Ossining, NY Homes

• 

  

  

  /5

  $120,000

  Pending

  • 1 Bed
  • 1 Bath
  • 750 Sq Ft

  165 S Highland Ave Unit C, Ossining, NY 10562

  This is an amazing opportunity for someone handy or a contractor, to get into homeownership if your a first time buyer! Or if you are selling your home and need to downsize. First time on the market in 40 years! Spacious one bedroom co-op near the Scarborough Metro North train station! Located across the street from Shoprite shopping plaza and close to all! No renting allowed, no dogs. This unit

  Imma Carletto Christie's Int. Real Estate

  165 S Highland Ave Unit C, Ossining, NY 10562
• 

  $1,410,000

  Sold Jul 22, 2025

  444 River Rd, Briarcliff Manor, NY 10510

  • 4 Beds
  • 3.5 Baths
  • 4,412 Sq Ft
  • Built 1984

  Last Sold Summary

  • 8% Above List Price
  • $320/SF
  • 20 Days On Market

  Current Estimated Value $1,529,362

  Last Listing Agent Hillary Landau Compass Greater NY, LLC

  444 River Rd, Briarcliff Manor, NY 10510
• 

  Est $1,111,315

  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

  • 6% Above List Price
  • $439/SF
  • 13 Days On Market

  • Last Sold Price $1,050,000
  • Dec 21, 2023

  Last Listing Agent Douglas Dill Houlihan Lawrence Inc.
• 

  

  

  /44

  $235,000

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft

  127 S Highland Ave Unit B3, Ossining, NY 10562

  Spacious two bedroom light & airy updated END-unit in heart of town offers easy affordable living. Wired for Verizon Fios/Spectrum/Cablevision. Common charges include taxes, heat, water, buildings/grounds and pool maintenance, insurance & parking. This is a one level first floor unit just a couple of steps up from the front door. Multiple ceiling fans and windows in every room and a/c units

  Jane Rodman Howard Hanna Rand Realty

  127 S Highland Ave Unit B3, 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
• 

  Est $1,567,505

  Not Listed For Sale

  335 Jaclyn Ln, Ossining, NY 10562

  • 4 Beds
  • 3.5 Baths
  • 3,294 Sq Ft
  • Built 1992

  335 Jaclyn Ln, Ossining, NY 10562

  Last Sold Summary

  • 14% Above List Price
  • $417/SF
  • 8 Days On Market

  • Last Sold Price $1,375,000
  • Dec 08, 2023

  Last Listing Agent Douglas Dill Houlihan Lawrence Inc.
• 

  

  /39

  $795,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,612 Sq Ft

  101 Spring Valley Rd, Ossining, NY 10562

  Historic farmhouse-style home with original character and some modern updatesSet on a nearly half-acre lot in a quiet, wooded area , detached barn adds flexibility (garage, storage, workshop).Includes large front porch and scenic, “bucolic” surroundings, Hardwood flooring throughout. Located near the Teatown Lake Reservation and major commuter routes, low taxes

  Ted Thompson Christie's Int. Real Estate

  101 Spring Valley Rd, Ossining, NY 10562
• 

  $715,000

  Sold Aug 01, 2025

  2 Jenkins Ct, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 2,112 Sq Ft
  • Built 2000

  Last Sold Summary

  • 5% Above List Price
  • $339/SF
  • 57 Days On Market

  Current Estimated Value $737,309

  Last Listing Agent Tina Ciufo William Raveis-New York LLC

  2 Jenkins Ct, Ossining, NY 10562
• 

  Est $795,884

  Not Listed For Sale

  17 Adams Rd, Ossining, NY 10562

  • 4 Beds
  • 2 Baths
  • 2,184 Sq Ft
  • Built 1958

  17 Adams Rd, Ossining, NY 10562

  Last Sold Summary

  • 18% Above List Price
  • $309/SF
  • 15 Days On Market

  • Last Sold Price $675,500
  • Jun 26, 2023

  Last Listing Agent Suzan Zeolla Houlihan Lawrence Inc.
• 

  

  /45

  $650,000

  Pending

  • 6 Beds
  • 4 Baths
  • 2,678 Sq Ft

  16 Maple Place, Ossining, NY 10562

  Two-Family Home with Bonus Living Space – Prime Ossining Location This versatile two-family home with bonus living space offers comfort, convenience, and investment potential, all within minutes of downtown Ossining. Set on a large lot with ample off-street parking, it’s an ideal choice for investors, extended living groups, or buyers seeking flexible living arrangements. Each unit is bright and

  Crystal Hawkins Syska Keller Williams NY Realty

  16 Maple Place, 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 $634,137

  Last Listing Agent Mark Seiden Mark Seiden Real Estate Team

  22 William St, Ossining, NY 10562
• 

  Est $1,801,883

  Not Listed For Sale

  50 Cloverhill Ln, Ossining, NY 10562

  • 5 Beds
  • 4.5 Baths
  • 5,006 Sq Ft
  • Built 2005

  50 Cloverhill Ln, Ossining, NY 10562

  Last Sold Summary

  • $359/SF
  • 24 Days On Market

  • Last Sold Price $1,799,000
  • Nov 07, 2024

  Last Listing Agent Maeck Fowler Julia B Fee Sothebys Int. Rlty
• 

  

  /42

  $569,000

  Pending

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  1C Calam Ave, Ossining, NY 10562

  Charming 3-bedroom, 1-bath ranch offering easy one-level living in a convenient Ossining location. This bright and inviting home features hardwood floors, an open-concept layout, and an updated kitchen and bathroom (2020). The renovated mudroom adds everyday functionality, while the partially finished walk-out basement provides flexible space for a recreation room, home office, gym, or additional

  Felix Hernandez Real Broker NY LLC

  1C Calam Ave, Ossining, NY 10562
• 

  $750,000

  Sold Jun 24, 2025

  255 Chadeayne Rd, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,310 Sq Ft
  • Built 1967

  Last Sold Summary

  • $325/SF
  • 110 Days On Market

  Current Estimated Value $795,866

  Last Listing Agent Douglas Dill Houlihan Lawrence Inc.

  255 Chadeayne Rd, Ossining, NY 10562
• 

  Est $1,661,158

  Not Listed For Sale

  1340 Kitchawan Rd, Ossining, NY 10562

  • 8 Beds
  • 6.5 Baths
  • 6,500 Sq Ft
  • Built 1906

  1340 Kitchawan Rd, Ossining, NY 10562

  Last Sold Summary

  • 64% Above List Price
  • $156/SF
  • 27 Days On Market

  • Last Sold Price $1,015,000
  • Apr 30, 2025

  Last Listing Agent Donna Ramundo Keller Williams Valley Realty
• 

  /2

  $850,000

  Pending

  • 3 Beds
  • 2.5 Baths
  • 2,250 Sq Ft

  23 Liberty St, Ossining, NY 10562

  THIS IS NOT JUST ANOTHER LISTING! Don't miss this RARE opportunity to own a newly constructed home in the heart of Westchester County. This thoughtfully designed, three-level residence is currently being built with modern energy-efficient standards and fitted with premium, top-tier appliances. Every aspect of this home has been crafted to deliver both style and functionality for today’s

  Paige Castiello Keller Williams Realty Group

  23 Liberty St, 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
• 

  Est $939,851

  Not Listed For Sale

  1709 Spring Valley Rd, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft
  • Built 1790

  1709 Spring Valley Rd, Ossining, NY 10562

  Last Sold Summary

  • 10% Above List Price
  • $477/SF
  • 18 Days On Market

  • Last Sold Price $855,000
  • Jul 07, 2023

  Last Listing Agent Cindy Glynn Compass Greater NY, LLC
• 

  

  /38

  $699,000

  Open Sun 2PM - 4PM

  • 7 Beds
  • 4 Baths
  • 2,990 Sq Ft

  67 State St, Ossining, NY 10562

  Perfect for investor or end-user. Located in the heart of the village, the structure sits on a 4,356-square-foot lot and offers a classic architectural style characteristic of the historic downtown Ossining area. This multi-family, 2 family with accessory unit ground floor unit. Property features 7 bedrooms and 4 bathrooms.

  Luis Morocho Motivated Access Realty Corp.

  67 State St, 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
• 

  Est $1,033,946

  Not Listed For Sale

  1137 Estates Dr, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft
  • Built 1997

  1137 Estates Dr, Ossining, NY 10562

  Last Sold Summary

  • 16% Above List Price
  • $330/SF
  • 41 Days On Market

  • Last Sold Price $895,000
  • Jul 28, 2023

  Last Listing Agent Peter Procino Coldwell Banker Realty
• 

  

  /45

  $679,000

  Pending

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

  58 Hudson Watch Dr, Ossining, NY 10562

  Get ready for easy living in this beautifully updated two bedroom plus den townhome in a prime location in the coveted Hudson Watch community. Don't miss this rare opportunity for a mint-condition home with Hudson River views from the 2nd level! W alls of windows, vaulted ceilings and skylights let in natural light throughout the residence. This impeccably maintained home is evident from the

  Susan Strawgate Code Houlihan Lawrence Inc.

  58 Hudson Watch Dr, Ossining, NY 10562
• 

  $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 $868,112

  Last Listing Agent Mauro Santucci Kane & Associates

  47 Stormytown Rd, Ossining, NY 10562
• 

  Est $842,020

  Not Listed For Sale

  376 Illington Rd, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft
  • Built 1929

  376 Illington Rd, Ossining, NY 10562

  Last Sold Summary

  • 19% Above List Price
  • $323/SF
  • 65 Days On Market

  • Last Sold Price $710,000
  • Oct 04, 2024

  Last Listing Agent Jeffrey Green Compass Greater NY, LLC
• 

  

  /50

  $999,998

  $98K PRICE DROP Pending

  • 4 Beds
  • 4.5 Baths
  • 3,031 Sq Ft

  18 Briarbrook Dr, Briarcliff Manor, NY 10510

  Tucked away near the heart of Briarcliff Manor, Scarborough Glen offers the perfect blend of comfort, convenience and community living. With beautifully maintained grounds, a clubhouse with exercise room and lounge, a community pool & playground, plus a peaceful setting, and easy access to shops, dining and the Metro North Scarborough Station train, it's easy to see why residents love calling

  Susan Strawgate Code Houlihan Lawrence Inc.

  18 Briarbrook Dr, 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 $914,917

  Last Listing Agent Cindy Cassuto Corcoran Legends Realty

  9 High Ridge Rd, Ossining, NY 10562
• 

  Est $790,564

  Not Listed For Sale

  5 Ridgeview Dr, Ossining, NY 10562

  • 4 Beds
  • 3 Baths
  • 2,192 Sq Ft
  • Built 1952

  5 Ridgeview Dr, Ossining, NY 10562

  Last Sold Summary

  • 12% Above List Price
  • $322/SF
  • 36 Days On Market

  • Last Sold Price $705,000
  • Feb 27, 2024

  Last Listing Agent J. Philip Faranda Howard Hanna Rand Realty
• 

  

  /30

  $575,000

  Pending

  • 3 Beds
  • 2 Baths
  • 1,520 Sq Ft

  15 Prospect Ave, Ossining, NY 10562

  Step into a welcoming three-bedroom, two full-bath home that’s ready to make your life easier. The bright sunroom gives you a perfect spot to relax, while the fully finished basement offers extra room to spread out. The primary bedroom has a walk-in closet, and outside, you’ll enjoy a large backyard for gatherings or quiet afternoons. Plus, the roof was just redone last week, and all new windows

  Besmira Ulaj Serhant LLC

  15 Prospect Ave, Ossining, NY 10562
• 

  $245,500

  Sold May 30, 2025

  114 Charter Cir Unit 114, Ossining, NY 10562

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft
  • Built 1961

  Last Sold Summary

  • 7% Below List Price
  • $273/SF
  • 43 Days On Market

  Last Listing Agent Dorothy Botsoe Dorothy Jensen Realty, Inc.

  114 Charter Cir Unit 114, Ossining, NY 10562
• 

  Est $638,524

  Not Listed For Sale

  18 Ridgeview Dr, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,365 Sq Ft
  • Built 1947

  18 Ridgeview Dr, Ossining, NY 10562

  Last Sold Summary

  • 1% Above List Price
  • $463/SF
  • 13 Days On Market

  • Last Sold Price $632,000
  • Nov 08, 2024

  Last Listing Agent Heather Bouza Compass Greater NY, LLC
• 

  

  /30

  $415,000

  Pending

  • 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
• 

  $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 $830,327

  Last Listing Agent Bopaul Sookdeo YourHomeSold Guaranteed Realty

  15 Cooper Dr, Ossining, NY 10562
• 

  Est $712,227

  Not Listed For Sale

  6 Morningside Dr, Ossining, NY 10562

  • 3 Beds
  • 2 Baths
  • 1,695 Sq Ft
  • Built 1950

  6 Morningside Dr, Ossining, NY 10562

  Last Sold Summary

  • 2% Above List Price
  • $413/SF
  • 20 Days On Market

  • Last Sold Price $700,000
  • Jul 16, 2024

  Last Listing Agent Suzanne Welch Coldwell Banker Realty
• 

  

  /48

  $769,999

  Pending

  • 3 Beds
  • 3 Baths
  • 1,824 Sq Ft

  10 Pine Brook Rd, Ossining, NY 10562

  Nestled on a quiet cul-de-sac and set on a spacious, level yard, this immaculate, move-in-ready 3BR/3BA contemporary home offers bright, open living with soaring cathedral ceilings, skylights, and oversized windows throughout. The main level features gleaming hardwood floors, a sun-filled living and dining area, 3 bedrooms and an updated kitchen with granite countertops and Bosch and Samsung

  Mavra Mita Howard Hanna Rand Realty

  10 Pine Brook Rd, Ossining, NY 10562
• 

  $650,000

  Sold Jul 21, 2025

  162 Club Ct, Ossining, NY 10562

  • 3 Beds
  • 2.5 Baths
  • 1,616 Sq Ft
  • Built 1986

  Last Sold Summary

  • 5% Above List Price
  • $402/SF
  • 14 Days On Market

  Current Estimated Value $660,714

  Last Listing Agent Eric Stein RE/MAX Distinguished Hms.&Prop

  162 Club Ct, Ossining, NY 10562
• 

  Est $774,332

  Not Listed For Sale

  18 Studio Hill Rd, Briarcliff Manor, NY 10510

  • 3 Beds
  • 3 Baths
  • 2,224 Sq Ft
  • Built 1964

  18 Studio Hill Rd, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 11% Above List Price
  • $315/SF
  • 13 Days On Market

  • Last Sold Price $700,000
  • Sep 24, 2024

  Last Listing Agent Susan Strawgate Code Houlihan Lawrence Inc.
• 

  

  /34

  $850,000

  • 2 Beds
  • 1.5 Baths
  • 900 Sq Ft

  227 Cedar Ln, Ossining, NY 10562

  Step back in time without sacrificing an ounce of comfort in this enchanting, 200-year-old hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history and contemporary ease. The interior showcases exceptional craftsmanship, featuring original wide-plank wood floors, a majestic stone fireplace, and a genuine Dutch door. The versatile

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

  227 Cedar Ln, Ossining, NY 10562
• 

  $490,000

  Sold Jun 03, 2025

  3 Sherman Place, Ossining, NY 10562

  • 4 Beds
  • 2.5 Baths
  • 2,300 Sq Ft
  • Built 2024

  Last Sold Summary

  • 11% Below List Price
  • $213/SF
  • 79 Days On Market

  Current Estimated Value $550,962

  Last Listing Agent Arif Baksh YourHomeSold Guaranteed Realty

  3 Sherman Place, Ossining, NY 10562
• 

  Est $827,525

  Not Listed For Sale

  3 Haymont Terrace, Briarcliff Manor, NY 10510

  • 4 Beds
  • 2 Baths
  • 2,436 Sq Ft
  • Built 1960

  3 Haymont Terrace, Briarcliff Manor, NY 10510

  Last Sold Summary

  • 34% Above List Price
  • $254/SF
  • 83 Days On Market

  • Last Sold Price $618,000
  • Mar 05, 2024

  Last Listing Agent Jamie Jamieson Compass Greater NY, LLC
• 

  

  /31

  $1,989,000

  • 4 Beds
  • 2.5 Baths
  • 3,550 Sq Ft

  41 Croton Dam Rd, Ossining, NY 10562

  Experience refined new construction living at 41 Croton Dam Road, a thoughtfully designed 2026-built single-family residence set on 1.38 acres with Hudson River views. Offering 3,550 square feet of elegant living space, this 4-bedroom, 2.5-bath home blends architectural sophistication with modern functionality. The main level features 10-foot ceilings, dramatic 8-foot front entry doors, custom

  Nicola Santucci Houlihan Lawrence Inc.

  41 Croton Dam Rd, Ossining, NY 10562

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