Ossining, NY Homes

• 

  Est $785,339

  Not Listed For Sale

  5 Tavano Rd, Ossining, NY 10562

  • 3 Beds
  • 3 Baths
  • 2,295 Sq Ft
  • Built 1967

  5 Tavano Rd, Ossining, NY 10562

  Last Sold Summary

  • 27% Below List Price
  • $468/SF
  • 30 Days On Market

  • Last Sold Price $1,075,000
  • Dec 18, 2024

  Last Listing Agent Diane Silverman Keller Williams NY Realty
• 

  

  

  /13

  $399,000

  Pending

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  1 Agate Ave, Ossining, NY 10562

  Are you thinking about making a move? This is the perfect opportunity you were waiting for! Westchester welcomes you to your new home sweet home! One family house for a first-time homebuyer or those who are seeking a serene retreat! Well-maintained frame house, sitting on a 30x160 lot, with an inviting front porch. Step inside to discover 2 bedrooms, a full bathroom, plus one car garage. Imagine

  Segundo Agudo City Homes Realty Group LLC

  1 Agate Ave, Ossining, NY 10562
• 

  $364,000

  Sold Sep 25, 2025

  16 Rockledge Ave Unit 3L-1, Ossining, NY 10562

  • 1 Bed
  • 1 Bath
  • 1,284 Sq Ft
  • Built 1970

  Last Sold Summary

  • 4% Above List Price
  • $283/SF
  • 27 Days On Market

  Current Estimated Value $378,000

  Last Listing Agent Anna Hawley Howard Hanna Rand Realty

  16 Rockledge Ave Unit 3L-1, Ossining, NY 10562
• 

  Est $699,456

  Not Listed For Sale

  25 Somerstown Rd, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,540 Sq Ft
  • Built 1928

  25 Somerstown Rd, Ossining, NY 10562

  Last Sold Summary

  • 5% Below List Price
  • $481/SF
  • 14 Days On Market

  • Last Sold Price $740,000
  • Jul 01, 2024

  Last Listing Agent Francie Malina Compass Greater NY, LLC
• 

  

  

  /28

  $1,345,000

  • 4 Beds
  • 2.5 Baths
  • 3,592 Sq Ft

  14 Wyche Way, Ossining, NY 10562

  Beautifully updated center hall Colonial, set on a private and professionally landscaped almost one-acre property on a quiet cul-de-sac in one of Ossining’s most desirable neighborhoods. This move-in ready home blends classic architecture with modern upgrades and a highly functional layout designed for today’s lifestyle. The centerpiece of the home is the newly installed Leicht kitchen, featuring

  John Oliveira Douglas Elliman Real Estate

  14 Wyche Way, Ossining, NY 10562
• 

  $596,370

  Sold Nov 19, 2025

  19 1st Ave, Ossining, NY 10562

  • 3 Beds
  • 1 Bath
  • 1,512 Sq Ft
  • Built 1930

  Last Sold Summary

  • $394/SF
  • 34 Days On Market

  Current Estimated Value $607,568

  Last Listing Agent Valerie Cascione Compass Greater NY, LLC

  19 1st Ave, Ossining, NY 10562
• 

  Est $638,189

  Not Listed For Sale

  27 Somerstown Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1928

  27 Somerstown Rd, Ossining, NY 10562

  Last Sold Summary

  • 16% Above List Price
  • $441/SF
  • 89 Days On Market

  • Last Sold Price $550,000
  • Jan 26, 2024

  Last Listing Agent Shirley Jacobs Houlihan Lawrence Inc.
• 

  

  /23

  $335,000

  Pending

  • 3 Beds
  • 1 Bath
  • 842 Sq Ft

  22 Lafayette Ave, Ossining, NY 10562

  Opportunity knocks. Are you looking for a starter house or is it time to downsize? 22 Lafayette Ave might be just what you've been looking for. Bring your vision and creativity to this cozy 3-bedroom, 1-bath ranch nestled on a quiet street in the heart of Ossining. Perfect for investors, contractors or handy buyers looking to build equity. Enter into a front porch leading to a living room, eat-in

  Jeffrey Hanrahan Keller Williams Realty Group

  22 Lafayette Ave, Ossining, NY 10562
• 

  $1,400,000

  Sold Jun 18, 2025

  95 Old Briarcliff Rd, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2.5 Baths
  • 3,259 Sq Ft
  • Built 1906

  Last Sold Summary

  • 17% Above List Price
  • $430/SF
  • 9 Days On Market

  Current Estimated Value $1,420,163

  Last Listing Agent Eileen O'Neill Houlihan Lawrence Inc.

  95 Old Briarcliff Rd, Briarcliff Manor, NY 10510
• 

  Est $676,383

  Not Listed For Sale

  17 Feeney Rd, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 1,650 Sq Ft
  • Built 1963

  17 Feeney Rd, Ossining, NY 10562

  Last Sold Summary

  • 2% Above List Price
  • $400/SF
  • 73 Days On Market

  • Last Sold Price $660,000
  • Feb 11, 2025

  Last Listing Agent Karen O'Connor Compass Greater NY, LLC
• 

  

  /32

  $775,000

  Open Sat 1PM - 3PM

  • 4 Beds
  • 3.5 Baths
  • 2,863 Sq Ft

  903 Pheasant Woods Rd, Briarcliff Manor, NY 10510

  Nestled in a quiet neighborhood, this spacious townhome offers the perfect combination of comfort, convenience, and privacy. The open-concept living and dining area is filled with natural light and features sliding doors leading to a private deck-an ideal spot for morning coffee, outdoor dining, or simply relaxing in a peaceful setting. The large eat-in kitchen offers ample space for cooking and

  Melissa Palley Julia B Fee Sothebys Int. Rlty

  903 Pheasant Woods Rd, Briarcliff Manor, NY 10510
• 

  $925,000

  Sold Jan 08, 2026

  59 Somerstown Rd, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 3,946 Sq Ft
  • Built 1840

  Last Sold Summary

  • 3% Above List Price
  • $234/SF
  • 32 Days On Market

  Current Estimated Value $929,517

  Last Listing Agent Janet Brand Houlihan Lawrence Inc.

  59 Somerstown Rd, Ossining, NY 10562
• 

  Est $583,444

  Not Listed For Sale

  60 Croton Dam Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,918 Sq Ft
  • Built 1732

  60 Croton Dam Rd, Ossining, NY 10562

  Last Sold Summary

  • 12% Above List Price
  • $271/SF
  • 18 Days On Market

  • Last Sold Price $520,000
  • Jun 21, 2024

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
• 

  

  /39

  $699,001

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

  16 Rockledge Ave Unit 2E2, Ossining, NY 10562

  This is a rare opportunity to own a truly exceptional residence with panoramic, year-round Hudson River views, something rarely found at this price point in Scarborough Manor. Designed for both comfort and sophistication, this expansive three-bedroom, two-bath home offers 9ft ceilings, oversized rooms, and abundant closet space throughout. The layout strikes the perfect balance between everyday

  Cynthia Leite ERA Insite Realty Services

  16 Rockledge Ave Unit 2E2, Ossining, NY 10562
• 

  $1,530,000

  Sold Mar 27, 2026

  383 Illington Rd, Ossining, NY 10562

  • 3 Beds
  • 3.5 Baths
  • 4,300 Sq Ft
  • Built 2006

  Last Sold Summary

  • 10% Below List Price
  • $356/SF
  • 215 Days On Market

  Current Estimated Value $1,513,208

  Last Listing Agent Annette Cicinelli Keller Williams Realty Partner

  383 Illington Rd, Ossining, NY 10562
• 

  Est $818,089

  Not Listed For Sale

  6 Cherry Hill Cir, Ossining, NY 10562

  • 3 Beds
  • 1.5 Baths
  • 2,356 Sq Ft
  • Built 1969

  6 Cherry Hill Cir, Ossining, NY 10562

  Last Sold Summary

  • 12% Above List Price
  • $309/SF
  • 25 Days On Market

  • Last Sold Price $729,000
  • Sep 12, 2023

  Last Listing Agent Joanne Daly Coldwell Banker Realty
• 

  

  /38

  $450,000

  Open Sat 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 930 Sq Ft

  20 Samstag Ave, Ossining, NY 10562

  20 Samstag Ave is the kind of home that sparks ideas the moment you enter. Tucked into an established Ossining neighborhood just minutes from the Hudson River, this classic 2-story Cape-style home with charming dormers and a cheerful red-painted front porch is ready for its next chapter, and for the right buyer, that chapter could be something special. Inside, three bedrooms, a full bath, and 930

  Alex Mashkin Keller Williams Realty Partner

  20 Samstag Ave, Ossining, NY 10562
• 

  $510,000

  Sold Feb 03, 2026

  16 Rockledge Ave Unit 3E1, Ossining, NY 10562

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

  Last Sold Summary

  • $249/SF
  • 52 Days On Market

  Current Estimated Value $378,000

  Last Listing Agent Marcia Sousa Weichert Realtors

  16 Rockledge Ave Unit 3E1, Ossining, NY 10562
• 

  Est $788,961

  Not Listed For Sale

  83 van Cortlandt Ave, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,032 Sq Ft
  • Built 1984

  83 van Cortlandt Ave, Ossining, NY 10562

  Last Sold Summary

  • 11% Above List Price
  • $349/SF
  • 13 Days On Market

  • Last Sold Price $710,000
  • Feb 02, 2024

  Last Listing Agent David Murillo eRealty Advisors, Inc
• 

  

  /50

  $1,680,000

  Pending

  • 5 Beds
  • 2.5 Baths
  • 4,550 Sq Ft

  230 Ridgecrest Rd, Briarcliff Manor, NY 10510

  Bucolic Privacy on 1.14 Acres, this spacious 5-bedroom Cape/Colonial set in the sought-after Ridgecrest area of Briarcliff Manor. Surrounded by perennial gardens, mature trees and natural beauty, this home offers exceptional privacy while remaining conveniently close to the Scarborough train station. A dramatic two-story entry hall welcomes you inside and leads to a sunken living room with access

  Elizabeth Harlow Compass Greater NY, LLC

  230 Ridgecrest Rd, Briarcliff Manor, NY 10510
• 

  $370,000

  Sold Sep 24, 2025

  3 Belleview Ave, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft
  • Built 1954

  Last Sold Summary

  • 18% Below List Price
  • $255/SF
  • 96 Days On Market

  Current Estimated Value $420,173

  Last Listing Agent Derek Greene Greene Realty Group

  3 Belleview Ave, Ossining, NY 10562
• 

  Est $618,868

  Not Listed For Sale

  64 Hudson Watch Dr, Ossining, NY 10562

  • 2 Beds
  • 3 Baths
  • 1,435 Sq Ft
  • Built 1987

  64 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 15% Above List Price
  • $376/SF
  • 11 Days On Market

  • Last Sold Price $540,000
  • Mar 08, 2024

  Last Listing Agent Josephine LaPietra PLI Realty
• 

  

  /42

  $789,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,302 Sq Ft

  23 Apple Ln, Briarcliff Manor, NY 10510

  Welcome to this wonderful Chilmark neighborhood home, nestled on over half an acre of level property and featuring a beautifully enclosed, fully fenced backyard. This 3-bedroom, 2 and a half bath home with a 2-car garage offers a seamless blend of style and relaxed living. At its center, sleek and bright, the fully renovated kitchen flows into the dining room and living room with fireplace, and

  Donna Gravenese Houlihan Lawrence Inc.

  23 Apple Ln, Briarcliff Manor, NY 10510
• 

  $490,000

  Sold Aug 26, 2025

  1 Brooke Club Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,825 Sq Ft
  • Built 1985

  Last Sold Summary

  • 2% Below List Price
  • $268/SF
  • 29 Days On Market

  Last Listing Agent Peter Giner Giner Real Estate Inc.

  1 Brooke Club Dr, Ossining, NY 10562
• 

  Est $658,158

  Not Listed For Sale

  52 Hudson Watch Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,752 Sq Ft
  • Built 1987

  52 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 19% Above List Price
  • $317/SF
  • 21 Days On Market

  • Last Sold Price $555,000
  • Jul 06, 2023

  Last Listing Agent Catherine Lederer ICAN Realty Corp
• 

  

  /42

  $1,599,000

  Open Sat 11:30AM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 4,370 Sq Ft

  273 Elm Rd, Briarcliff Manor, NY 10510

  Refined and timeless, this beautifully renovated 1930 Center Hall Colonial at 273 Elm Road blends classic architectural character with sophisticated modern living. Set on over an acre of private, landscaped grounds, the show-stopping original details include soaring ceilings, graceful archways, an oversized original fireplace, and a restored vintage butler’s pantry, replete with custom millwork.

  Susan Law Houlihan Lawrence Inc.

  273 Elm Rd, Briarcliff Manor, NY 10510
• 

  $470,000

  Sold Mar 26, 2026

  2 N Water St Unit 1A, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,148 Sq Ft
  • Built 1870

  Last Sold Summary

  • 4% Above List Price
  • $409/SF
  • 207 Days On Market

  Last Listing Agent Lynn Harmonay North Country Sothebys Int Rlt

  2 N Water St Unit 1A, Ossining, NY 10562
• 

  Est $733,559

  Not Listed For Sale

  60 Hudson Watch Dr, Ossining, NY 10562

  • 2 Beds
  • 3 Baths
  • 1,687 Sq Ft
  • Built 1987

  60 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • $434/SF
  • 7 Days On Market

  • Last Sold Price $732,000
  • Sep 13, 2024

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.
• 

  /2

  $2,100,000

  $900K PRICE DROP

  • Land
  • 5.92 Acres
  • $354,730 per Acre

  0 van Wyck St Unit KEY834077, Ossining, NY 10562

  Property located at Snowden Avenue & van Wyck Street. Site plan approval required. Plans available to review see attached flyer.Planned and designed for 48 unit four story building with views of Hudson River. 36 two bedroom & 16 one bedroom. Roof-top terrace overlooking the Hudson River, swimming pool, fitness area, pedestrian path connecting Van Wyck Street through the site and connecting to

  Barry Synnott Coldwell Banker Realty

  0 van Wyck St Unit KEY834077, Ossining, NY 10562
• 

  $1,205,000

  Sold Oct 10, 2025

  173B Chappaqua Rd, Briarcliff Manor, NY 10510

  • 5 Beds
  • 3.5 Baths
  • 3,866 Sq Ft
  • Built 1995

  Last Sold Summary

  • $312/SF
  • 33 Days On Market

  Current Estimated Value $1,469,282

  Last Listing Agent Christine DiChiara Coldwell Banker Realty

  173B Chappaqua Rd, Briarcliff Manor, NY 10510
• 

  Est $687,900

  Not Listed For Sale

  69 Hudson Watch Dr, Ossining, NY 10562

  • 1 Bed
  • 2.5 Baths
  • 1,793 Sq Ft
  • Built 1987

  69 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 10% Above List Price
  • $349/SF
  • 32 Days On Market

  • Last Sold Price $625,000
  • Jun 14, 2024

  Last Listing Agent Amber Thomas Compass Greater NY, LLC
• 

  

  /17

  $285,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,250 Sq Ft

  155 Charter Cir Unit 155, Ossining, NY 10562

  Welcome to this spacious townhouse-style co-op in Ossining, NY. This inviting home features 3 bedrooms and 1.5 bathrooms, offering plenty of space for comfortable living. The eat-in kitchen is perfect for everyday meals, and the in-unit laundry provides added convenience. The bright living area features sliding glass doors that lead to the back of the complex, offering a great spot to relax and

  Amanda Samuel RE/MAX Distinguished Hms.&Prop

  155 Charter Cir Unit 155, Ossining, NY 10562
• 

  $490,000

  Sold Oct 14, 2025

  5 Amawalk Ct, Ossining, NY 10562

  • 4 Beds
  • 1 Bath
  • 1,306 Sq Ft
  • Built 1954

  Last Sold Summary

  • 11% Below List Price
  • $375/SF
  • 61 Days On Market

  Current Estimated Value $520,900

  Last Listing Agent Rose Asprea Houlihan Lawrence Inc.

  5 Amawalk Ct, Ossining, NY 10562
• 

  Est $743,754

  Not Listed For Sale

  66 Hudson Watch Dr, Ossining, NY 10562

  • 1 Bed
  • 2.5 Baths
  • 1,695 Sq Ft
  • Built 1987

  66 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 1% Below List Price
  • $442/SF
  • 11 Days On Market

  • Last Sold Price $750,000
  • Jun 05, 2024

  Last Listing Agent Cindy Kief Corcoran Legends Realty
• 

  

  /29

  $1,450,000

  Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 4,290 Sq Ft

  352 Croton Dam Rd, Ossining, NY 10562

  Set privately on a beautifully landscaped property, this exceptional colonial at 352 Croton Dam Road offers the perfect blend of timeless design, modern updates, and everyday comfort. A grand two-story entry welcomes you into sun-filled interiors featuring hardwood floors, oversized windows, and thoughtfully designed living spaces throughout. The stunning renovated chef’s kitchen is the

  Sari Shaw Compass Greater NY, LLC

  352 Croton Dam Rd, Ossining, NY 10562
• 

  $480,000

  Sold May 07, 2026

  15 Steven Dr Unit 4, Ossining, NY 10562

  • 2 Beds
  • 2 Baths
  • 1,337 Sq Ft
  • Built 1988

  Last Sold Summary

  • 7% Above List Price
  • $359/SF
  • 16 Days On Market

  Last Listing Agent James Andrews Today Realty Corp.

  15 Steven Dr Unit 4, Ossining, NY 10562
• 

  Est $704,932

  Not Listed For Sale

  36 Hudson Watch Dr, Ossining, NY 10562

  • 1 Bed
  • 2.5 Baths
  • 1,847 Sq Ft
  • Built 1987

  36 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 7% Above List Price
  • $357/SF
  • 18 Days On Market

  • Last Sold Price $660,000
  • Nov 22, 2024

  Last Listing Agent Anthony Sibio Coldwell Banker Realty
• 

  

  /28

  $599,999

  $50K PRICE DROP Pending

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

  8 Hudson Watch Dr, Ossining, NY 10562

  Welcome to Hudson Watch, one of Ossining’s most sought-after townhome communities. This beautifully maintained unit offers a perfect blend of comfort and convenience, featuring a bright, open floor plan with seasonal Hudson River views. The main level boasts a spacious living area anchored by a cozy fireplace and sliding glass doors that lead to a private deck- ideal for morning coffee or sunset

  Sana Gilani Houlihan Lawrence Inc.

  8 Hudson Watch Dr, Ossining, NY 10562
• 

  $723,000

  Sold Jan 08, 2026

  7 Liberty St, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1820

  Last Sold Summary

  • 3% Above List Price
  • $543/SF
  • 20 Days On Market

  Current Estimated Value $703,269

  Last Listing Agent Elizabeth Harlow Compass Greater NY, LLC

  7 Liberty St, Ossining, NY 10562
• 

  Est $621,425

  Not Listed For Sale

  32 Hudson Watch Dr, Ossining, NY 10562

  • 2 Beds
  • 2.5 Baths
  • 1,730 Sq Ft
  • Built 1987

  32 Hudson Watch Dr, Ossining, NY 10562

  Last Sold Summary

  • 21% Above List Price
  • $298/SF
  • 54 Days On Market

  • Last Sold Price $515,000
  • Jan 08, 2024

  Last Listing Agent Maria Fitzgerald Compass Greater NY, LLC

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