Ossining Homes for Sale

Ossining, New York Homes for Sale

Ossining is a town that incorporates two villages, one of the same name and part of the village of Briarcliff Manor. Ossining is bordered to the west by the Hudson River, and the north by the Croton River. In 1685, Frederick Philipse bought our town from the Sint Sinck Indians, members of the Wappinger Confederacy. It constituted a part of the Manor of Philipsburg, which extended from Spuyten Duyvil Creek to the Croton River.

Because the last Lord of the Manor, Colonel Frederick Philipse, was a Loyalist during the Revolutionary War, the Manor was confiscated by the State in 1779. Subsequently, many of the former tenants bought their old farms from the State.

In 1813, the Village of Sing Sing was incorporated. In 1845, by an action of the state legislature, a new township was created from the northern part of the Town of Mount Pleasant. On the advice of an eminent Indian authority this new town was christened Ossinsing, a different form of Sing Sing. The next year the name was shortened to Ossining which proved easier to pronounce.

In 1901, local officials changed the name of the village to Ossining to avoid confusing goods made in the village with prison-made products that were at that time allowed to be sold on the open market. The village of Briarcliff, east of the village of Ossining, was settled during the nineteenth century, and was then called Whitson's Crossing after one of the early families. In 1902 it was incorporated as the village of Briarcliff Manor, the name was given to it by Walter W. Law founder and chief landowner.

Due to the history of the village, a number of Ossining structures are on the National Register of Historic Places, and the downtown shopping area is listed as the Downtown Ossining Historic District. In addition, the Sparta neighborhood has been designated a local historic district. Ossining’s role in New York’s heritage has been recognized by its inclusion, as one of only 14 areas, in an Urban Cultural Park System designed to attract visitors to the State.

Present day Ossining is a vital community with a vast range in types of housing, from the very modest to the luxurious estates, and a diversified population enjoying a healthy racial and religious mix. The Village of Ossining is situated within 3 square miles and according to the U.S. Bureau of Census, 2000 census 24,010 reside in this historic village on the Hudson River.

Ossining is ranked the No.2 best community to live in Westchester by Westchester Magazine, based on criteria such as diversity, housing costs, parks & recreation, property tax, proximity to NYC, safety, schools, and proximity to water, Nightlife, Shopping, and Downtown.

Ossining High School's former mascot and team name was the Indian however it is represented by the letter "O", and does not have a mascot after the Riverhawk was disliked by many after it was discovered by students that the Riverhawk is actually a flower and not a bird. This is still the subject of controversy today, and many students still wear old Indians jerseys and wear the headdress to games and pep rallies. 

Town of Ossining: www.townofossining.com
Village of Ossining: www.villageofossining.org
Village of Briarcliff Manor:www.briarcliffmanor.org
Ossining Union Free School District: http://www.ossiningufsd.org
Ossining Historical Society: www.ossininghistorical.org

 

Ossining Homes for Sale

$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
$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
$2,900,000
7 Beds ⋅ 7 Baths ⋅ 942815 MLS
Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country setting less than an hour on the express train from NYC. The main residence features a warm and welcoming checkerbox marble foyer opening to elegant formal rooms, and flowing to a cozy bar and family room overlooking the grounds through walls of windows. A sparkling chef’s kitchen, convenient butler’s pantry, and finely restored period details make the home ideal for both everyday living and entertaining. Upstairs, there is extensive accommodation, including a spacious primary suite with elevated views of the private lake, along with three additional bedrooms and multiple baths. A generous home office and dedicated home theater provide exceptional flexibility for work and leisure. The uppermost floor offers two more expansive bedrooms, or flex space for a creative studio. Beyond the main residence, the estate includes a 5-car garage connected to a stables complex by an elegant breezeway. An additional and completely remodelled 1-bedroom apartment above the stable wing, and a charming separate 2-bedroom stone cottage provide versatility for guests, multigenerational living, or rental/Airbnb income. Landscaped grounds with nature paths, sweeping lawns, and exceptional stonework make this a true retreat. Located in the quaint riverfront community of Ossining, known for its scenic Hudson views, vibrant downtown, and abundant parks and trails, this property offers a rare opportunity to own a thoughtfully preserved and modernized Hudson Valley estate.

83 Somerstown 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
$1,900,000
834077 MLS
Property located at Snowden Avenue & Van Wyck Street. Site plan approval required. Zoning CDD allowing for a multifamily development possibly 48 units. Views of the Hudson River and connecting to the Crawbockie Nature Preserve.

Van Wyck Street, Ossining
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 933442 MLS
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 to-be-built, 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. Masia, is the first of three luxury residences to be offered. Set on two acres and encompassing four bedrooms and three and 1/2 baths, the house is designed all on one level. Rendered in open plan, the kitchen, dining and living rooms are surrounded by floor to ceiling windows and three outdoor exposures-all centered on a free standing, wood burning fireplace. 9 1/2 to 10 1/2 foot ceilings with high clerestory windows and skylights flood the interior with natural light. 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 room, walk-in kitchen pantry, two-car garage and roof top deck are additional amenities. Designed and being 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.

94-3 Somerstown 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
$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
$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
$1,199,000
1002207 MLS
Mixed-use investment opportunity in the heart of Ossining! This commercial property features a restaurant space plus two residential apartments, offering excellent income-producing potential for investors, owner-operators, or those looking to add value over time. The apartments and building require some updating and repairs, and the pricing reflects the current condition, making this a fantastic opportunity to renovate and maximize returns. Conveniently located near shops, restaurants, transportation, and all that Ossining has to offer, this property presents strong upside potential in a desirable and growing river town community. *SOME PHOTOS ARE VIRTUALLY STAGED*

185 Main Street, Ossining
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