Ossining, NY Homes

• 

  $805,000 Sold Aug 12, 2025

  801 Syska Rd, Ossining, NY 10562

  • 2 Beds
  • 1.5 Baths
  • 1,328 Sq Ft
  • Built 1956

  Last Sold Summary

  • 15% Above List Price
  • $606/SF
  • 7 Days On Market

  Current Estimated Value $784,657

  Last Listing Agent Yona Strougo Compass Greater NY, LLC

  801 Syska Rd, Ossining, NY 10562
• 

  Est $1,117,184 Not Listed For Sale

  363 Long Hill Rd E, Briarcliff Manor, NY 10510

  363 Long Hill Rd E, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 2% Above List Price
  • 104 Days On Market

  Last Sold Price $1,100,000

  Last Listing Agent Jamey Gelardi Houlihan Lawrence Inc.
• 

  

  

  /50

  $3,300,000

  • 5 Beds
  • 7 Baths
  • 7,931 Sq Ft

  36 Revolutionary Rd, Briarcliff Manor, NY 10510

  The Essence of Westchester Luxury. A Grand Briarcliff Manor Estate sited on 3.83 Private Acres. Perfectly positioned between the Hudson River and Sleepy Hollow Country Club. World-class dining, shopping and Metro North train are nearby, blending convenience with serene privacy. The stately home boasts five spacious ensuite bedrooms, including a spectacular primary suite with a cozy fireplace, a

  Elaine Wasserman Houlihan Lawrence Inc.

  36 Revolutionary Rd, Briarcliff Manor, NY 10510
• 

  $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 $529,340

  Last Listing Agent Greg Kane Kane & Associates

  39 Hamilton Ave, Ossining, NY 10562
• 

  Est $362,085 Not Listed For Sale

  178 Cedar Ln, Ossining, NY 10562

  178 Cedar Ln, Ossining, NY 10562

  Last Sold Summary

  • 2% Above List Price
  • 126 Days On Market

  Last Sold Price $355,000

  Last Listing Agent ALEXIS MALSBURY Coldwell Banker Realty
• 

  

  /50

  $679,000 Pending

  • 5 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  33 Ryder Rd, Ossining, NY 10562

  FREE 12 MONTH HOME WARRANTY that covers electrical/plumbing/appliances/and MORE! This historically charming Center Hall Colonial Farmhouse is situated on almost an acre of pristine land. Own a piece of Westchester County history with this 1826 built farmhouse, enjoy 7' high ceilings, wide planked hardwood floors, and three working fireplaces. HUGE dry walkout basement with an enormous walk-up

  Justin Landon Howard Hanna Rand Realty

  33 Ryder Rd, Ossining, NY 10562
• 

  $850,000 Sold May 15, 2025

  19 High Ridge Rd, Ossining, NY 10562

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

  Last Sold Summary

  • 1% Below List Price
  • $313/SF
  • 15 Days On Market

  Current Estimated Value $884,807

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.

  19 High Ridge Rd, Ossining, NY 10562
• 

  Est $513,289 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

  • 8% Above List Price
  • $385/SF
  • 9 Days On Market

  Last Sold Price $475,000

  Last Listing Agent Stacey Sporn William Raveis Real Estate
• 

  

  /36

  $129,000 Pending

  • 1 Bath
  • 650 Sq Ft

  121 S Highland Ave Unit 5F, Ossining, NY 10562

  Welcome Home to the Best Deal in Ossining! Looking for a great price on a cozy place to come home to, after a hard day's work? Do you cherish Amazing Western Sky Sunsets? Then, you'll love Unit 5F at Parkview Cooperative, conveniently located on Route 9 in Ossining. This very large studio apartment lives like a 1 Bedroom Apt! It has a separated bedroom, giving you some privacy from the main

  Robert Pape Keller Williams NY Realty

  121 S Highland Ave Unit 5F, Ossining, NY 10562
• 

  $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 $899,304

  Last Listing Agent Wendy Nolan Houlihan Lawrence Inc.

  35 Mystic Dr, Ossining, NY 10562
• 

  Est $183,000 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

  • 66% Above List Price
  • $169/SF
  • 42 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Nancy Keller Keller Williams Realty Partner
• 

  

  /8

  $649,000 Pending

  • 5 Beds
  • 3 Baths
  • 1,944 Sq Ft

  132 Croton Ave, Ossining, NY 10562

  Great Investment! This great duplex allows you to live in one unit while the other unit rent covers most of the mortgage monthly payment (first floor and basement unit rent for $3,700, second floor unit rented for $1,850 monthly). Just A 15 minute walk to the Ossining train station. Bus stop right in front. Walk in distance to schools, shops and restaurants.seasonal views of the Hudson River.

  Guido Alvarez United Family Real Estate LLC

  132 Croton Ave, Ossining, NY 10562
• 

  $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 $654,024

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.

  407 Glenwood Dr, Briarcliff Manor, NY 10510
• 

  Est $689,116 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

  • 17% Above List Price
  • $348/SF
  • 270 Days On Market

  Last Sold Price $591,000

  Last Listing Agent Joe Hasselt Joe Hasselt Real Estate
• 

  

  /22

  $775,000 Open Sat 11AM - 12:30PM

  • 5 Beds
  • 2 Baths
  • 2,250 Sq Ft

  35 Havell St, Ossining, NY 10562

  Welcome to 35 Havell St, a legal two family home with a great oppottunity for owner occupied & rental income for the other unit. Unit 1 has 3 bedrooms, 1 full bath, living room, large eat in kitchen with access to backyard patio area. Full basement with plenty of storage, laundry area, mechanicals & 1 car garage. Unit 2 which is tenant occupied, has 2 bedrooms, 1 full bath, living room, large eat

  Elizabeth Kamp Kane & Associates

  35 Havell St, 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 $409,633

  Last Listing Agent Gary Leogrande Keller Williams NY Realty

  20 Maple Place, Ossining, NY 10562
• 

  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

  • $254/SF
  • 21 Days On Market

  Last Sold Price $435,000

  Last Listing Agent Pamela Rotando Coldwell Banker Realty
• 

  

  /37

  $449,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft

  15 Steven Dr Unit 4, Ossining, NY 10562

  Welcome to this bright and inviting two bedroom, two bathroom condo located in the desirable Hudson View development in Ossining. This beautifully designed home features dramatic lofted ceilings and an abundance of natural light, enhanced by multiple skylights that create an airy, open feel throughout. The spacious living area is highlighted by a charming wood burning fireplace, perfect for cozy

  James Andrews Today Realty Corp.

  15 Steven Dr Unit 4, 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 $183,000

  Last Listing Agent Peter Raider Real Broker NY LLC

  117 S Highland Ave Unit 6J, 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

  • $240/SF
  • 10 Days On Market

  Last Sold Price $934,500

  Last Listing Agent Arafat Ibrahim AI Realty Brokerage LLC
• 

  

  /48

  $5,500,000

  • 7 Beds
  • 5.5 Baths
  • 5,700 Sq Ft

  433 Arcady Rd, Ossining, NY 10562

  Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular

  Nancy Kennedy

  433 Arcady Rd, 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 $366,000 Not Listed For Sale

  16 Rockledge Ave Unit 6J2, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,560 Sq Ft
  • Built 1968

  16 Rockledge Ave Unit 6J2, Ossining, NY 10562

  Last Sold Summary

  • 37% Above List Price
  • $172/SF
  • 147 Days On Market

  Last Sold Price $268,000

  Last Listing Agent Iris Kalt Berkshire Hathaway Home Services
• 

  

  /23

  $599,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft

  22 Copley Ct Unit 22, Briarcliff Manor, NY 10510

  Beautifully maintained 2-bedroom, 2-bath condo in the highly desirable Copley Court community, just minutes from downtown Briarcliff Manor with its quaint shops and restaurants. This home features a fantastic open floor plan with an open kitchen and breakfast bar that flows seamlessly into the dining area and a spacious living room. Sliding glass doors lead to a covered porch overlooking the pool

  Maura Mcspedon William Raveis Real Estate

  22 Copley Ct Unit 22, Briarcliff Manor, NY 10510
• 

  $490,000 Sold Jul 31, 2025

  49 Pine Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,026 Sq Ft
  • Built 1963

  Last Sold Summary

  • 2% Above List Price
  • $478/SF
  • 36 Days On Market

  Current Estimated Value $507,872

  Last Listing Agent Kelly Castiglione Coldwell Banker Realty

  49 Pine Ave, Ossining, NY 10562
• 

  Est $637,041 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

  • 11% Above List Price
  • $367/SF
  • 39 Days On Market

  Last Sold Price $575,000

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
• 

  

  /26

  $224,000

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  123 S Highland Ave Unit B3, Ossining, NY 10562

  Welcome to Highland Terrace! This spacious 2-bedroom, 1-bath garden-style co-op offers 950 square feet of comfortable living. This first-floor unit features a bright layout with plenty of natural light throughout. Enjoy the convenience of assigned parking and the benefits of a well-maintained community complete with a pool and basketball court.Pet lovers will appreciate that this co-op is

  Taylor Cirillo Howard Hanna Rand Realty

  123 S Highland Ave Unit B3, 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 $691,014

  Last Listing Agent Brian Perez Century 21 Hire Realty

  5 Cedar Place, Ossining, NY 10562
• 

  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

  • $347/SF
  • 26 Days On Market

  Last Sold Price $450,500

  Last Listing Agent Madelyn Ricciardi Houlihan Lawrence Inc.
• 

  

  /41

  $439,000

  • 3 Beds
  • 2 Baths
  • 1,431 Sq Ft

  9 Briarcliff Dr S Unit 16, Ossining, NY 10562

  Opportunity awaits in the reputable Briarcliff Woods Development in Ossining, where space, light, and an exceptional layout set the stage for your vision. This spacious 3-bedroom, 2-bath condominium is thoughtfully designed to meet your lifestyle needs, offering a wealth of opportunities to personalize and transform it into your dream home. As you step inside, you're greeted by an expansive

  Lisa DaRos Houlihan Lawrence Inc.

  9 Briarcliff Dr S Unit 16, Ossining, NY 10562
• 

  $1,264,064 Sold Jun 24, 2025

  35 Candlewood Ct, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3.5 Baths
  • 2,715 Sq Ft
  • Built 1998

  Last Sold Summary

  • 29% Above List Price
  • $466/SF
  • 6 Days On Market

  Current Estimated Value $1,284,123

  Last Listing Agent Kathleen Griffin Houlihan Lawrence Inc.

  35 Candlewood Ct, Briarcliff Manor, NY 10510
• 

  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

  • $211/SF
  • 22 Days On Market

  Last Sold Price $190,000

  Last Listing Agent Jamie Jamieson Compass Greater NY, LLC
• 

  

  /37

  $1,795,000

  • 4 Beds
  • 4 Baths
  • 3,847 Sq Ft

  37 Hyatt Rd, Briarcliff Manor, NY 10510

  Set at the end of a quiet cul-de-sac on nearly two perfectly flat acres, 37 Hyatt Road offers a rare combination of privacy, usable land, and thoughtful custom design. The property is distinguished by its expansive level lawns and gunite pool, creating an exceptional setting for outdoor living, recreation, and entertaining. A covered patio extends the living space outdoors and provides a natural

  Adam Hade Compass Greater NY, LLC

  37 Hyatt Rd, Briarcliff Manor, NY 10510
• 

  $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 $638,996

  Last Listing Agent John Buoninfante Real Broker NY LLC

  7 Birchbrook Rd, Ossining, NY 10562
• 

  Est $933,316 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

  • 1% Below List Price
  • $348/SF
  • 79 Days On Market

  Last Sold Price $945,000

  Last Listing Agent Gay Marglin Houlihan Lawrence Inc.
• 

  

  /43

  $600,000 Open Sat 12PM - 2PM

  • 3 Beds
  • 1.5 Baths
  • 1,636 Sq Ft

  4 Spaulding Place, Ossining, NY 10562

  Welcome home to this beautifully updated and maintained American Foursquare full of original charm and tasteful modern upgrades. A picturesque and centrally located home in the Village of Ossining, just an hour north of NYC. A large, private front porch and entry welcomes you into the main floor of this classic home. You're lead into a gracious first floor layout — the living room with it's large

  Katelyn White Hudson River Line Realty

  4 Spaulding Place, 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 $610,420

  Last Listing Agent Patricia Wolny Corcoran Legends Realty

  73 van Cortlandt Ave, Ossining, NY 10562
• 

  Est $183,000 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

  • 14% Above List Price
  • $213/SF
  • 114 Days On Market

  Last Sold Price $159,900

  Last Listing Agent Lisa Emanuele ERA Insite Realty Services
• 

  

  /36

  $690,000

  • 2 Beds
  • 2.5 Baths
  • 1,850 Sq Ft

  42 Brooke View Dr, Ossining, NY 10562

  Welcome home to The Woods Condominium, a community in Westchester offering both proximity to NYC and recreation galore. This beautifully maintained three-level townhome has 2 bedrooms, 2.5 bathrooms, a finished basement, an additional room which can serve as bedroom or home office, and an attached garage. The finished basement boasts generous living space with two full size closets for storage

  Jonathan Minerick HomeCoin.com

  42 Brooke View Dr, 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 $349,320

  Last Listing Agent Jamarr Zellner REALHome Services & Solutions

  4 William St, Ossining, NY 10562

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