Ossining NY Homes For Sale

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Welcome to Ossining, a charming village nestled in Westchester County, New York. Known for its rich history and picturesque landscapes, Ossining offers a perfect blend of small-town charm and modern conveniences.

Located along the Hudson River, Ossining boasts stunning views and a vibrant community. With a variety of local shops, restaurants, and recreational activities, residents enjoy a high quality of life in this bustling village.

Ossining is also home to historic landmarks such as the Sing Sing Prison Museum and the breathtaking Kykuit estate, former home of the Rockefeller family. Outdoor enthusiasts will appreciate the numerous parks and trails in the area, perfect for hiking, biking, and enjoying the natural beauty of the Hudson Valley.

With top-rated schools and a strong sense of community, Ossining is a popular choice for families looking to settle down in a safe and welcoming environment. Easy access to public transportation and major highways makes commuting a breeze, whether you're heading to nearby cities or exploring all that Westchester County has to offer.

Whether you're searching for a cozy cottage or a spacious family home, Ossining has something for everyone. Come discover the beauty and charm of this vibrant village in the heart of Westchester County.

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Latest Ossining Listings

$539,999
1 Beds ⋅ 2 Baths ⋅ 1030990 MLS
Discover your dream home at 93 Bridle Path Road, nestled within the highly sought after Fox Hill Condominiums in Ossining, NY. This charming 2 level townhouse features a spacious 1 bedroom and a versatile loft, perfect for an office or study area. The first level boasts a modern galley kitchen with stainless steel appliances, a cozy living room with a wood burning fireplace, and a dining area that opens to a tranquil deck ideal for relaxing or entertaining. Enjoy the benefits of hardwood floors throughout, recessed lighting, and recently renovated kitchen and bathrooms. With a one car garage and additional driveway space, this property offers both convenience and comfort. Embrace the pet-friendly lifestyle and the serene, park-like setting of Fox Hill, which spans 45 wooded acres and includes amenities such as a pool, tennis court, basketball court, and playground. Located just 30 miles from New York City, with easy access to the Metro North rail line making your commute approximately 55 minutes, this home perfectly balances suburban tranquility with urban convenience. Don't miss the opportunity to make this peaceful retreat your own!

93 Bridle Path Road, Ossining
$950,000
4 Beds ⋅ 3 Baths ⋅ 1023457 MLS
Welcome to 61 Underhill! Expanded in approximately 2008, this spacious home offers far more space than first meets the eye. The substantial rear addition nearly doubled the size of the home, creating a layout that blends the character of the original residence with a newer, expansive living area featuring generous room sizes and an open feel. While the original portion of the home is ready for updating, the addition provides comfortable living today, offering buyers the opportunity to modernize over time while building equity. The thoughtfully designed layout creates two distinct living areas within the home, offering exceptional flexibility for extended family, long-term guests or those simply looking for additional space and privacy. The full unfinished basement offers excellent ceiling height and abundant square footage, presenting outstanding potential for future finished living space, recreation, storage or a workshop. Outside, the terraced backyard features multiple levels, a storage shed and a charming playhouse, offering plenty of outdoor space to restore and personalize. Conveniently located near shopping, restaurants, parks and major commuting routes, this is an excellent opportunity for buyers with vision to unlock the full potential of a home with exceptional space and versatility.

61 Underhill Road, Ossining
$624,000
1029679 MLS
Freshly refurbished and move-in ready, individually owned, Professional Condo! This prime first-floor two unit professional suite, formerly two separate adjacent medical offices, offers a versatile layout perfect for healthcare, therapy, or high-end administrative use. The space features two individual welcoming reception and administrative areas, private offices, a break room, and ample storage. Designed for efficiency, the units include ten office rooms, several equipped with its own sanitary station and two separate reception/waiting rooms for maximum privacy. Use one and lease out the other or bring your entire practice to this new professional location. Situated in a prestigious, high-visibility location, your business will benefit from maximum exposure with signage opportunities directly on busy Route 9. Don’t miss this opportunity to position your practice in one of Ossining’s most accessible and sought-after professional corridors.

100 S Highland, Ossining
$4,500,000
1029548 MLS
An exceptional investment opportunity at 37 Old Albany Post Road in Ossining, New York, featuring three industrial buildings situated on a spacious 1.9416-acre lot. The property comprises approximately 11,600 square feet of building space and is currently configured with five income-producing units, providing a diversified tenant base and multiple revenue streams. Additional income is generated through on-site parking, including a separate parking area with 16 spaces. The property currently produces approximately $30,455 in combined monthly building and parking income, totaling approximately $365,460 annually, with scheduled rent increases offering further income-growth potential. Current annual operating expenses are estimated at approximately $61,109, resulting in a projected net operating income of approximately $304,351. With substantial land, multiple buildings, strong existing cash flow, parking income and future upside, this property presents a compelling opportunity for investors seeking a well-located commercial asset in Westchester County. Bring an offer.

37 Old Albany Post Road, Ossining
$125,000
1 Beds ⋅ 1 Baths ⋅ 1027696 MLS
It's oh so quiet. This High Meadows top floor one bedroom, one bath is fresh and ready to go. Hard wood floors throughout, A sun filled living room with dining nook, new stove and refrigerator, lot's of closet space. A small hall leads to extra closets and the bedroom. High Meadows Cooperative features a common laundry and storage space around the back. 2 playgrounds and a basketball court are available as well. Reserved spot number 5 is a short walk to the door, street parking with permit. This gem is tucked away, off route 9, with easy access and close proximity to shopping, fitness center, trails, public transport, and highways, just 2 miles to the train station. The best of both worlds. Peaceful oasis, and convenient to the business district.

50 Charter Circle Unit #C, Ossining
$899,000
4 Beds ⋅ 3 Baths ⋅ 1027151 MLS
Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless character with modern updates. The main level offers an updated kitchen with granite countertops, stainless steel appliances, a gas Viking stove, laundry, and access to a private backyard. The oversized primary bedroom features elegant arch and tray ceilings. The walk out basement includes a finished recreation room and plenty of storage. The second floor apartment features an updated kitchen, three bedrooms, two full bathrooms, and access to a finished attic with a wainscoted ceiling, providing excellent income potential or additional living space. Conveniently located just 0.5 miles from the Ossining train station and close to downtown restaurants, shops, the farmers market, parks, schools, and major highways. A fantastic opportunity for homeowners and investors alike!

20 Waller Avenue, Ossining
$425,000
2 Beds ⋅ 2 Baths ⋅ 1006040 MLS
This adorable Ossining Schools gem awaits new owners to provide personal touches and TLC. It boast a welcoming entry leading to living room with charming details including arched doorway, built in shelving, and fireplace. Bright airy dining/flex room, 1st floor half bath, eat in kitchen with breakfast nook/ dining area and sliding door to patio. Climb the stairs to enjoy two sunny bedrooms each with double closets, and large full skylit bath including laundry hook up. With so much to offer it’s hard to determine but the best detail of this home may be the expansive private yard ready to become the entertainment center for its new owners. Don't sleep on this amazingly convenient location…less than 1 mile to two train stations (Scarborough and Ossining), 35 min to NYC, walking distance to market, and Ossining village shops. Near to bus, schools and more! This might just be the best deal in town. Apx. $1500 STAR tax saving available. Make your appointment today.

42 Revolutionary Road, Ossining
$625,000
4 Beds ⋅ 3 Baths ⋅ 1027201 MLS
Legal two-family Colonial tucked away on large cul-de-sac adjacent to Ossining's historic Sparta community. Originally built as a two-family (not a conversion), the home offers a practical layout with separate living spaces. The first floor apartment features 1 bedroom and 1 full bath, while the upper apartment spans the 2nd and 3rd floors with 3 bedrooms and 1.5 baths. The upper apartment can be accessed by either: 1) A private exterior staircase. 2) A shared enclosed stairwell with its own exterior entrance and separate lockable doors to each apartment. Whether you're looking for an owner-occupied property with rental income or a solid investment opportunity, this home offers flexibility and strong potential. Conveniently located just around the corner from Sparta Park, .5 miles from the Arcadian Shopping Center and .8 miles from the Scarborough Train Station for an easy commute to Manhattan.

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

42 Pershing Avenue, Ossining
$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
$599,000
3 Beds ⋅ 1 Baths ⋅ 1025170 MLS
This lovingly maintained, one level home offers the ideal location- so convenient to all and a beautiful level backyard....You will be impressed with the very private outdoor space ready for entertaining and warm weather enjoyment -a country neighborhood feel yet only 10 minutes to Metro North station- a 50 min express commute to Grand Central and 2-3 miles to Rt 9/ Taconic Parkway....A warm and welcoming ranch in the wonderful Rivertown of Ossining where comfort, charm, convenience and community come together....This cozy retreat offers spacious living and a dining area that seamlessly connects to the kitchen creating the perfect setting for everyday living and entertaining. Conveniently located first floor bedrooms provide added accessibility and ease. Step outside to a welcoming patio perfect for outdoor living, gardening or simply enjoying your own private oasis. Known for its rich history, vibrant downtown, beautiful river views and breathtaking sunsets, Ossining offers the charm of riverfront living with waterfront parks, scenic walking neighborhoods and vibrant dining and shopping. Nature lovers will appreciate nearby hiking trails, Teatown Nature Preserve, Veterans Park and the Ossining Farmers Market. If you you are looking for a move in condition home, tranquility, the ideal commuter location or a lifestyle that comes with Rivertown living, this home with gas heat/ cooking, town water & sewer could be just what you are looking for!

23 Gates Avenue, Ossining
$419,000
1 Beds ⋅ 1 Baths ⋅ 1025908 MLS
Welcome to Eagle Bay, a sought-after gated community overlooking the Hudson River in Ossining. This beautiful 1st floor unit is freshly painted and offers the perfect combination of privacy, convenience, and resort-style living. Relax on your private deck while enjoying a peaceful natural setting just minutes from Metro-North, shopping, and dining. The bright, open floor plan features hardwood floors throughout and a wood-burning fireplace that creates a warm and inviting living space. The updated eat-in kitchen is appointed with granite countertops, and the bedroom features a walk-in closet while the primary bath offers a relaxing Jacuzzi tub. Additional highlights include an assigned parking space and the washer/dryer in unit. Residents of Eagle Bay enjoy an exceptional lifestyle with outstanding amenities, including a swimming pool, tennis and basketball courts, clubhouse, fitness center, and playground. Ideally located near the vibrant villages of Ossining and Croton-on-Hudson, you'll have easy access to restaurants, shopping, parks, and Metro-North for a convenient commute to New York City.

101 Eagle Bay Drive, Ossining
$160,000
1 Beds ⋅ 1 Baths ⋅ 1024369 MLS
Welcome to this beautifully maintained, pet-friendly 1-bedroom co-op in desirable Ossining, offering the perfect blend of comfort, convenience, and a rare private patio. A spacious foyer welcomes you inside and leads to a thoughtfully designed layout featuring an updated bathroom, a functional kitchen with ample cabinet space, and a generously sized bedroom. The expansive living and dining area provides an ideal setting for both everyday living and entertaining, with a private back door opening directly to your patio, creating a seamless indoor-outdoor lifestyle. Nestled within a well-maintained garden-style community, residents enjoy exceptional amenities including an in-ground swimming pool, basketball court, scenic walking trails, beautifully landscaped grounds, plentiful guest parking, and an assigned parking space conveniently located just steps from the building. Ideally situated just minutes from Metro-North, the Taconic State Parkway, shopping, dining, parks, and the vibrant Ossining waterfront, this home offers the perfect balance of tranquility and accessibility. Whether you're purchasing your first home, downsizing, or searching for a commuter-friendly residence with sought-after outdoor space, this move-in-ready opportunity is one you won't want to miss.

129-3 S Highland Avenue Unit #A2, Ossining
$1,700,000
2 Beds ⋅ 2 Baths ⋅ 1023302 MLS
Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes. Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles of organic architecture, where walls of glass, natural materials, and thoughtful siting dissolve the boundaries between indoors and out. Built from Philippine mahogany, stone, slate, and glass, every detail was carefully considered to create harmony with the surrounding landscape. The result is a 2 bedroom 2 bathroom home that feels remarkably current nearly seventy years later. Inside, soaring glass walls frame the changing seasons while a dramatic stone fireplace anchors the main living space. Original built-ins, slate floors, rich mahogany, and a signature wraparound deck celebrate Henken's vision, while the thoughtfully updated kitchen and recent improvements allow the home to function beautifully for modern living. Designed using passive solar principles decades before sustainability became mainstream, the home captures the low winter sun for natural warmth while deep roof overhangs provide cooling shade throughout the summer additionally geothermal heating, solar, and other thoughtful updates bring modern all-electric comfort to the home. Complementing the main residence is a beautifully reimagined 1,200 square foot studio that expands the property's possibilities. Completely renovated, the space now offers a bedroom, full bath, living area, kitchenette, and a stunning spa-inspired sauna suite finished with terrazzo tile, warm Aspen wood, and premium contemporary materials throughout. Whether used as a guest retreat, artist's studio, wellness space, home office, or income-producing guest accommodation, it offers the same thoughtful design and craftsmanship found in the main home. Recent improvements, including a newly constructed carport, estate-style gravel driveway, high-performance siding, Energy Star windows, updated insulation, and new mechanical connections to the studio, ensure the property is ready for years of effortless enjoyment. The setting is every bit as extraordinary as the architecture. Wander your own seventeen-acre landscape, listen to the year-round stream, or spend the afternoon exploring nearby Teatown Lake Reservation. Just beyond, you'll find some of the Hudson Valley's most celebrated destinations, including Blue Hill at Stone Barns and The Farmer & The Fish. Nearby towns of Ridgefield, Pound Ridge, Katonah and Bedford, offer exceptional dining, galleries, farmers markets, and hiking. Metro-North provides easy access to New York City, making this an extraordinary full-time residence or one of the region's most remarkable weekend escapes. Architecturally significant homes of this caliber rarely become available. This is more than a residence—it's an opportunity to own a living piece of mid-century design history, thoughtfully preserved for the next generation.

1306 Grants Lane, Ossining
$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
$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
$750,000
3 Beds ⋅ 2 Baths ⋅ 1021208 MLS
Welcome to 39 Secor Road. Being sold strictly as-is and as a buy one get one with 37 Secor Road ( offered @ $85K CASH ONLY). You cannot pass on this deal. Get this rare investment opportunity for this two bedroom over 1-bedroom multi- family home that offers street parking or with the purchase of municipal parking pass, tenants can park right behind the building in the municipal lot. This home boasts unobstructed windows of the Hudson River views from both units and the windows in the basement. Priced to be sold as a package with the adjoining Single-family home at 37 Secor road. These two homes are on one deed with two separate tax lots, but they are adjoined with ONE furnace and one oil tank. The single-family home is being sold for cash only while a buyer can obtain financing for the two-bedroom multi-family home. This is an amazing opportunity for a first time or veteran investor. Both units are being sold strictly AS IS but boast two new rooves. The unfinished basement extends the length of both homes. Street parking for the multi-family home, but there is a municipal lot located behind the homes. They are a short distance to the Ossining training station and down-town Ossining alike. Both homes have access to basements. Unfinished basements have windows and exterior access if a buyer would like

39 Secor Road, Ossining
$950,000
4 Beds ⋅ 3 Baths ⋅ 1019889 MLS
Welcome to one of Ossining's most captivating homes, where breathtaking panoramic Hudson River views take center stage. Perfectly positioned on a quiet cul-de-sac in the sought-after Sparta neighborhood, this beautifully updated 4-bedroom, 2.5-bath residence offers an exceptional blend of style, comfort, and unforgettable scenery. From the moment you enter, you're greeted by abundant natural light and spectacular water views from nearly every level. The thoughtfully renovated kitchen flows seamlessly into the main living and dining spaces, while hardwood floors, two fireplaces, and oversized windows create a warm yet sophisticated atmosphere. Wake up to stunning river vistas from the bedrooms, then unwind each evening as the sun sets over the Hudson from your expansive wraparound patio. Designed for both entertaining and everyday living, the outdoor space features a private backyard with a stone fire pit—perfect for gathering with family and friends while enjoying the ever-changing beauty of the river. Located just moments from Sparta Park, the Ossining waterfront, restaurants, shopping, and the Scarborough Metro-North station, this home offers the perfect balance of tranquility and convenience. If you've been searching for a home with truly spectacular water views, timeless charm, and an unbeatable location, this is an opportunity you won't want to miss.

12 Riverview Court, Ossining
$675,000
3 Beds ⋅ 2 Baths ⋅ 1013329 MLS
Make every day, one of leisure and delight. Perched above the Hudson River, discover this impeccably maintained, spacious 3 bedroom, 2 full bath, at the highly coveted Scarborough Manor. High on the 6th floor, this corner unit has 9ft ceiling and oversized rooms, creating a most expansive and tranquil oasis. Its light wood floors, custom blinds/shades, sleek kitchen, and renovated baths mingle luxury with practicality. Best of all, you can enjoy majestic vistas from your private terrace and banquet of large windows. Allow yourself to be treated to a daily lifestyle that nurtures your spirit, as you enjoy the many amenities the complex offers: Clubhouse with fitness center, sauna, billiards, library, ping-pong, and event space • Outdoor Heated Pool surrounded by mature trees with Hudson River views • Beautiful Park-Like Grounds with walking paths and benches • 24/7 Gated Security for peace of mind and to accept your packages • Free Outdoor Parking for all (Indoor parking is wait listed at $85 per month) • Full Generator no power outages. Hallways redecorated one year ago with contemporary wallpaper and carpeting • Unique Features: Convenient laundry on each floor • New HVAC units in LR, Dining Room, and Bedrooms • New windows throughout • New lobby restoration underway • Storage units are on a wait list and the rent is ($30-$50/month). Scarborough Manor offers the best of both worlds – a tranquil, riverside setting with easy access to both the Scarborough and Ossining Metro-North stations, Route 9, and nearby shops and restaurants.

16 Rockledge Avenue Unit ##6E-1, Ossining
$929,000
3 Beds ⋅ 2 Baths ⋅ 1011357 MLS
Why wait for vacation when you can enjoy a retreat-like lifestyle every day? This exceptional, fully renovated Colonial with farmhouse charm is a rare Sears Roebuck Kit House circa 1927, seamlessly blending historic character with modern comforts. Thoughtfully updated throughout, the home features central air conditioning, remote-controlled blinds, renovated baths, and hardwood floors that enhance its timeless appeal. At the heart of the home is a beautifully designed custom kitchen featuring a stunning Viking range, soapstone countertops, and a large maple butcher block island. Whether preparing meals, entertaining guests, or gathering with family, this inviting space is as functional as it is beautiful. The spacious great room offers warmth and character with a wood-burning fireplace, creating a cozy setting for crisp autumn evenings and winter nights. Designed for both relaxation and entertaining, the expansive deck spans the length of the home and overlooks the picturesque barn and tranquil pond, creating a private outdoor oasis with a peaceful, country-inspired feel. The primary suite features custom built-in closets and an en-suite bath with a walk-in shower. Two additional bedrooms and a renovated hall bath complete the second level. The finished third-floor attic provides flexible space ideal for a home office, fitness studio, playroom, or creative retreat. The unfinished stone basement offers abundant storage, a laundry area, and direct access to the attached garage via a convenient walkway. Nestled on one of the area's most scenic and sought-after streets, this special property offers the perfect balance of privacy and accessibility, just minutes from the Taconic State Parkway, Metro-North, shopping, dining, and everyday conveniences. A truly unique opportunity to own a piece of history while enjoying all the comforts of modern living.

28 Inningwood Road, Ossining
$705,000
4 Beds ⋅ 2 Baths ⋅ 1011605 MLS
Beautifully maintained TWO FAMILY DUPLEX in the cherished, historic Sparta district! Each 1000 sq. foot apartment features two bedrooms, one updated bathroom, living room, kitchen, dining room and large bright 4 season sun sunroom. The full, unfinished basement features two laundry stations, one for each unit plus plenty of storage. Additional features include oak hardwood floors, stucco walls & solid wood trim. The shared backyard features a large hardwood deck for outdoor entertaining. Ample driveway and off-street parking. This home is very well-maintained. Apartments may enjoy some updating, but the bones of this beautiful property are excellent. Enjoy this incredible location featuring a short walk to the Arcadian Shopping, the Scarborough-on-Hudson train station to GCS, and the Hudson River Front. It doesn't get better than this! Taxes don't reflect STAR savings of $1,591 if qualified.

321 Spring Street, Ossining
$995,000
1008929 MLS
Site plan approved subdivision on historic Somerstown road in Ossining. Three lots each with a beautiful building site being all sold together. Roughed in driveway will become common drive to three homesites. Great opportunity to build.

94 Somerstown 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
$625,000
3 Beds ⋅ 3 Baths ⋅ 1013828 MLS
A tri-level gem, just minutes from downtown Ossining, this three bedroom home is perfect for those who need more space, but want less maintenance. Park either in the driveway or pull into the garage (with extra storage space). There is additional parking shortly down the street. Entering the home on the first floor, you will find a flexible bonus room, great for storage, an office or more. There are multiple closets here as well. Up one level is the open living and dining room. Centered on a wood-burning fireplace with granite hearth and featuring new floors, this is a wonderful space. There are sliding doors here, out to the rear deck and tree ensconced lawn beyond. The eat-in kitchen is well laid out, with good counter and cabinet space. Off of the kitchen, find the large balcony - a great place to enjoy a cup of tea in the early morning, or something a little stronger at the end of the day. Also on this floor is the hall bathroom and the large laundry closet. Up one more level, we reach the bedrooms. The primary bedroom, with an ensuite bathroom that has a tub and a shower, has a deep walk-in closet. In this room, and every bedroom, natural light shines through oversized windows with views out to trees. The second and third bedrooms share a full hall bath with a tub. In Ossining, there are few options for three bedroom condominiums. The Deerfield community has a beautiful, large pool - a perfect place to sunbathe even if you don't swim. There are also walking trails, easily accessible from this unit. All of this, just a short drive to shopping, restaurants and parks, and easily accessible to commuting by train or highway. What more can you ask for?

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