Ossining, NY Homes

• 

  

  

  /16

  $155,000

  $2K PRICE INCREASE Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  125 S Highland Ave Unit C5, Ossining, NY 10562

  Welcome to this beautifully maintained one-bedroom, one-bath co-op in the highly sought-after Highland Terrace complex in Ossining — where opportunities to own rarely become available. Filled with natural sunlight throughout, this inviting home offers a warm and airy atmosphere from the moment you step inside. The versatile entry foyer offers the perfect flex space to suit your lifestyle — ideal

  Tracie Tobacco Coldwell Banker Realty

  125 S Highland Ave Unit C5, Ossining, NY 10562
• 

  $540,000

  Sold Mar 23, 2026

  39 Hamilton Ave, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 2,198 Sq Ft
  • Built 1900

  Last Sold Summary

  • 4% Above List Price
  • $246/SF
  • 45 Days On Market

  Current Estimated Value $585,357

  Last Listing Agent Greg Kane Kane & Associates

  39 Hamilton Ave, Ossining, NY 10562
• 

  Est $525,008

  Not Listed For Sale

  94 Deer Run, Ossining, NY 10562

  • 1 Bed
  • 1.5 Baths
  • 1,234 Sq Ft
  • Built 1986

  94 Deer Run, Ossining, NY 10562

  Last Sold Summary

  • 9 Days On Market

  Last Listing Agent Stacey Sporn William Raveis Real Estate
• 

  

  

  /41

  $699,975

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,026 Sq Ft

  224 Willow Dr, Briarcliff Manor, NY 10510

  Welcome to 224 Willow Drive, a beautifully maintained and thoughtfully updated home offering 2,026 square feet of living space in the sought-after Briarcliff Manor community. This inviting 3-bedroom, 2.5-bath residence combines timeless charm, modern updates, and exceptional lifestyle amenities. The sun-filled interior features soaring cathedral ceilings, gleaming hardwood floors, and spacious

  Dean Nugent Mary Jane Pastor Realty

  224 Willow Dr, Briarcliff Manor, NY 10510
• 

  $925,000

  Sold Oct 06, 2025

  35 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • 8% Above List Price
  • $343/SF
  • 20 Days On Market

  Current Estimated Value $953,144

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  35 Mystic Dr, Ossining, NY 10562
• 

  Est $159,000

  Not Listed For Sale

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

  • Studio
  • 1 Bath
  • 650 Sq Ft
  • Built 1964

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

  Last Sold Summary

  • 42 Days On Market

  Last Listing Agent Nancy Keller Keller Williams Realty Partner
• 

  

  /49

  $575,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,266 Sq Ft

  311 Kemeys Cove, Briarcliff Manor, NY 10510

  This is a great opportunity to create your own masterpiece - unit needs to be renovated - nestled in the Kemey's Cove Condominium community of Briarcliff Manor awaits a ground level unit with spectacular water views- layout features: Entrance - Living room w/entrance closet - plus sliding doors out to private balcony to enjoy your morning coffee or sunsets at night while sipping wine and watching

  Diane Capone Berkshire Hathaway HS NY Prop

  311 Kemeys Cove, Briarcliff Manor, NY 10510
• 

  $653,000

  Sold Oct 22, 2025

  407 Glenwood Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,837 Sq Ft
  • Built 2001

  Last Sold Summary

  • 9% Above List Price
  • $355/SF
  • 19 Days On Market

  Current Estimated Value $682,441

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Est $663,173

  Not Listed For Sale

  25 Tappan Terrace, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2 Baths
  • 1,673 Sq Ft
  • Built 1956

  25 Tappan Terrace, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Eric Lebenson ERA Insite Realty Services
• 

  

  /26

  $949,000

  Pending

  • 4 Beds
  • 3 Baths
  • 3,012 Sq Ft

  6 Maria Ln, Ossining, NY 10562

  Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich

  Mark Boyland Keller Williams Realty Partner

  6 Maria Ln, Ossining, NY 10562
• 

  $320,000

  Sold Dec 29, 2025

  20 Maple Place, Ossining, NY 10562

  • 5 Beds
  • 1.5 Baths
  • 2,880 Sq Ft
  • Built 1870

  Last Sold Summary

  • 12% Below List Price
  • $111/SF
  • 284 Days On Market

  Current Estimated Value $494,898

  Last Listing Agent Gary Leogrande Keller Williams NY Realty

  20 Maple Place, Ossining, NY 10562
• 

  Est $417,360

  Not Listed For Sale

  9 Briarcliff Dr S Unit 2, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,065 Sq Ft
  • Built 1978

  9 Briarcliff Dr S Unit 2, Ossining, NY 10562

  Last Sold Summary

  • 20 Days On Market

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
• 

  

  /23

  $799,500

  Pending

  • 3 Beds
  • 2.5 Baths
  • 1,914 Sq Ft

  4 Cooper Dr, Ossining, NY 10562

  Enjoy easy living in this spacious, move-in-ready Raised Ranch featuring numerous updates and a functional floor plan. The bright kitchen offers abundant cabinetry, granite countertops, a breakfast bar, and stainless-steel appliances, while the adjacent dining area provides easy access to a two-tier deck, perfect for outdoor dining, entertaining, or just relaxing. Beautiful hardwood floors

  Janet Brand Houlihan Lawrence Inc.

  4 Cooper Dr, Ossining, NY 10562
• 

  $150,000

  Sold Jan 13, 2026

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

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1969

  Last Sold Summary

  • $200/SF
  • 9 Days On Market

  Current Estimated Value $159,000

  Last Listing Agent Peter Raider Real Broker NY LLC

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

  Est $604,306

  Not Listed For Sale

  222 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,390 Sq Ft
  • Built 1983

  222 Woods Brooke Cir, Ossining, NY 10562

  Last Sold Summary

  • 16 Days On Market

  Last Listing Agent Lena O'Neill Howard Hanna Rand Realty
• 

  

  /35

  $699,000

  Pending

  • 2 Beds
  • 3 Baths
  • 1,784 Sq Ft

  191 Horseshoe Cir, Ossining, NY 10562

  Welcome to 191 Horseshoe Circle, a beautifully designed contemporary townhouse at the sought after Fox Hill Condo Development in the Hudson Valley, Westchester County. This rare "C" End Unit is beautifully located in the heart of the development, surrounded by tranquility with an expansive deck for enjoying the outdoors. Cheery and spacious, this home has an open floor plan with combined Dining

  Heidi Henshaw Corcoran Legends Realty

  191 Horseshoe Cir, Ossining, NY 10562
• 

  $1,650,000

  Sold Apr 24, 2026

  2 Lodge Rd, Briarcliff Manor, NY 10510

  • 6 Beds
  • 5.5 Baths
  • 5,700 Sq Ft
  • Built 1996

  Last Sold Summary

  • $289/SF
  • 12 Days On Market

  Current Estimated Value $1,857,128

  Last Listing Agent Arya Rabinovits eRealty Advisors, Inc

  2 Lodge Rd, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1975

  224 Kemeys Cove Unit 2-24, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 41 Days On Market

  Last Listing Agent Stacy Levey William Raveis-New York, LLC
• 

  

  /49

  $649,000

  Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,530 Sq Ft

  73 Clinton Ave, Ossining, NY 10562

  Discover timeless elegance in this impeccably maintained 3-bedroom, 2-bath Colonial in the heart of Ossining. Blending classic charm with exceptional outdoor living, this beautiful home offers warmth, sophistication, and privacy at every turn.The inviting interior features a welcoming living room with a fireplace, creating the perfect gathering space for cozy evenings. A dedicated home

  Tana McGuire eXp Realty

  73 Clinton Ave, Ossining, NY 10562
• 

  $445,000

  Sold Oct 07, 2025

  705 Briarcliff Dr S, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,288 Sq Ft
  • Built 1977

  Last Sold Summary

  • 2% Above List Price
  • $345/SF
  • 46 Days On Market

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty

  705 Briarcliff Dr S, Ossining, NY 10562
• 

  Est $388,082

  Not Listed For Sale

  103 Eagle Bay Dr, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,089 Sq Ft
  • Built 1982

  103 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 22 Days On Market

  Last Listing Agent Nancy Kennedy Houlihan Lawrence Inc.
• 

  

  /32

  $655,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,927 Sq Ft

  8 Still Ct, Ossining, NY 10562

  Nestled in Ossining's coveted Sparta Historic District, this exceptional 1860 historic home offers timeless charm in one of Westchester's unique storied neighborhoods. Rich with character, this special property showcases preserved historical details including original plaster moldings and medallions, hardwood floors throughout, original stone walls, and beautiful rock gardens.The home offers

  Mary Ann Tighe Houlihan Lawrence Inc.

  8 Still Ct, Ossining, NY 10562
• 

  $699,000

  Sold Dec 19, 2025

  5 Cedar Place, Ossining, NY 10562

  • 3 Beds
  • 3 Baths
  • 2,272 Sq Ft
  • Built 1931

  Last Sold Summary

  • 4% Below List Price
  • $308/SF
  • 73 Days On Market

  Current Estimated Value $722,128

  Last Listing Agent Brian Perez Century 21 Hire Realty

  5 Cedar Place, Ossining, NY 10562
• 

  Est $316,000

  Not Listed For Sale

  16 Rockledge Ave Unit 4A-1, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,260 Sq Ft
  • Built 1968

  16 Rockledge Ave Unit 4A-1, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Marco Ricchiuti Compass Greater NY, LLC
• 

  

  /14

  $299,000

  Pending

  • 4 Beds
  • 2.5 Baths
  • 2,374 Sq Ft

  5 Maria Ln, Ossining, NY 10562

  Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private

  Anthony Lando Julia B Fee Sothebys Int. Rlty

  5 Maria Ln, Ossining, NY 10562
• 

  $635,000

  Sold Dec 16, 2025

  7 Birchbrook Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,049 Sq Ft
  • Built 1955

  Last Sold Summary

  • 2% Below List Price
  • $310/SF
  • 55 Days On Market

  Current Estimated Value $672,576

  Last Listing Agent John Buoninfante Real Broker NY LLC

  7 Birchbrook Rd, Ossining, NY 10562
• 

  Est $504,854

  Not Listed For Sale

  1010 Eagle Bay Dr, Ossining, NY 10562

  • 1 Bed
  • 2 Baths
  • 1,378 Sq Ft
  • Built 1982

  1010 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty
• 

  

  /39

  $699,000

  $50K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,286 Sq Ft

  32 Terrace Ave, Ossining, NY 10562

  This charming 3-bedroom, 2-bath home in the Village of Ossining, is a legal 2 family and is currently being used as a single family. Features include a small backyard, a detached 1-car garage, and a convenient location close to shops, transportation, and amenities.

  Jason Kerwar William Raveis Real Estate

  32 Terrace Ave, Ossining, NY 10562
• 

  $610,000

  Sold Nov 14, 2025

  73 van Cortlandt Ave, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,482 Sq Ft
  • Built 1882

  Last Sold Summary

  • 2% Above List Price
  • $412/SF
  • 56 Days On Market

  Current Estimated Value $632,994

  Last Listing Agent Patricia Wolny Corcoran Legends Realty

  73 van Cortlandt Ave, Ossining, NY 10562
• 

  Est $728,574

  Not Listed For Sale

  59 Briarbrook Dr, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 2,000 Sq Ft
  • Built 2001

  59 Briarbrook Dr, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Daniel Bucci Coldwell Banker Realty
• 

  

  /27

  $1,079,000

  $21K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,606 Sq Ft

  54 Allapartus Rd, Ossining, NY 10562

  Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping,

  Derek Greene Greene Realty Group

  54 Allapartus Rd, Ossining, NY 10562
• 

  $980,000

  Sold Jul 10, 2026

  10 Stone Ave, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 1960

  Last Sold Summary

  • 23% Above List Price
  • $456/SF
  • 12 Days On Market

  Current Estimated Value $793,735

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  10 Stone Ave, Ossining, NY 10562
• 

  Not Listed For Sale

  18 Charter Cir Unit 18, Ossining, NY 10562

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

  18 Charter Cir Unit 18, Ossining, NY 10562

  Last Sold Summary

  • 25 Days On Market

  Last Listing Agent Christine Naber RE/MAX Distinguished Hms.&Prop
• 

  

  /47

  $750,000

  • 3 Beds
  • 2 Baths
  • 2,110 Sq Ft

  39 Secor Rd, Ossining, NY 10562

  Welcome to 39 Secor Road. Being sold strictly as-is and as a buy one get one with 37 Secor Road ( offered @ $85K CASH ONLY). You cannot pass on this deal. Get this rare investment opportunity for this two bedroom over 1-bedroom multi- family home that offers street parking or with the purchase of municipal parking pass, tenants can park right behind the building in the municipal lot. This home

  Monica Cooper THD Homes LLC

  39 Secor Rd, Ossining, NY 10562
• 

  $343,350

  Sold Dec 22, 2025

  4 William St, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,160 Sq Ft
  • Built 1826

  Last Sold Summary

  • 26% Below List Price
  • $296/SF
  • 1,016 Days On Market

  Current Estimated Value $436,846

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  4 William St, Ossining, NY 10562
• 

  Not Listed For Sale

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,298 Sq Ft
  • Built 1975

  106 Kemeys Ave Unit 6, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
• 

  

  /6

  $2,295,000

  • 4 Beds
  • 3.5 Baths
  • 2,682 Sq Ft

  94 Somerstown Rd, Ossining, NY 10562

  Phase Two at Moradia is now offering a fabulous to-be-built new modern on Lot One. Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is a brand-new community of high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated

  David Turner Compass Greater NY, LLC

  94 Somerstown Rd, Ossining, NY 10562
• 

  $912,000

  Sold Sep 05, 2025

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

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Below List Price
  • $445/SF
  • 41 Days On Market

  Current Estimated Value $316,000

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.

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

  Not Listed For Sale

  648 Pinesbridge Rd, Ossining, NY 10562

  648 Pinesbridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Susan Pratt Coldwell Banker Realty
• 

  

  /31

  $690,000

  • 1 Bed
  • 1.5 Baths
  • 1,195 Sq Ft

  42 Hudson Watch Dr, Ossining, NY 10562

  Beautifully renovated one-bedroom townhouse with loft and attached garage in desirable Hudson Watch, tucked away on a cul-de-sac. This sun-filled home features hardwood floors, a stunning stone fireplace in the living room, and an open-concept floor plan perfect for modern living. The updated kitchen boasts white cabinetry, stainless steel appliances, quartz countertops, and recessed lighting,

  Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

  42 Hudson Watch Dr, Ossining, NY 10562

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