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

$4,350,000
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
$3,100,000
3 Beds ⋅ 5 Baths ⋅ 1019351 MLS
No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and superior hardware throughout. The woods in the house are too numerous to list, but some of them are Mahogany, Red Maple, Pecky Cypress, White Oak, Utile (Mahogany type), Amboyna, Birch, Curly Birch, Bubinga, Red Birch, Maple, Maple Burl, and Walnut. All of the baseboards are double or triple layered with different wood species. All of the light fixtures, window dressings, and appliances stay with the home. The gourmet kitchen contains a steam oven, double drawer freezer full-size refrigerator, built in microwave, warming drawer, six burner stove, double oven, ice maker, separate built-in vacuum cleaning system. Additional square footage is on the basement level. This is a wonderful home surrounded by greenery to entertain guests or enjoy your privacy. Please see video link for a virtual tour.

23 Inningwood 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
$1,350,000
5 Beds ⋅ 4 Baths ⋅ 1034206 MLS
A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details, including wide-plank pine floors, original farm doors, hand-crafted millwork, and three fireplaces. Offering exceptional versatility, the estate is ideally suited as a private country retreat, equestrian property, or multi-generational residence. Set on over five picturesque acres, the grounds are a true sanctuary. Enjoy peaceful mornings on the multi-level stone patios surrounded by mature landscaping and native plantings, or gather with family and friends on the expansive covered front porch. Equestrian enthusiasts will appreciate the six-stall horse barn, multiple paddocks, and riding arena, while the heated 20' x 50' in-ground pool, complete with its own stone patio and custom-built pergola, provides the perfect setting for summer relaxation. Historic stone walls, crafted from stones found on the property, and impressive steps built from reclaimed West Point stone further showcase the estate's remarkable heritage. A gracious front porch welcomes you into the center hall. The main level features a living room with a wood-burning fireplace, an intimate reading room, formal dining room, eat-in kitchen with its own fireplace, powder room, family room, laundry room, and walk-in pantry. The second level features a spacious primary suite, three additional bedrooms, and a full bath highlighted by a timeless clawfoot tub. The approximately 1,200-square-foot finished walk-out lower level offers exceptional flexibility, featuring a spacious living and dining area with wide-plank flooring, a former tiled summer kitchen, two bedrooms with hardwood flooring—one with a fireplace—a storage/mechanical room, and multiple exterior entrances, creating an ideal space for extended family, guests, or a potential mother/daughter arrangement with the appropriate approvals. While this private estate feels like a world away, it is just minutes from the Village of Ossining, the scenic Hudson River waterfront, and an array of restaurants, shops, parks, hiking trails, and recreational activities that make the Hudson Valley such a sought-after destination. Located approximately 45 minutes from New York City, this extraordinary estate presents a rare opportunity to own an authentic piece of American history while enjoying the privacy, beauty, and lifestyle of a truly exceptional country property. Estates of this significance, craftsmanship, and versatility are exceedingly rare and simply cannot be replicated.

15 Inningwood 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
$1,149,000
1048659 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
$1,099,222
1034832 MLS
Exceptional opportunity to own a legal 6-unit multifamily property with stable, long-term tenants. All six units, 4-two bedroom units and 2-three bedroom units, are leased through September 2027, providing immediate, reliable rental income and a strong 7% cap rate. This well-maintained building is ideally situated in a convenient location directly across from Park School and within walking distance to shops, restaurants, the train station, and additional schools, making it an attractive location for tenants. The property's utility setup is designed to help minimize owner expenses. Tenants are responsible for their own gas and electric, while the landlord pays for water. The building features seven electric meters, six gas meters, and six individual water heaters. Street parking is readily available. Whether you're expanding your investment portfolio or seeking a turnkey income-producing property, this is a rare opportunity to acquire a well-maintained asset with dependable cash flow and long-term lease stability. There are no audio recording devices inside this property.

17 19 Edward Street, Ossining
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