Ossining, NY Homes

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  /42

  $799,000

  • 4 Beds
  • 3 Baths
  • 1,368 Sq Ft

  143 N Highland Ave, Ossining, NY 10562

  Legal 3-family home, located in the heart of Ossining. Excellent 1st time buyer opportunity to live in one and rent two other units and parking lot to help pay the mortgage or great investment opportunity for passive income and build equity. Prime location-close to all, easy access to transportation, downtown, and Hudson River waterfront.

  

  Abraham Mathew

  CENTURY 21 DAWNS GOLD

  (914) 867-0383

  143 N Highland Ave, Ossining, NY 10562
• Explore Ossining

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  /26

  $4,500 per month

  • 1 Bed
  • 1.5 Baths
  • 1,452 Sq Ft
  • Townhouse for Rent

  8 Davids Ln, Ossining, NY 10562

  Liberty Knoll is a hidden sanctuary nestled in Ossining’s desirable Sparta neighborhood, just steps from the Hudson River. This light-filled 1-bedroom, 1.5-bath townhome offers an open, airy layout that blends contemporary comfort with warm, inviting living. The main level features a spacious living and dining area with an effortless flow for everyday living and entertaining, an updated powder

  

  Sara Reel

  Julia B Fee Sothebys Int. Rlty

  (914) 619-2721

  8 Davids Ln, Ossining, NY 10562
• 

  $2,500,000 Sold Sep 02, 2025

  652 Long Hill Rd W, Briarcliff Manor, NY 10510

  • 5 Beds
  • 5.5 Baths
  • 6,080 Sq Ft
  • Built 1956

  Last Sold Summary

  • 2% Below List Price
  • $411/SF
  • 15 Days On Market

  Current Estimated Value $2,446,561

  Last Listing Agent Jennifer Fischman Houlihan Lawrence Inc.

  652 Long Hill Rd W, Briarcliff Manor, NY 10510
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  Est $178,000 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  121 S Highland Ave Unit 2B, Ossining, NY 10562

  121 S Highland Ave Unit 2B, Ossining, NY 10562
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  /50

  $1,320,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,813 Sq Ft

  11 Knollwood Dr, Ossining, NY 10562

  Accepted offer. Enter through stately stone pillars and wrought iron gates to this exquisite Center Hall Colonial, perfectly set on nearly one acre of stunning, level, and fully fenced property. Every inch of this residence has been thoughtfully designed to offer an extraordinary combination of elegance, comfort, and functionality. The magnificent gourmet kitchen is a chef’s dream, featuring an

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 809-8240

  11 Knollwood Dr, Ossining, NY 10562
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  /37

  $7,000 per month

  • 3 Beds
  • 3.5 Baths
  • 3,112 Sq Ft
  • Condo for Rent

  2 Winterberry Ln, Briarcliff Manor, NY 10510

  Beautifully renovated 3–4 bedroom townhouse located in a peaceful community with a pool and basketball court. The home features an open layout with high ceilings, a loft overlooking the living and dining areas, and a skylight that fills the space with natural light. A cozy wood-burning fireplace adds warmth and charm. The first floor includes a bedroom with its own en-suite bathroom—perfect for

  

  Anil Soman

  Houlihan Lawrence Inc.

  (914) 677-2891

  2 Winterberry Ln, Briarcliff Manor, NY 10510
• 

  $510,000 Sold Sep 26, 2025

  8 Samstag Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,031 Sq Ft
  • Built 1922

  Last Sold Summary

  • 2% Above List Price
  • $495/SF
  • 105 Days On Market

  Current Estimated Value $505,706

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
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  Est $888,144 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 3,240 Sq Ft

  23 Mystic Dr, Ossining, NY 10562

  23 Mystic Dr, Ossining, NY 10562
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  /42

  $1,395,000

  • 4 Beds
  • 3 Baths
  • 2,564 Sq Ft

  270 Law Rd, Briarcliff Manor, NY 10510

  Classic Colonial ideally situated on one of Briarcliff Manor's most desirable streets, offering privacy, warmth, and timeless appeal. Lovingly maintained by the original owners, this 4-bedroom, 3-full-bath home is set in a very private location with a wooded backyard and close proximity to a cul-de-sac. Sun-filled interiors feature hardwood floors throughout, fireplaces in the living room and

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 685-8476

  270 Law Rd, Briarcliff Manor, NY 10510
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  /97

  $2,995 - $4,895 per month

  Harbor Square

  1 - 2 Beds

  3 Westerly Rd, Ossining, NY 10562

  1 month free on select units.

  3 Westerly Rd, Ossining, NY 10562
• 

  $1,210,000 Sold Sep 19, 2025

  32 Waterview Dr, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 3,246 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Above List Price
  • $373/SF
  • 34 Days On Market

  Current Estimated Value $1,162,680

  Last Listing Agent Eric Lebenson ERA Insite Realty Services

  32 Waterview Dr, Ossining, NY 10562
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  Est $711,000 Not Listed For Sale

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

  16 Rockledge Ave Unit 7J-2, Ossining, NY 10562

  16 Rockledge Ave Unit 7J-2, Ossining, NY 10562
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  /50

  $829,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,030 Sq Ft

  6 Ichabod Ln, Ossining, NY 10562

  Over $200,000 in updates since 2019 - Swim/Spa, Railing, Chimney, Attic and Garage Insulation, Bathrooms, Towel Warmer, Washer/Dryer, Gutters Lighting and Fixtures, Basement, Septic System, Deck and Stairs, Refinished Closets, Generator connection, Driveway Sealing, Sub Sewage Pump, Tree removal, Landscaping, Playground, Stove, Microwave, Dishwasher

  

  Joseph Iannibelli

  Keller Williams NY Realty

  (914) 814-6897

  6 Ichabod Ln, Ossining, NY 10562
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  /10

  $2,300 per month

  • 1 Bed
  • 1 Bath
  • 2,588 Sq Ft
  • Apartment for Rent

  43 Linden Ave Unit 1L, Ossining, NY 10562

  Charming One-Bedroom Rental in the Village of Ossining Spacious one-bedroom rental located in the Village of Ossining, featuring an updated kitchen with new appliances, new flooring, and fresh paint throughout. The unit includes a full bathroom and a welcoming entry area that can comfortably be used as a living space. All utilities are included, along with one dedicated parking space for added

  Aiman Haddadin Century 21 Alliance Realty Grp

  43 Linden Ave Unit 1L, Ossining, NY 10562
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  $379,000 Sold Nov 25, 2025

  16 Rockledge Ave Unit 7D1, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,284 Sq Ft
  • Built 1970

  Last Sold Summary

  • $295/SF
  • 18 Days On Market

  Last Listing Agent Sarah Mirza Mulhall Julia B Fee Sothebys Int. Rlty

  16 Rockledge Ave Unit 7D1, Ossining, NY 10562
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  94 Charter Cir Unit 94, Ossining, NY 10562

  94 Charter Cir Unit 94, Ossining, NY 10562
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  /10

  $4,000,000 Pending

  • Land
  • 15.55 Acres
  • $257,235 per Acre

  620 Sleepy Hollow Rd, Briarcliff Manor, NY 10510

  Discover the potential of 620 Sleepy Hollow Rd, an expansive 15.55-acre parcel of raw land in the picturesque Briarcliff Manor. This unique property offers a rare opportunity for buyers seeking to create their dream estate or invest in a prime location. With over 677,358 square feet, this lot provides ample space for various development possibilities, whether you envision a private residence, a

  

  Peter Raider

  Real Broker NY LLC

  (914) 928-2662

  620 Sleepy Hollow Rd, Briarcliff Manor, NY 10510
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  /14

  $2,400 per month

  Audubon Living

  1 Bed

  38 1/2 Wolden Rd, Ossining, NY 10562

  Audubon Living is located in Ossining, a beautiful Rivertown in Northern Westchester. The property offers close proximity to Metro North and major highways for convenient commuting. Audubon Living is located in the residential area of Ossining, close to the High School, and a short distance from downtown, which offers many local restaurants, brewery, and the historical Aqueduct Trail. There are

  38 1/2 Wolden Rd, Ossining, NY 10562
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  $640,000 Sold Aug 18, 2025

  107 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,246 Sq Ft
  • Built 1996

  Last Sold Summary

  • 2% Above List Price
  • $285/SF
  • 12 Days On Market

  Current Estimated Value $650,386

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  107 Glenwood Dr, Briarcliff Manor, NY 10510
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  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft

  338 N State Rd Unit 3F, Briarcliff Manor, NY 10510

  338 N State Rd Unit 3F, Briarcliff Manor, NY 10510
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  /27

  $199,900 Pending

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562

  Discover this charming, updated two-bedroom co-op in highly sought-after Highland Terrace. This unique unit offers the convenience of both a main building entrance and its own private entry. Inside, you'll find a spacious and bright primary bedroom with ample closet space, while the versatile second bedroom That is currently being utilized as a home office. Abundant windows fill the living areas

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 483-3103

  135 - 6 Highland Ave S Unit D1, Ossining, NY 10562
• 

  

  /22

  $1,700 per month

  • 1 Bath
  • 730 Sq Ft
  • Apartment for Rent

  175 Main St Unit 2R, Ossining, NY 10562

  Bright, sun-filled, industrial-style second-floor walk-up (no elevator) studio within the Downtown Ossining Historic District— an ideal blend of comfort, convenience, and Hudson Valley charm. This open-plan unit features large windows, a kitchenette, three-quarter bathroom and storage space. Conveniently located near shops, restaurants, cafes, parks, and the Ossining waterfront;

  Lindsey Green Houlihan Lawrence Inc.

  175 Main St Unit 2R, Ossining, NY 10562
• 

  $845,000 Sold Oct 07, 2025

  31 Murray Ln, Ossining, NY 10562

  • 3 Beds
  • 4 Baths
  • 2,068 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Above List Price
  • $409/SF
  • 15 Days On Market

  Current Estimated Value $814,832

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

  31 Murray Ln, Ossining, NY 10562
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  14 Charter Cir, Ossining, NY 10562

  14 Charter Cir, Ossining, NY 10562
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  /43

  $775,000

  • 3 Beds
  • 1.5 Baths
  • 2,151 Sq Ft

  7 Bracken Rd, Ossining, NY 10562

  A great place to call home, this raised ranch–style home sits on 0.52 acres and provides inviting living spaces in Ossining, just outside the town center. The foyer leads into a spacious living room with a large bay window that fills the space with natural light. An open layout leads into the formal dining room and continues into a four-season sunroom with oversized windows overlooking the

  Ana Bermeo Keller Williams Realty Partner

  7 Bracken Rd, Ossining, NY 10562
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  /24

  $1,839 - $3,400 per month

  Cortlandt Living

  Studio - 4 Beds

  24 Claremont Gardens, Ossining, NY 10562

  More than an apartment community, Cortlandt Ridge is your home. We offer affordable one, two, three, and four apartments and townhomes for rent in central Ossining, NY, near North Highland Avenue. Our homes are unique. Not only are they comfortable, they're stylish, too. Fully equipped featuring new kitchens and designer cabinetry. We have just what you need to live well in Westchester

  24 Claremont Gardens, Ossining, NY 10562
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  $1,225,000 Sold Nov 14, 2025

  106 Mystic Dr, Ossining, NY 10562

  • 3 Beds
  • 3.5 Baths
  • 3,638 Sq Ft
  • Built 1998

  Last Sold Summary

  • 11% Above List Price
  • $337/SF
  • 9 Days On Market

  Last Listing Agent Jody Toth Corcoran Legends Realty

  106 Mystic Dr, Ossining, NY 10562
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  310 N State Rd Unit 1C, Briarcliff Manor, NY 10510

  310 N State Rd Unit 1C, Briarcliff Manor, NY 10510
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  /35

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,418 Sq Ft

  110 Morningside Dr, Ossining, NY 10562

  Welcome Home and discover this charming ranch-style residence nestled in one of Ossining’s most sought-after neighborhoods. Surrounded by nature and set on nearly an acre (0.85 acres) of beautifully landscaped property, this Single Family home offers comfort with 3 beds and 2 baths, lives like 2,000+ sq/ft with finished Basement, 2+ Car Garage, privacy, and timeless appeal.Enjoy a sun-filled

  Luis Morgado HomeSmart Homes & Estates

  110 Morningside Dr, Ossining, NY 10562
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  /29

  $5,500 per month

  • 4 Beds
  • 3.5 Baths
  • 2,297 Sq Ft
  • Townhouse for Rent

  305 Glenwood Dr Unit 3-3, Briarcliff Manor, NY 10510

  Welcome to 305 Glenwood—an updated 4-bedroom, 3.5-bath townhome located in the highly desirable Scarborough Glen community. Enter through the front door or the attached garage into a welcoming foyer that leads to the beautifully updated eat-in kitchen featuring shaker cabinets, stainless steel appliances, and a comfortable breakfast area. This level also includes a powder room, a formal dining

  Carolyn Constantine Coldwell Banker Realty

  305 Glenwood Dr Unit 3-3, Briarcliff Manor, NY 10510
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  $1,025,013 Sold Sep 05, 2025

  144 Hungerford Rd N, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2.5 Baths
  • 2,416 Sq Ft
  • Built 1998

  Last Sold Summary

  • 5% Above List Price
  • $424/SF
  • 13 Days On Market

  Current Estimated Value $1,011,414

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  144 Hungerford Rd N, Briarcliff Manor, NY 10510
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  43 Charter Cir, Ossining, NY 10562

  43 Charter Cir, Ossining, NY 10562
• 

  

  /22

  $675,000 Pending

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  19 Donald Ln, Ossining, NY 10562

  Located along a peaceful cul-de-sac in Ossining, there is a quiet grace to 19 Donald Lane. This beautifully maintained home welcomes you with sun-filled rooms and a sense of calm. As you walk up the new flagstone walkway and enter through the front door, you're greeted by the spacious living room lit by bay windows setting the tone for relaxed mornings or hosting evening guests. The open layout

  Luke Joachim Redfin Real Estate

  19 Donald Ln, Ossining, NY 10562
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  /15

  $2,400 - $2,795 per month

  WaterView Living

  1 - 2 Beds

  42 Cedar Ln, Ossining, NY 10562

  Waterview Living, located in Ossining NY, offers beautiful views of the Hudson River, with updated apartments and wonderful amenities. The property is situated between major highways, easy access to Metro North, and a short distance from the bustling downtown area of Ossining. There is much to do and see in this historic Rivertown. With local restaurants and the Sing Sing Kill Brewery downtown,

  42 Cedar Ln, Ossining, NY 10562
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  $630,000 Sold Dec 09, 2025

  10 Mohegan Rd, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,362 Sq Ft
  • Built 1929

  Last Sold Summary

  • $463/SF
  • 38 Days On Market

  Last Listing Agent Francie Malina Compass Greater NY, LLC

  10 Mohegan Rd, Ossining, NY 10562
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  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  211 Schrade Rd Unit 2C, Briarcliff Manor, NY 10510

  211 Schrade Rd Unit 2C, Briarcliff Manor, NY 10510
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  /27

  $589,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,886 Sq Ft

  126 Whitetail Cir, Ossining, NY 10562

  Welcome to Deerfield! This desirable End-Unit Condo offers the perfect blend of comfort and convenience. Featuring an attached garage, private balcony, and an abundance of natural light. The spacious layout includes an open-concept living and dining area as well as an updated kitchen with sliders leading to the balcony. Enjoy the privacy of an end unit and the amenities of the Deerfield

  Kathleen Courtney Coldwell Banker Realty

  126 Whitetail Cir, Ossining, NY 10562
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  /10

  $2,900 per month

  • 2 Beds
  • 1 Bath
  • 850 Sq Ft
  • Apartment for Rent

  2 John St, Ossining, NY 10562

  Totally renovated 2 bedroom, 1 bath apartment with tons of natural light and beautiful hardwood floors. Entry into mudroom then staircase upstairs to living room/dining area, eat-in-kitchen, bedroom, bedroom and full bath. Apartment comes with 1 parking space. Tenant is responsible for electric, gas and cable. Heat and hot water are included.

  Jason Kerwar William Raveis Real Estate

  2 John St, Ossining, NY 10562
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  $627,000 Sold Mar 31, 2025

  6 2nd Ave, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,460 Sq Ft
  • Built 1931

  Last Sold Summary

  • 9% Above List Price
  • $429/SF
  • 16 Days On Market

  Current Estimated Value $635,068

  Last Listing Agent Sheldon Wiggins

  6 2nd Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 959 Sq Ft

  121 S Highland Ave Unit L1, Ossining, NY 10562

  121 S Highland Ave Unit L1, Ossining, NY 10562

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