Ossining, NY Homes

• 

  

  

  /16

  $155,000

  $2K PRICE INCREASE

  • 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
• 

  $625,000

  Sold Sep 02, 2025

  7 Fuller Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 1,692 Sq Ft
  • Built 1963

  Last Sold Summary

  • 10% Above List Price
  • $369/SF
  • 18 Days On Market

  Current Estimated Value $658,050

  Last Listing Agent Amy Dmytryshyn Corcoran Legends Realty

  7 Fuller Rd, Ossining, NY 10562
• 

  Est $158,000

  Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1964

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

  Last Sold Summary

  • 27 Days On Market
• 

  

  

  /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
• 

  $3,100,000

  Sold Sep 24, 2025

  41 Austin Place, Briarcliff Manor, NY 10510

  • 5 Beds
  • 7.5 Baths
  • 9,783 Sq Ft
  • Built 2007

  Last Sold Summary

  • 3% Above List Price
  • $317/SF
  • 53 Days On Market

  Current Estimated Value $3,171,215

  Last Listing Agent Hillary Landau Compass Greater NY, LLC

  41 Austin Place, Briarcliff Manor, NY 10510
• 

  Est $720,658

  Not Listed For Sale

  9 River Pkwy, Briarcliff Manor, NY 10510

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft
  • Built 1976

  9 River Pkwy, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 270 Days On Market
• 

  

  /50

  $2,175,000

  • 3 Beds
  • 4.5 Baths
  • 3,178 Sq Ft

  107 Tower Hill Rd, Briarcliff Manor, NY 10510

  Make your dreams come true! Rare opportunity to own this beautiful and charming, mint-condition Cape Cod Colonial home on the grounds of SHCC adjacent to the 6th & 7th holes of the private golf course. Sleepy Hollow Country Club is ranked as #52 of America's greatest golf courses by Golf Digest & as #77 in the world by Golf magazine. Young roof (2015), young windows, young hot water boiler

  Susan Strawgate Code Houlihan Lawrence Inc.

  107 Tower Hill Rd, Briarcliff Manor, NY 10510
• 

  $1,675,000

  Sold Aug 06, 2025

  95 Marlborough Rd, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft
  • Built 1952

  Last Sold Summary

  • 21% Above List Price
  • $625/SF
  • 10 Days On Market

  Current Estimated Value $1,660,970

  Last Listing Agent Amy Via Houlihan Lawrence Inc.

  95 Marlborough Rd, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  17 Steven Dr Unit 3, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,710 Sq Ft
  • Built 1995

  17 Steven Dr Unit 3, Ossining, NY 10562

  Last Sold Summary

  • 21 Days On Market
• 

  

  /49

  $575,000

  • 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
• 

  $650,000

  Sold Oct 01, 2025

  23 Ann St, Ossining, NY 10562

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft
  • Built 1897

  Last Sold Summary

  • $361/SF
  • 58 Days On Market

  Current Estimated Value $663,928

  Last Listing Agent Eric Schatz Schatz Realty Group

  23 Ann St, Ossining, NY 10562
• 

  Not Listed For Sale

  79 Main St, Ossining, NY 10562

  • 8 Beds
  • 4 Baths
  • 3,888 Sq Ft
  • Built 1880

  79 Main St, Ossining, NY 10562

  Last Sold Summary

  • 10 Days On Market
• 

  

  /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
• 

  $280,000

  Sold Dec 30, 2025

  129 S Highland Ave Unit C-2, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,047 Sq Ft
  • Built 1961

  Last Sold Summary

  • $267/SF
  • 91 Days On Market

  Last Listing Agent Linda Williams Century 21 Alliance Realty Grp

  129 S Highland Ave Unit C-2, Ossining, NY 10562
• 

  Est $674,252

  Not Listed For Sale

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  • 2 Beds
  • 2.5 Baths
  • 1,566 Sq Ft
  • Built 2015

  8 Robert Rinaldi Ln, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 39 Days On Market
• 

  

  /35

  $699,000

  • 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
• 

  $999,000

  Sold Apr 24, 2026

  7 Dunn Ln, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 1,800 Sq Ft
  • Built 1950

  Last Sold Summary

  • 2% Above List Price
  • $555/SF
  • 29 Days On Market

  Current Estimated Value $974,907

  Last Listing Agent Greg Kochanov Compass Greater NY, LLC

  7 Dunn Ln, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  506 Kemeys Cove Unit 506, Ossining, NY 10562

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

  506 Kemeys Cove Unit 506, Ossining, NY 10562

  Last Sold Summary

  • 26 Days On Market
• 

  

  /43

  $1,795,000

  Pending

  • 4 Beds
  • 4.5 Baths
  • 4,327 Sq Ft

  26 Plumwood Rd, Briarcliff Manor, NY 10510

  Beautifully sited on a quiet cul-de-sac alongside the golf course, this gracious center hall Colonial combines exceptional scale, timeless design, and an enviable Briarcliff Manor location, close to award-winning schools. Thoughtfully designed for both everyday living and entertaining, this home offers 4 bedrooms and 4.5 baths, including a spacious primary suite with heated floors and custom

  Jessica Cunningham

  26 Plumwood Rd, Briarcliff Manor, NY 10510
• 

  $280,000

  Sold Sep 17, 2025

  92 Charter Cir Unit 92, Ossining, NY 10562

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

  Last Sold Summary

  • 2% Above List Price
  • $295/SF
  • 14 Days On Market

  Last Listing Agent Valerie Cascione Compass Greater NY, LLC

  92 Charter Cir Unit 92, Ossining, NY 10562
• 

  Not Listed For Sale

  123 S Highland Ave Unit B5, Ossining, NY 10562

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

  123 S Highland Ave Unit B5, Ossining, NY 10562

  Last Sold Summary

  • 22 Days On Market
• 

  

  /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
• 

  $605,000

  Sold Feb 21, 2026

  126 Whitetail Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,886 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $321/SF
  • 23 Days On Market

  Current Estimated Value $606,090

  Last Listing Agent Kathleen Courtney Coldwell Banker Realty

  126 Whitetail Cir, Ossining, NY 10562
• 

  Est $950,915

  Not Listed For Sale

  45 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1996

  45 Mystic Dr, Ossining, NY 10562

  Last Sold Summary

  • 79 Days On Market
• 

  

  /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
• 

  $625,000

  Sold Sep 02, 2025

  233 Woods Brooke Cir, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,475 Sq Ft
  • Built 1985

  Last Sold Summary

  • $424/SF
  • 26 Days On Market

  Current Estimated Value $640,272

  Last Listing Agent Carl Baker Ball Property Management LLC

  233 Woods Brooke Cir, Ossining, NY 10562
• 

  Est $158,000

  Not Listed For Sale

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

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

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

  Last Sold Summary

  • 114 Days On Market
• 

  

  /27

  $1,085,000

  $15K 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
• 

  $164,000

  Sold Oct 29, 2025

  131 S Highland Ave Unit A3, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft
  • Built 1962

  Last Sold Summary

  • 3% Above List Price
  • $219/SF
  • 58 Days On Market

  Last Listing Agent Amit Shah Compass Greater NY, LLC

  131 S Highland Ave Unit A3, Ossining, NY 10562
• 

  Est $509,983

  Not Listed For Sale

  1210 Eagle Bay Dr, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1982

  1210 Eagle Bay Dr, Ossining, NY 10562

  Last Sold Summary

  • 26 Days On Market
• 

  

  /25

  $1,550,000

  Pending

  • 5 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  33 Hirst Rd, Briarcliff Manor, NY 10510

  Located on a desirable cul-de-sac street in sought-after Briarcliff Manor, this fully renovated, contemporary-style, spacious ranch combines privacy, panoramic views, and a flowing, open floor plan filled with natural sunlight. Perfect for those seeking the ease of main-level living, the home also offers extensive additional space and rooms on the lower level. The sunny, open, eat-in kitchen has

  Lisa Goodrich - Zedlovich Guard Hill Realty

  33 Hirst Rd, Briarcliff Manor, NY 10510
• 

  $515,000

  Sold Jan 29, 2026

  61 Snowden Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,516 Sq Ft
  • Built 1957

  Last Sold Summary

  • 3% Above List Price
  • $340/SF
  • 30 Days On Market

  Current Estimated Value $533,912

  Last Listing Agent Paul Leis North Country Sothebys Int Rlt

  61 Snowden Ave, Ossining, NY 10562
• 

  Est $184,000

  Not Listed For Sale

  129 S Highland Ave Unit B4, Ossining, NY 10562

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

  129 S Highland Ave Unit B4, Ossining, NY 10562

  Last Sold Summary

  • 23 Days On Market
• 

  

  /42

  $675,000

  • 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 (mls#973600, offered @ $85K). 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
• 

  $377,500

  Sold Jan 13, 2026

  16 Rockledge Ave Unit 7J, Ossining, NY 10562

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

  Last Sold Summary

  • 2% Below List Price
  • $239/SF
  • 122 Days On Market

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  16 Rockledge Ave Unit 7J, Ossining, NY 10562
• 

  Not Listed For Sale

  123 S Highland Ave Unit B4, Ossining, NY 10562

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

  123 S Highland Ave Unit B4, Ossining, NY 10562

  Last Sold Summary

  • 360 Days On Market
• 

  

  /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
• 

  $635,000

  Sold Jul 21, 2025

  45 Lee Ave, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 1,274 Sq Ft
  • Built 1962

  Last Sold Summary

  • 7% Above List Price
  • $498/SF
  • 16 Days On Market

  Current Estimated Value $644,790

  Last Listing Agent Suzanne Lagle Houlihan Lawrence Inc.

  45 Lee Ave, Ossining, NY 10562
• 

  Est $377,156

  Not Listed For Sale

  7 Nicole Cir Unit 7, Ossining, NY 10562

  • 1 Bed
  • 2 Baths
  • 1,127 Sq Ft
  • Built 1987

  7 Nicole Cir Unit 7, Ossining, NY 10562

  Last Sold Summary

  • 82 Days On Market
• 

  

  /16

  $500,000

  • 3 Beds
  • 3 Baths
  • 1,992 Sq Ft

  237 Spring St, Ossining, NY 10562

  Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments.There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage

  Peggy Wunderlich Douglas Elliman Real Estate

  237 Spring St, Ossining, NY 10562

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