Ossining, NY Real Estate | Ossining, NY Just Listed Homes for Sale

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 Additional Information: Amenities:Storage,ParkingFeatures:1 Car Attached,Storage: Garage,

48 Lincoln Place, 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

$125,000

1 Beds ⋅ 1 Baths ⋅ 1027696 MLS

It's oh so quiet. This High Meadows top floor one bedroom, one bath is fresh and ready to go. Hard wood floors throughout, A sun filled living room with dining nook, new stove and refrigerator, lot's of closet space. A small hall leads to extra closets and the bedroom. High Meadows Cooperative features a common laundry and storage space around the back. 2 playgrounds and a basketball court are available as well. Reserved spot number 5 is a short walk to the door, street parking with permit. This gem is tucked away, off route 9, with easy access and close proximity to shopping, fitness center, trails, public transport, and highways, just 2 miles to the train station. The best of both worlds. Peaceful oasis, and convenient to the business district.

50 Charter Circle Unit #C, 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

$1,850

1 Beds ⋅ 1 Baths ⋅ 1028019 MLS

Renovated 1 Bedroom apartment located in Historic Downtown Ossining! Close to shops, train, school, etc. This beautiful unit features hardwood floors, granite counters, stainless appliances, as well as central AC/Heat. Come take a look and you won't want to leave!

195 Main Street Unit #5, Ossining

$6,975

3 Beds ⋅ 4 Baths ⋅ 1025140 MLS

Beautifully updated and move in ready! This spacious home offers flexibility, comfort, and style. Featuring 3 bedrooms and a versatile office/den on the main level that can easily serve as a 4th bedroom, guest room, or work-from-home space. The updated kitchen opens seamlessly to the main living and dining areas, while hardwood floors and renovated bathrooms add timeless appeal throughout. Step outside to an oversized wraparound deck overlooking a large, private backyard, perfect for entertaining, relaxing, or enjoying the outdoors. Additional highlights include a full bathroom on main level, second-floor laundry, two-car attached garage, and ample storage throughout. The finished lower level features its own private entrance, kitchenette, full bathroom, and laundry, providing exceptional flexibility for additional living space, guests, a home office, recreation, or extended living needs. Conveniently located near parks, schools, major highways, and Metro-North. This home offers the ideal combination of space, modern updates, and commuter convenience. A rare rental opportunity in Ossining!

275 Croton Dam 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

$3,500

1 Beds ⋅ 1 Baths ⋅ 1026994 MLS

Welcome to Eagle Bay, a sought-after gated community overlooking the Hudson River in Ossining. This beautiful 1st floor unit is freshly painted and offers the perfect combination of privacy, convenience, and resort-style living. Relax on your private deck while enjoying a peaceful natural setting just minutes from Metro-North, shopping, and dining. The bright, open floor plan features hardwood floors throughout and a wood-burning fireplace that creates a warm and inviting living space. The updated eat-in kitchen is appointed with granite countertops, and the bedroom features a walk-in closet while the primary bath offers a relaxing Jacuzzi tub. Additional highlights include an assigned parking space and the washer/dryer in unit. Residents of Eagle Bay enjoy an exceptional lifestyle with outstanding amenities, including a swimming pool, tennis and basketball courts, clubhouse, fitness center, and playground. Ideally located near the vibrant villages of Ossining and Croton-on-Hudson, you'll have easy access to restaurants, shopping, parks, and Metro-North for a convenient commute to New York City.

101 Eagle Bay Drive, 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

$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

$419,000

1 Beds ⋅ 1 Baths ⋅ 1025908 MLS

Welcome to Eagle Bay, a sought-after gated community overlooking the Hudson River in Ossining. This beautiful 1st floor unit is freshly painted and offers the perfect combination of privacy, convenience, and resort-style living. Relax on your private deck while enjoying a peaceful natural setting just minutes from Metro-North, shopping, and dining. The bright, open floor plan features hardwood floors throughout and a wood-burning fireplace that creates a warm and inviting living space. The updated eat-in kitchen is appointed with granite countertops, and the bedroom features a walk-in closet while the primary bath offers a relaxing Jacuzzi tub. Additional highlights include an assigned parking space and the washer/dryer in unit. Residents of Eagle Bay enjoy an exceptional lifestyle with outstanding amenities, including a swimming pool, tennis and basketball courts, clubhouse, fitness center, and playground. Ideally located near the vibrant villages of Ossining and Croton-on-Hudson, you'll have easy access to restaurants, shopping, parks, and Metro-North for a convenient commute to New York City.

101 Eagle Bay Drive, Ossining

$160,000

1 Beds ⋅ 1 Baths ⋅ 1024369 MLS

Welcome to this beautifully maintained, pet-friendly 1-bedroom co-op in desirable Ossining, offering the perfect blend of comfort, convenience, and a rare private patio. A spacious foyer welcomes you inside and leads to a thoughtfully designed layout featuring an updated bathroom, a functional kitchen with ample cabinet space, and a generously sized bedroom. The expansive living and dining area provides an ideal setting for both everyday living and entertaining, with a private back door opening directly to your patio, creating a seamless indoor-outdoor lifestyle. Nestled within a well-maintained garden-style community, residents enjoy exceptional amenities including an in-ground swimming pool, basketball court, scenic walking trails, beautifully landscaped grounds, plentiful guest parking, and an assigned parking space conveniently located just steps from the building. Ideally situated just minutes from Metro-North, the Taconic State Parkway, shopping, dining, parks, and the vibrant Ossining waterfront, this home offers the perfect balance of tranquility and accessibility. Whether you're purchasing your first home, downsizing, or searching for a commuter-friendly residence with sought-after outdoor space, this move-in-ready opportunity is one you won't want to miss.

129-3 S Highland Avenue Unit #A2, 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

$3,750

2 Beds ⋅ 2 Baths ⋅ 1023785 MLS

Move in to the completely remodeled 92 South Highland; thoughtfully designed with you in mind. This 2 bed 1.5 bath unit has been given an expansive, open-concept layout with contemporary finishes; so you will feel at home the moment you walk through the door. The fully equipped kitchen is outfitted with Samsung appliances, a stunning 10 foot quartzite island, and slab vent hood. The bathroom has stunningly appointed with floor to ceiling large format tiling, a marble adorned wet room complete with rain head and freestanding tub. This home has everything you could want and more, from 10ft ceilings, wide plank wood flooring, fully dimmable recessed lighting, central air, customizable storage, oversized windows- filling the home with natural light, W/D, assigned parking, and private outdoor space. Discover the best of Ossining, 92 S Highland is conveniently located walking distance from the Village’s shops, restaurants, library, school, MTA, and is easy for commuting.

92 S Highland Avenue Unit #2, Ossining

$9,000

5 Beds ⋅ 5 Baths ⋅ 1025513 MLS

Experience refined living at 45 Wolden Road, a fully furnished and move-in-ready residence offering five bedrooms, four-and-a-half bathrooms, expansive living spaces, a private in-ground pool, and generous driveway parking. Distinctive architectural details, multiple fireplaces, inviting outdoor entertaining areas, and nearly an acre of property create a private retreat designed for both everyday comfort and gracious hosting. Convenient access to Ossining’s Metro-North station provides Hudson Line service to Grand Central, making the home well suited for Manhattan commuters and those relocating to Westchester. Residents also enjoy a vibrant Hudson River community with downtown shops, waterfront destinations, local parks, recreational facilities, and access to the Ossining School District.

45 Wolden Road, Ossining

$2,300

1 Beds ⋅ 1 Baths ⋅ 1025361 MLS

Step into this beautifully renovated, turn-key top-floor one-bedroom apartment in the heart of the historic Town of Ossining. Thoughtfully redesigned with high-end finishes and eclectic charm, this one-of-a-kind residence is ready for immediate occupancy. The stunning contemporary kitchen features sleek countertops, new cabinetry, and a full suite of brand-new stainless steel appliances. The stylishly renovated bathroom offers modern fixtures and designer finishes, while freshly painted walls and updated flooring create a bright, inviting atmosphere throughout. The spacious living room is the centerpiece of the home, showcasing a striking stone-tiled decorative fireplace flanked by custom built-in bookshelves, adding warmth, character, and a unique architectural focal point. Large windows fill the apartment with natural light, enhancing its comfortable and distinctive vibe. Perfectly situated just steps from the vibrant downtown Ossining waterfront district, you'll enjoy easy access to local shops, cafés, restaurants, and parks. The nearby Ossining Metro-North station provides a convenient commute to Grand Central Terminal. Heat and water are included in the rent, and one garage space is available for $150 per month. Experience modern living with timeless character in this exceptional apartment!

56 S Highland Avenue Unit #D1, 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

$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

$700,000

2 Beds ⋅ 3 Baths ⋅ 1020813 MLS

Coveted Hudson Watch offers the perfect blend of convenience and River Town living. Ideally located just 1.1 miles from the Hudson Line Metro-North station and 1.6 miles from Louis Engel Waterfront Park. Locals enjoy the scenic RiverWalk Park paths, and all the charm of historic Ossining. This spacious two-story corner townhouse welcomes you with a natural stone foyer, vaulted ceilings and skylights that bathe the home in soft natural light throughout the day. Designed for easy everyday living and effortless entertaining. The open floor plan flows from one inviting space to the next seamlessly connecting indoor and outdoor living. The one step down living room is anchored by a wood-burning fireplace and sliding glass doors to a private patio surrounded by mature landscaping, creating a peaceful outdoor retreat. The patio has a remote operated sunshade. The thoughtfully updated kitchen features natural stone countertops and backsplash, stainless steel appliances, an abundance of cabinets and oversized windows overlooking lush green space that adds an inviting setting for casual dining. The adjacent dining area continues the home's open floor plan. Offering exceptional flexibility, the first-floor primary suite features a beautifully updated bath with a spa tub, separate shower, walk-in closets, and large windows. This generous space could also serve as a family room depending on your lifestyle. A nearby office or den easily functions as a second bedroom and is complemented by a full hall bath. A full-size washer and dryer are conveniently tucked away and direct access to the attached one-car garage complete the first floor. The second-floor primary en-suite is an unexpected bedroom or bonus room option, offering vaulted ceilings with skylights, a spacious bath complete with oversized soaking tub, separate shower, double vanity, walk-in closets & additional eave storage. This flexible additional space is particularly special. The current owner has meticulously landscaped the perimeter of the home and patio, enhancing both privacy around the patio and year-round beauty. Hudson Watch residents enjoy outstanding community amenities including a swimming pool, tennis and pickleball courts, a resident dog park, and wide tree-lined streets where distant Hudson River views are enjoyed from the neighborhood's elevated hilltop setting. Historic Ossining has become one of Westchester's vibrant River Towns, celebrated for its waterfront restaurants, boutique shopping, farmers markets, hiking trails, parks, and a welcoming community that embraces both nature and culture.

61 Hudson Watch Drive Unit #61, 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

$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

$655,000

3 Beds ⋅ 2 Baths ⋅ 1011379 MLS

Nestled in Ossining's coveted Sparta Historic District, this exceptional 1860 historic home offers timeless charm in one of Westchester's unique storied neighborhoods. Rich with character, this special property showcases preserved historical details including original plaster moldings and medallions, hardwood floors throughout, original stone walls, and beautiful rock gardens. The home offers 3 bedrooms, 1.5 baths, an office or bonus room, 2 staircases, a working wood-burning fireplace, a large front sitting porch, a rear porch, and a full attic with abundant storage and lots of potential. Beautiful double tiered backyard. Thoughtful updates have been made over the years, including a newly updated bathroom, a tastefully refreshed kitchen, exterior painting, new basement and attic windows, new above ground oil tank and oil line, new roof, copper chimney flashing and a repaved driveway. Ideal commuter location! Approximately 1/2 mile from Metro North. Leave your car at home! A rare opportunity to own a home filled with history, charm, and meaningful improvements in one of Sparta's most treasured settings

8 Still Court, Ossining

$425,000

2 Beds ⋅ 2 Baths ⋅ 976452 MLS

Welcome to Scarborough Manor, one of Westchester's most sought-after riverside co-op communities — where resort-style living meets everyday convenience along the scenic Hudson River. This beautifully appointed, recently updated two-bedroom, two-bath residence offers what may be the community's most prized feature: breathtaking, unobstructed Hudson River views that greet you from the moment you step inside. You will revel in the daily dose of beauty every time you walk out onto your private terrace and take in the sweeping river panorama — whether with your morning coffee or an evening glass of wine. Inside, the apartment has been thoughtfully updated throughout with new modern lighting, refinished parquet floors, and a refreshed kitchen, including updated appliances, counter, sink, backsplash, knobs, and cabinet refinishing. The spacious living area flows naturally to the terrace, making the river views a seamless extension of your living space. Both bedrooms are generously sized, and two full bathrooms offer comfort and flexibility for residents and guests alike. Beyond your front door, Scarborough Manor delivers a true resort lifestyle. Newly renovated hallways and soon-to-be-redone lobby set a refined tone the moment you arrive. Residents also enjoy a stunning heated pool, elegant clubhouse with fitness center, sauna, billiards, library, and ping-pong lounge. Take strolls or have a picnic in the beautifully landscaped walking paths and quiet seating areas along the property overlooking the water. The community features 24-hour gated security, complimentary outdoor parking, solar, and a full-building backup generator. And the location couldn't be more convenient — just a short distance to the Scarborough Metro-North station for an easy commute to Manhattan, with shopping and dining minutes away at the Arcadian Shopping Center, downtown Ossining, and nearby towns such as Sleepy Hollow, Tarrytown, Pleasantville, and Briarcliff Manor. This area is full of culture, recreation, and ongoing events for all ages and interests. Please note that applicants must meet the Co-Op's purchase criteria. Estimated Monthly maintenance is $2,184. This is Hudson River living at its finest - come see for yourself! Paradise Found!

16 Rockledge Avenue Unit #5P-2, Ossining

$750,000

3 Beds ⋅ 2 Baths ⋅ 1021208 MLS

Welcome to 39 Secor Road. Being sold strictly as-is and as a buy one get one with 37 Secor Road ( offered @ $85K CASH ONLY). You cannot pass on this deal. Get this rare investment opportunity for this two bedroom over 1-bedroom multi- family home that offers street parking or with the purchase of municipal parking pass, tenants can park right behind the building in the municipal lot. This home boasts unobstructed windows of the Hudson River views from both units and the windows in the basement. Priced to be sold as a package with the adjoining Single-family home at 37 Secor road. These two homes are on one deed with two separate tax lots, but they are adjoined with ONE furnace and one oil tank. The single-family home is being sold for cash only while a buyer can obtain financing for the two-bedroom multi-family home. This is an amazing opportunity for a first time or veteran investor. Both units are being sold strictly AS IS but boast two new rooves. The unfinished basement extends the length of both homes. Street parking for the multi-family home, but there is a municipal lot located behind the homes. They are a short distance to the Ossining training station and down-town Ossining alike. Both homes have access to basements. Unfinished basements have windows and exterior access if a buyer would like

39 Secor Road, Ossining

$4,500

3 Beds ⋅ 2 Baths ⋅ 1015488 MLS

Awesome In Ossining! Clean, crisp and ready to move right in to this perfect rental on a quiet cul-de-sac where the green space is inviting and the gigantic dining deck is exciting! An open floor plan with lots of natural light makes living here a breeze. Comforts? How about an eat-in kitchen with a terrific prep and party island! Central air-conditioning and well insulated walls keep things comfortable and tight. Three bedrooms, a large flowing living room & dining space plus a vast finished lower level for fun, recreation and flexibility of lifestyle. Game night? Ping-pong? Movie night? There is a tone of space and a cozy fireplace! A laundry room with loads of storage, closets and closets and closets AND a true 2 car garage with a level driveway that can park all your friends and family. Al this and just moments from Veterans Park, and 7 minutes to Croton train station with a 46 express commute to GCT and so near to Croton Gorge Park, picnic areas, Teatown, shops, restaurants, schools...AWEsome AWESSINING!

8 Duers Court, 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

$675,000

3 Beds ⋅ 2 Baths ⋅ 1013329 MLS

Make every day, one of leisure and delight. Perched above the Hudson River, discover this impeccably maintained, spacious 3 bedroom, 2 full bath, at the highly coveted Scarborough Manor. High on the 6th floor, this corner unit has 9ft ceiling and oversized rooms, creating a most expansive and tranquil oasis. Its light wood floors, custom blinds/shades, sleek kitchen, and renovated baths mingle luxury with practicality. Best of all, you can enjoy majestic vistas from your private terrace and banquet of large windows. Allow yourself to be treated to a daily lifestyle that nurtures your spirit, as you enjoy the many amenities the complex offers: Clubhouse with fitness center, sauna, billiards, library, ping-pong, and event space • Outdoor Heated Pool surrounded by mature trees with Hudson River views • Beautiful Park-Like Grounds with walking paths and benches • 24/7 Gated Security for peace of mind and to accept your packages • Free Outdoor Parking for all (Indoor parking is wait listed at $85 per month) • Full Generator no power outages. Hallways redecorated one year ago with contemporary wallpaper and carpeting • Unique Features: Convenient laundry on each floor • New HVAC units in LR, Dining Room, and Bedrooms • New windows throughout • New lobby restoration underway • Storage units are on a wait list and the rent is ($30-$50/month). Scarborough Manor offers the best of both worlds – a tranquil, riverside setting with easy access to both the Scarborough and Ossining Metro-North stations, Route 9, and nearby shops and restaurants.

16 Rockledge Avenue Unit ##6E-1, Ossining

$699,000

2 Beds ⋅ 3 Baths ⋅ 1018107 MLS

Welcome to 191 Horseshoe Circle, a beautifully designed contemporary townhouse at the sought after Fox Hill Condo Development in the Hudson Valley, Westchester County. This rare "C" End Unit is beautifully located in the heart of the development, surrounded by tranquility with an expansive deck for enjoying the outdoors. Cheery and spacious, this home has an open floor plan with combined Dining Area and Living Room with gas Fireplace. The large Eat-in-Kitchen features a breakfast nook where beautiful light pours in to welcome your day. The first floor includes a Flex Space area that can be used as a private Guest Room - Full Bathroom and Closet are attached. While perfect for people who wish to avoid steps, this space is also ideal for Office, Den or Exercise use. Upstairs has 2 lovely Bedrooms, both En-suite. The pretty Primary Bedroom is roomy and features an attached dressing room, multiple closets and large Bathroom with Shower and separate Tub. The second upstairs Bedroom is also ensuite with full bathroom. Laundry area/closet is conveniently located off the first floor foyer. The 2-Car Garage and driveway accommodates parking for six cars. Additional storage shelving is found in the garage. Much of the interior has been painted in the past 1-2 years. Hot Water Heater replaced 4/2025. Fox Hill is well maintained, includes beautiful amenities - Pool, Tennis, Basketball, Playground, Swings - and is Pet friendly. Tucked away but close enough to highway and train stations 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, West Point, hiking, more.

191 Horseshoe Circle, Ossining

$1,200,000

3 Beds ⋅ 4 Baths ⋅ 1015078 MLS

Wisteria & Wood: A Craftsman Masterpiece in the Heart of Teatown Tucked into nearly an acre of lush, private landscape in Croton-on-Hudson's most coveted enclave, this custom-built Craftsman residence is where architectural intention meets natural serenity. From the moment you arrive — welcomed by a wisteria-draped pergola and a stunning Belgian block driveway and courtyard — it's clear this home was designed with both beauty and purpose in mind. Inside, the open floor plan unfolds with the effortless flow that today's lifestyle demands. Walls of windows flood the rooms with natural light, while rich hardwood floors, recessed lighting, and an abundance of storage on every level create a home that feels both elevated and completely livable. The wood-burning fireplace anchors the living space with warmth and character, and a stunning wall of built-in bookcases adds depth and personality. Just off the living room, a den offers the perfect balance of connection and privacy — ideal as a reading room, media space, or quiet retreat. The chef's kitchen is appointed with top-of-the-line stainless steel appliances and opens seamlessly to both the dining room and living area — a layout made for entertaining and everyday connection alike. Step outside to the back deck and discover a deeply private outdoor retreat, where nature sets the stage for al fresco dining, morning coffee, or simply doing nothing at all. The spacious primary suite offers a true escape with a generous walk-in closet and a spa bath. Two additional bedrooms feature soaring beamed ceilings and large closets, sharing a full hall bath. The entry level delivers exceptional function with a large mudroom with custom coat cubbies, plus a beautifully finished flex space — ideal as a home office, studio, or guest suite — with a brand new ensuite modern bath. Three bedrooms. with the flexibility to live like 4, and three and a half baths. Craftsmanship in every corner. And then there's the setting. Spectacular rock outcroppings and ancient boulders punctuate the grounds with dramatic natural character, while towering mature trees — including a graceful dogwood and a statuesque magnolia — frame the yard in seasonal beauty. Walk to Teatown Lake Reservation for hiking and birding, or be in Croton village, the Hudson River waterfront, and the Metro-North station in just ten minutes — where a 48-minute express carries you directly into New York City. All within the award-winning Croton-Harmon School District. This is not just a home. It is a way of living.

1821 Spring Valley Road, Ossining

$929,000

3 Beds ⋅ 2 Baths ⋅ 1011357 MLS

Why wait for vacation when you can enjoy a retreat-like lifestyle every day? This exceptional, fully renovated Colonial with farmhouse charm is a rare Sears Roebuck Kit House circa 1927, seamlessly blending historic character with modern comforts. Thoughtfully updated throughout, the home features central air conditioning, remote-controlled blinds, renovated baths, and hardwood floors that enhance its timeless appeal. At the heart of the home is a beautifully designed custom kitchen featuring a stunning Viking range, soapstone countertops, and a large maple butcher block island. Whether preparing meals, entertaining guests, or gathering with family, this inviting space is as functional as it is beautiful. The spacious great room offers warmth and character with a wood-burning fireplace, creating a cozy setting for crisp autumn evenings and winter nights. Designed for both relaxation and entertaining, the expansive deck spans the length of the home and overlooks the picturesque barn and tranquil pond, creating a private outdoor oasis with a peaceful, country-inspired feel. The primary suite features custom built-in closets and an en-suite bath with a walk-in shower. Two additional bedrooms and a renovated hall bath complete the second level. The finished third-floor attic provides flexible space ideal for a home office, fitness studio, playroom, or creative retreat. The unfinished stone basement offers abundant storage, a laundry area, and direct access to the attached garage via a convenient walkway. Nestled on one of the area's most scenic and sought-after streets, this special property offers the perfect balance of privacy and accessibility, just minutes from the Taconic State Parkway, Metro-North, shopping, dining, and everyday conveniences. A truly unique opportunity to own a piece of history while enjoying all the comforts of modern living.

28 Inningwood Road, Ossining

$705,000

4 Beds ⋅ 2 Baths ⋅ 1011605 MLS

Beautifully maintained TWO FAMILY DUPLEX in the cherished, historic Sparta district! Each 1000 sq. foot apartment features two bedrooms, one updated bathroom, living room, kitchen, dining room and large bright 4 season sun sunroom. The full, unfinished basement features two laundry stations, one for each unit plus plenty of storage. Additional features include oak hardwood floors, stucco walls & solid wood trim. The shared backyard features a large hardwood deck for outdoor entertaining. Ample driveway and off-street parking. This home is very well-maintained. Apartments may enjoy some updating, but the bones of this beautiful property are excellent. Enjoy this incredible location featuring a short walk to the Arcadian Shopping, the Scarborough-on-Hudson train station to GCS, and the Hudson River Front. It doesn't get better than this! Taxes don't reflect STAR savings of $1,591 if qualified.

321 Spring Street, Ossining

$439,000

1 Beds ⋅ 2 Baths ⋅ 1015764 MLS

Welcome to 2 David's Lane, where you will find a charming one-bedroom, corner townhouse in Ossining. This home offers a wonderful opportunity to enjoy comfortable, low-maintenance living in a desirable Westchester community. This thoughtfully designed home features a bright and inviting layout with a comfortable living space, a functional kitchen, and a cozy bedroom retreat. The open flow of the main living area creates a welcoming atmosphere, perfect for relaxing at the end of the day or entertaining guests. The kitchen offers convenient functionality with plenty of potential to make the space your own. The spacious bedroom provides a peaceful place to unwind, while the overall layout maximizes comfort and ease of living. Enjoy the benefits of townhouse living with the privacy and convenience of your own home, along with the added appeal of a well-maintained community setting. Whether you’re a first-time buyer, looking to downsize, or seeking a place that offers simplicity without sacrificing location, this home provides the perfect opportunity. Ideally located near Ossining’s vibrant downtown, restaurants, parks, shopping, and Metro-North transportation, this home offers the perfect blend of comfort and convenience. Come see all that this delightful townhouse has to offer!

2 Davids Lane, Ossining

$625,000

4 Beds ⋅ 3 Baths ⋅ 1015576 MLS

Welcome to 10 Susquehanna Road, a well-maintained 4-bedroom, 2.5-bath home offering 1,752 square feet of living space on a level 0.23-acre property in Ossining. The main level features a spacious living room with fireplace, formal dining room, kitchen, two bedrooms, a hall bath, hardwood flooring, and a mudroom/laundry room with access to the rear porch. The upper level offers two additional bedrooms, a full bath, a half bath, and a walk-in hall closet. A full unfinished basement provides abundant storage and future potential. Thoughtfully maintained over the years, the home features updated windows, mechanical systems, a newer front entry door, and other improvements that enhance comfort, efficiency, and everyday living. Located within the Ossining Union Free School District and just minutes from downtown Ossining's restaurants, cafes, shopping, waterfront parks, and Hudson River attractions, this home offers an ideal balance of convenience and recreation. Nearby points of interest include Richard G. Wishnie Park and the Ossining Reservoir walking path (directly behind the home), Croton Point Park, Teatown Lake Reservation, Louis Engel Waterfront Park, Bethany Arts Community, and the historic Sing Sing Kill Brewery district. Commuters will appreciate easy access to Route 9, the Taconic State Parkway, and both the Ossining and Croton-Harmon Metro-North stations, providing direct service to Grand Central Terminal and convenient connectivity throughout Westchester, New York City, and the Hudson Valley. Combining valuable updates, comfortable living spaces, outdoor enjoyment, and a highly convenient location, this property presents an exceptional opportunity to enjoy all that Ossining has to offer. Call today!

10 Susquehanna Road, Ossining

$2,850

2 Beds ⋅ 1 Baths ⋅ 1012943 MLS

Welcome to this 2 bedroom 1 bathroom located in the heart of Ossining! Offering a comfortable and functional layout, this rental features spacious bedrooms a full kitchen, a full bathroom and versatile flexibility perfect for everyday living. Enjoy the added convenience of one dedicated parking space with hot water included. Located close to shopping, dining, public transportation, and major roadways this apartment offers both comfort and convenience for your daily lifestyle.

188 Spring Street Unit #4, Ossining

$249,000

2 Beds ⋅ 1 Baths ⋅ 1013780 MLS

Opportunity knocks in the heart of Ossining. Best value home on the market right now!!! This 2-bedroom, 1-bath Colonial offers tremendous potential for investors, contractors, renovators, and buyers seeking a value-add project. The home is ready for its next chapter and presents the chance to restore, reimagine, or redevelop to suit your vision. Featuring a traditional Colonial layout and a manageable lot size, this property provides a rare opportunity to create value in a desirable Westchester County location. Conveniently located near local amenities, transportation, shopping, dining, and major commuter routes. Property is being sold strictly as-is. Cash buyers, renovation loan purchasers, and experienced investors will appreciate the possibilities this property presents. Bring your imagination and unlock the potential of this Ossining opportunity.

126 Croton Avenue, Ossining

$507,000

2 Beds ⋅ 1 Baths ⋅ 1014067 MLS

Charming Cape Cod in Indian Village – Move-In Ready! A rare opportunity to own a home with a backyard sanctuary. Tucked away in the desirable Indian Village neighborhood, this recently remodeled and tastefully updated cape cod is turnkey and ready for its next owner. Offering the perfect blend of charm, comfort, and potential, this home presents the perfect starter home. An oversized deck overlooks your own private garden oasis perfect for entertaining, gardening, or simply relaxing in a peaceful setting surrounded by lush greenery, blooming flowers, and mature vegetation. Additional features include a full walkout basement offering ample storage and future expansion possibilities. With its thoughtful updates, inviting outdoor spaces, and endless potential, this home is ready to be enjoyed from day one.

53 Pleasantville Road, 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

$699,000

5 Beds ⋅ 2 Baths ⋅ 1013271 MLS

FULLY AVAILABLE as of 7-7-2026. Well-maintained two-unit property in the heart of Ossining, fully renovated in 2020 and offering a strong combination of space, convenience, and versatility. The building features a spacious three-bedroom second floor unit that is ready for immediate occupancy over a two-bedroom unit, providing an ideal opportunity for owner-occupants or investors. Both units benefit from updated finishes completed during the 2020 renovation, offering modern functionality while maintaining a practical layout. The second floor unit has a back enclosed porch with access to a fenced in back yard. The property is located within one mile of two Metro-North Hudson Line train stations, providing convenient access for commuters. Ideally situated close to local shops, parks, schools, major highways, and public transportation, this property offers excellent accessibility and everyday convenience. A solid option for those seeking a turnkey multi-family home in a well-connected Westchester location.

1 Edward Street, Ossining

$1,350,000

6 Beds ⋅ 4 Baths ⋅ 1013182 MLS

Built in 1870 and lovingly restored by its current owners, this Queen Anne Victorian at 28 Hamilton Avenue sits in the heart of Historic Ossining. Both yards are planted with apple, cherry, Asian pear, pawpaw, hazelnut, raspberry, blueberry, and strawberry, along with a working vegetable garden — a rare thing to find alongside a home of this character. Approach through a deep front yard bursting with pollinators, wisteria draping the covered porches. The house keeps its greatest surprise for later — the breathtaking views of the Hudson River and the Palisades are revealed as you move deeper inside, unfolding room by room. Cross the double-door vestibule into a gracious foyer with soaring double-height ceilings, rich wainscoting, inlaid parquet floors, and a staircase anchored by an elaborately turned newel post — all presided over by the first of four hand-carved ceramic tile fireplaces. The main level was built for both formal entertaining and comfortable everyday living. Two spacious living rooms, each with its own ceramic tile fireplace, open into a sun-drenched den with a spectacular coffered wood ceiling, three walls of windows, and doors facing each other — one to the front porch, one to the rear. The formal dining room, with its own fireplace and a sweeping Hudson River School-inspired mural, connects to a well-appointed kitchen with an original farmhouse sink, a corner butler's pantry with intact original cabinetry, and discreet service stairs tucked behind. Throughout, the turret windows with their curved glass are a signature of the era, and of this street. Step out the back and the Hudson opens before you — wide, silver, and immediate — framed by a terraced garden and a covered rear porch made for long evenings. This is the river that stirred a generation of painters to invent an American landscape tradition, that carried commerce and dreams in equal measure, that poets and wanderers have stood before and felt genuinely small. It is your backyard now. Upstairs, four bedrooms include a primary suite of nearly 20 by 18 feet, wrapped in a turret bay, with a screened balcony, ensuite bath, and the kind of proportions that are simply not built anymore. The current owners have thoughtfully upgraded the electrical and insulation throughout the attic, creating a series of carefully considered spaces — a serene room for yoga, meditation, or quiet work, a jewel-like sitting room with leaded diamond windows, a full bath, and at the crown of it all, a lookout tower lined with curved bookshelves and wide-plank floors, from which this house has contemplated the mighty Hudson for 155 years. A ten minute walk brings you to Metro North and 45 minutes later, Grand Central. Historic downtown Ossining — its shops, restaurants, and the extraordinary Sing Sing Museum — is at your doorstep. A rare opportunity to live inside a piece of history, on the banks of one of the great rivers of the world.

28 Hamilton Avenue, Ossining

$629,900

2 Beds ⋅ 3 Baths ⋅ 1012453 MLS

First time on market! 2 bedroom, 2.5 bath end unit Hamlet on Spring Pond condo gives you all the convenience of a condominium and the feel of a single family home. You'll love being nestled among the woods with a nearby pond, waterfall, clubhouse, tennis court and pool. The kitchen features stainless steel appliances, granite counters, and a sunny dining area. The formal dining room overlooks a sunken living room with a woodburning fireplace and sliding doors to the rear deck and wooded grounds. The primary suite has tons of closet space, a generously sized en suite bath, and a balcony. The second floor laundry offers ease and convenience, and the second bedroom is roomy and sunny. Located with convenient proximity to highways and all that nearby Ossining village has to offer.

70 Spring Pond Drive, Ossining

$619,000

2 Beds ⋅ 2 Baths ⋅ 1012195 MLS

Welcome to 54 Mystic Drive, a bright corner end-unit townhouse-style condo in the desirable gated community of Mystic Pointe. This inviting multi-level home offers a flexible layout with wonderful natural light, enhanced by recently installed Andersen windows and patio door, including several large windows that brighten the living room, dining area, breakfast nook, and kitchen. The main level features an open living and dining area with a gas fireplace and access to a stone patio, creating an easy flow for everyday living and entertaining. The eat-in kitchen offers a charming breakfast nook, recessed lighting, and a comfortable connection to the main living space. A powder room completes this level. Upstairs, both bedrooms feature high ceilings, and the spacious primary bedroom includes a large walk-in closet and access to an upper-level den/office, ideal for working from home, reading, hobbies, or quiet retreat space. The full bath includes a whirlpool tub. The finished lower level adds a family room/recreation space, laundry area, and access to the attached 1-car garage with remote-control door. Enjoy the ease of low-maintenance living in Mystic Pointe, known for its beautifully landscaped setting and resort-style amenities including a clubhouse, fitness center, pool, playground, tennis/pickleball court, and nature trail, with convenient access to Croton-Harmon Metro-North, shopping, dining, and major roadways.

54 Mystic Drive, Ossining

$3,995,000

7 Beds ⋅ 6 Baths ⋅ 1012192 MLS

Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular 7-bedroom main residence, where grand, light-filled rooms showcase timeless craftsmanship and sweeping vistas from nearly every window. Multiple primary suites and en suite bedrooms provide exceptional comfort and flexibility for hosting overnight guests. The property also features a 5-bedroom, 2 bath, caretaker’s home and a historic carriage house with a 5-car garage, horse stalls, a chicken house, and a sheep house—ideal for equestrian pursuits, hobby farming, or simply enjoying the pastoral lifestyle. Whether you envision a private compound, event venue, or generational retreat, this setting offers endless possibilities. With its rich heritage, refined elegance, and serene privacy, Old Dam Farm is more than a property—it’s a place to create memories that will last a lifetime.

433 Arcady Road, Ossining

$639,222

3 Beds ⋅ 1 Baths ⋅ 1011590 MLS

Welcome to this beautifully maintained vintage Colonial, ideally situated on a desirable corner lot in the heart of the village. Combining classic character with thoughtful updates, this spacious home offers comfortable living both inside and out. The first floor features hardwood floors, high ceilings, a bright eat-in kitchen, dining room, an inviting living room, and laundry off the kitchen. Upstairs, you'll find 3 generously sized bedrooms and a hall bath. A walk-up attic and expansive basement provide abundant storage and future possibilities. Outdoor living is equally impressive, with a fully fenced yard, expansive stone patio perfect for entertaining, front and rear porches, and an above-ground oil tank. A detached two-car garage and driveway offer off-street parking for up to four vehicles. Conveniently located within walking distance of schools, parks, village amenities, shops, restaurants, and public transportation, this home offers the perfect blend of historic charm, modern convenience, and exceptional outdoor space. Don’t miss this opportunity to enjoy village living at its best! There are no audio recording devices inside this property.

219 Spring Street, Ossining

$575,000

2 Beds ⋅ 3 Baths ⋅ 1010405 MLS

Tucked within the beautifully maintained Woods in Westchester, this townhome offers a wonderful opportunity to create a home that reflects your own style and vision. Privately situated amid mature landscaping, the setting is peaceful and inviting, with a sunny patio and private balcony providing comfortable outdoor spaces to relax and enjoy the surroundings. The interior features a bright eat-in kitchen, spacious living area, a versatile loft ideal for a home office or den, central air, second-floor laundry, and an attached garage. Residents enjoy a sparkling pool, tennis court, walking paths, a scenic pond, and professionally maintained grounds, creating an easy, low-maintenance lifestyle. The Woods is ideally located just minutes from the Croton-Harmon Metro-North station, major parkways, shopping, dining, parks, and the Hudson River waterfront. Situated with convenient access to the many conveniences and amenities of Croton-on-Hudson, Ossining, and the surrounding areas of Briarcliff Manor. Whether you're looking for low-maintenance living, outdoor amenities, or an easy Westchester lifestyle, 122 Woods Brooke Circle is the wonderful place for you!

122 Woods Brooke Circle, Ossining

$2,500

1 Beds ⋅ 1 Baths ⋅ 1009795 MLS

Bright and inviting 2nd-floor rental apartment located in a well-maintained multi-family home in the charming Town and Village of Ossining. This sun-filled residence offers beautiful natural light throughout the day and spectacular sunset views, creating a warm and welcoming atmosphere. A standout feature of this large apartment is the bonus office room, perfect for working from home, studying, creative pursuits, or additional flex space to suit your lifestyle. Conveniently situated just a 10-minute walk to the Ossining Metro-North Station, providing approximately a 50-minute commute to Grand Central Terminal. Enjoy easy access to local bus lines, parks, supermarkets, laundromats, museums, and a variety of international dining options. Residents will appreciate the vibrant community amenities, including creative arts programs, recreational activities, and access to indoor swimming facilities. This desirable location combines small-town charm with outstanding convenience, making it an excellent place to call home. Don't miss this opportunity to enjoy comfortable living in one of Westchester County's most sought-after river towns.

269 Spring Street Unit #2nd Floor, Ossining

$949,000

4 Beds ⋅ 3 Baths ⋅ 1000282 MLS

Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich espresso cabinetry, quartz countertops, stainless steel appliances, a stylish tile backsplash, recessed lighting, and a large center island with seating. The open flow connects seamlessly to the dining room and main living areas, creating an inviting atmosphere for gatherings large and small. The spacious primary suite includes a private en-suite bath, while two additional bedrooms and a full bath round out the first floor. The finished lower level offers exceptional versatility with a separate entrance, additional family room, a full bath, another bedroom and a bonus room flexible for a home office, gym, or crafts. Enjoy the beautifully usable outdoor space complete with a patio and above-ground pool, perfect for relaxing or entertaining. Additional features include generous storage, an attached garage, and a convenient location close to shopping, parks, schools, and major commuter routes. A rare opportunity with endless possibilities for today’s lifestyle.

6 Maria 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

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