Ossining, NY Homes

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  /39

  $549,000 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,470 Sq Ft

  707 Eagle Bay Dr, Ossining, NY 10562

  Carefree Rivertown Living Surrounded by Nature – Rare End Unit with 2 Deeded GaragesEnjoy effortless living in this bright and spacious end-unit townhome. 2-bedroom, 2.5-bath home featuring a fireplace and a beautiful sunroom that feels like a private treehouse escape. Perfect for reading, relaxing, or enjoying the view year-round.A rare find, this home includes two deeded detached

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 758-0173

  707 Eagle Bay Dr, Ossining, NY 10562
• Explore Ossining

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  /97

  $3,095 - $4,995 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
• 

  $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 $2,455,736

  Last Listing Agent Jennifer Fischman Houlihan Lawrence Inc.

  652 Long Hill Rd W, Briarcliff Manor, NY 10510
• 

  Est $156,000 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
• 

  

  

  /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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  /21

  $3,400 per month

  • 2 Beds
  • 1.5 Baths
  • 1,396 Sq Ft
  • Condo for Rent

  56 Hudson View Hill, Ossining, NY 10562

  Welcome to 56 Hudson View Hill. A bright and spacious 2-bedroom, 1.5-bath townhouse nestled in the sought-after Riverview Condominium community in Ossining. This charming home offers over 1,400 sq ft of living space, featuring a sun-filled living room with a cozy fireplace and sliding glass doors that open to a private deck perfect for relaxing or entertainingEnjoy cooking in the eat-in

  Ken Scala Century 21 Scala Group

  56 Hudson View Hill, Ossining, NY 10562
• 

  $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

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
• 

  Est $899,450 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
• 

  

  /27

  $199,900

  • 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
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  /18

  $2,299 - $2,995 per month

  Audubon Living

  1 - 2 Beds

  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
• 

  $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
• 

  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
• 

  

  /16

  $150,000 Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  117 S Highland Ave Unit 6J, Ossining, NY 10562

  Welcome to your perfect home-away-from-the-hustle! Step into this beautifully maintained 750-square-foot haven featuring thoughtful design and abundant natural light throughout. The well-appointed kitchen with new appliances, and updated bathroom create a perfect foundation for daily living, while the spacious bedroom provides a peaceful retreat after busy days. Ossining offers the perfect

  

  Peter Raider

  Real Broker NY LLC

  (914) 908-6292

  117 S Highland Ave Unit 6J, Ossining, NY 10562
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  /22

  $3,600 per month

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft
  • Condo for Rent

  42 Briarcliff Dr S Unit 4- 2, Ossining, NY 10562

  Welcome to this exceptionally spacious and lovely car cared for a condo in the highly sought after Briarcliff Woods community. Walk into this gorgeous top to bottom, renovated unit with gracious dining room, that conveniently transitions to the stunning eat in kitchen that has been updated with designer, cabinetry, and modern finishes. All the conveniences of in unit laundry. You'll love the

  Joseph Midyett Christie's Int. Real Estate

  42 Briarcliff Dr S Unit 4- 2, Ossining, NY 10562
• 

  $175,000 Sold Jan 10, 2025

  119 S Highland Ave Unit 4A, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 895 Sq Ft
  • Built 1964

  Last Sold Summary

  • $196/SF
  • 22 Days On Market

  Last Listing Agent Michael LaMorte Christie's Int. Real Estate

  119 S Highland Ave Unit 4A, Ossining, NY 10562
• 

  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
• 

  

  /19

  $505,000 Pending

  • 2 Beds
  • 1 Bath
  • 1,151 Sq Ft

  5 Glen St, Ossining, NY 10562

  Imagine the lifestyle you can create in this appealing Victorian, where a welcoming rocking chair front porch sets the tone and modern updates enhance timeless charm. Unwind in the inviting living room with gas fireplace, custom built-in and elegant bow window. Cook and dine with ease in the beautifully renovated eat-in kitchen. Thoughtful touches like radiant heated floors, pot filler, and

  

  Sheri Wolfe

  Berkshire Hathaway HS NY Prop

  (914) 635-2594

  5 Glen St, 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
• 

  $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
  • 900 Sq Ft

  14 Charter Cir, Ossining, NY 10562

  14 Charter Cir, Ossining, NY 10562
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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
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  /9

  $3,750 per month

  • 4 Beds
  • 1 Bath
  • 1,548 Sq Ft
  • Apartment for Rent

  17 Hamilton Ave, Ossining, NY 10562

  4 Br+Nursury APARTMENT, upper two levels of an Attractive classic Colonial, Fresh Paint, lovely trim, side street, Walk to Parks, Trains and Busses, Living Room/Dining Area, Kitchen, 2 Big Br, 2 medium/small Br and a Nursery/Office. Walk to Ossining Central Village and River Front Activities galore, 17 restaurants, Riverfront Food Truck Friday concert series, close to Aqueduct Trailway, Farmers

  Eric Schatz Schatz Realty Group

  17 Hamilton Ave, Ossining, NY 10562
• 

  $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 $656,421

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  107 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  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
• 

  

  /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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  /15

  $2,399 - $3,195 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
• 

  $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

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

  31 Murray Ln, Ossining, NY 10562
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  43 Charter Cir, Ossining, NY 10562

  43 Charter Cir, Ossining, NY 10562
• 

  

  /23

  $199,000 Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  147 Charter Cir Unit 147, Ossining, NY 10562

  Step into this fabulous duplex townhouse-style cooperative, boasting its own private entrance on a picturesque, tree-lined street. The main level unfolds into an inviting layout, featuring a bright and spacious living room, a dedicated dining room perfect for entertaining, and a well-appointed kitchen. Ascend to the second floor where you'll discover two generously sized bedrooms, each offering

  

  Sherry Wiggs

  Houlihan Lawrence Inc.

  (914) 647-6619

  147 Charter Cir Unit 147, Ossining, NY 10562
• 

  

  /17

  $2,675 per month

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

  79 Main St Unit 2W, Ossining, NY 10562

  Completely renovated in 2025, this charming second-floor two-bedroom, one-bath apartment blends modern style with village convenience. Located in the heart of Ossining, it’s just a short walk to the Metro-North train station—making your NYC commute easy and stress-free.Enjoy weekend strolls to the lively Farmers Market, local cafes, restaurants, and the scenic Hudson River waterfront. The

  Altagracia Grace Patalano BHHS River Towns Real Estate

  79 Main St Unit 2W, Ossining, NY 10562
• 

  $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
• 

  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
• 

  

  /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
• 

  

  /35

  $2,792 - $15,469 per month

  Terraces on the Hudson

  1 - 3 Beds

  217 N Highland Ave, Ossining, NY 10562

  Avalon Ossining, only 1 mile from the Ossining Metro-North Railroad Station, offers thoughtfully designed 1, 2, and 3 bedroom luxury apartments that include contemporary kitchens with Energy Star appliances, walk-in closets, and a washer/dryer. Community amenities include a state-of-the-art fitness center and outdoor swimming pool, on-site children’s play area, and outdoor grilling areas.

  217 N Highland Ave, Ossining, NY 10562
• 

  $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 $999,377

  Last Listing Agent Jeanne Beckley Howard Hanna Rand Realty

  144 Hungerford Rd N, Briarcliff Manor, NY 10510
• 

  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
• 

  

  /50

  $1,350,000 Pending

  • 6 Beds
  • 7 Baths
  • 4,495 Sq Ft

  9 Gualtiere Ln, Ossining, NY 10562

  Panoramic Hudson River Views | Custom Architecture | Resort-Style Amenities |Discover an extraordinary sanctuary, where every detail has been carefully curated to create an unparalleled living experience. This architecturally stunning residence seamlessly blends sophisticated design with the natural beauty of its coveted river view location.Make a memorable entrance through the property’s

  Irina Fiorella Coldwell Banker Realty

  9 Gualtiere Ln, Ossining, NY 10562
• 

  

  /17

  $3,850 per month

  • 2 Beds
  • 1.5 Baths
  • 1,765 Sq Ft
  • Townhouse for Rent

  1 Spring Pond Dr, Ossining, NY 10562

  Beautiful, bright end-unit condo featuring 2 bedrooms and 1.5 baths in Spring Pond. This home offers an eat-in kitchen with ample cabinet space, a new stove and refrigerator, and stainless-steel appliances. Enjoy hardwood floors in both the living room and dining area, plus a deck off the dining area. Both upper-level decks have also been newly replaced, and the entire unit has been freshly

  Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

  1 Spring Pond Dr, Ossining, NY 10562
• 

  $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
• 

  Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  119 S Highland Ave Unit 3E, Ossining, NY 10562

  119 S Highland Ave Unit 3E, Ossining, NY 10562

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