Ossining, NY Homes

• 

  

  

  /30

  $423,000

  $8K PRICE INCREASE

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

  16 Rockledge Ave Unit 5K-1, Ossining, NY 10562

  Welcome to Scarborough Manor, A Co-Op That Offers The Perfect Balance Of Tranquility And Convenience. This Fifth-Floor Beauty Offers A Rare Opportunity To Reside In A Serene And Sophisticated Setting Along The Majestic Hudson River. This Two Bedroom, Two Bath Stunner Has Nine Foot Ceilings, Oversized Rooms, And Tons Of Closet Space. This Unit Is Ideal For Hosting Intimate Gatherings Or Enjoying

  Candace D'Addario Coldwell Banker Realty

  16 Rockledge Ave Unit 5K-1, Ossining, NY 10562
• 

  $206,000

  Sold Nov 12, 2025

  119 S Highland Ave Unit 1B, Ossining, NY 10562

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft
  • Built 1964

  Last Sold Summary

  • 18% Above List Price
  • $229/SF
  • 211 Days On Market

  Last Listing Agent Alex Hernandez Real Broker NY LLC

  119 S Highland Ave Unit 1B, Ossining, NY 10562
• 

  Est $725,967

  Not Listed For Sale

  4 Mystic Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,974 Sq Ft
  • Built 1996

  4 Mystic Dr, Ossining, NY 10562

  Last Sold Summary

  • 44 Days On Market

  Last Listing Agent Nancy Strong Douglas Elliman Real Estate
• 

  

  

  /10

  $249,000

  $50K PRICE DROP Pending

  • 2 Beds
  • 1 Bath
  • 849 Sq Ft

  126 Croton Ave, Ossining, NY 10562

  Opportunity knocks in the heart of Ossining. Best value home on the market right now!!! This 2-bedroom, 1-bath Colonial offers tremendous potential for investors, contractors, renovators, and buyers seeking a value-add project. The home is ready for its next chapter and presents the chance to restore, reimagine, or redevelop to suit your vision. Featuring a traditional Colonial layout and a

  Arya Rabinovits eRealty Advisors, Inc

  126 Croton Ave, Ossining, NY 10562
• 

  $116,000

  Sold Aug 27, 2025

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

  • 1 Bath
  • 650 Sq Ft
  • Built 1973

  Last Sold Summary

  • 3% Below List Price
  • $178/SF
  • 34 Days On Market

  Current Estimated Value $159,000

  Last Listing Agent Dina Lewis Dorothy Jensen Realty, Inc.

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

  Not Listed For Sale

  360 N State Rd Unit 1I, Ossining, NY 10510

  • 1 Bed
  • 1 Bath
  • 950 Sq Ft
  • Built 1950

  360 N State Rd Unit 1I, Ossining, NY 10510

  Last Sold Summary

  • 160 Days On Market

  Last Listing Agent Wendy Phillips Corcoran Legends Realty
• 

  

  /50

  $899,000

  • 4 Beds
  • 3 Baths
  • 2,664 Sq Ft

  20 Waller Ave, Ossining, NY 10562

  Don't miss this opportunity to own a charming owner occupied only two family home full of character, situated on a beautiful corner lot with a welcoming front porch, great curb appeal, and a detached 2 car garage. This sun filled home features oversized windows, high ceilings, hardwood floors, original wood doors, thick floor moldings, and high hats throughout both units, blending timeless

  Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

  20 Waller Ave, Ossining, NY 10562
• 

  $500,000

  Sold Jan 07, 2026

  22 William St, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,116 Sq Ft
  • Built 1893

  Last Sold Summary

  • 25% Above List Price
  • $236/SF
  • 29 Days On Market

  Current Estimated Value $647,910

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  22 William St, Ossining, NY 10562
• 

  Est $686,343

  Not Listed For Sale

  2 Robert Rinaldi Ln, Ossining, NY 10562

  • 2 Beds
  • 4 Baths
  • 1,614 Sq Ft
  • Built 2015

  2 Robert Rinaldi Ln, Ossining, NY 10562

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.
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  /34

  $850,000

  • 2 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  227 Cedar Ln, Ossining, NY 10562

  A Rare 200-Year-Old Log Cabin Sanctuary with Subdivision/Expansion Potential! Step back in time without sacrificing an ounce of modern comfort in this enchanting, hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history, contemporary ease, and incredible future value with a potential buildable lot included. The interior showcases

  Josephine O'Leary Weir Julia B Fee Sothebys Int. Rlty

  227 Cedar Ln, Ossining, NY 10562
• 

  $630,000

  Sold Aug 07, 2026

  63 Deerfield Ln Unit 63, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,547 Sq Ft
  • Built 1986

  Last Sold Summary

  • 3% Above List Price
  • $407/SF
  • 60 Days On Market

  Last Listing Agent Thomas Burns Coldwell Banker Realty

  63 Deerfield Ln Unit 63, Ossining, NY 10562
• 

  Not Listed For Sale

  0 Burns Place Unit ONEH6329441, Briarcliff Manor, NY 10510

  0 Burns Place Unit ONEH6329441, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 89 Days On Market

  Last Listing Agent Ramanjit Dhanoa eXp Realty
• 

  

  /34

  $749,000

  Pending

  • 3 Beds
  • 3 Baths
  • 1,930 Sq Ft

  124 Cedar Ln, Ossining, NY 10562

  Set on a sprawling 1.41-acre lot with rolling lawn, this beautifully updated 3-bedroom, 1 full/2 half bath Raised Ranch offers the space and privacy that's hard to find so close to the city. Inside, a flexible layout flows easily between everyday living and entertaining, centered around a new kitchen with stainless steel appliances and granite countertops. The generous living room overlooks the

  Magdalena Konkola Houlihan Lawrence Inc.

  124 Cedar Ln, Ossining, NY 10562
• 

  $699,000

  Sold Jun 03, 2026

  155 Club Ct, Ossining, NY 10562

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

  Last Sold Summary

  • $437/SF
  • 20 Days On Market

  Current Estimated Value $696,180

  Last Listing Agent Michael LaMorte eXp Realty

  155 Club Ct, Ossining, NY 10562
• 

  Not Listed For Sale

  16 Maria Ln, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 3,427 Sq Ft
  • Built 1887

  16 Maria Ln, Ossining, NY 10562

  Last Sold Summary

  • 33 Days On Market

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team
• 

  

  /31

  $1,350,000

  $225K PRICE INCREASE

  • 6 Beds
  • 3.5 Baths
  • 4,546 Sq Ft

  28 Hamilton Ave, Ossining, NY 10562

  Built in 1870 and lovingly restored by its current owners, this Queen Anne Victorian at 28 Hamilton Avenue sits in the heart of Historic Ossining. Both yards are planted with apple, cherry, Asian pear, pawpaw, hazelnut, raspberry, blueberry, and strawberry, along with a working vegetable garden — a rare thing to find alongside a home of this character. Approach through a deep front yard bursting

  Zoya Litinetskaya Compass Greater NY, LLC

  28 Hamilton Ave, Ossining, NY 10562
• 

  $606,000

  Sold Jul 28, 2026

  5 Meadowbrook Dr, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,560 Sq Ft
  • Built 1958

  Last Sold Summary

  • 1% Above List Price
  • $388/SF
  • 17 Days On Market

  Current Estimated Value $616,339

  Last Listing Agent Daniel Berger RE/MAX Prestige Properties

  5 Meadowbrook Dr, Ossining, NY 10562
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  Not Listed For Sale

  9 Barnes Rd, Ossining, NY 10562

  • 4 Beds
  • 4.5 Baths
  • 4,583 Sq Ft
  • Built 1797

  9 Barnes Rd, Ossining, NY 10562

  Last Sold Summary

  • 37 Days On Market

  Last Listing Agent Sena Baron William Raveis-New York, LLC
• 

  

  /32

  $675,000

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

  56 Pond View Ct, Ossining, NY 10562

  Welcome to this well maintained 2-bedroom 2.5 bathroom end-unit townhouse in the Woods where comfort, space and easy-living come together. Freshly painted throughout and featuring brand new carpeting, this home offers a clean, move in ready interior with a bright and welcoming atmosphere. Discover the added privacy and abundance of natural light that comes with an end-unit location. Recent

  Sarah Mirza Mulhall Julia B Fee Sothebys Int. Rlty

  56 Pond View Ct, Ossining, NY 10562
• 

  $965,000

  Sold Oct 09, 2025

  15 Deertree Ln, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Above List Price
  • $335/SF
  • 56 Days On Market

  Last Listing Agent Iris Lu-Notis Coldwell Banker Realty

  15 Deertree Ln, Briarcliff Manor, NY 10510
• 

  Not Listed For Sale

  130 Pinesbridge Rd, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 2,644 Sq Ft
  • Built 1946

  130 Pinesbridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 168 Days On Market

  Last Listing Agent Natalia Wixom Compass Greater NY, LLC
• 

  

  /19

  $624,000

  $236K PRICE DROP Pending

  • 4 Beds
  • 2.5 Baths
  • 3,128 Sq Ft

  398 Illington Rd, Ossining, NY 10562

  A Charming Farmhouse Style Home, Carefully Restored to Blend Historic Character with Modern Comfort. Nestled on 3 acres of landscaped grounds, this inviting residence offers spacious living and serene privacy just minutes from local amenities and commuting routes. The renovations that were made still kept its original charm. Features like the woodwork, beamed ceilings, built-in cabinets, and

  Joann Perna Guardian Realty Center, LLC

  398 Illington Rd, Ossining, NY 10562
• 

  $485,000

  Sold Dec 12, 2025

  313 Saddle Trail Unit 31-3, Ossining, NY 10562

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

  Last Sold Summary

  • 8% Above List Price
  • $425/SF
  • 12 Days On Market

  Last Listing Agent Mary Ann Tighe Houlihan Lawrence Inc.

  313 Saddle Trail Unit 31-3, Ossining, NY 10562
• 

  Not Listed For Sale

  50 Spring Valley Rd, Ossining, NY 10562

  • 3 Beds
  • 5 Baths
  • 3,902 Sq Ft
  • Built 1897

  50 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 388 Days On Market

  Last Listing Agent Michael Clemente DeSimone Real Estate
• 

  

  /32

  $979,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,904 Sq Ft

  29 Winterberry Ln, Briarcliff Manor, NY 10510

  Welcome to 29 Winterberry Lane, a beautifully updated townhome in Briarcliff Manor's sought-after Wyndcrest community, offering 3 bedrooms, 2.5 baths, and roughly 2,904 square feet of turnkey living space in the highly sought after Briarcliff Manor school district. Set at the end of the cul-de-sac, just steps from the pool, this home offers extra privacy along with balconies and spacious outdoor

  Rachel Lacoste Houlihan Lawrence Inc.

  29 Winterberry Ln, Briarcliff Manor, NY 10510
• 

  $915,000

  Sold Mar 27, 2026

  47 Stormytown Rd, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 2,424 Sq Ft
  • Built 1953

  Last Sold Summary

  • 4% Above List Price
  • $377/SF
  • 13 Days On Market

  Current Estimated Value $906,079

  Last Listing Agent Mauro Santucci Kane & Associates

  47 Stormytown Rd, Ossining, NY 10562
• 

  Not Listed For Sale

  49 Spring Valley Rd, Ossining, NY 10562

  • 5 Beds
  • 3 Baths
  • 2,754 Sq Ft
  • Built 1855

  49 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 75 Days On Market

  Last Listing Agent Matthew Valvano Berkshire Hathaway HS NY Prop
• 

  

  /36

  $650,000

  Pending

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft

  310 Kemeys Ave Unit 3-10, Briarcliff Manor, NY 10510

  As nice as they come. Hudson River views. Totally renovated from top to bottom. New kitchen, new baths, new flooring, new crown molding, recessed lighting, ceiling fans and speakers, new a/c units, expanded and organized closets, new separate laundry closet. Open Living Room/Dining Area with Hudson River Views and slider to patio with awning. Super-efficient galley kitchen outfitted with Bosch

  Stacy Levey William Raveis-New York, LLC

  310 Kemeys Ave Unit 3-10, Briarcliff Manor, NY 10510
• 

  $930,000

  Sold Jan 22, 2026

  9 High Ridge Rd, Ossining, NY 10562

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

  Last Sold Summary

  • 3% Above List Price
  • $343/SF
  • 30 Days On Market

  Current Estimated Value $934,744

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty

  9 High Ridge Rd, Ossining, NY 10562
• 

  Est $818,112

  Not Listed For Sale

  801 Syska Rd, Ossining, NY 10562

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

  801 Syska Rd, Ossining, NY 10562

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Yona Strougo Compass Greater NY, LLC
• 

  

  /11

  $125,000

  Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  50 Charter Cir Unit C, Ossining, NY 10562

  It's oh so quiet. This High Meadows top floor one bedroom, one bath is fresh and ready to go. Hard wood floors throughout, A sun filled living room with dining nook, new stove and refrigerator, lot's of closet space. A small hall leads to extra closets and the bedroom. High Meadows Cooperative features a common laundry and storage space around the back. 2 playgrounds and a basketball court are

  Ali Alvarez Houlihan Lawrence Inc.

  50 Charter Cir Unit C, Ossining, NY 10562
• 

  $800,000

  Sold Jul 14, 2026

  25 William St, Ossining, NY 10562

  • 7 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • Built 1880

  Last Sold Summary

  • 16% Below List Price
  • $360/SF
  • 119 Days On Market

  Current Estimated Value $827,667

  Last Listing Agent Etan Hakimi Mitra Hakimi Realty Group LLC

  25 William St, Ossining, NY 10562
• 

  Est $934,243

  Not Listed For Sale

  796 Pinesbridge Rd, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 2,900 Sq Ft
  • Built 1870

  796 Pinesbridge Rd, Ossining, NY 10562

  Last Sold Summary

  • 48 Days On Market

  Last Listing Agent Patricia Schiller Patricia Schiller Real Est Co.
• 

  

  /30

  $639,500

  • 4 Beds
  • 2 Baths
  • 1,463 Sq Ft

  42 Pershing Ave, Ossining, NY 10562

  Welcome home to this beautifully maintained 4-bedroom, 2-bath Cape Cod nestled in one of the desirable Hudson Valley River towns. Combining classic charm with everyday comfort, this move-in-ready home features gleaming hardwood floors, spacious living areas, and a flexible floor plan perfect for today's lifestyle.The private backyard offers a peaceful retreat with a patio ideal for outdoor

  Janet Brand Houlihan Lawrence Inc.

  42 Pershing Ave, Ossining, NY 10562
• 

  $775,000

  Sold Aug 20, 2025

  15 Cooper Dr, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 2,742 Sq Ft
  • Built 1961

  Last Sold Summary

  • 13% Below List Price
  • $283/SF
  • 103 Days On Market

  Current Estimated Value $830,569

  Last Listing Agent Bopaul Sookdeo YourHomeSold Guaranteed Realty

  15 Cooper Dr, Ossining, NY 10562
• 

  Est $810,961

  Not Listed For Sale

  800 Syska Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,196 Sq Ft
  • Built 1955

  800 Syska Rd, Ossining, NY 10562

  Last Sold Summary

  • 66 Days On Market

  Last Listing Agent John Buoninfante Real Broker NY LLC
• 

  

  /6

  $1,899,000

  • 4 Beds
  • 3.5 Baths
  • 2,693 Sq Ft

  94 Somerstown Rd, Ossining, NY 10562

  Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is abrand-new community of to-be-built, 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 and private-ranging between 1 1/2 and 3 acres. Masia, is the first

  David Turner Compass Greater NY, LLC

  94 Somerstown Rd, Ossining, NY 10562
• 

  $2,380,000

  Sold Jul 06, 2026

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3.5 Baths
  • 3,282 Sq Ft
  • Built 1957

  Last Sold Summary

  • 21% Below List Price
  • $725/SF
  • 83 Days On Market

  Current Estimated Value $2,608,138

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC

  132 Ridgecrest Rd, Briarcliff Manor, NY 10510
• 

  Est $1,106,521

  Not Listed For Sale

  265 Chadeayne Rd, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,392 Sq Ft
  • Built 1968

  265 Chadeayne Rd, Ossining, NY 10562

  Last Sold Summary

  • 13 Days On Market

  Last Listing Agent Douglas Dill Houlihan Lawrence Inc.
• 

  

  /3

  $650,000

  Pending

  • 4 Beds
  • 2 Baths
  • 1,667 Sq Ft

  24 Fuller Rd, Ossining, NY 10562

  Beautiful 4-bedroom, 2 full bath home located on a quiet cul-de-sac in Ossining, offering a comfortable layout and inviting indoor-outdoor living. The main level features an open-concept design connecting the eat-in kitchen and living room, highlighted by modern stainless steel appliances, beautiful moldings, and expansive windows that fill the home with natural light, creating an ideal setting

  Joseph Lukic Compass Greater NY, LLC

  24 Fuller Rd, Ossining, NY 10562

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