Ossining, NY Homes

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  /41

  $1,800,000

  • 5 Beds
  • 5 Baths
  • 4,223 Sq Ft

  16 Hall Rd, Briarcliff Manor, NY 10510

  Welcome to 16 Hall Rd, where the cul-de-sac is quiet enough to stroll, and the house itself feels like it's been designed just for you. You've been thinking about this move for a while now. Maybe the city apartment that once felt exciting has started to feel a little tight. Maybe you've been eyeing bigger spaces in the suburbs, but have not found the one that checks every box without needing a

  

  Hillary Landau

  Compass Greater NY, LLC

  (914) 326-0785

  16 Hall Rd, Briarcliff Manor, NY 10510
• Explore Ossining

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  /26

  $3,800 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
• 

  $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 $507,371

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
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  Est $183,000 Not Listed For Sale

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

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

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

  Last Sold Summary

  • 5% Above List Price
  • $194/SF
  • 27 Days On Market

  Last Sold Price $174,900

  Last Listing Agent Evelyn Romero BHHS River Towns Real Estate
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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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  /97

  $3,150 - $4,295 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 $1,169,671

  Last Listing Agent Eric Lebenson ERA Insite Realty Services

  32 Waterview Dr, Ossining, NY 10562
• 

  Est $893,936 Not Listed For Sale

  23 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 3,240 Sq Ft
  • Built 1996

  23 Mystic Dr, Ossining, NY 10562

  Last Sold Summary

  • 23% Above List Price
  • $224/SF
  • 14 Days On Market

  Last Sold Price $725,000

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty
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  /34

  $1,299,000

  • 3 Beds
  • 3.5 Baths
  • 2,976 Sq Ft

  8 Justine Ct, Briarcliff Manor, NY 10510

  First time on the market! Come enjoy a carefree lifestyle in the sought-after Rosecliff community. Beautifully built by Toll Brothers, this elegant 3-bedroom home is located at the end of a small cul-de-sac. This sun-lit home features hardwood floors throughout, 9-foot ceilings on the main level, formal living room and dining room and an open kitchen with stainless steel appliances, and breakfast

  

  Maria Teresa Duguet

  Houlihan Lawrence Inc.

  (914) 340-0561

  8 Justine Ct, Briarcliff Manor, NY 10510
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  /25

  $5,600 per month

  • 4 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • House for Rent

  16 Minkel Rd, Ossining, NY 10562

  Beautiful 4-bedroom, 3.5-bath single-family home located in a quiet residential neighborhood offering great space and flexibility. The main level features a bright living room filled with natural light and highlighted by a bay window, an open kitchen with nice countertops, and a dining room perfect for everyday living. A cozy den provides additional space for a home office or sitting

  Jason Schmeltzer Coldwell Banker Realty

  16 Minkel Rd, Ossining, NY 10562
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  $870,000 Sold Feb 12, 2026

  40 Magnolia Rd, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 2,614 Sq Ft
  • Built 1961

  Last Sold Summary

  • 3% Below List Price
  • $333/SF
  • 83 Days On Market

  Current Estimated Value $909,305

  Last Listing Agent Denyse Fecteau Denyse M. Fecteau

  40 Magnolia Rd, Briarcliff Manor, NY 10510
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  Est $366,000 Not Listed For Sale

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

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1970

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

  Last Sold Summary

  • 9% Above List Price
  • $212/SF
  • 93 Days On Market

  Last Sold Price $335,000

  Last Listing Agent Eric Lebenson ERA Insite Realty Services
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  /48

  $985,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,548 Sq Ft

  21 Candlewood Ct, Briarcliff Manor, NY 10510

  Set on a private cul-de-sac with no through traffic, this home offers a quiet, tucked-away setting where daily life feels a touch more calm. From the moment you enter, the sightline lands where it should: a Westchester Magazine-recognized kitchen, Scandinavian-leaning and defined by clean lines, bright space, and a turquoise glass-tile focal wall that reads like water. With two islands, living

  

  Valerie Cascione

  Compass Greater NY, LLC

  (914) 935-7320

  21 Candlewood Ct, Briarcliff Manor, NY 10510
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  /14

  $2,400 - $2,499 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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  $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

  Current Estimated Value $366,000

  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

  94 Charter Cir Unit 94, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1961

  94 Charter Cir Unit 94, Ossining, NY 10562

  Last Sold Summary

  • $211/SF
  • 80 Days On Market

  Last Sold Price $200,000

  Last Listing Agent Kimberly Renzi Coldwell Banker Realty
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  /26

  $245,000 Pending

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  9 Geneva Rd Unit 9, Ossining, NY 10562

  Welcome to this beautifully updated co-op in the sought-after High Meadow complex, where timeless style meets everyday convenience. The main level offers a bright, airy flow with an inviting living room, dining area, and a beautifully renovated kitchen featuring new cabinetry, quartz countertops, and a classic subway tile backsplash. Barn doors add character and charm while opening to a laundry

  

  Valerie Cascione

  Compass Greater NY, LLC

  (914) 685-5423

  9 Geneva Rd Unit 9, Ossining, NY 10562
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  /20

  $3,950 per month

  • 3 Beds
  • 2 Baths
  • 1,150 Sq Ft
  • Apartment for Rent

  5 Brandreth St Unit 2A, Ossining, NY 10562

  Come see this bright, stylish 3BR/2BA Apartment in downtown Ossining! The unit is teeming with elegance and offers many great amenities, including Central Air, BIG Closets, and Hi-End Finishes. Just 48 minutes by Train to GCS, and Close to restaurants, recreation, and shopping! The apartment is on the 2nd floor and has lovely light quality and views from the bedrooms. Enjoy Hardwood Floors in

  Jenifer Ross eXp Realty

  5 Brandreth St Unit 2A, 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 $659,910

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

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

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

  • 2 Beds
  • 2 Baths
  • 1,050 Sq Ft
  • Built 1950

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

  Last Sold Summary

  • $252/SF
  • 80 Days On Market

  Last Sold Price $265,000

  Last Listing Agent Donna McKenna Edlund Coldwell Banker Realty
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  /42

  $1,395,000 Pending

  • 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) 483-3155

  270 Law Rd, Briarcliff Manor, NY 10510
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  /24

  $2,000 - $2,800 per month

  Cortlandt Living

  Studio - 2 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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  $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 $848,639

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

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

  14 Charter Cir, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1961

  14 Charter Cir, Ossining, NY 10562

  Last Sold Summary

  • $253/SF
  • 19 Days On Market

  Last Sold Price $227,500

  Last Listing Agent George Khury Keller Williams Realty Group
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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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  /30

  $2,975 per month

  • 2 Beds
  • 1 Bath
  • 1,100 Sq Ft
  • Apartment for Rent

  56 S Highland Ave Unit 1B, Ossining, NY 10562

  Step into a spacious, fully renovated, turn-key lifestyle with this extraordinary first-floor apartment in the heart of historic Town of Ossining. This extra-large 2-bedroom residence has been meticulously transformed with high-end finishes, ready for immediate occupancy. Brand-new, Contemporary Kitchen: A chef's delight featuring sleek countertops, new cabinetry, and a full suite of brand-new,

  Christina DiMinno Julia B Fee Sothebys Int. Rlty

  56 S Highland Ave Unit 1B, Ossining, NY 10562
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  $500,000 Sold Feb 24, 2026

  14 Gates Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,276 Sq Ft
  • Built 1920

  Last Sold Summary

  • 17% Below List Price
  • $392/SF
  • 188 Days On Market

  Current Estimated Value $552,046

  Last Listing Agent Tim Rothman Compass Greater NY, LLC

  14 Gates Ave, Ossining, NY 10562
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  Not Listed For Sale

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

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1950

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

  Last Sold Summary

  • $221/SF
  • 182 Days On Market

  Last Sold Price $210,000

  Last Listing Agent Michelle Drenga Weichert Realtor Future Vision
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  /38

  $249,999

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft

  16 Rockledge Ave Unit 2MM-2, Ossining, NY 10562

  Perched gracefully above the majestic Hudson River, this beautifully renovated one-bedroom home is ready to welcome you in. Nestled within the highly sought-after, gated Scarborough Manor community, you’ll be greeted by the gatekeeper each time you arrive—an immediate sense of comfort and care. This sun-soaked, south-facing unit feels bright and uplifting from the moment you step inside.

  

  Loretta Fleming Chiavetta

  Coldwell Banker Realty

  (914) 353-4296

  16 Rockledge Ave Unit 2MM-2, Ossining, NY 10562
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  /17

  $2,400 - $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
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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

  Current Estimated Value $938,031

  Last Listing Agent Jody Toth Corcoran Legends Realty

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

  43 Charter Cir, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1962

  43 Charter Cir, Ossining, NY 10562

  Last Sold Summary

  • $242/SF
  • 20 Days On Market

  Last Sold Price $230,000

  Last Listing Agent SANDRA MAHON BHHS Hudson Valley Properties
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  /28

  $599,999 Pending

  • 2 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  5 Robert Rinaldi Ln, Ossining, NY 10562

  Welcome to this beautifully maintained 2-bedroom, 2.5-bath single-family home built in 2015, tucked away on a quiet cul-de-sac in one of the area’s most desirable and commuter-friendly communities. Offering modern design, open-concept living, and low-maintenance ease, this home presents a rare opportunity in today’s limited inventory market. The sun-filled main level features rich hardwood

  

  Ciara Walsh

  Houlihan Lawrence Inc.

  (914) 546-4460

  5 Robert Rinaldi Ln, Ossining, NY 10562
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  /11

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 800 Sq Ft
  • Apartment for Rent

  55 Woodside Ave Unit 1A, Briarcliff Manor, NY 10510

  Beautifully designed 2-bedroom, 2-bath residence offers the perfect balance of modern comfort, convenience, and location. This spacious 800 sq ft apartment features modern amenities such as high efficiency heating & air conditioning with individual climate control, high end all black Samsung kitchen appliances including dishwasher, microwave, and refrigerator/freezer. Enjoy the convenience of the

  Jamey Gelardi Houlihan Lawrence Inc.

  55 Woodside Ave Unit 1A, Briarcliff Manor, NY 10510
• 

  $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 $1,044,459

  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

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

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • Built 1954

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

  Last Sold Summary

  • $274/SF
  • 18 Days On Market

  Last Sold Price $260,000

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
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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
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  /119

  $2,250 - $7,500 per month

  • 1 - 5 Beds
  • 4 Baths
  • 680 Sq Ft
  • House for Rent

  275 Croton Dam Rd, Ossining, NY 10562

  This beautifully maintained 2017 stand-alone modern home offers privacy, space, and upscale living on just under an acre of level property. Featuring 4 bedrooms and 3 full bathrooms across 2,950 square feet, the home is thoughtfully designed with hardwood floors and an open-concept main level ideal for both everyday living and entertaining.The expansive living room flows seamlessly into a

  275 Croton Dam Rd, 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

  Current Estimated Value $626,059

  Last Listing Agent Francie Malina Compass Greater NY, LLC

  10 Mohegan Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  121 S Highland Ave Unit L1, Ossining, NY 10562

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

  121 S Highland Ave Unit L1, Ossining, NY 10562

  Last Sold Summary

  • $193/SF
  • 16 Days On Market

  Last Sold Price $185,000

  Last Listing Agent Amarish J. Khan Apollo Real Properties, Inc.

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