Ossining, NY Real Estate | Ossining, NY Single Family Homes for Sale

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

$850,000

3 Beds ⋅ 4 Baths ⋅ 1004287 MLS

PRICED TO SELL! THIS ONE WON'T LAST!!! Discover this beautifully maintained home in Hawkes Crossing, offering a comfortable layout and low-maintenance lifestyle. The home features 3 spacious bedrooms, 2.5 bathrooms, and an additional room that can be used as a 4th bedroom, home office, or flex space. The main level includes a formal dining room, an open kitchen, and a flowing floor plan that makes everyday living and entertaining easy. Cathedral ceilings add to the home's spacious feel, while walk-in closets provide plenty of storage. Additional features include a two-car garage, backyard fire pit, sprinkler system, and a finished basement with approximately 680 square feet of additional living space. The lower level also includes a separate 430-square-foot storage room with potential for a home gym, recreation room, media room, or additional finished space. This area was expanded through excavation work completed during foundation and basement improvements, creating additional headroom and allowing for enhanced structural support. The monthly maintenance fee of $218 includes landscaping and snow removal, making homeownership even more convenient. Located in a desirable neighborhood and move-in ready, this home offers space, flexibility, and value. Don't miss this opportunity to make it your own.

1 Thornton Hill, Ossining

$540,000

3 Beds ⋅ 2 Baths ⋅ 1001582 MLS

Full of warmth, character, and timeless appeal, this charming colonial home offers a wonderful blend of classic details, comfortable living spaces, and an exceptional location in the heart of Ossining. Set on a beautiful property with a spacious yard, this special home provides the perfect backdrop for gardening, entertaining, outdoor play, or simply enjoying a quiet evening outdoors. Inside, you'll find inviting spaces filled with character, including a welcoming living room, formal dining room, bonus room ideal for a home office, den, or playroom, and a large eat-in kitchen that serves as the heart of the home. A convenient main-level laundry area, three bedrooms, one-and-a-half baths, and a full unfinished basement complete the home's functional and flexible layout. The outdoor space is truly a standout feature. The expansive yard offers endless possibilities for recreation, gardening, gatherings with family and friends, or creating your own private retreat. Whether hosting summer barbecues, enjoying morning coffee on the porch, or watching the seasons change, this property offers a lifestyle that is increasingly hard to find. Ideally located just minutes from downtown Ossining, you'll enjoy easy access to local restaurants, cafes, shops, parks, and the popular Ossining Farmers Market. Nature lovers will appreciate nearby waterfront parks, scenic trails, and recreation opportunities along the Hudson River. Commuters will love the convenience of the Ossining Metro-North station, offering direct access to New York City while allowing you to enjoy all the charm and community of Rivertown living. Rich in character, filled with potential, and situated in one of Westchester's most vibrant riverfront communities, 33 Maurice Avenue is a place you'll be proud to call home.

33 Maurice Avenue, Ossining

$699,222

3 Beds ⋅ 3 Baths ⋅ 1004746 MLS

Bring your vision and make this spacious split-level home your own! Set on over an acre of level, park-like property, this home offers a rare opportunity to create the lifestyle you've been dreaming of in a serene and convenient location. Freshly enhanced with newly painted exterior surfaces, a brand-new walkway, front patio, and a new above-ground oil tank, the property is ready for its next chapter. Inside, a bright and inviting floor plan features a generously sized living room with a fireplace, a dining room perfect for entertaining, and a comfortable den for everyday living. The home offers a primary bedroom suite, two additional bedrooms, hall bath, and large pull stair attic. The existing kitchen provides the perfect canvas for customization and renovation to suit your personal style and needs. A true highlight is the expansive addition featuring a hobby shop and storage room with a cathedral ceiling and door to the outdoors—ideal for creative pursuits, a workshop, studio space, or additional recreation area. Enjoy peaceful views from the enclosed rear porch overlooking the beautifully maintained backyard. A fenced section offers endless possibilities as a dog run, garden area, or private outdoor retreat. As an added bonus, the property includes rights to 24 acre Stillwater Lake, where residents enjoy access to a private beach with lifeguard, swimming, boating, kayaking, paddle boarding, and pedal boating in a tranquil natural setting. Conveniently located near major parkways, shopping, and scenic hiking and walking trails, this property combines privacy, space, and accessibility. With great bones, abundant living space, and exceptional outdoor amenities, this is a wonderful opportunity to create your dream home in a highly desirable setting. There are no audio recording devices inside this property.

10 Lakeview Road, Ossining

$1,750,000

9 Beds ⋅ 8 Baths ⋅ 1005133 MLS

Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining

$299,000

4 Beds ⋅ 3 Baths ⋅ 1004901 MLS

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

5 Maria Lane, Ossining

$599,000

3 Beds ⋅ 2 Baths ⋅ 1004276 MLS

Charming Cape Cod on a .23-acre lot in desirable Ossining — comfortable now with plenty of room to personalize. This 3-bedroom, 1.5-bath home offers classic curb appeal, a bright living area, and a flexible layout that adapts to your needs. The spacious yard provides room for gardening, play, or outdoor entertaining. Enjoy easy access to local shops, schools, parks, and commuter routes while making this home your own — whether you prefer simple cosmetic updates or a thoughtful remodel to add value. Move in now and add your finishing touches over time. Schedule a showing today to discover the possibilities.

5 Meadowbrook Drive, Ossining

$1,085,000

4 Beds ⋅ 3 Baths ⋅ 1002953 MLS

Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping, dining, and everyday essentials. The Croton-Harmon Train Station is even closer, while convenient access to Route 9A and the Taconic State Parkway makes commuting throughout Westchester and beyond easily accessible. Thoughtfully redesigned and extensively reconstructed under architectural plans, the home features spacious light-filled living areas, a dramatic vaulted great room ceiling, and an architect-designed wall of glass that brings natural light and the surrounding landscape into the heart of the home. Multiple Marvin door systems were designed to create seamless indoor-outdoor flow and future deck integration. The home was designed with a similar footprint across both levels, resulting in an exceptionally large lower level that dramatically expands the usable space of the home and offers substantial flexibility for workshop space, storage, recreation, future finishing, home business use, gym space, or other expanded uses rarely found in the area. The kitchen and main living spaces were rebuilt from the foundation up during the 2008 reconstruction and create a true chef’s kitchen experience, featuring radiant heated flooring beneath large-format tile, custom-built cabinetry, an oversized 5’ x 7’ island, a large built-in KitchenAid refrigerator, KitchenAid dishwasher, and a Thermador professional oven. The kitchen was intentionally designed with exceptional spacing and flow for cooking, entertaining, and everyday living, creating an openness rarely found in homes of this style. A large high-ceiling lower level was also added during the reconstruction, offering excellent flexibility as a workshop, workspace, storage area, gym, hobby space, or potential future finished area. The lower level also includes a second laundry setup with an additional washer and dryer. The spacious primary suite addition includes a large ensuite bath with jacuzzi tub, oversized shower, and private water closet. A second primary-style bedroom offers its own ensuite bathroom with shower and direct access to the backyard, creating excellent flexibility for guests, extended family, multigenerational living, or private workspace use. A second primary bathroom was also fully renovated in 2025. The rare 4-car tandem garage configuration, expansive multi-driveway parking setup with space for approximately 20 vehicles, and oversized lower level create exceptional flexibility for car enthusiasts, collectors, hobbyists, workshop use, home business needs, or anyone seeking substantial additional storage and utility space rarely found in northern Westchester. Additional highlights include a central vacuum system with multiple in-wall outlets and kitchen kick-plate crumb sweeper, fireplace-ready buildout with propane option, generator-ready electrical infrastructure, alarm system, updated water systems, and numerous structural and mechanical improvements completed over the years. A unique opportunity to enjoy peaceful acreage, architectural character, exceptional utility space, commuter convenience, and a level of flexibility rarely found in one property.

54 Allapartus Road, Ossining

$650,000

4 Beds ⋅ 2 Baths ⋅ 1001998 MLS

Beautiful 4-bedroom, 2 full bath home located on a quiet cul-de-sac in Ossining, offering a comfortable layout and inviting indoor-outdoor living. The main level features an open-concept design connecting the eat-in kitchen and living room, highlighted by modern stainless steel appliances, beautiful moldings, and expansive windows that fill the home with natural light, creating an ideal setting for both everyday living and entertaining. A finished lower level provides additional versatile living space suitable for a family room, recreation area, workspace, fitness setup, or other lifestyle needs. Enjoy outdoor gatherings on the spacious deck overlooking the backyard, along with the convenience of an attached one-car garage. Located within the Ossining Union Free School District and just minutes from downtown Ossining’s restaurants, cafes, waterfront parks, and the Hudson River. Nearby points of interest include Croton Point Park, Teatown Lake Reservation, Louis Engel Waterfront Park, Bethany Arts Community, and the historic Sing Sing Kill Brewery district. Convenient commuter access to Route 9, the Taconic State Parkway, and the Croton-Harmon and Ossining Metro-North stations provides direct service to Grand Central Terminal and easy connectivity throughout Westchester and the Hudson Valley. Call today!

24 Fuller Road, Ossining

$2,295,000

4 Beds ⋅ 4 Baths ⋅ 1002298 MLS

Phase Two at Moradia is now offering a fabulous to-be-built new modern on Lot One. Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is a brand-new community of high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated and private-ranging between 1 1/2 and 3 acres. MIES is the second of three luxury residences to be offered. Set on two acres and encompassing four bedrooms and three and one half bathrooms the house is designed to take advantage of the natural surroundings. Rendered in open plan, the kitchen, dining and living rooms are surrounded by large windows and three outdoor exposures-all centered on a free standing, wood burning fireplace. 9 1/2 to 14 foot ceilings with high clerestory windows and skylights flood the interior with sunlight. A covered deck is adjacent to the living area. High quality finishes include wood clad Andersen windows, Restoration hardware bathroom vanities, Herman Miller lighting, five-panel solid fir interior doors, and five-inch white oak floors. A dedicated laundry closet, kitchen pantry, two-car garage are additional amenities. Designed and built by local Westchester developers, Atelier Atlantic, the new community is conceived as modern homes for the new century. Principals Jennifer and Pascal Smith Couti, who live and work in the Ossining, are leveraging their extensive experience as home designers to bring the project to life and to skillfully integrate the residences into a cohesive and elegant new community. The project is an extraordinary opportunity to fulfill the dream of purchasing a newly-built modern home on a wonderful parcel of beautiful land.

94 Somerstown Road, Ossining

$715,000

2 Beds ⋅ 3 Baths ⋅ 1002512 MLS

Set in Ossining, NY, this Colonial-style home offers the space, layout, and location so many buyers are searching for. A welcoming front porch leads you inside to a foyer opening into the bright living room, where high ceilings and a large bay window create an airy and inviting atmosphere. The open layout continues into the formal dining room, creating a comfortable flow to the eat-in kitchen featuring custom cabinetry, tiled flooring, and peninsula seating, along with direct access to the backyard. Hardwood floors throughout the living and dining areas add warmth and character to the home. A conveniently located half bathroom completes the main level. Upstairs, the second level offers two generously sized bedrooms with custom shelving, hardwood flooring, an office/den, along with a spacious full bathroom. The walk-up attic provides additional space for a home office, playroom, or extra storage. The basement adds even more versatility with a laundry area including washer and dryer, utility space, family room, a full bathroom, and walk-out access. Outside, enjoy a large driveway with parking for 5+ cars, a spacious bluestone patio ideal for gatherings, and a large shed for additional storage. Additional highlights include a Navien hot water system installed in 2024 and a new 200-amp electrical service panel. Conveniently located near downtown Ossining, residents can enjoy nearby restaurants, shopping centers, the Ossining waterfront along the Hudson River, Louis Engel Waterfront Park, the Old Croton Aqueduct Trail, Croton Point Park, and the Ossining Train Station providing an easy commute to New York City.

119 Croton Avenue, Ossining

$1,450,000

4 Beds ⋅ 4 Baths ⋅ 995572 MLS

Set privately on a beautifully landscaped property, this exceptional colonial at 352 Croton Dam Road offers the perfect blend of timeless design, modern updates, and everyday comfort. A grand two-story entry welcomes you into sun-filled interiors featuring hardwood floors, oversized windows, and thoughtfully designed living spaces throughout. The stunning renovated chef’s kitchen is the centerpiece of the home, complete with custom cabinetry, expansive granite countertops, premium stainless steel appliances, designer lighting, and a large center island ideal for gathering and entertaining. The adjoining family room with fireplace creates a warm and inviting atmosphere, while formal living and dining rooms provide elegant spaces for hosting. A versatile first-floor office/playroom with French doors offers flexibility for today’s lifestyle needs. Upstairs, the luxurious primary suite features an expansive bedroom, spa-like bath, and generous closet space. Spacious secondary bedrooms and beautifully updated baths complete the upper level. Outside, enjoy sweeping lawns, mature trees, and a peaceful private setting perfect for outdoor entertaining, play, or simply relaxing in nature. This move-in ready home combines classic colonial charm with sophisticated modern updates, all conveniently located near parks, schools, shopping, dining, and major commuting routes. A rare opportunity to own a turnkey home with space, style, and privacy in one of Westchester’s most desirable settings.

352 Croton Dam Road, Ossining

$749,999

3 Beds ⋅ 3 Baths ⋅ 991726 MLS

Welcome to 22 Quail Hollow Road, a well-maintained 3-bedroom, 2.5-bath Colonial offering 2,354 square feet of living space on a quiet cul-de-sac in Ossining, New York. The main level features a spacious living room with a vaulted ceiling that flows into a family room, kitchen with a breakfast nook and formal dining room creating an open and comfortable setting for everyday living and entertaining. A sliding glass door that opens directly to the deck, extending the living area outdoors for dining and relaxation. The large primary suite is features a walk-in closet and an en-suite bath. Two additional bedrooms and a hall bath complete the bedroom level. Set on a quiet cul-de-sac, the property offers a calm residential setting with the convenience of nearby amenities. This home is close to local parks and nature preserves, including Teatown Lake Reservation, offering access to hiking trails and outdoor activities. Transportation options, major roadways, and nearby train service provide connectivity to surrounding Westchester communities and beyond.

22 Quail Hollow Road, Ossining

$450,000

3 Beds ⋅ 1 Baths ⋅ 995689 MLS

20 Samstag Ave is the kind of home that sparks ideas the moment you enter. Tucked into an established Ossining neighborhood just minutes from the Hudson River, this classic 2-story Cape-style home with charming dormers and a cheerful red-painted front porch is ready for its next chapter, and for the right buyer, that chapter could be something special. Inside, three bedrooms, a full bath, and 930 square feet of light-filled living space stretch across two levels. The walls have stories to tell, the spaces invite imagination, and every room offers an opportunity to restore, reinvent, or simply bring fresh life to what is already here. The standout living room features warm knotty-pine wood paneling and an incredible mid-century modern built-in shelf and wall divider that feels straight out of another era. It's the kind of architectural detail you simply cannot recreate with a quick trip to a big box store. The kitchen offers a more updated counterpoint with maple-tone cabinetry, a gas range, and tile flooring that flows through the main level, while the upstairs bedrooms tuck under classic Cape sloped ceilings, ideal as cozy retreats or a quiet home office. Outdoors, one of the home's most surprising gifts comes into view: a generous, fully fenced backyard with mature shade trees, a level lawn, and a private rear entry. It's a rare bonus at this price point and a versatile space for entertaining, gardening, or simply enjoying the outdoors. The basement adds another layer of potential. Whether the vision is a workshop, studio, recreation space, or simply more room to spread out, the opportunity is there for someone willing to bring it to life. The location does a lot of the heavy lifting, too. Ossining is one of the Hudson Valley's most loved river towns and one of the smartest commutes north of the city. The Croton Metro-North and other stations on the Hudson Line are just a short drive away, putting Grand Central roughly 45 to 55 minutes from your front door, making this an ideal opportunity. Downtown Ossining is minutes from the house, with its growing roster of restaurants, cafes, and shops, the Sing Sing Kill Greenway, and Louis Engel Waterfront Park where the Hudson and the Palisades stretch out in front of you. Weekends nearby look like the Old Croton Aqueduct trail, Teatown Lake Reservation, Rockefeller State Park Preserve, and the antique-and-eatery rhythm of neighboring Croton-on-Hudson and Sleepy Hollow. For buyers who appreciate homes with character, history, and room to create something personal without giving up an easy commute to NYC, 20 Samstag Ave offers a rare opportunity to shape a space into something truly your own.

20 Samstag Avenue, Ossining

$880,000

4 Beds ⋅ 3 Baths ⋅ 990966 MLS

Vacation at Home! Gracious 4 bedroom, 2 1/2 bathroom, covered front porch colonial home with a gorgeous in-ground heated pool, located in a non-through street, residential neighborhood in the Town of New Castle section of Ossining. Set far back from the road, this one-acre lot offers a private backyard featuring a huge paver patio, a sprawling lawn and tree-lined backyard, including a Japanese Zen garden, plus the separately fenced pool area. Hardwood floors throughout. Updated kitchen (6 seat breakfast bar, granite counters & stainless steel appliances) and updated bathrooms, windows & central air, plus meticulous maintenance makes for easy living. Propane heats the pool and is for the gas range & dryer, and can be hooked up to the outdoor BBQ too! Nothing to do but pack your bags (don't forget to include a swim suit) and move right in. The 805 SF basement is not included in the SF, but offers great potential. Extra refrigerator in basement included. See special features sheet for additional highlights. Floor plans and PCDS attached as well.

119 Edgewood Road, Ossining

$850,000

2 Beds ⋅ 2 Baths ⋅ 996003 MLS

A Rare 200-Year-Old Log Cabin Sanctuary with Subdivision/Expansion Potential! Step back in time without sacrificing an ounce of modern comfort in this enchanting, hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history, contemporary ease, and incredible future value with a potential buildable lot included. The interior showcases exceptional craftsmanship, featuring original wide-plank wood floors, a majestic stone fireplace, and a genuine Dutch door. The versatile layout includes two bedrooms plus an alcove and 1.5 baths highlighted by a hand-painted sink. A large, vintage-inspired country kitchen serves as the heart of the home, boasting a herringbone-patterned original brick floor, 1940s decor, and modern appliances including a dishwasher and washer-dryer. The exterior is a true nature lover's sanctuary, featuring a cedar shingle roof, a classic porch with Adirondack furniture, and a sophisticated bluestone slate patio. The expansive grounds are home to a picturesque pond and babbling brook that attract magnificent wildlife. While providing total seclusion, this property is remarkably accessible, located just five minutes from the Croton-on-Hudson train station and local supermarkets. Enjoy being minutes away from Hudson River dining, boating, and Teatown Lake Reservation, with an easy commute of less than one hour to New York City and a 50-minute drive to Thunder Ridge skiing. It is located in a Historic area near Old Croton Aqueduct and Senesqua Park. The community offers 17 parks, including a Westchester River Walk, hiking trails, views of the Hudson, and the Haverstraw-Ossining Ferry. Amenities include an indoor town pool, a Farmers Market, and local dining options. Community events include the Hudson River Music Festival and Teatown Annual Hudson River EagleFest.

227 Cedar Lane, Ossining

$1,345,000

4 Beds ⋅ 3 Baths ⋅ 995878 MLS

Beautifully updated center hall Colonial, set on a private and professionally landscaped almost one-acre property on a quiet cul-de-sac in one of Ossining’s most desirable neighborhoods. This move-in ready home blends classic architecture with modern upgrades and a highly functional layout designed for today’s lifestyle. The centerpiece of the home is the newly installed Leicht kitchen, featuring sleek European cabinetry, premium appliances, contemporary finishes, and abundant workspace and storage. The kitchen opens seamlessly to the home’s main living areas, creating an ideal flow for both everyday living and entertaining. Sun-filled interiors include spacious formal living and dining rooms, a welcoming family room with fireplace, and generously sized bedrooms with ample closet space. The primary suite offers a private retreat with an en-suite bath and peaceful views of the surrounding property. Large windows throughout the home bring in natural light and enhance the bright, airy feel of the interiors. Additional features include an unfinished basement offering excellent storage or future expansion potential, as well as a spacious 3-car garage. The expansive level backyard provides exceptional outdoor space for entertaining, recreation, gardening, or future enhancements. Mature trees and established landscaping create a private and tranquil setting while still being conveniently located near shopping, dining, parks, schools, and close to both the Saw Mill and Taconic State Parkways, as well as two Metro-North train stations for an easy commute to Manhattan.

14 Wyche Way, Ossining

$899,000

3 Beds ⋅ 3 Baths ⋅ 986851 MLS

Set on a quiet cul-de-sac with seasonal river views and unforgettable sunsets, this beautifully maintained Colonial offers the perfect balance of style, comfort, and everyday ease. Built in 2004 and gently lived in, the home is filled with natural light, highlighted by high ceilings, generous proportions, and a seamless, inviting flow. The main level features formal living and dining rooms, a powder room, and a bright, functional kitchen that opens to a cozy den with fireplace and sliding glass doors to the deck; perfect for relaxed indoor-outdoor living. A convenient laundry/mudroom connects directly to the two-car garage. Upstairs, the spacious primary suite serves as a private retreat with a spa-like bath, including a jetted tub and separate shower. Two additional large bedrooms, a full hall bath, and a flexible bonus space, ideal for a home office or creative use, complete the second level. The walk-out lower level offers high ceilings, generous storage, sliding doors to the backyard, and plumbing already in place for a future bathroom; ready to be finished to suit your needs. Recent updates include a new driveway, new boiler and hot water heater, new dishwasher, and updated central air. Ideally located near Metro-North, parks, shopping, and everyday conveniences, this move-in ready home delivers space, flexibility, and a setting that truly stands out.

3 Birch Court, Ossining

$599,000

3 Beds ⋅ 3 Baths ⋅ 989545 MLS

A charm-filled village home with river views, timeless details, and the ease of modern updates. This beautiful antique Colonial offers a rare blend of character, light, and convenience. From the moment you arrive, the Hudson River and Palisades set the tone, followed by a welcoming covered front porch and the warmth of beautiful woodwork and period details inside. The main level features an updated kitchen with counter seating, open to a bright breakfast room with walls of windows and access to the patio, along with a living room, reading nook, first-floor bedroom, and full bath. Upstairs, the primary suite offers river views, an updated ensuite bath, and walk-in closet, while a spacious second bedroom, updated hall bath, and second-floor laundry add everyday ease. A sunlit studio with glass doors provides flexible bonus space ready to suit your needs. Thoughtful improvements including updated heating and electrical systems, a new roof, driveway, patio, and retaining walls enhance the home, while lovely gardens and mature fruiting apple, plum, and peach trees add to its special appeal. All just moments from town, train, restaurants, parks, schools, and the farmers market.

41 Clinton Avenue, Ossining

$675,000

3 Beds ⋅ 3 Baths ⋅ 977440 MLS

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

24 Highview Road, Ossining

$1,095,000

5 Beds ⋅ 3 Baths ⋅ 977120 MLS

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

27 Allapartus Circle, Ossining

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