Ossining, NY Real Estate | Ossining, NY 3 Bathroom Homes for Sale

Love the NYC loft lifestyle, but not the NYC-sized floor plan—or price tag? Welcome to The Penthouse. Set within a reimagined historic 1820s schoolhouse, this dramatic tri-level penthouse loft delivers the attitude of a downtown loft with the space, light and breathing room Manhattan forgot to include. The result? Something seriously cool—and anything but ordinary. The Entertaining Level sets the tone with soaring volume, exposed brick elements, original wood beams, exposed copper piping, hardwood floors and distinctive low-set windows that help fill the space with natural light. An elevated kitchen with granite counters and stainless-steel appliances overlooks the expansive open-concept living and dining area, creating one incredible backdrop for entertaining or simply hanging out at home. A powder room completes the level. Then there’s The Loft—perched above and overlooking the entertaining space below. Skylights bring in even more natural light, while the open design gives you a completely different perspective on the architecture of The Penthouse. Home office, studio, lounge, reading retreat or creative escape—it’s the kind of flexible space that makes loft living so much fun. The Private Level changes gears completely. Two generously sized bedrooms each enjoy their own private en-suite bath. The oversized primary suite features a huge walk-in closet and spacious bath with double sinks and a jetted whirlpool tub. The second bedroom has its own beautifully refreshed en-suite bath with brand-new tile. In-unit laundry is conveniently tucked into this level as well. And here’s something you won’t see in the photos: some of the most impressive improvements in The Penthouse are hidden behind the finished walls. Extensive sound-control upgrades were incorporated into select walls and ceilings using additional framing and separation, ROCKWOOL mineral-wool insulation, spray foam and heavier 5/8-inch drywall. The primary-bedroom ceiling received its own extensive insulated assembly, all designed with acoustic comfort and reduced sound transmission in mind. Drenched in natural light? Absolutely. Drenched in noise? This renovation took that on from the inside out. And then there’s Ossining. Hudson River waterfront parks, marinas, downtown shops and cafes, the Old Croton Aqueduct Trail and Metro-North are all nearby—giving you the space and character of Hudson Valley living without giving up your connection to NYC. And when Manhattan calls? Metro-North express service can have you at Grand Central in under 50 minutes. Two assigned parking spaces and dedicated private storage round it all out—two more things Manhattan generally forgets to include. Historic character. Downtown attitude. Suburban breathing room. Three incredible levels. Serious sound-control improvements. This isn’t another suburban condo. This is The Penthouse—and that’s exactly the point.

88 Broadway Unit #PH4, Ossining

$806,000

3 Beds ⋅ 3 Baths ⋅ 1049363 MLS

Large 3-bedroom, 2.5 bath, 2,914 square foot single family colonial home on 54,132 square foot wooded lot. Home is a short drive into town and Hudson train station to Riverdale. Make it your own. Jump on this great deal before its gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other records to their satisfaction before bidding. No inspection contingencies in contract. Absolutely no repairs before closing. This property is sold As-Is. This is a REO auction property.

6 Brookside Lane, Ossining

$925,000

4 Beds ⋅ 3 Baths ⋅ 1047406 MLS

Exceptional value in a spectacular setting. Welcome to this beautifully renovated Dutch Colonial, an elegant blend of timeless architectural character, refined modern updates, and Hudson River views. Bathed in natural light and thoughtfully designed for both gracious living and entertaining, this exceptional home offers a rare combination of style, comfort, and an extraordinary setting. The beautifully renovated chef’s kitchen serves as the heart of the home, featuring crisp white cabinetry, quartz countertops, generous storage, and a seamless connection to the dining spaces. The inviting living room is anchored by a beautiful fireplace and enhanced by elegant French doors opening to a covered patio. Beyond, the expansive west-facing deck captures spectacular Hudson River vistas and provides an idyllic setting for outdoor entertaining, quiet relaxation, and magnificent sunsets. A private office or study, with sliding glass doors leading to the deck, offers an inspiring workspace surrounded by beautiful views. A beautifully renovated full bath completes the main level. Upstairs, the spacious primary suite is a serene retreat, featuring a generous walk-in dressing area and a luxurious, spa-inspired bath with a soaking tub, separate shower, and picturesque views. Three additional well-proportioned bedrooms and another beautifully updated full bath provide exceptional flexibility for family and guests. Additional amenities include a built-in speaker system throughout much of the home, an expansive yard, abundant parking, an oversized garage, and a full basement offering substantial storage and versatile possibilities for recreation, hobbies, etc... A rare opportunity at an attractive price, this beautifully renovated home pairs exceptional Hudson River views with sophisticated updates, generous living spaces, and an extraordinary setting.

27 Ryder Road, Ossining

$895,000

2 Beds ⋅ 3 Baths ⋅ 1045247 MLS

There is something very special about Mystic Pointe, you feel it as soon as you enter through the gates. 33 Mystic Drive is a tri-level, end unit, Biscayne model home in the heart of Mystic, overlooking the Nature Trail. It offers a traditional layout with an eat-in kitchen, living and dining areas with sliding glass doors to one of the decks, a powder room, and access to the two-car garage all on the main level. The upper level has two generous bedrooms, two full baths, and a den/office room. The lower level is a wonderful all-around everything room, with sliding glass doors to the oversized deck, a generous walk-in storage closet, a laundry room, plus an additional storage room and utility room. One of the few homes with double decks for double entertaining! And Mystic Pointe has so much to offer: two pools, one adult and one for children; a clubhouse with a full kitchen and gym; a tennis/pickleball court; and a warm, welcoming community with weekly bridge nights, book club, and so much more. And since you don't have to mow the lawn, shovel the snow, or repair the exterior of your home, you will have plenty of time to enjoy it all.

33 Mystic Drive, Ossining

$839,000

3 Beds ⋅ 3 Baths ⋅ 1038194 MLS

Welcome to 61 Ganung Drive, a spacious 3-bedroom, 3-bath home situated on .65 acres in the Town of Ossining. Offering privacy, versatility, and exceptional outdoor living, this property has so much to offer. Step inside to a welcoming sunken living room with skylights and a dining room featuring a wood-burning fireplace, filling the space with natural light while creating a warm and inviting atmosphere. The downstairs offers additional living space with its own private entrance, full bath, living room, office, and wood-burning stove, making it ideal for a variety of uses. A Certificate of Occupancy is currently in progress for a possible fourth bedroom on the lower level, offering even more flexibility and potential. Central air adds comfort throughout the warmer months. The backyard is where this home truly shines. Ryder Park borders the rear of the property, creating a wonderfully private setting with no homes directly behind you. The fenced-in yard is designed for entertaining and everyday enjoyment, featuring a heated above-ground pool, two decks, gazebo, basketball court, and plenty of space to relax and gatherings. A newer shed, approximately four years old, provides additional outdoor storage. A two-car garage, cobblestone-lined half-moon driveway, and ample parking add to the home’s convenience. Enjoy your own private retreat while remaining conveniently located just 2 miles from the train station. With its spacious property, incredible outdoor entertaining areas, privacy, flexible living space, and commuter-friendly location, 61 Ganung Drive is a home that truly needs to be experienced.

61 Ganung Drive, Ossining

$649,000

3 Beds ⋅ 3 Baths ⋅ 1035810 MLS

Discover timeless elegance in this impeccably maintained 3-bedroom, 2-bath Colonial in the heart of Ossining. Blending classic charm with exceptional outdoor living, this beautiful home offers warmth, sophistication, and privacy at every turn. The inviting interior features a welcoming living room with a fireplace, creating the perfect gathering space for cozy evenings. A dedicated home office provides an ideal setting for remote work, study, or creative pursuits. Thoughtfully designed living spaces throughout reflect pride of ownership and meticulous care. Step outside into a truly enchanting backyard reminiscent of an English garden. Surrounded by mature natural privacy borders, this serene outdoor retreat offers beauty and tranquility in every season. Enter through the elegant wrought-iron driveway gate and enjoy the covered patio, perfect for outdoor dining and entertaining, as well as the enclosed sitting room where you can relax while taking in the peaceful garden views. Completing the property is a detached two-car garage, providing ample space for parking, storage, or a workshop. This exceptional Colonial combines refined indoor living with spectacular outdoor spaces, creating a home that is as inviting as it is unforgettable. Conveniently located near shopping, restaurants, parks, schools, and major commuting routes, this is a rare opportunity to own a truly special Ossining property.

73 Clinton Avenue, Ossining

$975,000

4 Beds ⋅ 3 Baths ⋅ 1033661 MLS

Welcome to 39 Park Drive, a beautifully updated Colonial nestled on a quiet cul-de-sac. Set on .74 private acres, this move-in ready 4-bedroom, 2.5-bath home offers 2,363 square feet of thoughtfully designed living space, including a main-level office that can easily serve as a fifth bedroom, convenient main-floor laundry, a finished lower-level ideal for recreation, a home office, or additional living space, and abundant storage throughout. The renovated 2022 kitchen features an electric double oven, pot filler, recessed lighting, and opens to inviting living areas highlighted by both a wood-burning fireplace and gas stove. The spacious primary suite includes a his-and-her walk-in closet with a custom Closets by Design system, a dedicated vanity area, and an updated bath with a new sink and vanity (2022). Recent improvements include a new roof (2025), wood siding re-stained (2025), front and rear walkways and steps (2026), new three-zone boiler (2021), central air conditioning (2016), EV charger (2023), hot tub (2024), custom blackout blinds throughout the entire home (2025), and a newer dishwasher (2025). Additional highlights include an attached two-car garage, level & private backyard, fully insulated attic, kitchen, and garage, plus plywood attic flooring for additional dry storage, a SimpliSafe security system with transferable service, and a proactive Terminix contract. Conveniently located near parks, shopping, dining, schools, and major commuter routes, this meticulously maintained home offers the perfect blend of comfort, flexibility, modern updates, and peaceful suburban living.

39 Park 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

$4,150

3 Beds ⋅ 3 Baths ⋅ 1028255 MLS

Welcome home to this charming single-family colonial in the heart of Ossining. Conveniently located near all the essential amenities- Metro North, schools, shops, restaurants, yet tucked away on a quiet cul de sac. This home features a newly updated eat-in kitchen equipped GE appliances, quartz countertops and low maintenance LVP flooring. Open your sliding glass doors to a beautiful, spacious deck that overlooks a lush green lawn. Upstairs, the primary bedroom offers a king size bed, a remodeled (2022) bathroom, and a spacious closet for ample storage. Downstairs a partially finished basement provides an additional 600 sq feet of living space that is the perfect escape for a home office, play space, or media room. Complete with extra storage and laundry so you'll never have to go to the laundromat again! Fresh paint and new carpet throughout. Not to mention you can pull into the driveway and park in your own single car garage with easy access to the kitchen. The convenience of village living along with the tranquility of the Hudson River make this home a true gem. Minimum Credit Score: 700 or higher. Income Requirement: Gross monthly income must be at least 3 times the monthly rent. Verification: Proof of income (recent pay stubs or tax returns) and background/credit checks required for all adults Additional Information: Amenities:Storage,ParkingFeatures:1 Car Attached,Storage: Garage,

48 Lincoln Place, Ossining

$850,000

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

$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

$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

$899,000

4 Beds ⋅ 3 Baths ⋅ 1026827 MLS

Welcome to this beautiful 4 bedroom, 2 full bath, 1 half bath home offering stunning water views and views of the Hudson River and Mario M. Cuomo bridge. Thoughtfully designed with spacious living areas and inviting outdoor spaces, this home combines comfort, charm, and an exceptional setting. Step inside through the impressive two story foyer, where soaring ceilings create a bright and welcoming first impression. The home's spacious layout provides plenty of room for everyday living, entertaining, and working from home. Enjoy peaceful mornings or relaxing evenings on the expansive front porch while taking in the scenic views. The large rear yard offers abundant outdoor space for gatherings, gardening, recreation, or simply enjoying the privacy and natural surroundings. Additional features include an attached garage, generous living space, and an ideal location in Ossining. Conveniently located just minutes from the Ossining Metro-North Station,

5 Gualtiere Lane, Ossining

$799,500

3 Beds ⋅ 3 Baths ⋅ 1021307 MLS

Enjoy easy living in this spacious, move-in-ready Raised Ranch featuring numerous updates and a functional floor plan. The bright kitchen offers abundant cabinetry, granite countertops, a breakfast bar, and stainless-steel appliances, while the adjacent dining area provides easy access to a two-tier deck, perfect for outdoor dining, entertaining, or just relaxing. Beautiful hardwood floors enhance the main level, while the lower-level family room features a brick fireplace, new flooring, a mini-split A/C system, and sliding glass doors leading to a large backyard with plenty of space for recreation, gardening, or play. Recent improvements include an updated heating system, newly installed A/C system, and beautifully renovated primary and hall bathrooms. An oversized two-car attached garage provides exceptional storage and everyday convenience. Ideally located close to transportation, shopping, restaurants, and everyday amenities, this well-maintained home offers the perfect combination of comfort, updates, and location.

4 Cooper Drive, Ossining

$749,000

3 Beds ⋅ 3 Baths ⋅ 1024026 MLS

Set on a sprawling 1.41-acre lot with rolling lawn, this beautifully updated 3-bedroom, 1 full/2 half bath Raised Ranch offers the space and privacy that's hard to find so close to the city. Inside, a flexible layout flows easily between everyday living and entertaining, centered around a new kitchen with stainless steel appliances and granite countertops. The generous living room overlooks the lush yard, while an enclosed porch and newly expanded composite deck invite you to relax and take in the natural surroundings. The primary suite features a walk-in closet, and two additional bedrooms share a hall bathroom. Downstairs, a family room with a wood-burning fireplace and a versatile bonus room with a half bath add even more room to spread out. From a new roof and siding to replacement windows and solar panels, this home has been thoughtfully upgraded from top to bottom and a long driveway with a two-car garage means parking and storage are covered too. The location is just as impressive: less than 5 minutes to the Croton-Harmon and 7 minutes from Ossining Metro-North stations, with easy highway access and nearby gems like Teatown Nature Preserve, Cedar Lane Park, and the Hudson River, plus local shops and restaurants. Loved for years by its family, this home offers room to grow, space for pets, and quiet moments with nature, a rare opportunity in a truly desirable commuter location.

124 Cedar Lane, Ossining

$975,000

3 Beds ⋅ 3 Baths ⋅ 1022746 MLS

This charming renovated farmhouse offers 3,000 sq ft of living space and is nestled at the very end of a quiet cul-de-sac providing exceptional privacy and adjacent to protected parklands with scenic walking trails, and the Hudson River. The home features a newly added first floor primary suite complete with a tray ceiling, recessed lighting, oversized walk-in closet, and an adjoining home office all on its own HVAC system, creating the perfect private retreat. The custom kitchen offers granite countertops, custom cabinetry, GE appliances, and a sunny breakfast alcove. The kitchen flows seamlessly into the formal dining room and inviting living room with a wood-burning fireplace and access to the charming covered front porch. The separate and spacious family room on the south side of the home is filled with natural light from a wall of windows with access through sliding glass doors to the patio and fully fenced rear yard. Upstairs you will find two generously sized bedrooms and a versatile bonus room, ideal as a fourth bedroom, home office, laundry room or den. Additional features include a large detached two-car garage with expansive storage, newly installed generator, alarm system with video cameras, multiple laundry hook-ups including a second washer & dryer in the basement. There is also a cover front porch, and two patio areas around the property. Located just 1.5 miles from the Ossining train station! The location is truly exceptional. Situated at the entrance to the Crawbuckie Nature Preserve, this home offers immediate access to appx 20 acres of woodlands with walking trails winding through mature forest along the Hudson River. Enjoy scenic overlooks, observation platforms, and year-round hiking and nature just steps from your front door. This unique combination of character, modern updates, and an unparalleled natural setting makes this home a rare opportunity.

44 Beach Road, Ossining

$850,000

3 Beds ⋅ 3 Baths ⋅ 1010331 MLS

Offered for the first time ever, 21 Hawkes Avenue is a one of a kind contemporary residence in the Town of Ossining custom built by its current owner, an accomplished contractor, and designed by architect Jim Picone. Completed in 1983 and thoughtfully improved over the years, the home sits on a private, wooded 1.5-acre parcel originally acquired in 1980. A winding, tree-lined driveway leads to the residence, which is perfectly positioned atop a gentle rise overlooking beautifully maintained grounds. Defined by dramatic rooflines, soaring ceilings, expansive windows, and striking geometric forms, the home was designed to blur the line between indoors and out while embracing its natural surroundings. Surrounded by mature specimen trees, stone edged gardens, broad lawns, and woodland, the property offers exceptional privacy. A historic stone wall borders a gently flowing creek at the edge of the property, creating a peaceful setting rich with wildlife and seasonal beauty. Stone and timber steps lead to a covered entry and welcoming foyer. Inside, open concept living spaces feature exposed beam ceilings, stained softwood floors, and abundant natural light. A dramatic two-story dining area framed by towering trapezoidal windows serves as the heart of the home. The renovated kitchen features custom light green cabinetry, slate countertops sourced from a Vermont quarry, newer appliances, and a custom breakfast table and island inspired by George Nakashima. Glass doors connect the dining area to the wraparound deck, creating seamless indoor/outdoor living. A spacious living area provides the perfect setting for relaxing or entertaining. The main level also includes a full bath, private office or den with cathedral ceilings and built-ins, pantry, laundry room, and generous storage. A wood-burning stove adds warmth and ambiance during the winter months. The custom staircase rises to a light-filled second floor with vaulted ceilings and clerestory windows. The primary suite offers a renovated bath, ample closet space, and serene views of the surrounding landscape. Two additional bedrooms, each featuring signature trapezoidal windows, share a full bath. Above, a charming loft provides flexible space for play, storage, or a cozy retreat. The lower level includes a spacious one car garage with a 220V/40-amp outlet suitable for a Level II EV charger, ample storage space, as well as a workshop and utility room. A permitted accessory apartment, added in 2000, offers approximately 350 square feet with a private entrance, full kitchen, washer/dryer, radiant floor heat, cooling, and yard views. Ideal for rental income, guests, an au pair, in-laws, or a home office, it adds tremendous flexibility and value. Designed with energy efficiency in mind, the home's southern exposure provides passive solar warmth in winter. Solar panels were installed in 2023, and a whole-house automatic generator was added in 2024. Seven mini-split systems provide efficient heating and cooling throughout. Additional features include central vacuum, a monitored security system, and a woodshed stocked with a two-year supply of split hardwood. Despite its private, retreat-like setting, the home enjoys a convenient Ossining location near Route 9A, Route 134, shopping, schools, and everyday amenities. Croton-Harmon Metro-North Station is approximately ten minutes away, offering express service to Grand Central Terminal in roughly 40-45 minutes. Lovingly maintained by its original owners for more than four decades, 21 Hawkes Avenue presents a rare opportunity to own a thoughtfully designed home where architecture, craftsmanship, and nature exist in perfect harmony.

21 Hawkes Avenue, 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

$625,000

3 Beds ⋅ 3 Baths ⋅ 1013828 MLS

A tri-level gem, just minutes from downtown Ossining, this three bedroom home is perfect for those who need more space, but want less maintenance. Park either in the driveway or pull into the garage (with extra storage space). There is additional parking shortly down the street. Entering the home on the first floor, you will find a flexible bonus room, great for storage, an office or more. There are multiple closets here as well. Up one level is the open living and dining room. Centered on a wood-burning fireplace with granite hearth and featuring new floors, this is a wonderful space. There are sliding doors here, out to the rear deck and tree ensconced lawn beyond. The eat-in kitchen is well laid out, with good counter and cabinet space. Off of the kitchen, find the large balcony - a great place to enjoy a cup of tea in the early morning, or something a little stronger at the end of the day. Also on this floor is the hall bathroom and the large laundry closet. Up one more level, we reach the bedrooms. The primary bedroom, with an ensuite bathroom that has a tub and a shower, has a deep walk-in closet. In this room, and every bedroom, natural light shines through oversized windows with views out to trees. The second and third bedrooms share a full hall bath with a tub. In Ossining, there are few options for three bedroom condominiums. The Deerfield community has a beautiful, large pool - a perfect place to sunbathe even if you don't swim. There are also walking trails, easily accessible from this unit. All of this, just a short drive to shopping, restaurants and parks, and easily accessible to commuting by train or highway. What more can you ask for?

83 Deerfield Lane, Ossining

$500,000

3 Beds ⋅ 3 Baths ⋅ 1005194 MLS

Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments. There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage was probably originally a stable. The water main and sewer lines were replaced in 2025

237 Spring Street, Ossining

$724,222

2 Beds ⋅ 3 Baths ⋅ 1008140 MLS

Experience turnkey luxury in this beautifully renovated corner unit at The Woods, where every detail has been thoughtfully updated from top to bottom. The heart of the home is the custom high-end Bilotta kitchen, featuring a granite center island with seating, Bosch stainless steel appliances, induction cooktop, pantry, and under-cabinet lighting. The open-concept main level is ideal for both everyday living and entertaining, showcasing a custom fireplace, a sophisticated leathered quartzite bar, a private first-floor office, and a stylish powder room. Additional upgrades include updated electrical, baseboards, windows, recessed lighting, custom blinds, luxury vinyl flooring, and a redesigned balustrade. Upstairs, the spacious primary suite offers a true retreat with a luxurious spa-inspired bath featuring an oversized rainforest shower with marble seat and niche, dual quartzite vanity, and a custom walk-in closet illuminated by a skylight. The second level also includes an updated hall bath, a secondary bedroom with new carpeting, and an enclosed bonus room perfect for guests, a home office, or recreation space. Modern comforts continue with a Navien tankless boiler and hot water system providing efficient, unlimited hot water. Outdoors, relax on the private covered patio surrounded by beautifully landscaped specimen plantings, including Japanese maple and hydrangeas. A significant value-add: the $15,000 roof assessment has already been paid in full. Residents enjoy access to community amenities including a pool and tennis courts, offering a low-maintenance lifestyle in a desirable setting. There are no audio recording devices inside this property.

86 Woods Brooke Terrace, Ossining

$299,000

4 Beds ⋅ 3 Baths ⋅ 1004901 MLS

Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private woodland retreat, you are minutes from the best of the Hudson Valley. Commuting is a breeze with easy access to the Taconic State Parkway and both the Ossining and Croton-Harmon Metro-North stations. Enjoy an unmatched lifestyle surrounded by local culture and nature. You're just a short drive from daily conveniences, schools, and parks, as well as other local highlights including Teatown Lake Reservation, Kitchawan Preserve, Sunny Ridge, the North County Trailway, the historic Jacob Burns Film Center and both Sleepy Hollow Country Club and Hudson National. Bring your architect, your contractor, and your imagination. Property being sold strictly as-is.

5 Maria Lane, Ossining

$1,079,000

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

$550,000

6 Beds ⋅ 3 Baths ⋅ 991931 MLS

Legal 2-family opportunity in the heart of Ossining offering exceptional value, versatility, and upside potential. Priced at $550,000, this spacious property features a 5-bedroom, 3 full bath layout plus a separate studio apartment with its own private entrance—ideal for investors or owner-occupants looking to generate rental income. Set on a 7,405 sq ft lot, the home offers approximately 2,276 sq ft of living space with classic architectural charm including a mansard-style roof, covered front porch, and original details throughout. The property features multiple living areas, generous room sizes, and flexible layout options to accommodate extended living or rental configurations. Interior spaces offer a blend of character and opportunity. Bright rooms with hardwood floors, large windows, and high ceilings provide great natural light. Kitchens and baths are functional with room for updates, making this a strong value-add opportunity. Separate living quarters allow for privacy between units, enhancing rental appeal. The exterior offers a large private driveway with ample off-street parking, a rare find in this area, along with a spacious backyard and patio area—perfect for outdoor use, entertaining, or future improvements. A detached structure and additional outdoor space provide even more potential. Located on a quiet residential street, the property is just minutes from downtown Ossining, shops, restaurants, parks, and the Hudson River waterfront. Commuters will appreciate easy access to Metro-North, offering a convenient commute to NYC. The area continues to see strong demand due to proximity to major employment hubs including White Plains, Tarrytown, and Stamford. With comparable multi-family properties in Ossining selling significantly higher, this property presents a compelling opportunity to build equity and maximize returns. Whether you are looking to invest, renovate, or live in one unit while renting the other, this is a property with strong income potential and long-term growth. A rare chance to own a legal 2-family with a separate studio in a sought-after Westchester location.

41 Ellis Place, Ossining

$675,000

3 Beds ⋅ 3 Baths ⋅ 977440 MLS

Welcome to 24 Highview Road, a classic Split-Level home offering the perfect blend of privacy and potential on a rare 1.32-acre lot in the Town of New Castle. This 3-bedroom, 2.1-bathroom residence features 1,959 square feet of living space with several recent high-value mechanical and interior upgrades. The main level boasts a spacious living room with a cozy fireplace and a seamless flow into the dining area. Notable recent improvements include: Interior Refresh (2024): Freshly painted rooms and brand-new vinyl flooring throughout the lower level. Updated Bathroom: A newly renovated bathroom adds modern comfort to the home. Mechanical Peace of Mind: Equipped with a Generac whole-house generator (2022) and a brand-new above-ground oil tank (2025). Ample Storage: Featuring two scuttle-access attics and a full basement for all your storage needs. The primary bedroom offers a truly unique feature: a structural rooftop column with a C/O for a telescope, perfect for the hobbyist stargazer. Outside, the expansive property includes a shed and a secondary structure (formerly a coop), offering endless possibilities for gardening or outdoor recreation. Conveniently located in the Ossining school district with an attached 2-car garage, this home is ready for its next chapter.

24 Highview Road, Ossining

$1,095,000

5 Beds ⋅ 3 Baths ⋅ 977120 MLS

This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed Main house layout features an expansive family room with wood-burning fireplace perfect for everyday gathering, first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room. The main floor features walls of windows showcasing the sylvan setting and a formal dining room that flows seamlessly into a spacious living room. The eat-in kitchen, complete with a charming breakfast nook, is easily accessible and well-suited for casual dining. This level also includes three additional bedrooms, including one with a private en-suite bath, two bedrooms share a well-appointed hall bath, and a laundry room. The Detached 3 car garage with guest quarters and guest patio with built-in wood grill and woodland views add to this retreat.

27 Allapartus Circle, Ossining

$5,800

4 Beds ⋅ 3 Baths ⋅ 974694 MLS

Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed layout, featuring a first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room and an expansive family room with wood-burning fireplace perfect for everyday gathering. The main level is designed for both entertaining and comfort, showcasing a formal dining room that flows seamlessly into a spacious living room. The eat-in kitchen, complete with a charming breakfast nook, is easily accessible and well-suited for casual dining. This level also includes three additional bedrooms, including one with a private en-suite bath, while the remaining two bedrooms share a well-appointed hall bath. There is another laundry room on this level as well. Excludes detached garage building. This distinctive compound blends timeless craftsmanship with modern livability, all set in the highly sought-after Teatown area, offering seclusion without sacrificing proximity to trains, parks, and major highways.

27 Allapartus Circle, Ossining

$624,000

4 Beds ⋅ 3 Baths ⋅ 946519 MLS

A Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Modern Comfort. Nestled on 3 acres of landscaped grounds, this inviting residence offers spacious living and serene privacy just minutes from local amenities and commuting routes. The renovations that were made still kept its original charm. Features like the woodwork, beamed ceilings, built-in cabinets, and hardwood floors that have been preserved. The formal dining room has a stone fireplace and large windows that let in plenty of light. Convenient to the Taconic State Parkway! Yorktown Schools.

398 Illington Road, Ossining

$650,000

2 Beds ⋅ 3 Baths ⋅ 945915 MLS

Two family home for sale. Each apartment is a very large one bedroom apartment. Private driveway and garage parking. Convenient to shopping and services including supermarkets, local shops and eateries, and Bee-Line bus service with access to Ossining Hudson Line train for NYC commuting. This is an unapproved short sale. There are tenants occupying the home so we must provide them with 48 hour notice before showing the home.

12 Broad Avenue, Ossining

$850,000

3 Beds ⋅ 3 Baths ⋅ 884984 MLS

THIS IS NOT JUST ANOTHER LISTING! Don't miss this RARE opportunity to own a newly constructed home in the heart of Westchester County. This thoughtfully designed, three-level residence is currently being built with modern energy-efficient standards and fitted with premium, top-tier appliances. Every aspect of this home has been crafted to deliver both style and functionality for today’s discerning homeowner. The interior layout offers a seamless blend of practicality and elegance. A fully finished basement provides versatile space for storage, recreation, or a home office. The main level features a welcoming foyer, an open-concept kitchen with a butler’s pantry, a formal dining room, and a bright, spacious living area—ideal for both everyday living and entertaining. The home includes three well-proportioned bedrooms, highlighted by a luxurious primary suite complete with an ensuite bath and a generous walk-in closet. Located in the desirable community of Ossining, the property affords easy access to scenic Hudson River views, public transportation options, and a vibrant downtown filled with restaurants, cafes, and local shops—all within walking distance. This home presents an exceptional opportunity for families looking to settle in before the new school year begins, offering not just a fresh start, but a brand-new home built with care, comfort, and quality in mind.

23-096 Liberty Street, Ossining

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