Ossining, NY Homes for Sale

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  $1,200,000

  • 5 Beds
  • 3.5 Baths
  • 3,866 Sq Ft

  173B Chappaqua Rd, Briarcliff Manor, NY 10510

  Nestled on a tranquil private road, this stunning Colonial home seamlessly blends timeless elegance with modern comfort. Featuring five spacious bedrooms and four bathrooms with recent upgrades including new roof, HVAC and water heater. This home offers the perfect balance of charm, functionality, and luxury.From the inviting rocking chair front porch to the resort-style backyard, every

  Christine DiChiara Coldwell Banker Realty

  173B Chappaqua Rd, Briarcliff Manor, NY 10510
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  /50

  $750,000

  • 3 Beds
  • 2.5 Baths
  • 1,385 Sq Ft

  21 Tappan Terrace, Briarcliff Manor, NY 10510

  This marvelous house on a quiet cul-de-sac is an absolute gem! With a huge Office/Den and Recreation Room downstairs NOT included in the square footage, this house truly lives like a much larger home than many in this desired neighborhood. These extra spaces also will give any new owner tremendous flexibility to make the home THEIRS, with so many possibilities for comfort and convenience. On the

  Eric Lebenson ERA Insite Realty Services

  21 Tappan Terrace, Briarcliff Manor, NY 10510
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  /27

  $1,350,000

  • 7 Beds
  • 4 Baths
  • 4,800 Sq Ft

  858 Pleasantville Rd, Briarcliff Manor, NY 10510

  Rare Investment Opportunity in Coveted Briarcliff Manor; Welcome to this exceptional multi-family home located in the highly desirable village of Briarcliff Manor, offering both a strong income-producing investment and the potential to live in one unit while collecting rental income from the others. Located within the award-winning Briarcliff Manor School District, this property presents a unique

  Nancy Beard Houlihan Lawrence Inc.

  858 Pleasantville Rd, Briarcliff Manor, NY 10510
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  /15

  $495,000

  • 4 Beds
  • 1 Bath
  • 1,268 Sq Ft

  35 Ann St, Ossining, NY 10562

  Charming Colonial in Prime Ossining Location!Welcome to this well-maintained single-family Colonial nestled in the heart of Ossining, NY. This inviting home offers 4 spacious bedrooms and 1 full bathroom, with the convenience of a first-floor bedroom—perfect for guests or flexible living arrangements.Located in a great neighborhood, this property combines classic charm with modern

  Chaim Lebrecht eRealty Advisors, Inc

  35 Ann St, Ossining, NY 10562
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  /15

  $565,000

  • 4 Beds
  • 2 Baths
  • 1,560 Sq Ft

  37 Ann St, Ossining, NY 10562

  Opportunity Knocks in Ossining, NY!Don’t miss this incredible investment opportunity in a sought-after location! This income-producing 2-family home offers a steady revenue stream and is priced to sell. Whether you're a savvy investor or a first-time buyer looking to live in one unit and rent the other, this property delivers.Located in the heart of Ossining, close to transportation,

  Chaim Lebrecht eRealty Advisors, Inc

  37 Ann St, Ossining, NY 10562
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  $698,000 Open Sat 11AM - 1PM

  • 4 Beds
  • 3 Baths
  • 1,932 Sq Ft

  18 Jenkins Ct, Ossining, NY 10562

  Tucked away at the end of a quiet cul-de-sac, this charming Cape cod is the kind of home that just feels good from the moment you arrive. With 4 bedrooms, and 3 full bathrooms, there’s plenty of room to spread out, grow, and make lasting memories. Step inside through a stylish glass-paneled front door and into a sunlit foyer that sets the tone for the rest of the house. The kitchen—spacious and

  Eva Casoria eXp Realty

  18 Jenkins Ct, Ossining, NY 10562
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  /45

  $945,000

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft

  15 Deertree Ln, Briarcliff Manor, NY 10510

  Welcome home to the charming and historic village of Briarcliff Manor in the Rivertowns of Northern Westchester! A highly desirable Wyndcrest community within the Briarcliff School District and in a very convenient location. The building structures feature a classic exterior and geometric elements in the interior, situated in a cul-de-sac with scenic views of rock and mountains within the

  Iris Lu-Notis Coldwell Banker Realty

  15 Deertree Ln, Briarcliff Manor, NY 10510
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  $506,000 Open Sun 12PM - 2PM

  • 2 Beds
  • 2 Baths
  • 1,283 Sq Ft

  83 Hudson Point Ln, Ossining, NY 10562

  Welcome to your next home - a stylish 2-bedroom condo where modern living meets comfort, and where your four-legged family members are warmly welcomed! Hudson Point is a lovely pet friendly complex overlooking the historic Hudson. Enjoy stunning sunsets in this 2 bedroom, 2 bath end unit with partial seasonal river views. Step inside and discover an open-concept living space filled with natural

  Luba Sydor Houlihan Lawrence Inc.

  83 Hudson Point Ln, Ossining, NY 10562
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  $699,000

  • 5 Beds
  • 3 Baths
  • 2,100 Sq Ft

  20 Pine Ave, Ossining, NY 10562

  This huge 5-bedroom, 3-bathroom home, is beautifully maintained and tucked away on a quiet, tree-lined residential street in the heart of Ossining has 2 bedrooms conveniently located on the main level for folks not wanting to walk up steps, guest accommodations, or a private home office setup.Even more room downstairs, the fully renovated basement which has a separate entrance and full

  Marc Giles eXp Realty

  20 Pine Ave, Ossining, NY 10562
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  /20

  $670,000

  • 3 Beds
  • 2 Baths
  • 1,604 Sq Ft

  5 Sabrina Ln, Ossining, NY 10562

  Beautifully maintained raised ranch nestled in a quiet Ossining Neighborhood-just minutes from Hudson River trails,local parks,and Metro North.Whether you’re commuting to NYC or escaping into nature,this home offers the best of both worlds.Featuring:3 bedrooms,2 full bathrooms,1,604 sqft interior on a 7,405 sqft lot.large kitchen,finished basement with laundry.2 car garage,long driveway,Built in

  Brad Turner AVWAR Realty

  5 Sabrina Ln, Ossining, NY 10562
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  /5

  $599,000

  • 3 Beds
  • 1 Bath
  • 1,276 Sq Ft

  14 Gates Ave, Ossining, NY 10562

  Welcome to 14 Gates Avenue, a unique opportunity in the heart of Ossining. This charming single-family home is being sold as-is, offering endless potential for renovation, expansion, or investment. Included in the sale is a valuable additional parcel of land, providing added privacy, space, or future development possibilities.Set on a quiet, tree-lined street, this property features a classic

  Tim Rothman Compass Greater NY LLC

  14 Gates Ave, Ossining, NY 10562
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  $650,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  23 Ann St, Ossining, NY 10562

  TWO FAMILY HOME - FULLY AVAILABLE - temp off market 100% renovation. Quality materials and workmanship. First level has 2 Br, second floor has 2 large Br and one small one. The attic is a big walk up finished storage area. Newer boiler and oil tank. Short walk to everything that makes Ossining a great place to live. Coffee Shops, Farmers Market, restaurants', Fairs, Festivals, River Front

  Eric Schatz Schatz Realty Group

  23 Ann St, Ossining, NY 10562
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  $699,000 Open Sat 1PM - 2:30PM

  • 5 Beds
  • 3 Baths
  • 2,000 Sq Ft

  33 Ann St, Ossining, NY 10562

  Two-Family Home!! Here is a wonderful opportunity for a picturesque Colonial home near the Hudson River in desirable Ossining. Originally built in 1902, the charming clapboard property with its cute green shutters has since been expanded and is currently configured as a two-family residence. The possibilities are endless!The home presents beautifully with its postcard-perfect fenced

  Matthew Bizzarro Bizzarro Agency, LLC

  33 Ann St, Ossining, NY 10562
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  $1,499,000

  • 3 Beds
  • 3.5 Baths
  • 4,300 Sq Ft

  383 Illington Rd, Ossining, NY 10562

  Welcome to 383 Illington Road – an amazing, oversized 3 bedroom colonial that lives like a 4 bedroom, with 10 foot ceilings, nestled on over 5 acres of picturesque, level land in the highly sought-after Yorktown Central School District. This exceptional property offers privacy, space, and convenience, including an additional lot with an adorable treehouse for everyone to enjoy. All just minutes

  Annette Cicinelli Keller Williams Realty Partner

  383 Illington Rd, Ossining, NY 10562
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  $928,000

  • 2 Beds
  • 3.5 Baths
  • 2,745 Sq Ft

  17 Deertree Ln, Briarcliff Manor, NY 10510

  Welcome to this move-in ready end-unit townhome that lives like a 3 bedroom in the highly sought-after Wyndcrest community, crafted by GDC, in the charming village of Briarcliff Manor. Designed with a modern aesthetic and a thoughtful layout, this home offers comfort, style, and convenience in equal measure. The beautifully updated eat-in kitchen features granite countertops, a classic tile

  Suzan Zeolla Houlihan Lawrence Inc.

  17 Deertree Ln, Briarcliff Manor, NY 10510
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  /24

  $514,999

  • 2 Beds
  • 2.5 Baths
  • 1,265 Sq Ft

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510

  Welcome to 608 Kemeys Cove, a beautifully maintained 2-bedroom, 2.5-bathroom duplex condominium nestled in the sought-after Kemeys Cove community in Briarcliff Manor. Step inside to a spacious and thoughtfully designed layout that flows seamlessly between the living, dining, and kitchen areas—ideal for today’s lifestyle. The primary bedroom suite offers a serene retreat with a private bathroom

  Kareem Kirby Keller Williams Realty NYC Grp

  608 Kemeys Cove Unit 6-08, Briarcliff Manor, NY 10510
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  $829,000

  • 3 Beds
  • 2.5 Baths
  • 2,741 Sq Ft

  401 Glenwood Dr, Briarcliff Manor, NY 10510

  Welcome to this inviting end unit townhome in the coveted Scarborough Glen community, offering a harmonious blend of space, style, and convenience. This residence boasts four fully finished levels and a serene, private wooded backyard. The sun-drenched, open-concept living and dining area is adorned with elegant hardwood floors, a cozy gas fireplace, and seamless access to a spacious private

  Stephen Lasko Compass Greater NY, LLC

  401 Glenwood Dr, Briarcliff Manor, NY 10510
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  /30

  $1,899,000

  • 5 Beds
  • 3.5 Baths
  • 4,034 Sq Ft

  205 River Rd, Briarcliff Manor, NY 10510

  Welcome to 205 River Road, a rare opportunity to own a fully renovated luxury home in Westchester County with breathtaking Hudson River views. This 5-bedroom, 3.5-bath colonial sits on a beautifully landscaped large lot in Briarcliff Manor’s highly desirable River Road neighborhood overlooking the majestic Hudson River, a quiet, tucked-away setting known for its natural beauty, privacy, and

  Lindsay DiLoreto Houlihan Lawrence Inc.

  205 River Rd, Briarcliff Manor, NY 10510
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  $549,999

  • 2 Beds
  • 2.5 Baths
  • 1,444 Sq Ft

  50 Snowden Ave, Ossining, NY 10562

  Welcome to 50 Snowden Avenue, Ossining, NY, a distinguished end unit nestled in the heart of Westchester County. This property offers a harmonious blend of comfort and convenience, making it an ideal choice for discerning buyers. With 1,990 square feet of thoughtfully designed living space, this home features two bedrooms and two and a half bathrooms, including a spacious master suite that

  Cynthia Geiger Corcoran Legends Realty

  50 Snowden Ave, Ossining, NY 10562
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  /30

  $775,000

  • 3 Beds
  • 2 Baths
  • 2,658 Sq Ft

  459 Illington Rd, Ossining, NY 10562

  Yorktown School District – Charming Colonial in Sought-After Teatown Neighborhood.Move right into this charming three-bedroom colonial, beautifully situated in the highly desirable T-Town neighborhood. Set on two serene, park-like acres with protected, undeveloped land directly across the road, this home offers both privacy and natural beauty. The spacious interior includes a large eat-in

  Jonathan Gumowitz Coldwell Banker Signature Prop

  459 Illington Rd, Ossining, NY 10562
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  /19

  $280,000

  • 3 Beds
  • 2 Baths
  • 1,047 Sq Ft

  129 S Highland Ave Unit C-2, Ossining, NY 10562

  This beautifully spacious renovated co-op unit offers 3 bedroom, 2 full bath an open floor plan for easy living. Located in much desirable Highland Terrace community. Well maintained curb appeal landscaping. This unit offers beautiful vinyl floors throughout the unit and sun filled windows. Living room is complimented with private patio and garden for outdoor living to experiencing the natural

  Linda Williams Century 21 Alliance Realty Grp

  129 S Highland Ave Unit C-2, Ossining, NY 10562
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  $700,000

  • 4 Beds
  • 3.5 Baths
  • 2,900 Sq Ft

  11C Piping Rock Dr, Ossining, NY 10562

  Nestled at the end of the serene and private Piping Rock Drive, this stunning colonial home offers a perfect blend of elegance, comfort, and convenience. As you approach, the expansive driveway ensures ample parking, while the attached one-car garage provides seamless access to the property. To the side of the garage, a charming, covered patio invites you to enjoy morning coffee or unwind in the

  Paige Castiello Keller Williams Realty Group

  11C Piping Rock Dr, Ossining, NY 10562
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  $675,000

  • 4 Beds
  • 2 Baths
  • 1,408 Sq Ft

  58 Yale Ave, Ossining, NY 10562

  Exceptional Two-Family Opportunity in Ossining, NY! This versatile property offers a fantastic chance for first-time buyers or investors to maximize their investment. With one unit freshly vacated, move right in and rent out the second to help cover your mortgage. The home features an attached two-car garage, providing ample parking and storage space. What truly sets this property apart is the

  Chaim Lebrecht eRealty Advisors, Inc

  58 Yale Ave, Ossining, NY 10562
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  /19

  $529,000

  • 2 Beds
  • 2.5 Baths
  • 1,102 Sq Ft

  88 Broadway Unit 4, Ossining, NY 10562

  Experience the perfect blend of historic charm and modern comfort in this sun-drenched 2 bed, 2.5 bath condo located in a beautifully converted antique schoolhouse. This distinctive residence pairs original architectural character with contemporary finishes. Soaring vaulted ceilings with exposed beams and oversized windows flood the space with natural light, enhancing the open, airy ambiance. The

  Sandra Santos-Lacey Coldwell Banker Realty

  88 Broadway Unit 4, Ossining, NY 10562
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  $1,223,000

  • 4 Beds
  • 3 Baths
  • 2,950 Sq Ft

  320 Illington Rd, Ossining, NY 10562

  Kitchawan Farmhouse built approx. 1850 featuring all up-to-date amenities. Stylish Kitchen w/cherry wood cabinetry, granite counters, Wolf gas stove, Subzero Refrigerator. & additional 2 refrigerator draws in cabinets.. Enter the Formal Dining Room and extra large Living Room with wood burning original fireplace and freshly stained & polished wide plank floors. Continue on to the Family Room,

  Janet Auer Coldwell Banker Realty

  320 Illington Rd, Ossining, NY 10562
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  $549,000 Open Sun 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,488 Sq Ft

  16 Forest Ave, Ossining, NY 10562

  Welcome to 16 Forest Avenue, an elegant retreat nestled in the charming enclave of Ossining, NY. This beautifully appointed residence offers an exquisite blend of sophistication and comfort across a generous 1,488 square feet.Step inside and be greeted by gleaming hardwood floors that lead you through a spacious layout featuring four well-appointed bedrooms and two pristine bathrooms.

  Korab Krasniqi Compass Greater NY, LLC

  16 Forest Ave, Ossining, NY 10562
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  /46

  $6,400,000

  • 11 Beds
  • 6.5 Baths
  • 9,481 Sq Ft

  335 Croton Dam Rd, Ossining, NY 10562

  Nestled in the heart of the picturesque Hudson Valley, this stunning Tudor-style mansion is a true dream estate. Boasting an impressive 9,481 sq ft of living space, this magnificent property is situated on 50 acres of meticulously landscaped gardens, making it one of the most sought-after locations in the county.The estate features a 3-acre lake with a charming boathouse, a sparkling pool, a

  Dalia Valdes Julia B Fee Sothebys Int. Rlty

  335 Croton Dam Rd, Ossining, NY 10562
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  /17

  $440,000

  • 1 Bed
  • 1.5 Baths
  • 1,064 Sq Ft

  10 Sparta View Unit 30, Ossining, NY 10562

  Perfectly maintained townhouse in the Liberty Knoll complex, offering a modern touch with peaceful living. Hardwood flooring, recessed lighting, custom California closet, full half bath, private laundry. The lower levels offers more space as a finished rec room with hardwood flooring, office or possible bedroom. Leading to a walkout patio and backyard offers awesome and peaceful relaxation. It

  Amarish J. Khan Apollo Real Properties, Inc.

  10 Sparta View Unit 30, Ossining, NY 10562
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  /36

  $475,000

  • 3 Beds
  • 1 Bath
  • 1,526 Sq Ft

  25 Belleview Ave, Ossining, NY 10562

  Choose your Hudson view from your front porch or second floor enclosed balcony in this superb village stunner. This 3 bedroom home has preserved its vintage charm, thanks to the owner's care, with an attractive and artistic color scheme, hardwood floors, sconce lights, and artisan early 20th century millwork. The kitchen has a breakfast bar, and a pass through to the formal dining room,

  J. Philip Faranda Howard Hanna Rand Realty

  25 Belleview Ave, Ossining, NY 10562
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  /2

  $3,000,000

  • Land
  • 6 Acres
  • $506,757 per Acre

  0 van Wyck St Unit KEY834077, Ossining, NY 10562

  Property located at Snowden Avenue & van Wyck Street. Site plan approval required. Plans available to review see attached flyer.Planned and designed for 48 unit four story building with views of Hudson River. 36 two bedroom & 16 one bedroom. Roof-top terrace overlooking the Hudson River, swimming pool, fitness area, pedestrian path connecting Van Wyck Street through the site and

  Barry Synnott Coldwell Banker Realty

  0 van Wyck St Unit KEY834077, Ossining, NY 10562
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  /5

  $279,000

  • Land
  • 0.27 Acre
  • $1,033,333 per Acre

  50 Hunter St, Ossining, NY 10562

  Located in the heart of Ossining, this .27-acre vacant lot offers incredible potential with stunning, unobstructed views of the Hudson River. Situated just moments from the train station, shopping, and dining options, this centrally located property is perfect for a variety of development possibilities (buyers must verify with the town).Whether you're looking to build a luxury single-family

  Debra Tricarico Houlihan Lawrence Inc.

  50 Hunter St, Ossining, NY 10562
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  /49

  $4,300,000

  • 6 Beds
  • 7 Baths
  • 6,571 Sq Ft

  177 Old Briarcliff Rd, Briarcliff Manor, NY 10510

  Welcome to Boxwood: A Timeless RetreatBoxwood offers a unique blend of classic Williamsburg Colonial architecture and thoughtful modern upgrades, creating a warm and inviting home that caters to both comfort and elegance. Situated on 3.895 acres of beautifully maintained grounds, this gated property provides a peaceful escape while remaining functional and accommodating for modern living.The home

  Timothy Hegarty Houlihan Lawrence Inc.

  177 Old Briarcliff Rd, Briarcliff Manor, NY 10510
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  $2,900,000

  • 14 Beds
  • 7.5 Baths
  • 15,530 Sq Ft

  139 Scarborough Rd, Briarcliff Manor, NY 10510

  Seize this rare opportunity to own an iconic estate rich in history, dating back to the 1890s. This distinguished property, known as “The Manor House,” was built for and live in by Walter Law, the founder of The Village of Briarcliff Manor. Constructed on Brier Cliff Farms, originally acquired from James Stillman, then-President of National City Bank (now Citibank), the estate at 139 Scarborough

  Elana Zimmerman Julia B Fee Sothebys Int. Rlty

  139 Scarborough Rd, Briarcliff Manor, NY 10510
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  $750,000

  • 6 Beds
  • 2.5 Baths
  • 3,720 Sq Ft

  33 Ryder Rd, Ossining, NY 10562

  Calling all antique lovers! On the hilltop of Ryder Road in Ossining sits an historic property going back centuries, on the market for the first time in decades. The 33 Ryder Road 1826 farmhouse, claimed to be Ossining's oldest residence by The Citizen Register of 1936, is oozing with original charm, including its huge rocking chair front porch, 7' high ceilings, wide plank hardwood floors and

  Lynn Harmonay North Country Sothebys Int Rlt

  33 Ryder Rd, Ossining, NY 10562
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  /2

  $195,000

  • Land
  • 1.69 Acres
  • $115,385 per Acre

  7 Hawkes Ave, Ossining, NY 10562

  Partially wooded 1.69 acre lot in Ossining.

  Anthony Matra Hudson Edge Real Estate LLC

  7 Hawkes Ave, Ossining, NY 10562
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  /2

  $398,200

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft

  4 William St, Ossining, NY 10562

  The property is occupied so all potential buyers are asked to check with city and tax records to determine actual bedroom, bathroom counts and all details on this property listed above to their satisfaction. This is an AS-IS foreclosed/REO property. Do not disturb occupants or walk on property. Buyers’ premium paid at closing by buyer. *** Seller makes no guarantees about property’s condition,

  Christopher Rose REALHome Services & Solutions

  4 William St, Ossining, NY 10562
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  $350,000

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562

  Inspirational. Awe inspiring. Witness first-hand the most stunning panoramic Hudson River views from EVERY room of this large two-bedroom, two-bathroom coop apartment in exceptional, Scarborough Manor—a gated community in Ossining, NY. This unit has exquisite, unobstructed southern views of one of the most poetically beautiful rivers in the world. The primary bedroom ensuite has its own

  Melissa Terman River Realty Services, Inc.

  16 Rockledge Ave Unit 5B1, Ossining, NY 10562
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  /14

  $265,000

  • 2 Beds
  • 1 Bath
  • 951 Sq Ft

  135 Main St Unit 203, Ossining, NY 10562

  Exciting 2-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. Walk to train, restaurants, stores, farmers market, festivals, waterfront park, community recreation center, library, and more. Cats and dogs friendly (limit 2 per unit)! As an owner, you can obtain a parking permit for both the village and train station. This property is a part of "fair and affordable"

  Igor Krasnoperov Rising Star Realty

  135 Main St Unit 203, Ossining, NY 10562
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  /2

  $446,200

  • 1 Bed
  • 1.5 Baths
  • 1,139 Sq Ft

  14 Bridle Path Rd, Ossining, NY 10562

  Welcome to 14 Bridle Path Road, a condominium with incredible potential in Ossining's sought-after Fox Hill complex. This 1986 built 1 bedroom, 1 and a half bath condo/townhome sits in a wooded quiet community. It will need repairs but has so much potential. Make it your own. Jump on this great deal before its gone! All buyers are responsible to confirm City, County, Zoning, Tax, and other

  Jamarr Zellner REALHome Services & Solutions

  14 Bridle Path Rd, Ossining, NY 10562

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