Ossining, NY Homes

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  /11

  $575,000

  $10K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,440 Sq Ft

  58 State St, Ossining, NY 10562

  Income-producing duplex in a desirable location! Has 5 bedrooms and two baths total. 3 bedrooms 1 bath in one unit, 2 bedrooms 1 bath in second unit. This well-maintained property offers two units with strong rental history and consistent cash flow. Ideal for investors or owner-occupants looking to offset their mortgage. Features include separate utilities, spacious layouts, and convenient access

  Amarish J. Khan Apollo Real Properties, Inc.

  58 State St, Ossining, NY 10562
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  /12

  $4,000 Per Month

  • 2 Beds
  • 1.5 Baths
  • 1,183 Sq Ft
  • Apartment for Rent

  1 Depot Square Unit 201, Ossining, NY 10562

  Be the first tenant to enjoy this stunning brand-new bi-level apartment at Depot Plaza, offering breathtaking Hudson River views and an unbeatable location directly across from the train station. Designed with a chic, modern aesthetic reminiscent of a SoHo loft, this exceptional residence combines style, comfort, and convenience. The main level features a spacious open-concept living and dining

  Mark Seiden Mark Seiden Real Estate Team

  1 Depot Square Unit 201, Ossining, NY 10562
• 

  $999,999

  Sold Jul 29, 2026

  2 Deertree Ln, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2.5 Baths
  • 2,326 Sq Ft
  • Built 1996

  Last Sold Summary

  • 11% Above List Price
  • $430/SF
  • 16 Days On Market

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  2 Deertree Ln, Briarcliff Manor, NY 10510
• 

  Est $615,946

  Not Listed For Sale

  223 Horseshoe Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,592 Sq Ft
  • Built 1986

  223 Horseshoe Cir, Ossining, NY 10562

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Angela Schuler William Raveis Real Estate
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  /43

  $950,000

  • 4 Beds
  • 2.5 Baths
  • 2,214 Sq Ft

  12 Riverview Ct, Ossining, NY 10562

  Welcome to one of Ossining's most captivating homes, where breathtaking panoramic Hudson River views take center stage. Perfectly positioned on a quiet cul-de-sac in the sought-after Sparta neighborhood, this beautifully updated 4-bedroom, 2.5-bath residence offers an exceptional blend of style, comfort, and unforgettable scenery. From the moment you enter, you're greeted by abundant natural

  David Thomsen HomeSmart Homes & Estates

  12 Riverview Ct, Ossining, NY 10562
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  /6

  $2,100 Per Month

  • 1 Bath
  • 400 Sq Ft
  • Apartment for Rent

  1123 Pleasantville Rd Unit 2D, Briarcliff Manor, NY 10510

  Luxury rental living in downtown Briarcliff Manor! This new construction elevator building is now offering studio, 1 bedroom and 2 bedroom units. A unique boutique-style rental opportunity, with only 8 units available. Unit 2D is a STUDIO apartment featuring an open layout. This unit is bright and sunny thanks to the large windows bringing in natural light. As you step inside, you'll be greeted

  Cord Stahl Julia B Fee Sothebys Int. Rlty

  1123 Pleasantville Rd Unit 2D, Briarcliff Manor, NY 10510
• 

  $650,000

  Sold Sep 25, 2025

  6 Agate Ave, Ossining, NY 10562

  • 6 Beds
  • 2 Baths
  • 2,243 Sq Ft
  • Built 1897

  Last Sold Summary

  • 8% Above List Price
  • $290/SF
  • 41 Days On Market

  Current Estimated Value $679,920

  Last Listing Agent JoElla Deliberto Houlihan Lawrence Inc.

  6 Agate Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  316 Kemeys Ave, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft
  • Built 1974

  316 Kemeys Ave, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Elyse Pace Berkshire Hathaway HS NY Prop
• 

  

  /23

  $2,489,222

  • 5 Beds
  • 4.5 Baths
  • 5,391 Sq Ft

  517A Old Chappaqua Rd, Briarcliff Manor, NY 10510

  Exquisite new 5 bedroom, 4.1 bath center hall colonial to be built offering refined luxury and timeless architectural elegance in an exceptional cul-de-sac setting. Perfectly positioned on just shy of one acre and backing the serene wooded grounds of the Edith Macy Center, this residence blends privacy, prestige, and natural beauty. A rare opportunity exists to fully customize finishes,

  Mark Seiden Mark Seiden Real Estate Team

  517A Old Chappaqua Rd, Briarcliff Manor, NY 10510
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  /25

  $9,000 Per Month

  • 5 Beds
  • 4.5 Baths
  • 4,290 Sq Ft
  • House for Rent

  45 Wolden Rd, Ossining, NY 10562

  Experience refined living at 45 Wolden Road, a fully furnished and move-in-ready residence offering five bedrooms, four-and-a-half bathrooms, expansive living spaces, a private in-ground pool, and generous driveway parking. Distinctive architectural details, multiple fireplaces, inviting outdoor entertaining areas, and nearly an acre of property create a private retreat designed for both everyday

  Abraham Fernandez Serhant LLC

  45 Wolden Rd, Ossining, NY 10562
• 

  $660,000

  Sold Jun 30, 2026

  19 Forest Ave, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,328 Sq Ft
  • Built 1920

  Last Sold Summary

  • 10% Above List Price
  • $497/SF
  • 24 Days On Market

  Current Estimated Value $617,311

  Last Listing Agent Lucille Ettere Houlihan Lawrence Inc.

  19 Forest Ave, Ossining, NY 10562
• 

  Est $506,867

  Not Listed For Sale

  19 Lincoln Place Unit 31, Ossining, NY 10562

  • 2 Beds
  • 1.5 Baths
  • 1,250 Sq Ft
  • Built 1966

  19 Lincoln Place Unit 31, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Patti Kolman ERA Insite Realty Services
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  /27

  $975,000

  • 4 Beds
  • 2.5 Baths
  • 2,363 Sq Ft

  39 Park Dr, Ossining, NY 10562

  Welcome to 39 Park Drive, a beautifully updated Colonial nestled on a quiet cul-de-sac. Set on .74 private acres, this move-in ready 4-bedroom, 2.5-bath home offers 2,363 square feet of thoughtfully designed living space, including a main-level office that can easily serve as a fifth bedroom, convenient main-floor laundry, a finished lower-level ideal for recreation, a home office, or additional

  Renee Macklin William Raveis-New York LLC

  39 Park Dr, Ossining, NY 10562
• 

  $245,000

  Sold Jul 02, 2026

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

  • 1 Bed
  • 1 Bath
  • 736 Sq Ft
  • Built 1970

  Last Sold Summary

  • 2% Below List Price
  • $333/SF
  • 27 Days On Market

  Current Estimated Value $316,000

  Last Listing Agent Loretta Fleming Chiavetta Coldwell Banker Realty

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

  Est $673,356

  Not Listed For Sale

  226 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,885 Sq Ft
  • Built 1983

  226 Woods Brooke Cir, Ossining, NY 10562

  Last Sold Summary

  • 109 Days On Market

  Last Listing Agent Catia Leon eXp Realty
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  /40

  $700,000

  • 2 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  34 Briarbrook Dr, Briarcliff Manor, NY 10510

  Welcome to effortless living in the highly desirable Scarborough Glen community. Beautifully updated and impeccably maintained, this move-in ready home offers the perfect combination of spacious living and a private natural setting. Step inside to discover hardwood floors throughout the main living areas, complemented by brand new carpeting in the bedrooms, loft, and finished lower level. The

  Stephen Zondorak Astor Lane Realty

  34 Briarbrook Dr, Briarcliff Manor, NY 10510
• 

  $510,000

  Sold May 12, 2026

  312A Spring St, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 3,687 Sq Ft
  • Built 2004

  Last Sold Summary

  • 7% Below List Price
  • $138/SF
  • 91 Days On Market

  Current Estimated Value $834,652

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  312A Spring St, Ossining, NY 10562
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  Not Listed For Sale

  312 Saddle Trail, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,616 Sq Ft
  • Built 1986

  312 Saddle Trail, Ossining, NY 10562

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Diane Silverman Keller Williams NY Realty
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  /37

  $929,000

  • 3 Beds
  • 2 Baths
  • 1,917 Sq Ft

  28 Inningwood Rd, Ossining, NY 10562

  Why wait for vacation when you can enjoy a retreat-like lifestyle every day?This exceptional, fully renovated Colonial with farmhouse charm is a rare Sears Roebuck Kit House circa 1927, seamlessly blending historic character with modern comforts. Thoughtfully updated throughout, the home features central air conditioning, remote-controlled blinds, renovated baths, and hardwood floors that

  Suzanne Lagle Houlihan Lawrence Inc.

  28 Inningwood Rd, Ossining, NY 10562
• 

  $799,000

  Sold Sep 24, 2025

  1002 Kitchawan Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 2,067 Sq Ft
  • Built 1900

  Last Sold Summary

  • $387/SF
  • 45 Days On Market

  Current Estimated Value $811,075

  Last Listing Agent Joanne Debellis Debellis Real Estate LLC

  1002 Kitchawan Rd, Ossining, NY 10562
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  Est $519,921

  Not Listed For Sale

  214 Horseshoe Cir, Ossining, NY 10562

  • 1 Bed
  • 1.5 Baths
  • 1,141 Sq Ft
  • Built 1986

  214 Horseshoe Cir, Ossining, NY 10562

  Last Sold Summary

  • 57 Days On Market

  Last Listing Agent Lynn Harmonay North Country Sothebys Int Rlt
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  /36

  $660,000

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,482 Sq Ft

  7 Brook Place, Ossining, NY 10562

  Charming on the outside but updated and modern on the inside! Spacious living room has large bay window and also boasts a fireplace for those cold winter nights. Through the oversized doorway is the dining room which is large enough to host friends and family for both informal occasions and the holidays. The updated kitchen (2024) with heated flooring will make any chef happy. From the kitchen

  Diane Herlihy BHHS River Towns Real Estate

  7 Brook Place, Ossining, NY 10562
• 

  $715,000

  Sold Jul 24, 2026

  31 Saddle Trail Unit 5, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,601 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $447/SF
  • 12 Days On Market

  Last Listing Agent Lisa Berliner Coldwell Banker Realty

  31 Saddle Trail Unit 5, Ossining, NY 10562
• 

  Est $1,089,155

  Not Listed For Sale

  25 Briarbrook Dr, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3.5 Baths
  • 3,007 Sq Ft
  • Built 2001

  25 Briarbrook Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Renata Douglass Houlihan Lawrence Inc.
• 

  

  /23

  $439,000

  Pending

  • 1 Bed
  • 1.5 Baths
  • 1,109 Sq Ft

  2 Davids Ln, Ossining, NY 10562

  Welcome to 2 David's Lane, where you will find a charming one-bedroom, corner townhouse in Ossining. This home offers a wonderful opportunity to enjoy comfortable, low-maintenance living in a desirable Westchester community. This thoughtfully designed home features a bright and inviting layout with a comfortable living space, a functional kitchen, and a cozy bedroom retreat. The open flow of the

  Marlena Mucci The Select Team, LLC

  2 Davids Ln, Ossining, NY 10562
• 

  $802,000

  Sold Jun 29, 2026

  34 Piping Rock Dr, Ossining, NY 10562

  • 2 Beds
  • 3 Baths
  • 2,288 Sq Ft
  • Built 1987

  Last Sold Summary

  • $351/SF
  • 43 Days On Market

  Current Estimated Value $796,374

  Last Listing Agent Maureen Verre Houlihan Lawrence Inc.

  34 Piping Rock Dr, Ossining, NY 10562
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  Not Listed For Sale

  203 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Built 1996

  203 Glenwood Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Deborah Valentino Houlihan Lawrence Inc.
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  /24

  $350,000

  Pending

  • 1 Bed
  • 1 Bath
  • 1,250 Sq Ft

  16 Rockledge Ave Unit 2D1, Ossining, NY 10562

  Discover The Perfect Blend Of Tranquility And Convenience In This Stunning Second Floor End Unit At Scarborough Manor. This Beautifully Appointed One Bedroom, One Bathroom Apartment Offers Breathtaking Seasonal Views Of The Hudson River, All While Providing A Serene Woodland Ambiance That Makes You Feel Miles Away From It All. Step Inside To Find Soaring 9 Foot Ceilings And An Oversized Living

  Candace D'Addario Coldwell Banker Realty

  16 Rockledge Ave Unit 2D1, Ossining, NY 10562
• 

  $950,000

  Sold Jul 01, 2026

  31 Orchard Rd, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2.5 Baths
  • 1,550 Sq Ft
  • Built 1961

  Last Sold Summary

  • 1% Above List Price
  • $613/SF
  • 32 Days On Market

  Current Estimated Value $937,240

  Last Listing Agent James Maurno Berkshire Hathaway HS NY Prop

  31 Orchard Rd, Briarcliff Manor, NY 10510
• 

  Est $705,873

  Not Listed For Sale

  241 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 1,950 Sq Ft
  • Built 1984

  241 Woods Brooke Cir, Ossining, NY 10562

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Andrea O'Brien Douglas Elliman Real Estate
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  /44

  $425,000

  Pending

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

  16 Rockledge Ave Unit 5P-2, Ossining, NY 10562

  Welcome to Scarborough Manor, one of Westchester's most sought-after riverside co-op communities — where resort-style living meets everyday convenience along the scenic Hudson River. This beautifully appointed, recently updated two-bedroom, two-bath residence offers what may be the community's most prized feature: breathtaking, unobstructed Hudson River views that greet you from the moment you

  Jenifer Ross eXp Realty

  16 Rockledge Ave Unit 5P-2, Ossining, NY 10562
• 

  $120,000

  Sold Feb 20, 2026

  5-7 Hill St, Ossining, NY 10562

  • Land
  • 4,356 Sq Ft
  • $1,200,000 per Acre

  Last Sold Summary

  • 20% Below List Price
  • 97 Days On Market

  Last Listing Agent Greg Kane Kane & Associates

  5-7 Hill St, Ossining, NY 10562
• 

  Est $586,817

  Not Listed For Sale

  28 Spring Pond Dr, Ossining, NY 10562

  • 1 Bed
  • 1.5 Baths
  • 1,753 Sq Ft
  • Built 1985

  28 Spring Pond Dr, Ossining, NY 10562

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.
• 

  

  /33

  $1,289,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 3,606 Sq Ft

  31 Burns Place, Briarcliff Manor, NY 10510

  Set on a quiet, tree-lined street this beautifully maintained raised ranch offers the perfect blend of space, comfort, and convenience within the highly regarded Briarcliff Manor School District. Thoughtfully updated and expanded, the home features 4 bedrooms plus a dedicated office, 2.5 baths, and a flexible living space designed for today’s lifestyle. Sun-filled interiors, hardwood floors, and

  Heather Monachelli Coldwell Banker Realty

  31 Burns Place, Briarcliff Manor, NY 10510
• 

  $635,000

  Sold Apr 07, 2026

  5 Robert Rinaldi Ln, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,344 Sq Ft
  • Built 2015

  Last Sold Summary

  • 6% Above List Price
  • $472/SF
  • 11 Days On Market

  Last Listing Agent Ciara Walsh Houlihan Lawrence Inc.

  5 Robert Rinaldi Ln, Ossining, NY 10562
• 

  Est $650,607

  Not Listed For Sale

  302 Chase Ct, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,601 Sq Ft
  • Built 1986

  302 Chase Ct, Ossining, NY 10562

  Last Sold Summary

  • 62 Days On Market

  Last Listing Agent David Wenzel Century 21 Alliance Realty Grp
• 

  

  /19

  $215,000

  Pending

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  133 S Highland Ave Unit 5B, Ossining, NY 10562

  Welcome to Highland Terrace, a light-filled, top-floor end unit in a pet-friendly community. This bright and well-maintained two-bedroom apartment features an updated kitchen with granite counters, newer appliances, and a convenient pass-through to the living and dining area. The spacious living room offers plenty of space and great natural light, while both bedrooms include good sized closets. A

  Magdalena Konkola Houlihan Lawrence Inc.

  133 S Highland Ave Unit 5B, Ossining, NY 10562
• 

  $1,860,000

  Sold Dec 15, 2025

  39 Admiral Wordens Ln, Briarcliff Manor, NY 10510

  • 4 Beds
  • 5.5 Baths
  • 4,500 Sq Ft
  • Built 2000

  Last Sold Summary

  • 1% Above List Price
  • $413/SF
  • 45 Days On Market

  Current Estimated Value $1,923,393

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  39 Admiral Wordens Ln, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  5 High Ridge Rd, Ossining, NY 10562

  • 3 Beds
  • 4 Baths
  • 2,700 Sq Ft
  • Built 1996

  5 High Ridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Jamie Fosgate Nestedge Realty
• 

  

  /35

  $749,999

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,354 Sq Ft

  22 Quail Hollow Rd, Ossining, NY 10562

  Welcome to 22 Quail Hollow Road, a well-maintained 3-bedroom, 2.5-bath Colonial offering 2,354 square feet of living space on a quiet cul-de-sac in Ossining, New York. The main level features a spacious living room with a vaulted ceiling that flows into a family room, kitchen with a breakfast nook and formal dining room creating an open and comfortable setting for everyday living and

  Cynthia Geiger Corcoran Legends Realty

  22 Quail Hollow Rd, Ossining, NY 10562

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