Ossining, NY Homes

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  $849,999

  Open Sat 10AM - 1PM

  • 4 Beds
  • 1.5 Baths
  • 2,096 Sq Ft

  97 Morningside Dr, Ossining, NY 10562

  Offered for the first time in over 60 years and a rare opportunity to own a piece of history! This historic mid-nineteenth century farmhouse sits on 1.3 private acres bordering the protected land of Ryder Park, ensuring permanent privacy and an undisturbed natural setting. This four bedroom, one and a half bathroom home has charm and character everywhere you look. Exposed beams, wood flooring,

  

  Alycia Forbes

  Tag Realty & Property Mang

  97 Morningside Dr, Ossining, NY 10562
• Explore Ossining

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  /32

  $7,000 Per Month

  • 4 Beds
  • 3 Baths
  • 1,880 Sq Ft
  • House for Rent

  6 Scarborough Cir, Ossining, NY 10562

  Freshly painted 4 bedroom, 3 bath home features cathedral ceilings in the main living space, updated kitchen with sliding glass door to deck overlooking spacious yard with Hudson River Views. Main floor also has a masterbedroom with river views and private bath with oversized shower, 2 additional bedrooms and full hall bath. Lower level features a family room with traditional wood burning

  

  Donna McKenna Edlund

  Coldwell Banker Realty

  6 Scarborough Cir, 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 $514,473

  Last Listing Agent Maureen McEnroe Joyce Realty Corp

  8 Samstag Ave, Ossining, NY 10562
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  Est $159,000

  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

  • 27 Days On Market

  Last Listing Agent Evelyn Romero BHHS River Towns Real Estate
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  /15

  $425,000

  Pending

  • 2 Beds
  • 1 Bath
  • 1,446 Sq Ft

  32 Ferris Place, Ossining, NY 10562

  This charming colonial in the heart of the village maintains many original features and awaits your touches. Once you enjoy the ample parking and enclosed porch overlooking the quiet, tree-lined street you'll behold a classic entry foyer, living room, and dining room with classic woodwork. The small rear porch beholds the gently sloping rear yard and 2-car garage. The kitchen also has a genrously

  

  J. Philip Faranda

  Howard Hanna Rand Realty

  32 Ferris Place, Ossining, NY 10562
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  Starting at $2,875 Per Month

  • 1 - 2 Beds

  3 Westerly Rd, Ossining, NY 10562

  1 month free on select units.

  Harbor Square

  

  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 $1,187,612

  Last Listing Agent Eric Lebenson ERA Insite Realty Services

  32 Waterview Dr, Ossining, NY 10562
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  Est $316,000

  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

  • 93 Days On Market

  Last Listing Agent Eric Lebenson ERA Insite Realty Services
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  $550,000

  Pending

  • 6 Beds
  • 3 Baths
  • 2,276 Sq Ft

  41 Ellis Place, Ossining, NY 10562

  Legal 2-family opportunity in the heart of Ossining offering exceptional value, versatility, and upside potential. Priced at $550,000, this spacious property features a 5-bedroom, 3 full bath layout plus a separate studio apartment with its own private entrance—ideal for investors or owner-occupants looking to generate rental income. Set on a 7,405 sq ft lot, the home offers approximately 2,276

  

  Paula Esteves

  Century 21 Full Service Realty

  41 Ellis Place, Ossining, NY 10562
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  $3,700 Per Month

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

  8 Davids Ln, Ossining, NY 10562

  Rare and expansive 1-bedroom triplex with office/den/finished basement offering approximately 1,450 square feet of living space, featuring a large bonus room ideal for a home office, den, or entertaining space. This sun-filled residence enjoys beautiful natural light throughout, with morning sun in the kitchen and warm sunset light in the living room. The multi-level layout provides a unique

  

  Sara Reel

  Julia B Fee Sothebys Int. Rlty

  8 Davids Ln, Ossining, NY 10562
• 

  $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 $908,572

  Last Listing Agent Denyse Fecteau Denyse M. Fecteau

  40 Magnolia Rd, Briarcliff Manor, NY 10510
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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

  • 19 Days On Market

  Last Listing Agent George Khury Keller Williams Realty Group
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  $3,500,000

  • 10 Beds
  • 5.5 Baths
  • 8,881 Sq Ft

  335 Croton Dam Rd, Ossining, NY 10562

  Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing

  

  Hillary Landau

  Compass Greater NY, LLC

  335 Croton Dam Rd, Ossining, NY 10562
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  Starting at $2,400 Per Month

  • 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

  Audubon Living

  

  38 1/2 Wolden Rd, Ossining, NY 10562
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  $386,000

  Sold Jun 05, 2026

  16 Rockledge Ave Unit 6K-2, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,580 Sq Ft
  • Built 1968

  Last Sold Summary

  • 9% Above List Price
  • $244/SF
  • 36 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  16 Rockledge Ave Unit 6K-2, Ossining, NY 10562
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  Not Listed For Sale

  119 S Highland Ave Unit 6H, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,212 Sq Ft
  • Built 1965

  119 S Highland Ave Unit 6H, Ossining, NY 10562

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Chintan Trivedi RE/MAX In The City
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  /31

  $242,000

  • 2 Beds
  • 1.5 Baths
  • 950 Sq Ft

  135 S Highland Ave Unit 5D6, Ossining, NY 10562

  Welcome to Highland Terrace, a desirable co-op community in the heart of Ossining. This 2-bedroom, 1.5-bath residence offers comfortable living space with plenty of natural light, spacious rooms, and great storage throughout. Enjoy the convenience of common laundry, assigned parking, and access to the community pool. Highland Terrace is close to Metro-North, shops, restaurants, schools, parks,

  

  Michael Vasquez

  eXp Realty

  135 S Highland Ave Unit 5D6, Ossining, NY 10562
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  Starting at $2,000 Per Month

  • 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

  Cortlandt Living

  

  24 Claremont Gardens, 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 $316,000

  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

  43 Charter Cir, Ossining, NY 10562

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

  43 Charter Cir, Ossining, NY 10562

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent SANDRA MAHON BHHS Hudson Valley Properties
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  /23

  $175,000

  $15K PRICE DROP

  • 1 Bath
  • 500 Sq Ft

  225 Schrade Rd Unit 1E, Briarcliff Manor, NY 10510

  Bright and sunny studio apartment located in the highly desirable Briar Hill community. This move-in ready unit features an updated kitchen with granite countertops, a microwave, and a dishwasher are included. Major improvements include replacement windows installed in 2000 and a roof completed in 2003. Monthly maintenance includes heat and hot water for added value and convenience. Residents

  

  Cristina Gameiro

  Howard Hanna Rand Realty

  225 Schrade Rd Unit 1E, Briarcliff Manor, NY 10510
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  /17

  Starting at $2,400 Per Month

  • 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,

  WaterView Living

  

  42 Cedar Ln, Ossining, NY 10562
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  $580,000

  Sold Aug 10, 2026

  53 Pleasantville Rd, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 1,152 Sq Ft
  • Built 1960

  Last Sold Summary

  • 14% Above List Price
  • $503/SF
  • 18 Days On Market

  Current Estimated Value $510,275

  Last Listing Agent Jennifer Rivera Houlihan Lawrence Inc.

  53 Pleasantville Rd, Ossining, NY 10562
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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

  • 18 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
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  /40

  $1,150,000

  • 4 Beds
  • 2.5 Baths
  • 2,859 Sq Ft

  629 Scarborough Rd, Briarcliff Manor, NY 10510

  Some homes ask you to imagine what they could be. This one is already there and waiting for you. This classic colonial has been lovingly updated and impeccably maintained by owners/designer who cared about every detail. Large, sun-drenched rooms, a layout that feels both timeless and completely livable, and the big-ticket items already handled: new roof, new HVAC, new kitchen and appliances, new

  

  Hillary Landau

  Compass Greater NY, LLC

  629 Scarborough Rd, Briarcliff Manor, NY 10510
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  /17

  Starting at $2,950 Per Month

  • 1 - 2 Beds

  87 Hawkes Ave, Ossining, NY 10562

  CONTACT US DIRECTLY, NO BROKER FEE!!! WESTCHESTER MAGAZINE BUILDER AWARD FINALIST FOR BEST LUXURY MULTIFAMILY PROPERTY- PARTH KNOLLS is Luxury at your Leisure with the look and feel of single-family home living. Most apartments feature a study, which is perfect for your home office. Onsite indoor and assigned outdoor parking, spacious oversized units, In-unit full-sized Washer & Dryer in your

  Parth Knolls Apartments

  

  87 Hawkes Ave, 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 $688,030

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

  107 Glenwood Dr, Briarcliff Manor, NY 10510
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  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

  • 16 Days On Market

  Last Listing Agent Amarish J. Khan Apollo Real Properties, Inc.
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  /48

  $2,895,000

  Pending

  • 5 Beds
  • 4.5 Baths
  • 5,368 Sq Ft

  91 Chestnut Hill Ln, Briarcliff Manor, NY 10510

  Set privately at the end of a quiet cul-de-sac, this fully updated modern smart home is a rare offering, architecturally refined, impeccably maintained, and designed for the way people want to live today. Five bedrooms and four and a half baths are spread across three finished levels, beginning with a first-floor bedroom suite equally suited for guests, extended family, or a private home office,

  

  Hillary Landau

  Compass Greater NY, LLC

  91 Chestnut Hill Ln, Briarcliff Manor, NY 10510
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  /10

  $2,600 Per Month

  • 2 Beds
  • 1 Bath
  • Condo for Rent

  22 Upper Croton Ave Unit 2, Ossining, NY 10562

  Property Id: 2750975 Apartment Address: 22 Upper Croton Ave Ossining, NY 10562 - Apt 2 Number of Bedrooms and Rent: 2BR $2600 Discover a charming 2-bedroom apartment with spacious bedrooms that provide room to live, work, and relax. The adorable kitchen area and cozy bathroom create a welcoming atmosphere you'll love. AMCL Realty Angela

  22 Upper Croton Ave Unit 2, 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 $868,334

  Last Listing Agent Daniella Ingenito Compass Greater NY, LLC

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

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

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1965

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

  Last Sold Summary

  • 28 Days On Market

  Last Listing Agent Debra Goodwin Corcoran Legends Realty
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  /26

  $325,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,300 Sq Ft

  161 Charter Cir Unit 161, Ossining, NY 10562

  A rare three-bedroom opportunity in High Meadow, this corner townhouse-style co-op offers the space, privacy, and flexibility that are hard to find in co-op living, with a thoughtful two-level layout that feels more like a private home. The main level features an updated kitchen with in-unit washer/dryer, easy flow for living and dining, and an updated powder room. Upstairs, three generously

  

  Valerie Cascione

  Compass Greater NY, LLC

  161 Charter Cir Unit 161, Ossining, NY 10562
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  $3,100

  Total Monthly Price

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

  8 Old Albany Post Rd Unit C, Ossining, NY 10562

  Welcome home to this bright and beautiful 800 sq. ft. apartment featuring 2 bedrooms and 2 full bathrooms with parking. The layout includes a modern kitchen with stainless steel appliances, and washer and dryer. Enjoy access to a private yard, perfect for relaxing or entertaining.Ideally located within walking distance to the train, with easy access to major highways, scenic walking

  8 Old Albany Post Rd Unit C, Ossining, NY 10562
• 

  $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 $536,805

  Last Listing Agent Tim Rothman Compass Greater NY, LLC

  14 Gates Ave, Ossining, NY 10562
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  Est $159,000

  Not Listed For Sale

  117 S Highland Ave Unit 3F, Ossining, NY 10562

  • 1 Bath
  • 650 Sq Ft
  • Built 1964

  117 S Highland Ave Unit 3F, Ossining, NY 10562

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Joanna Concepcion eXp Realty
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  /47

  $499,000

  Pending

  • 3 Beds
  • 3 Baths
  • 2,463 Sq Ft

  4 Steven Dr Unit 1, Ossining, NY 10562

  A rare three-bedroom condo with the kind of extra space that makes daily life feel easier. This spacious tri-level end unit offers a flexible layout that lives more like a home, with ground-level entry, main-level living, a finished lower level, and a detached garage.The main level features wood floors, an updated kitchen with counter seating, a dining area, and a living room with a fireplace

  

  Valerie Cascione

  Compass Greater NY, LLC

  4 Steven Dr Unit 1, Ossining, NY 10562
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  /18

  $1,650

  Total Monthly Price

  • 1 Bed
  • 1 Bath
  • 900 Sq Ft
  • Condo for Rent

  25 S Highland Ave Unit apartment 1, Ossining, NY 10562

  Studio Apt with Heat and hot water included. Private entrance close to train station, walking distance and bus stops. No pets 1 month security Nice area freshly painted

  25 S Highland Ave Unit apartment 1, 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

  Current Estimated Value $844,105

  Last Listing Agent Jody Toth Corcoran Legends Realty

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

  117 S Highland Ave Unit 5H, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1963

  117 S Highland Ave Unit 5H, Ossining, NY 10562

  Last Sold Summary

  • 50 Days On Market

  Last Listing Agent Dina DiPaola-Gulli Keller Williams Realty Group

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