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$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
$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
$639,500
4 Beds ⋅ 2 Baths ⋅ 1021344 MLS
Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle. The private backyard offers a peaceful retreat with a patio ideal for outdoor dining, entertaining, or simply relaxing. Experience the best of Hudson Valley living with convenient access to the scenic Hudson River waterfront, parks, hiking and biking trails, local restaurants, shopping, and year-round community events. Whether you're commuting, exploring the outdoors, or enjoying the vibrant Rivertown lifestyle, this home offers the perfect balance of tranquility and convenience. Don't miss this opportunity to own a beautiful home in one of the Hudson Valley's most sought-after communities.

42 Pershing Avenue, Ossining
$698,000
4 Beds ⋅ 3 Baths ⋅ 1023097 MLS
Charm meets flexibility in this rare Ossining find! A legal mother-daughter bungalow ranch that feels like a secret waiting to be discovered! Tucked back from the road amid mature plantings and lush landscaping, this home delivers a bright, cheerful, private pocket of comfort. Step inside to a sun-drenched three-season room with recessed lighting, then through French doors into a warm kitchen with abundant cabinets and granite countertops. A dining area with oversized windows keeps the light flowing all day, opening into a family room with a fireplace, large bay window, and a door to the back deck. The first-floor primary bedroom features an en-suite bath and is joined by two additional bedrooms and a hall bath, with hardwood floors throughout the main level. A standout feature is the legal mother-daughter suite, complete with its own private entrance, summer kitchen, bedroom, full bath, and living/dining area. Ideal for multigenerational living, guests, or extra income potential. Out back, a fenced-in yard feels like your own private retreat - leafy, tucked away, and made for slow mornings and long summer nights. Fire up the grill on the spacious deck, linger under the stars, or lose an afternoon in the gardens. Ideally located close to the Croton train station (and the villages of both Croton-on-Hudson and Ossining, with plenty of amenities, shopping, and eateries nearby. Well-priced and move-in ready, this one won’t sit on the market long. Schedule your showing today.

7 Ogden Road, Ossining
$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
$1,700,000
2 Beds ⋅ 2 Baths ⋅ 1023302 MLS
Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes. Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles of organic architecture, where walls of glass, natural materials, and thoughtful siting dissolve the boundaries between indoors and out. Built from Philippine mahogany, stone, slate, and glass, every detail was carefully considered to create harmony with the surrounding landscape. The result is a 2 bedroom 2 bathroom home that feels remarkably current nearly seventy years later. Inside, soaring glass walls frame the changing seasons while a dramatic stone fireplace anchors the main living space. Original built-ins, slate floors, rich mahogany, and a signature wraparound deck celebrate Henken's vision, while the thoughtfully updated kitchen and recent improvements allow the home to function beautifully for modern living. Designed using passive solar principles decades before sustainability became mainstream, the home captures the low winter sun for natural warmth while deep roof overhangs provide cooling shade throughout the summer additionally geothermal heating, solar, and other thoughtful updates bring modern all-electric comfort to the home. Complementing the main residence is a beautifully reimagined 1,200 square foot studio that expands the property's possibilities. Completely renovated, the space now offers a bedroom, full bath, living area, kitchenette, and a stunning spa-inspired sauna suite finished with terrazzo tile, warm Aspen wood, and premium contemporary materials throughout. Whether used as a guest retreat, artist's studio, wellness space, home office, or income-producing guest accommodation, it offers the same thoughtful design and craftsmanship found in the main home. Recent improvements, including a newly constructed carport, estate-style gravel driveway, high-performance siding, Energy Star windows, updated insulation, and new mechanical connections to the studio, ensure the property is ready for years of effortless enjoyment. The setting is every bit as extraordinary as the architecture. Wander your own seventeen-acre landscape, listen to the year-round stream, or spend the afternoon exploring nearby Teatown Lake Reservation. Just beyond, you'll find some of the Hudson Valley's most celebrated destinations, including Blue Hill at Stone Barns and The Farmer & The Fish. Nearby towns of Ridgefield, Pound Ridge, Katonah and Bedford, offer exceptional dining, galleries, farmers markets, and hiking. Metro-North provides easy access to New York City, making this an extraordinary full-time residence or one of the region's most remarkable weekend escapes. Architecturally significant homes of this caliber rarely become available. This is more than a residence—it's an opportunity to own a living piece of mid-century design history, thoughtfully preserved for the next generation.

1306 Grants Lane, Ossining
$525,000
3 Beds ⋅ 2 Baths ⋅ 1024303 MLS
A true brick home in the Village of Ossining, offering beautiful sunset and river views, tremendous character, low taxes, and a location that’s hard to beat — just minutes to the train station, riverfront dining, and Teatown Nature Preserve. This 3-bedroom, 2-bath home features 1,240 sq ft across the main floors, plus a 340 sq ft walk-out lower level and a walk-up attic ideal for an artist loft, studio, or storage. Inside, original exposed beam ceilings and a striking stone-and-brick fireplace with a Jotul wood stove sets an unmistakable tone. Outside, enjoy a rare three-tiered outdoor living setup: a brick patio off the lower level, a large deck off the kitchen, and an upper balcony with year-round views of the Mario Cuomo Bridge and Croton Point Park — expanding to a full 180-degree Hudson River panorama in winter. The lower level includes a convenient kitchenette for guests or extended living. Classic brick architecture, arched window lintels, mature trees, a large rear yard, and a storage shed complete this home with genuine architectural soul.

33 Cedar Lane, Ossining
$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
$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
$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
$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
$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
$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
$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
$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
$750,000
3 Beds ⋅ 2 Baths ⋅ 1008226 MLS
Welcome to the peace and tranquility of Morningside Drive. Nestled in a highly desirable location, this well-maintained home offers expansive frontage, ensuring exceptional privacy and a serene setting on almost 1 acre. The spacious primary suite features a private bath and walk-in closet, while beautiful hardwood floors run throughout the home. The inviting living room, anchored by a stunning stone fireplace, creates the perfect gathering space for holidays and special occasions. Sliding glass doors open to a deck overlooking the quiet, picturesque property, providing the ideal place to relax and enjoy nature. Recent updates include a new oil tank (2026), furnace (2024), Corian kitchen countertops offering peace of mind for years to come. The fully finished lower level adds extra space not included in the Sq Ft, totaling 2400sq ft of versatile living space, ideal for a recreation room, home office, gym, or potential in-law or au pair suite. Conveniently located near parks, shopping, dining, and major highways, this home combines privacy with accessibility. Car enthusiasts and entertainers alike will appreciate the oversized two-car attached garage and abundant parking. Enjoy the convenience of walking to Ryder Park, featuring three ball fields, a picnic pavilion, basketball courts, tennis and pickleball courts, walking trails, and a playground. A rare opportunity to enjoy spacious living and a peaceful setting in a sought-after neighborhood.

110 Morningside Drive, Ossining
$729,000
3 Beds ⋅ 2 Baths ⋅ 1008426 MLS
Charming front porch colonial on tree lined Street. Front door opens to entry hall, large dining room and living room with hardwood floors, arched walkways between rooms. Beautifully updated kitchen with island and stainless appliances, half bath. A first floor bonus room that can be used as a bedroom or den/office. Upstairs leads to three bedrooms, a full bath, hardwood floors throughout, updated fixtures. Basement has laundry and utilities and storage space plus a playroom. The big deck outback looks over the yard parking for 3+ cars Taxes do not reflect basic star exemption of $1,555.

55 Sherwood Avenue, Ossining
$599,000
3 Beds ⋅ 1 Baths ⋅ 1010005 MLS
A beautifully cared-for 1929 Colonial with the sweetest feel, 16 Sherwood blends timeless character, warmth, and everyday ease. This darling home offers original charm, with beautiful wood floors, restored original interior doors with glass knobs, and thoughtful details throughout. A welcoming vestibule opens to a spacious living room anchored by a wood-burning fireplace with built-ins on either side. A French door leads to a wonderful three-season enclosed porch, extending the living space and creating the perfect spot for morning coffee, reading, or relaxed evenings. The formal dining room offers a classic setting for gathering, while the vintage charming kitchen has been meticulously maintained and includes a dishwasher, gas cooking, and easy access to the composite deck and lower level. Upstairs are three comfortable bedrooms and a nicely sized full bath. The lower level offers laundry, storage, and flexible space. Additional highlights include ductless AC, gas heat, a private driveway, detached two-car garage, low-maintenance deck, a welcoming front walkway, and beautifully established plantings that frame both the front and rear of the property. Set on a level property in one of Ossining’s lovely neighborhoods, close to parks, schools, shops, restaurants, the Hudson River, village conveniences, and under two miles to Metro-North. Classic, comfortable, and truly special.

16 Sherwood Avenue, Ossining
$3,500,000
10 Beds ⋅ 6 Baths ⋅ 999615 MLS
Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing sophistication or convenience, this is the ultimate retreat. From the moment you arrive, the estate feels transported from another era. A winding cobblestone driveway crafted from salvaged historic Bronx street stones loops through rolling lawns, curated gardens, and towering trees before revealing the magnificent manor overlooking its own private 3-acre pond. The original boathouse sits at the water’s edge, while a heated pool, tennis court, Japanese garden, orchard, vegetable and berry gardens, greenhouse, and heated pottery studio create a lifestyle reminiscent of a private European country estate. The nearly 9,000-square-foot residence is rich with warmth, grandeur, and unforgettable architectural detail. The awe-inspiring Great Room is nothing short of spectacular, anchored by a massive stone fireplace, soaring 40-foot oak-beamed ceilings, and dramatic walls of glass opening to sweeping pond views. Every room tells a story, from the stately oak-paneled library and elegant entertaining spaces to intimate sitting rooms, hidden carved staircases, and beautifully preserved plaster walls that showcase the home’s old-world craftsmanship. Designed for luxurious multi-generational living and grand entertaining alike, the estate features 10 bedrooms spread across thoughtfully designed wings, including guest accommodations and private caretaker quarters. The newly renovated primary suite rivals a five-star hotel, complete with its own fireplace, lounge/office with kitchenette, spa-like bath, dressing room, and tranquil views over the grounds. Nearly every fireplace throughout the home is operational, bringing warmth and romance to every season. Three separate tax lots, including an additional lot near the guest house, add a level of rarity and long-term value seldom found in estates of this caliber. Modern upgrades quietly support the property’s timeless elegance, including heated garages, multiple propane generators, upgraded well systems, mixed central air, and extensive utility and storage spaces. Private, historic, and impossibly romantic, this is more than a home. It is a destination, a lifestyle, and a once-in-a-generation opportunity to own one of the Hudson Valley’s most magical estates, all within easy reach of New York City.

335 Croton Dam Road, Ossining
$684,900
4 Beds ⋅ 3 Baths ⋅ 1007357 MLS
Nestled on a quiet cul-de-sac, this well-maintained home offers the perfect blend of comfort, functionality, and indoor-outdoor living in the Town of Ossining. The main level features an open floor plan with a spacious living and dining area, a large stone breakfast counter bar, two bedrooms, and a full bathroom. Upstairs, you’ll find two additional bedrooms with a second full bathroom, providing flexible living arrangements. Add an additional 300 s.f. for the finished lower level which offers a generous recreation/great room and a full bathroom, creating additional space for entertaining, hobbies, a home office, or extended living needs. Step outside to enjoy the backyard, designed for relaxation and entertaining, complete with a gazebo situated on a cement brick foundation with permits. A long driveway provides ample off-street parking. Additional highlights include an updated boiler less than five years old, oil heat, Con Edison electric service, municipal water, and utility systems that have been consistently maintained for efficient year-round operation. Conveniently located near parks, shopping, dining, transportation, and local amenities, this property offers a desirable combination of space, convenience, and value. All information, including but not limited to taxes, assessments, permits, square footage, utility costs, school information, and property condition, is deemed reliable but not guaranteed and should be independently verified by purchasers and their representatives.

22 Oakbrook Road, Ossining
$829,000
3 Beds ⋅ 3 Baths ⋅ 1000674 MLS
Summer starts here! Nestled on a stunning park-like property surrounded by mature trees and lush landscaping, this beautifully maintained 3-bedroom, 3 full bathroom home offers the perfect blend of privacy, comfort, and timeless style. The sun-filled main level features an open-concept layout with gleaming hardwood floors, a spacious living room anchored by an oversized picture window overlooking the backyard, and a beautifully appointed chef's kitchen complete with custom cabinetry, granite countertops, stainless steel appliances, and a large center island with an induction cooktop. The adjoining dining area provides an ideal setting for both everyday living and entertaining, with direct access to the expansive stone patio and backyard. The primary suite offers a peaceful retreat, while two additional bedrooms and a well-appointed full bath provide flexibility for family, guests, or home office needs. The fully finished lower level significantly expands the living space and offers endless possibilities, featuring a large recreation area, a full bathroom, and a convenient wet bar, ideal for extended family, guests, hobbies, fitness, or work-from-home needs. Adding even more potential, the home includes a full unfinished attic offering abundant storage space and exciting possibilities for future expansion. Outside, enjoy the tranquil setting from the spacious patio overlooking the sprawling backyard, perfect for entertaining, gardening, play, or simply relaxing in nature.

8 Riverview Farm Road, Ossining

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