restaurants, music, hiking, West Point, more. Come take a look before this beauty is gone!

113 Woods Brooke Circle, 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

135 South Highland Ave Unit #3B3, Ossining

$223,000

2 Beds ⋅ 1 Baths ⋅ 1058239 MLS

Sun-drenched and spacious, this two-bedroom, one bathroom co-op in the desirable Highland Terrace offers the perfect blend of serene nature and urban convenience. The versatile layout begins with a welcoming foyer, currently utilized as a flexible bonus space. A generous kitchen features abundant cabinet storage and sleek stainless-steel appliances, flowing seamlessly into a bright, airy living room bathed in natural light. The primary bedroom provides expansive closet space, while the flexible second bedroom is ideal for guests, a home office, or additional living area. Residents enjoy exceptional community amenities, including a refreshing swimming pool, basketball court and access to the historic Old Croton Aqueduct Trail—a paradise for outdoor enthusiasts and their pets in this pet-friendly community. Ideally situated less than two miles from the Ossining Metro-North station, this home provides a seamless commute while keeping you close to the natural beauty and vibrant energy of the Hudson River region. An exceptional opportunity for those seeking space, style, and accessibility that combines privacy, luxury, and convenience—a rare opportunity to own a truly turnkey home in one of Ossining's most sought-after complexes. Close to all shopping and amenities. Laundry and storage located in the basement of this building. Come see your new home in the exquisite Hudson Valley! ***Be advised that there are carpet rules. 100% of all BR's & LR are required to have fully padded, tacked down carpet. ***

135 South Highland Ave Unit #3B3, Ossining

$215,000

1 Beds ⋅ 1 Baths ⋅ 1057950 MLS

Why rent when you can own? Welcome to your new home! In the heart of the Village of Ossining, is this charming 1-bedroom condo that offers the perfect combination of comfort and convenience! Enjoy a vibrant, walkable lifestyle with easy access to the train station, restaurants, shops, farmers' market, seasonal festivals, waterfront park, community recreation center, library, and more. Pet-friendly for both cats and dogs, with a maximum of two pets per unit. There is also laundry facilities in the basement available to all residents. Each unit has its own storage unit for added convenience. Owners may also obtain parking permits for both Village and train station parking. A new parking garage is currently being built behind the building providing more parking options as seen in the aerial photos. This property is part of the "Fair and Affordable" housing program and is subject to HOME Program affordability requirements. Prospective purchaser(s) must meet applicable income eligibility guidelines, be a first time homebuyer and occupy the unit as their primary residence; investors are not permitted. As of September 2026, household income may not exceed 80% of the Westchester County Area Median Income (AMI), with the following limits: 1 occupant: $95,000, 2 occupants: $108,600, 3 occupants: $122,150 - Income limits are subject to change. There is a $30,000 Westchester County subsidy is available for this unit which has already been accounted for in the listing price. Note: Photos have been digitally enhanced for informational purposes only. Property is being sold as-is. AGENTS: Please review the confidential remarks and all MLS attachments for additional requirements, eligibility information, and further instructions.

135 Main Street Unit #302, Ossining

$675,000

2 Beds ⋅ 3 Baths ⋅ 1058726 MLS

Beautifully updated and meticulously maintained, this townhouse-style home at The Woods in Westchester makes settling in easy and staying home a pleasure. Rich walnut hardwood floors set the tone throughout, while the open living and dining area invites you to gather around the wood-burning fireplace. Sliders open to the patio for easy indoor-outdoor living. The renovated kitchen with upgraded appliances, offers a pass-through that keeps the cook part of the conversation. A powder room completes the main level. A new staircase with hardwood treads and rails leads to two bedrooms, each with its own en-suite bath. The spacious primary suite features a California Closets system and a skylit bath with a step-in shower and a soaking tub. An office or bonus room opens to a balcony, a lovely spot to take a break between tasks. Second-floor laundry adds everyday convenience. The care goes well beyond what you see. Upgrades include a high-efficiency condensing boiler with on-demand hot water (2022), energy-efficient windows and sliders, smart thermostats, Lutron switches and outlets, custom window treatments, central air, and an insulated attic. Even the one-car garage gets special treatment, with SwissTrax flooring and a Wi-Fi-enabled door opener. The exterior has been refreshed with vinyl siding (2021) and a new roof and gutters with leaf guards (2025). The seller has paid the special assessments for these projects in full. The community offers a pool, tennis court, and landscaped grounds with a fountain. With the HOA handling exterior maintenance, landscaping, pool upkeep, and snow removal, you'll have more time to enjoy it all.

172 Woods Brooke Circle, 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

$679,000

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.